Preface

Terpenes belong to the diverse class of chemical constituents isolated from materials found in nature (plants, fungi, insects, marine organisms, plant pathogens, animals and endophytes). These metabolites have simple-to-complex structures derived from Isopentyl diphosphate (IPP), dimethylallyl diphosphate (DMAPP), mevalonate and deoxyxylulose biosynthetic pathways. Terpenes play a very important role in human health and have significant biological activities (anticancer, antimicrobial, anti-inflammatory, antioxidant, anti-allergic, skin permeation enhancer, anti-diabetic, immunomodulatory, anti-insecticidal). According to new research, cineole (a spicy eucalyptus-derived flavoring oil) terpenes are ready to be directly converted to biofuel as soon as they are produced. This book provides an overview and highlights recent research in the phytochemical and biological understanding of terpenes and terpenoids and explains the most essential functions of these kinds of secondary metabolites isolated from natural sources.

#### **Dr. Shagufta Perveen** Professor,

Distinguish Professor, FRSC-UK, Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

#### **Dr. Areej Al-Taweel**

Professor, Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

**1**

**Figure 1**).

**Chapter 1**

and Terpenoids

*Shagufta Perveen*

have unique skeletons.

**2. Hemiterpene**

**1. Terpenes and terpenoids**

Introductory Chapter: Terpenes

Terpenes are the largest class of secondary metabolites found in nature (plants, fungus, marine organisms, animals). Terpenes are mainly present as a main constituent of essential oils. It consists of isoprene units (CH2=C(CH3)CH=CH2, C5H8) which are known as the building block of all types of terpenes, containing five carbon and eight hydrogen atoms. Monoterpenes have two isoprene units (C10), sesquiterpenes have three (C15), diterpenes have four (C20), sesterpene have five (C25), triterpenes have six (C30) and tetraterpenes have eight isoprene units (C40). Terpenes and terpenoids based chemical constituents are characterized by different chemical diversity with a wide range of therapeutic effects. This class of metabolites has been an enormous source of novel medicinal agents. Many terpenoids or terpenoid derivatives are used as traditional drugs with different medicinal values identified from different natural sources. *Artemisia annua* (sweet wormwood) a medicinal plant belongs to the family Asteraceae provided a drug artemisinin and its related derivatives which used as an antimalarial drug all over the world. Scientists Professor Tu Youyou was awarded Nobel Prize 2015 in Physiology or Medicine for her efforts toward the discovery of this important drug. Artemisinin and its derivatives are mainly sesquiterpenes (fifteen Carbons containing terpenes) which is known as a magical drug which served as the foundation for antimalarial treatment. Currently, many research groups have been reported the therapeutic potential of terpenes and its extract (terpene rich plant extracts) against anticancer, anti-inflammatory and SARS-CoV-2 and performed many tests and screenings. Many studies have been done for testing the efficacy of cannabis terpene for the treatment of this new viral infections [1, 2]. This chapter provides information about recently published terpenes which showed significant biological activities

Hemiterpenes are the basic unit of terpenes and its consists of five carbon atoms (CH2=C(CH3)CH=CH2) or one isoprene unit. It is usually found in different types of plants especially Coniferous, Willow and Oaks. Many types of hemiterpenes have isolated from different marine derived fungi (*Acremonium persicinum*, *Penicillium bialowiezense*) which are known as merohemiterpenoid]. Herein, we are discussing some of the recently published chemical diverse emiterpenes (**Table 1**,

#### **Chapter 1**

## Introductory Chapter: Terpenes and Terpenoids

*Shagufta Perveen*

#### **1. Terpenes and terpenoids**

Terpenes are the largest class of secondary metabolites found in nature (plants, fungus, marine organisms, animals). Terpenes are mainly present as a main constituent of essential oils. It consists of isoprene units (CH2=C(CH3)CH=CH2, C5H8) which are known as the building block of all types of terpenes, containing five carbon and eight hydrogen atoms. Monoterpenes have two isoprene units (C10), sesquiterpenes have three (C15), diterpenes have four (C20), sesterpene have five (C25), triterpenes have six (C30) and tetraterpenes have eight isoprene units (C40). Terpenes and terpenoids based chemical constituents are characterized by different chemical diversity with a wide range of therapeutic effects. This class of metabolites has been an enormous source of novel medicinal agents. Many terpenoids or terpenoid derivatives are used as traditional drugs with different medicinal values identified from different natural sources. *Artemisia annua* (sweet wormwood) a medicinal plant belongs to the family Asteraceae provided a drug artemisinin and its related derivatives which used as an antimalarial drug all over the world. Scientists Professor Tu Youyou was awarded Nobel Prize 2015 in Physiology or Medicine for her efforts toward the discovery of this important drug. Artemisinin and its derivatives are mainly sesquiterpenes (fifteen Carbons containing terpenes) which is known as a magical drug which served as the foundation for antimalarial treatment. Currently, many research groups have been reported the therapeutic potential of terpenes and its extract (terpene rich plant extracts) against anticancer, anti-inflammatory and SARS-CoV-2 and performed many tests and screenings. Many studies have been done for testing the efficacy of cannabis terpene for the treatment of this new viral infections [1, 2]. This chapter provides information about recently published terpenes which showed significant biological activities have unique skeletons.

#### **2. Hemiterpene**

Hemiterpenes are the basic unit of terpenes and its consists of five carbon atoms (CH2=C(CH3)CH=CH2) or one isoprene unit. It is usually found in different types of plants especially Coniferous, Willow and Oaks. Many types of hemiterpenes have isolated from different marine derived fungi (*Acremonium persicinum*, *Penicillium bialowiezense*) which are known as merohemiterpenoid]. Herein, we are discussing some of the recently published chemical diverse emiterpenes (**Table 1**, **Figure 1**).


#### **Table 1.**

*Source and biological activities of some hemiterpenes.*

#### **3. Monoterpenes**

These types of terpenes consist on ten carbon atom or two isoprene units. Each type of monoterpenes has a particular aroma for the related plant such as: Citrus, grapes, rose etc. Many monoterpenes and their isomers have been isolated from different marine sources. Herein, we are discussing some of the recently published monoterpenes (**Table 2**, **Figure 2**).


**3**

**Figure 2.**

**Table 2.**

**4. Sesquiterpenes**

*Structure of monoterpene.*

Sesquiterpenes are the class of terpenes with C15 carbon atoms having many uses like medicine, sanitary, agriculture, cosmetics and foods. These types of terpenes have many biological activities like, antibacterial, antifungal, antiviral and

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

> *rigidus* found in China

red seaweed *Plocamium maxillosum*

Callistrilones H & I *Callistemon* 

Plaxenones A & B South African

*Source and biological activities of some monoterpenes.*

**Name Source Activity Ref**

Melodinines Y1 It showed cytotoxicity toward six cancer cell

Compounds exhibited moderate inhibitory activities against HSV- 1 with IC50 values of 10.00 ± 2.50 and 12.50 ± 1.30 μM, respectively.

Plaxenones A and B were evaluated for activity against the metastatic breast carcinoma (MDA-MB-231) cell line and showed moderate antiproliferative effects with IC50 values of 10.78 ± 1.01 and 22.30 ± 1.13 μM, respectively.

lines. The new modification of the isolated compounds expands the chemical diversity of this family. Cytotoxicity assays have demonstrated that compound significantly inhibited HL-60 cancer cell line, presenting with a great opportunity to discover promising natural

agents for new antitumor leadings.

[6]

[7]

[8]

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*


#### **Table 2.**

*Terpenes and Terpenoids-Recent Advances*

Securiterpenoside G *Securidaca* 

(±)-Cytorhizophin A, Cytorhizophin B

**Table 1.**

*inappendiculata* found in China

Endophytic fungus *Cytospora rhizophorae* from the plant *Morinda officinalis*

*Source and biological activities of some hemiterpenes.*

**2**

**3. Monoterpenes**

*N*-glucopyranosyl vincosamide, vincosamide

*Structure of hemiterpene.*

**Figure 1.**

monoterpenes (**Table 2**, **Figure 2**).

*Psychotria leiocarpa* Leaves found in Brazil

These types of terpenes consist on ten carbon atom or two isoprene units. Each type of monoterpenes has a particular aroma for the related plant such as: Citrus, grapes, rose etc. Many monoterpenes and their isomers have been isolated from different marine sources. Herein, we are discussing some of the recently published

**Name Source Activity Ref**

anti-dengue agent.

Vincosamide with a preliminary dose-dependent activity inhibiting at 50 μg mL−1 99% of DENV infectious particles in the conditioned medium of infected HepG2 culture can be highlighted among the other isolated alkaloids as a potential

**Name Source Activity Ref**

100 μg mL−1.

The potential anti-inflammatory activities of compounds were evaluated through inhibiting nitric oxide (NO) overproduction in LPSstimulated mouse macrophage RAW264.7 model. Cell viability was measured by the MTT assay. None of them showed the obvious cytotoxicity at the dosage of 50 *μ*M and significant antiinflammatory activities (IC50 145.3, 57.5 *μ*M, respectively). Dexamethasone was used as

[3]

[4]

[5]

positive control (IC50 2.5 *μ*M).

These compounds were evaluated for antimicrobial activities against the bacteria *Escherichia coli* and *Staphylococcus aureus*. However, all of them were found to be devoid of significant activity even at a concentration of

*Source and biological activities of some monoterpenes.*

#### **Figure 2.** *Structure of monoterpene.*

#### **4. Sesquiterpenes**

Sesquiterpenes are the class of terpenes with C15 carbon atoms having many uses like medicine, sanitary, agriculture, cosmetics and foods. These types of terpenes have many biological activities like, antibacterial, antifungal, antiviral and ant insecticidal which provokes the researcher to work on the sesquiterpene rich natural sources. It is usually found in Asteraceae family plants. Herein we are tabulating few important sesquiterpene with their structure and biological information (**Table 3**, **Figure 3**).


#### **Table 3.**

*Source and biological activities of some sesquiterpenes.*

**Figure 3.** *Structure of sesquiterpene.*

#### **5. Diterpenes**

It consists on C20 carbon atom having four isoprene units. These are very famous class of compounds as many are using in market for curing cancer


**5**

**Figure 4**).

**Table 4.**

**6. Sesterpenes**

ogy (**Table 5**, **Figure 5**).

**7. Meroterpenes**

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

> *Trichoderma atroviride* FKI-3849 from a soil sample

*Basilicum polystachyon*

*paniculata* from Thailand

*Abies Nukiangensis* found in China

Wickerols A & B Fungus

Andrographolide *Andrographis* 

*Source and biological activities of some diterpenes.*

Nukiangendines A & B

Stachyonic acid A & B

disease such as; Taxol and etc. Herein, we are summarizing few recently published diterpenes structures, sources, origin and biological activities (**Table 4**,

**Name Source Activity Ref**

investigated.

Wickerol A was highly active against two A/ H1N1 viruses, but not active against two A/

Compounds were subjected to an in vitro bioassay for anti-hepatitis C virus (HCV) infection activity. Nukiangendine A exhibits a significant effect at 10 μM with an inhibition rate of 70.0%, compared to 99.0% for sofosbuvir (the positive control) at 0.01 μM.

Stachyonic acids A & B was tested for cytotoxicity against human cells, breast and melanoma along with primary neonatal foreskin fibroblast cells. Mixture of both showed limited cytotoxicity toward all cell lines

Stachyonic acid A, was found to display potent inhibitory activity against dengue virus.

The study demonstrated anti-SARS-CoV-2 activity of *A. paniculata* and andrographolide using a Calu-3-based anti-SARS-CoV-2 assay. Potent anti-SAR-CoV-2 activities, together with the favorable cytotoxicity profiles, support further development of *A. paniculata* extract and especially andrographolide as a monotherapy or in combination with other effective drugs against SARS-CoV-2 infection. [13, 14]

[15]

[16, 17]

[18]

H3N2 viruses or a B-type virus.

Sesterpenes are the small class of terpenoids family which consists on twenty-five carbon atoms (tricyclic 5-8-5 carbotricyclic core, five isoprene units). These types of constituents usually found in plants, fungus culture, insects and marine organism. Sesterterpenes type compounds has complex structures due to the presence of many ring systems which makes its unique skeletons. These compounds have significant biological activities such as cytotoxic, nematocidal, anti-influenza, enzyme inhibition, anti-inflammatory and antimicrobial activities. In this chapter we are discussing, some recently published sesterterpene, including their structures, source, origin and pharmacol-

Meroterpenes are mainly found in marine organisms and abundant in brown algae and other natural sources like microorganisms and invertebrates (sponges and


*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

**Table 4.**

*Terpenes and Terpenoids-Recent Advances*

*Carpesium minus*

Endophytic *Penicillium* sp. found in China

Cedarwood oil

*Source and biological activities of some sesquiterpenes.*

Cedrol *Cedrus atlantica*

(**Table 3**, **Figure 3**).

Minusolide G

Penisarins A & B

**Table 3.**

ant insecticidal which provokes the researcher to work on the sesquiterpene rich natural sources. It is usually found in Asteraceae family plants. Herein we are tabulating few important sesquiterpene with their structure and biological information

**Name Source Activity Ref**

cleavage of PARP.

It exhibited cytotoxic activities against MDA-MB-231, A549, and HCT-116 cells with IC50 values of 6.1 ± 0.2, 8.4 ± 0.6, and 3.7 ± 0.6 μM, respectively. It induced the apoptosis of HCT-116 cells via suppression of PARP and promoting

Penisarin B showed significant cytotoxicities against two human cancer cell lines, HL-60 and SMMC-7721, with IC50 values of 3.6 ± 0.2 and 3.7 ± 0.2 μM, respectively.

Cedrol-treated mice exhibited no significant differences in body weight and improved TMZ-induced liver damage. These results imply that cedrol may be a potential novel agent for combination treatment with TMZ for GBM therapy that deserves further investigation.

[9]

[10]

[11]

[12]

It consists on C20 carbon atom having four isoprene units. These are very famous class of compounds as many are using in market for curing cancer

**Name Source Activity Ref**

The antiproliferative activity of compounds was screened against CCRF-CEM leukemia cells using a fixed concentration of 30 μM. Dose response curve of (2*R*)-ent-2 hydroxyisopimara-8(14),15-dien showed IC50 values of ≤ 50 μM against CCRF-CEM, MDAMB-231-pcDNA and HCT116 (p53+/+).

Edible rhizomes of *Kaempferia galanga* found in India

**4**

**5. Diterpenes**

Kaemgalangols

B-D

*Structure of sesquiterpene.*

**Figure 3.**

*Source and biological activities of some diterpenes.*

disease such as; Taxol and etc. Herein, we are summarizing few recently published diterpenes structures, sources, origin and biological activities (**Table 4**, **Figure 4**).

#### **6. Sesterpenes**

Sesterpenes are the small class of terpenoids family which consists on twenty-five carbon atoms (tricyclic 5-8-5 carbotricyclic core, five isoprene units). These types of constituents usually found in plants, fungus culture, insects and marine organism. Sesterterpenes type compounds has complex structures due to the presence of many ring systems which makes its unique skeletons. These compounds have significant biological activities such as cytotoxic, nematocidal, anti-influenza, enzyme inhibition, anti-inflammatory and antimicrobial activities. In this chapter we are discussing, some recently published sesterterpene, including their structures, source, origin and pharmacology (**Table 5**, **Figure 5**).

#### **7. Meroterpenes**

Meroterpenes are mainly found in marine organisms and abundant in brown algae and other natural sources like microorganisms and invertebrates (sponges and

### **Figure 4.**

*Structure of diterpene.*


**7**

**Figure 6.**

*Structure of meroterpene.*

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

**Figure 6**).

**Figure 5.**

*Structure of sesterterpene.*

Gancochlearols

E − I

**Table 6.**

Peniclactone C Endophytic

fungus *Penicillium* sp. GDGJ-285

*Source and biological activities of some meroterpenes.*

Ganoderma cochlear

tunicates). These types of compounds have many chemical diversities. Herein, we are discussing some recently published biological active meroterpenes (**Table 6**,

**Name Source Activity Ref**

Bioassays showed that peniclactone C inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC50 value of 39.03 μM.

Biological results revealed the significantly inhibitory effects of the Gancochlearols E – I on COX-2 activity and the migration of TNBC cells. In results not only enrich the structure type of meroterpenoids in Ganoderma, but also present novel structural template for developing nonsteroidal anti-inflammatory drug (NSAID) and anti-cancer drug against metastatic TNBC.

[21]

[22]

**Table 5.** *Source and biological activities of some sesterpenes.* *Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

**Figure 5.** *Structure of sesterterpene.*

*Terpenes and Terpenoids-Recent Advances*

**6**

**Table 5.**

**Figure 4.**

*Structure of diterpene.*

Manoalide derivatives

Drophiobiolins A & B

**Name Source Activity Ref**

from 2 to 10 μM.

10 μM.

manoalide derivatives demonstrated cytotoxic activities against several human cancer cell lines with IC50 values ranging

Both of the newly identified ophiobolins showed significant phytotoxicity. Drophiobolins A & B exhibited cytotoxicity against Hela B cells with an IC50 value of

[19]

[20]

Sponge *Luffariella variabilis* from the South China Sea

*Dreschslera gigantea s* found in China

*Source and biological activities of some sesterpenes.*

tunicates). These types of compounds have many chemical diversities. Herein, we are discussing some recently published biological active meroterpenes (**Table 6**, **Figure 6**).


#### **Table 6.**

*Source and biological activities of some meroterpenes.*

**Figure 6.** *Structure of meroterpene.*


**Table 7.** *Source and biological activities of some triterpenes.*

**9**

**Author details**

Shagufta Perveen

Riyadh, Kingdom of Saudi Arabia

provided the original work is properly cited.

Department of Pharmacognosy, College of Pharmacy, King Saud University,

\*Address all correspondence to: shagufta792000@yahoo.com; shakhan@ksu.edu.sa

© 2021 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium,

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

from the squalene biosynthesis (**Table 7**, **Figure 7**).

A major class of secondary metabolites are known as triterpenes and it usually contains thirty carbons consisting of six isoprene units. Different class of triterpenes are known as lanostanes, euphanes,holostanes, tetranortriterpenoids, cycloartanes, cucurbitanes, dammaranes, tirucallanes, quassinoids, oleananes, lupanes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes which derived

**8. Tripterpenes**

**Figure 7.** *Structure of triterpene.*

### **8. Tripterpenes**

*Terpenes and Terpenoids-Recent Advances*

Arenarosides A *Polycarpaea* 

Longipetalol A Dichapetalum

Periploside A5 Root barks of

*Source and biological activities of some triterpenes.*

Ganoweberianones

A & B

**Table 7.**

*arenaria* found in

Fruiting bodies of Basidiomycete *Ganoderma weberianum*

longipetalum

*Periploca sepium*

Brazil

**Name Source Activity Ref**

Compound displayed promising

These compounds were evaluated for Ganoweberianone A exhibited significant antimalarial activity against *Plasmodium falciparum* K1 (multidrug-resistant strain)

Compound exhibited inhibitory effects on nitric oxide production in lipopolysaccharide-

Periploside showed significant suppressive effects on T lymphocyte proliferation with IC50 values ranging from 0.16 to 3.9 *μ*M and displayed potent inhibitory activity on B lymphocyte proliferation with IC50 data at between 0.17 and 5.9 *μ*M. IC50 data of Periploside A5 were 0.30 *μ*M and 0.55 *μ*M for T and B lymphocytes, and with the most favorite selective index values 176 and 96.9,

with an IC50 value of 0.050 μM.

induced RAW264.7 macrophages.

respectively.

antiangiogenesis effects with IC50 values <5 μM in the test system used. It exhibited the most potent inhibitory effects, not only in cancer cell proliferation but also in angiogenic activities.

[23]

[24]

[25]

[26]

**8**

**Figure 7.**

*Structure of triterpene.*

A major class of secondary metabolites are known as triterpenes and it usually contains thirty carbons consisting of six isoprene units. Different class of triterpenes are known as lanostanes, euphanes,holostanes, tetranortriterpenoids, cycloartanes, cucurbitanes, dammaranes, tirucallanes, quassinoids, oleananes, lupanes, friedelanes, ursanes, hopanes, serratanes, isomalabaricanes which derived from the squalene biosynthesis (**Table 7**, **Figure 7**).

### **Author details**

Shagufta Perveen Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Kingdom of Saudi Arabia

\*Address all correspondence to: shagufta792000@yahoo.com; shakhan@ksu.edu.sa

© 2021 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

### **References**

[1] Diniz LRL, Castillo-P Y, Hatem A. Elshabrawy, Filho CSMV, de Sousa DP. Bioactive Terpenes and Their Derivatives as Potential SARS-CoV-2 Proteases Inhibitors from Molecular Modeling Studies. Biomolecules 2021;11(74). DOI: 10.3390/biom 11010074.

[2] Anil MS, Shalev N, Vinayaka AC, Nadarajan S, D Namdar, Belausov E, Shoval I, Mani KA, Mechrez G, Kolta H. Cannabis compounds exhibit antiinfammatory activity in vitro in COVID-19-related infammation in lung epithelial cells and pro-infammatory activity in macrophages. Scientifc Reports. 2021;11;1462. DOI: 10.1038/ s41598-021-81049-2

[3] Yang C, Wang Z, Qiu Y, Zha H,Yang X. New hemiterpene and furolactone-type lignan glycosides from *Securidaca inappendiculata* Hassk. Phytochemistry Letters. 2020; 37:42-46. DOI: 10.1016/j.phytol.2020.04.001

[4] Liu H, Tan H, Wang W, Zhang W, Chen Y, Li S, Liu Z, Lia H, Zhang W. Cytorhizophins A and B, benzophenonehemiterpene adducts from the endophytic fungus Cytospora rhizophorae. Organic Chemistry Frontries. 2019; 6:591-596. DOI: 10.1039/C8QO01306C

[5] Costa JO, Barboza RS, Valente LMM, Gomes TWM, Gallo B, Berrueta LA, Guimarães-Andrade IP, Gavino-Leopoldinod D, Assunção-Miranda I. One-Step Isolation of Monoterpene Indole Alkaloids from Psychotria leiocarpa. Leaves and Their Antiviral Activity on Dengue Virus Type-2. Brazilian Chemical Society. 2020:10(31): 2104-2113. DOI: 10.21577/0103-5053.20200111

[6] Cao J-Q, Wu Y, Zhong Y-L, Li N-P, Chen M, Li M-M, Ye W-C, Wang L. Antiviral Triketone-PhloroglucinolMonoterpene Adducts from Callistemon rigidus. Chemistry & Biodiversity 2018;15: e1800172. DOI: 10.1002/ cbdv.201800172

[7] Knotta MG, de la Marec J.A, Edkinsc AL, Zhangd A, Stillmand MJ, Boltone JJ, Antunesf EM, Beukes DR. Plaxenone A and B: Cytotoxic halogenated monoterpenes from the South African red seaweed Plocamium maxillosum. Phytochemistry Letters. 2019;29:182-185. DOI: 10.1016/j. phytol.2018.12.009

[8] Fa-Lei Zhang, Juan He, Tao Feng, Ji-Kai Liu. Melodinines Y1–Y4, four monoterpene indole alkaloids from Melodinus henryi. RSC Advances. 2021, 11, 23-29. DOI:10.1039/D0RA09819A

[9] Zhu L, Liu X-Q, Lin Y-L, Wang W-L, Luo J-G, Kong L-Y. Cytotoxic Germacranolides from the Whole Plant of *Carpesium minus.* Journal of Natural Products. 2020 25;83(11):3230-3238. DOI: 10.1021/acs.jnatprod.0c00428

[10] Li W, Shao YT, Yin TP, Yan H, Shen BC, Li YY, Xie HD, Sun ZW, Ma YL. Penisarins A and B, Sesquiterpene Coumarins Isolated from an Endophytic *Penicillium* sp. Journal of Natural Products. 2020, 83(11):3471- 3475. DOI: 10.1021/acs. jnatprod.0c00393

[11] Chang K-F, Huang X-F, Chang J-T, Huang Y-C, Lo W-S, Hsiao C-Y, Tsai N-M. Cedrol, a Sesquiterpene Alcohol, Enhances the Anticancer Efficacy of Temozolomide in Attenuating Drug Resistance via Regulation of the DNA Damage Response and MGMT Expression. Journal of Natural Products. 2020;23;83(10):3021-3029. DOI: 10.1021/acs.jnatprod.0c00580

[12] Elshamy AI, Mohamed TA, Swapana N, Yoneyama T, Noji M, Efferth T, Hegazy M-EF, Akemi

**11**

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

Umeyama. Cytotoxic polyoxygenated isopimarane diterpenoids from the edible rhizomes of *Kaempferia galanga* (kencur). Industrial Crops & Products 2020; 158:112965. DOI:10.1016/j.

Charoensutthivarakul S, Wongtra koongate P, Pitiporn S, Chaopreecha J, Kongsomros S, Jearawuttanakul K,

*Andrographis paniculata* Extract and Its Major Component Andrographolide in Human Lung Epithelial Cells and Cytotoxicity Evaluation in Major Organ Cell Representatives. Journal of Natural Products*.* 2021;84(4):1261-

Wannalo W, Phisit K, Chuti pongtanate S, Borwornpinyo S, Thitithanyanont A, Hongeng S. Anti-SARS-CoV-2 Activity of

1270. DOI: 10.1021/acs. jnatprod.0c01324

0c01026

0c00836

10.1039/d1qo00173f

bioorg.2021.104706

[19] Luo X, Wang Q, Tang X, Xu J, Wang M, Li P, Li G. Cytotoxic Manoalide-Type Sesterterpenes from the Sponge *Luffariella variabilis* Collected in the South China Sea. Journal of Natural Products. 2021;84(1): 61-70. DOI: 10.1021/acs.jnatprod.

[20] Zatout R, Masi M , Sangermano F, Vurro M, Zonno MC, Santoro E, Viola Calabrò V, Superchi S, Evidente A. Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by *Dreschslera gigantea.* Journal of Natural Products. 2020;83(11):3387- 3396. DOI: 10.1021/acs.jnatprod.

[21] Mo T-X, Huang X-S, Zhang W-X, Schäberle TF, Qin J-K, Zhou D-X, Qin X-Y, Xu Z-L, Li J, Yang R-Y. A series of meroterpenoids with rearranged skeletons from an endophytic fungus *Penicillium* sp. GDGJ-285. Organic Chemistry Frontiers. 2021. DOI:

[22] Li Y-P, Jiang X-T, Qin F-Y, Zhang H-X, Cheng Y-X. Gancochlearols E-I, meroterpenoids from *Ganoderma cochlear* against COX-2 and triple negative breast cancer cells and the absolute configuration assignment of ganomycin K. Bioorganic Chemistry 2021;109: 104706. DOI: 10.1016/j.

[13] Yamamoto T, Izumi N, Ui H, Sueki A, Masuma R, Nonaka K, Hirose T, Sunazuka T, Nagai T, Yamada H, Ōmura S, Shiomi K.

virus diterpenes produced by *Trichoderma atroviride* FKI-3849. Tetrahedron. 2012;45(68):9267-9271.

DOI:10.1016/j.tet.2012.08.066

[14] Deng J, Ning Y, Tian H, Gui J. Divergent Synthesis of Antiviral Diterpenes Wickerols A and B. Journal

of American Chemical Society*.*

jacs.9b11838

2020;142(10), 4690-4695. DOI: 10.1021/

[15] LiLi-Y, Zhang O, Wu J-J, Xue L-J, Chen L-M, Tian J-M, Xu Z-N, Chen Y, Yang X-W, Hao X-J, Li J. Nukiangendines A and B, two novel 13,14-*seco-*abietanes from *Abies nukiangensis.* Tetrahedron Letters. 2019;10(60):751-753. DOI: 10.1016/j.tetlet.2019.02.008

[16] Tan YP, Houston SD, Modhiran N, Savchenko AI, Boyle GM, Young PR, Watterson D, Williams C.M. Stachyonic Acid: A Dengue Virus Inhibitor from *Basilicum Polystachyon*. Chemistry A Eurpion Journal 2019; 25:5664-5667. DOI:10.1002/chem.201900591

[17] Yuen P. Tan, Sevan D. Houston, Naphak Modhiran, Andrei I. Savchenko, Glen M. Boyle, Paul R. Young, Daniel Watterson, Craig M. Williams. Stachyonic Acid: A Dengue Virus Inhibitor from *Basilicum Polystachyon*.

Chemistry A Eurpion Journal 2019;25,5664-5667. DOI:10.1002/

Pewkliang Y, Thongsri P,

[18] Sa-ngiamsuntorn K, Suksatu A,

Kanjanasirirat P, Manopwisedjaroen S,

chem.201900591

Wickerols A and B: novel anti-influenza

indcrop.2020.112965

*Introductory Chapter: Terpenes and Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.98261*

Umeyama. Cytotoxic polyoxygenated isopimarane diterpenoids from the edible rhizomes of *Kaempferia galanga* (kencur). Industrial Crops & Products 2020; 158:112965. DOI:10.1016/j. indcrop.2020.112965

[13] Yamamoto T, Izumi N, Ui H, Sueki A, Masuma R, Nonaka K, Hirose T, Sunazuka T, Nagai T, Yamada H, Ōmura S, Shiomi K. Wickerols A and B: novel anti-influenza virus diterpenes produced by *Trichoderma atroviride* FKI-3849. Tetrahedron. 2012;45(68):9267-9271. DOI:10.1016/j.tet.2012.08.066

[14] Deng J, Ning Y, Tian H, Gui J. Divergent Synthesis of Antiviral Diterpenes Wickerols A and B. Journal of American Chemical Society*.* 2020;142(10), 4690-4695. DOI: 10.1021/ jacs.9b11838

[15] LiLi-Y, Zhang O, Wu J-J, Xue L-J, Chen L-M, Tian J-M, Xu Z-N, Chen Y, Yang X-W, Hao X-J, Li J. Nukiangendines A and B, two novel 13,14-*seco-*abietanes from *Abies nukiangensis.* Tetrahedron Letters. 2019;10(60):751-753. DOI: 10.1016/j.tetlet.2019.02.008

[16] Tan YP, Houston SD, Modhiran N, Savchenko AI, Boyle GM, Young PR, Watterson D, Williams C.M. Stachyonic Acid: A Dengue Virus Inhibitor from *Basilicum Polystachyon*. Chemistry A Eurpion Journal 2019; 25:5664-5667. DOI:10.1002/chem.201900591

[17] Yuen P. Tan, Sevan D. Houston, Naphak Modhiran, Andrei I. Savchenko, Glen M. Boyle, Paul R. Young, Daniel Watterson, Craig M. Williams. Stachyonic Acid: A Dengue Virus Inhibitor from *Basilicum Polystachyon*. Chemistry A Eurpion Journal 2019;25,5664-5667. DOI:10.1002/ chem.201900591

[18] Sa-ngiamsuntorn K, Suksatu A, Pewkliang Y, Thongsri P, Kanjanasirirat P, Manopwisedjaroen S, Charoensutthivarakul S, Wongtra koongate P, Pitiporn S, Chaopreecha J, Kongsomros S, Jearawuttanakul K, Wannalo W, Phisit K, Chuti pongtanate S, Borwornpinyo S, Thitithanyanont A, Hongeng S. Anti-SARS-CoV-2 Activity of *Andrographis paniculata* Extract and Its Major Component Andrographolide in Human Lung Epithelial Cells and Cytotoxicity Evaluation in Major Organ Cell Representatives. Journal of Natural Products*.* 2021;84(4):1261- 1270. DOI: 10.1021/acs. jnatprod.0c01324

[19] Luo X, Wang Q, Tang X, Xu J, Wang M, Li P, Li G. Cytotoxic Manoalide-Type Sesterterpenes from the Sponge *Luffariella variabilis* Collected in the South China Sea. Journal of Natural Products. 2021;84(1): 61-70. DOI: 10.1021/acs.jnatprod. 0c01026

[20] Zatout R, Masi M , Sangermano F, Vurro M, Zonno MC, Santoro E, Viola Calabrò V, Superchi S, Evidente A. Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by *Dreschslera gigantea.* Journal of Natural Products. 2020;83(11):3387- 3396. DOI: 10.1021/acs.jnatprod. 0c00836

[21] Mo T-X, Huang X-S, Zhang W-X, Schäberle TF, Qin J-K, Zhou D-X, Qin X-Y, Xu Z-L, Li J, Yang R-Y. A series of meroterpenoids with rearranged skeletons from an endophytic fungus *Penicillium* sp. GDGJ-285. Organic Chemistry Frontiers. 2021. DOI: 10.1039/d1qo00173f

[22] Li Y-P, Jiang X-T, Qin F-Y, Zhang H-X, Cheng Y-X. Gancochlearols E-I, meroterpenoids from *Ganoderma cochlear* against COX-2 and triple negative breast cancer cells and the absolute configuration assignment of ganomycin K. Bioorganic Chemistry 2021;109: 104706. DOI: 10.1016/j. bioorg.2021.104706

**10**

*Terpenes and Terpenoids-Recent Advances*

[1] Diniz LRL, Castillo-P Y, Hatem A. Elshabrawy, Filho CSMV, de Sousa DP. Monoterpene Adducts from Callistemon rigidus. Chemistry & Biodiversity 2018;15: e1800172. DOI: 10.1002/

[7] Knotta MG, de la Marec J.A, Edkinsc AL, Zhangd A, Stillmand MJ, Boltone JJ, Antunesf EM, Beukes DR.

Plaxenone A and B: Cytotoxic halogenated monoterpenes from the South African red seaweed Plocamium maxillosum. Phytochemistry Letters. 2019;29:182-185. DOI: 10.1016/j.

[8] Fa-Lei Zhang, Juan He, Tao Feng, Ji-Kai Liu. Melodinines Y1–Y4, four monoterpene indole alkaloids from Melodinus henryi. RSC Advances. 2021, 11, 23-29. DOI:10.1039/D0RA09819A

[9] Zhu L, Liu X-Q, Lin Y-L, Wang W-L,

Germacranolides from the Whole Plant of *Carpesium minus.* Journal of Natural Products. 2020 25;83(11):3230-3238. DOI: 10.1021/acs.jnatprod.0c00428

[10] Li W, Shao YT, Yin TP, Yan H, Shen BC, Li YY, Xie HD, Sun ZW, Ma YL. Penisarins A and B,

3475. DOI: 10.1021/acs. jnatprod.0c00393

Sesquiterpene Coumarins Isolated from an Endophytic *Penicillium* sp. Journal of Natural Products. 2020, 83(11):3471-

[11] Chang K-F, Huang X-F, Chang J-T, Huang Y-C, Lo W-S, Hsiao C-Y, Tsai N-M. Cedrol, a Sesquiterpene Alcohol, Enhances the Anticancer Efficacy of Temozolomide in Attenuating Drug Resistance via Regulation of the DNA Damage Response and MGMT

Expression. Journal of Natural Products.

2020;23;83(10):3021-3029. DOI: 10.1021/acs.jnatprod.0c00580

[12] Elshamy AI, Mohamed TA, Swapana N, Yoneyama T, Noji M, Efferth T, Hegazy M-EF, Akemi

Luo J-G, Kong L-Y. Cytotoxic

cbdv.201800172

phytol.2018.12.009

Derivatives as Potential SARS-CoV-2 Proteases Inhibitors from Molecular Modeling Studies. Biomolecules 2021;11(74). DOI: 10.3390/biom

[2] Anil MS, Shalev N, Vinayaka AC, Nadarajan S, D Namdar, Belausov E, Shoval I, Mani KA, Mechrez G, Kolta H. Cannabis compounds exhibit antiinfammatory activity in vitro in COVID-

19-related infammation in lung epithelial cells and pro-infammatory activity in macrophages. Scientifc Reports. 2021;11;1462. DOI: 10.1038/

s41598-021-81049-2

[3] Yang C, Wang Z, Qiu Y,

Cytorhizophins A and B,

10.1039/C8QO01306C

Zha H,Yang X. New hemiterpene and furolactone-type lignan glycosides from *Securidaca inappendiculata* Hassk. Phytochemistry Letters. 2020; 37:42-46. DOI: 10.1016/j.phytol.2020.04.001

[4] Liu H, Tan H, Wang W, Zhang W, Chen Y, Li S, Liu Z, Lia H, Zhang W.

benzophenonehemiterpene adducts from the endophytic fungus Cytospora rhizophorae. Organic Chemistry Frontries. 2019; 6:591-596. DOI:

[5] Costa JO, Barboza RS, Valente LMM, Gomes TWM, Gallo B, Berrueta LA, Guimarães-Andrade IP, Gavino-Leopoldinod D, Assunção-Miranda I. One-Step Isolation of Monoterpene Indole Alkaloids from Psychotria leiocarpa. Leaves and Their Antiviral Activity on Dengue Virus Type-2. Brazilian Chemical Society. 2020:10(31): 2104-2113. DOI: 10.21577/0103-5053.20200111

[6] Cao J-Q, Wu Y, Zhong Y-L, Li N-P, Chen M, Li M-M, Ye W-C, Wang L. Antiviral Triketone-Phloroglucinol-

Bioactive Terpenes and Their

11010074.

**References**

#### *Terpenes and Terpenoids-Recent Advances*

[23] Nguyen N-L, Vo T-H, Lin Y-C, Liaw C-C , Lu M-K , Cheng J-J, Chen M-C, Kuo Y-H. Arenarosides A-G, Polyhydroxylated Oleanane-Type Saponins from *Polycarpaea arenaria* and their Cytotoxic and Antiangiogenic Activities. Journal of Natural Products. 2021;84(2):259-267. DOI: 10.1021/acs. jnatprod.0c00919

[24] Isaka M, Chinthanom P, Vichai V, Sommai S, Choeyklin R. Ganowe berianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete Ganoderma weberianum. *Journal of Natural Products* 2020;83(11):3404- 3412. DOI: 10.1021/acs. jnatprod.0c00879

[25] Zhang D-L, Li M, Han G-F, Li S-Y, Jin D-J, Tang S-A. Longipetalol A: A Highly Modified Triterpenoid from *Dichapetalum longipetalum.* Journal of Natural Products. 2021. DOI: 10.1021/ acs.jnatprod.1c00068.

[26] Shao X-C, Chen Z-H, Liu S-S, Wu F, Mu H-Y, Wei W-H, Feng Y, Zuo J-P, Zhang J-Q, He S-J, Zhao W-*M. minor* immunosuppressive spiroorthoester group-containing pregnane glycosides from the root barks of *Periploca sepium.* Bioorganic Chemistry 2021; 108:104641. DOI: 10.1016/j.bioorg.2021.104641

**13**

**Chapter 2**

*Paco Noriega*

**1. Introduction**

compounds [2].

families of secondary metabolites.

**Abstract**

Terpenes in Essential Oils:

human well-being makes them extremely important.

2C-Methyl-D-erythirol-4-phosphate (MEP) route [1].

Traditionally they are classified as [3]:

**Keywords:** terpenes, essential oils, bioactivity, chemical analysis

Terpenes are chemical molecules synthesized from isoprene, 2-methyl-1,3 butadiene which are polymerized, thus obtaining one of nature's most diversified

The chemical diversity of terpenes is determined by the polymerization capacity of isoprene; because of this their classification is linked to the addition of five carbons to the basic molecular unit. The biosynthesis of the chemical precursors of isoprene, dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) is produced by two diversified metabolic routes, the mevalonate route (MEV) and the

DMAPP and IPP are hemiterpenes and are responsible of forming the various subclasses of compounds that make up the terpenes. Additionally, these isoprene polymers can be linear or can form rings and adhere to their structure oxygen and nitrogen atoms. The approximate number of known terpenes is close to 55,000

Hemiterpenes. These are constituted by five carbon atoms and are the basic units

of the terpenes, the best-known example is 2-methyl-1,3 butadiene or isoprene.

Bioactivity and Applications

Secondary metabolites from plant organisms have always been excellent options for the pharmaceutical, cosmetic, and food industries. Essential oils are a type of metabolites found in vegetables, and their chemical composition is diverse; however, monoterpenes and sesquiterpenes are inside the most abundant molecules. These terpenes have a diverse chemical composition that range from a simple molecule with carbon and hydrogen to more complex molecules with oxygenated organic groups, such as alcohols, aldehydes, ketones, and ethers. Many of these molecules with 10 and 15 carbon atoms have an especially important biological activity, being important the antimicrobial, antifungal, antioxidant, anti-inflammatory, insecticide, analgesic, anticancer, cytotoxic, among others. Some of these substances are potentially toxic, and hence, they should be handled with caution, especially when they are pure. They are easily obtained by different methods, and their industrial value grows every year, with a market of several million dollars. This chapter seeks to provide a better understanding of this type of bioactive molecules, with an emphasis in those whose information is remarkable in the scientific literature and whose value for health and

#### **Chapter 2**

*Terpenes and Terpenoids-Recent Advances*

Kuo Y-H. Arenarosides A-G, Polyhydroxylated Oleanane-Type Saponins from *Polycarpaea arenaria* and their Cytotoxic and Antiangiogenic Activities. Journal of Natural Products. 2021;84(2):259-267. DOI: 10.1021/acs.

jnatprod.0c00919

3412. DOI: 10.1021/acs. jnatprod.0c00879

acs.jnatprod.1c00068.

[23] Nguyen N-L, Vo T-H, Lin Y-C, Liaw C-C , Lu M-K , Cheng J-J, Chen M-C,

[24] Isaka M, Chinthanom P, Vichai V, Sommai S, Choeyklin R. Ganowe berianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete Ganoderma weberianum. *Journal of Natural Products* 2020;83(11):3404-

[25] Zhang D-L, Li M, Han G-F, Li S-Y, Jin D-J, Tang S-A. Longipetalol A: A Highly Modified Triterpenoid from *Dichapetalum longipetalum.* Journal of Natural Products. 2021. DOI: 10.1021/

[26] Shao X-C, Chen Z-H, Liu S-S, Wu F, Mu H-Y, Wei W-H, Feng Y, Zuo J-P, Zhang J-Q, He S-J, Zhao W-*M. minor* immunosuppressive spiroorthoester group-containing pregnane glycosides from the root barks of *Periploca sepium.* Bioorganic Chemistry 2021; 108:104641. DOI: 10.1016/j.bioorg.2021.104641

**12**

## Terpenes in Essential Oils: Bioactivity and Applications

*Paco Noriega*

#### **Abstract**

Secondary metabolites from plant organisms have always been excellent options for the pharmaceutical, cosmetic, and food industries. Essential oils are a type of metabolites found in vegetables, and their chemical composition is diverse; however, monoterpenes and sesquiterpenes are inside the most abundant molecules. These terpenes have a diverse chemical composition that range from a simple molecule with carbon and hydrogen to more complex molecules with oxygenated organic groups, such as alcohols, aldehydes, ketones, and ethers. Many of these molecules with 10 and 15 carbon atoms have an especially important biological activity, being important the antimicrobial, antifungal, antioxidant, anti-inflammatory, insecticide, analgesic, anticancer, cytotoxic, among others. Some of these substances are potentially toxic, and hence, they should be handled with caution, especially when they are pure. They are easily obtained by different methods, and their industrial value grows every year, with a market of several million dollars. This chapter seeks to provide a better understanding of this type of bioactive molecules, with an emphasis in those whose information is remarkable in the scientific literature and whose value for health and human well-being makes them extremely important.

**Keywords:** terpenes, essential oils, bioactivity, chemical analysis

#### **1. Introduction**

Terpenes are chemical molecules synthesized from isoprene, 2-methyl-1,3 butadiene which are polymerized, thus obtaining one of nature's most diversified families of secondary metabolites.

The chemical diversity of terpenes is determined by the polymerization capacity of isoprene; because of this their classification is linked to the addition of five carbons to the basic molecular unit. The biosynthesis of the chemical precursors of isoprene, dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP) is produced by two diversified metabolic routes, the mevalonate route (MEV) and the 2C-Methyl-D-erythirol-4-phosphate (MEP) route [1].

DMAPP and IPP are hemiterpenes and are responsible of forming the various subclasses of compounds that make up the terpenes. Additionally, these isoprene polymers can be linear or can form rings and adhere to their structure oxygen and nitrogen atoms. The approximate number of known terpenes is close to 55,000 compounds [2].

Traditionally they are classified as [3]:

Hemiterpenes. These are constituted by five carbon atoms and are the basic units of the terpenes, the best-known example is 2-methyl-1,3 butadiene or isoprene.

Monoterpenes. These are constituted by 10 carbon atoms, resulting from the union of two units of isoprene, which are abundant in essential oils. Some important substances are: pinene, myrcene, limonene, thujene, etc.

Sesquiterpenes. These are formed by 15 carbon atoms, which are the result of the junction of three units of isoprene, some examples are: bisabolene, zingiberene, germacrene, caryophyllene, etc.

Diterpenes. These are formed by 20 carbon atoms or four units of isoprene; some important compounds are retinol, taxol and phytol.

Triterpenes. Squalene and several phytosterols such as sitosterol stand out among the terpenes containing 30 carbon atoms or six units of isoprene.

Tetraterpenes. These are constituted by 40 carbon atoms and eight units of isoprene, many of them are dyes like carotenes, among these the most important are carotene, lycopene and bixin.

Polyterpenes. These are composed of more than 40 carbon atoms; they are often found in gums and latex of various plant species.

#### **2. Essential oils**

Essential oils are common secondary metabolites in vegetables. From 10 to 200 compounds can be found in an essential oil, and their main characteristic is their ability to evaporate at room temperature. The chemical variability in an oil is significant; however, its components can be classified into three large groups (**Figure 1**).

Terpenes are the majority group, being monoterpenes and sesquiterpenes the most abundant. These can be present as hydrocarbons, consisting of carbon and

**15**

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

substances are isovaleraldehyde or dodecanal.

ketones, and ethers.

anethole or carvacrol.

*cyminum*.

metabolites.

**3. Chemical analysis**

compounds from essential oils [4].

as nuclear magnetic resonance imaging.

hydrogen, or can have various functional groups such as alcohols, thiols, aldehydes,

The second group of importance is aromatic compounds, many of them with an important biological activity such as derivatives of cinnamaldehyde, thymol,

There is a third miscellaneous group in a lower proportion that groups various molecules such as hydrocarbons, aldehydes, ketones, esters, etc. Examples of these

The extraction processes are diverse, depending on the part of the plant used; the simplest and most widespread is the extraction by distillation with steam current, which does not require expensive equipment. Other methods are mechanical extraction used mainly to obtain oil from citrus pericarps, extraction using solvents which is useful when components can be affected by high temperatures and extraction using a supercritical CO2 current, which does not need high temperatures while maintaining

About 4000 species have been investigated by their ability to produce essential oils, but only about 30 are marketed massively globally; their main use is intended for the cosmetic industry and aromatherapy, although several of the compounds from essences could be valuable to the pharmaceutical industry. There are certainly still species whose essential oils have not been analyzed in their chemical composition or in their bioactivity, which could be interesting as a source of new secondary

Since they are volatile metabolites, their low boiling points make it possible to have them as steam in a remarkably simple way; for this reason the ideal analysis is

The use of capillary columns has made it possible to have defined separations in essential oils that exceed 100 compounds, usually chromatographic separation is made in nonpolar columns with 95% dimethylpolysiloxane, due to the fact that several components of an essential oil contain polar groups such as hydroxyl (OH); the realization of these components using columns of intermediate polarity has been made. Both assays result in a complete chemical inquiry of molecules and are complementary. The correct structural elucidation is performed by combining several analyses such as comparison with spectrum databases and the theoretical and experimental determination of the retention rates of the compounds. For this purpose, there are databases, being the most used the "Identification of essential oil components by gas chomatography/mass spectrometry," with approximately 4000

The GC/MS technique is limited in the fact that it is ineffective in evaluating stereoisomers, in such cases it is necessary to use chiral columns or techniques such

the chemistry of molecules, but it is very expensive to implement.

gas chromatography with GC/MS mass spectrometry.

Essential oils are usually found in low concentrations in plant organisms, ranging from 0.1 to 1%. They can exceed this value as is the case of clove oil with up to 10%, and are present in all plant organs and leaves: *Mentha piperita*, *Origanum majorana*, *Thymus vulgaris*; flowers: *Rosa damascena*, *Matricaria chamomilla*, *Lavandula officinale*; stems: *Cinnamomum verum*, *Ocotea quixos*, *Santalum álbum*; roots: *Valeriana officinale*; fruits: *Citrus bergamia*; rhizomes: *Zingiber officinale, Curcuma longa*; and seeds: *Pimpinella anisum*, *Syzygium aromaticum* and *Cuminum* 

**Figure 1.** *Main molecules of essential oils.*

#### *Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

*Terpenes and Terpenoids-Recent Advances*

germacrene, caryophyllene, etc.

carotene, lycopene and bixin.

**2. Essential oils**

(**Figure 1**).

substances are: pinene, myrcene, limonene, thujene, etc.

some important compounds are retinol, taxol and phytol.

found in gums and latex of various plant species.

Monoterpenes. These are constituted by 10 carbon atoms, resulting from the union of two units of isoprene, which are abundant in essential oils. Some important

Sesquiterpenes. These are formed by 15 carbon atoms, which are the result of the junction of three units of isoprene, some examples are: bisabolene, zingiberene,

Diterpenes. These are formed by 20 carbon atoms or four units of isoprene;

Triterpenes. Squalene and several phytosterols such as sitosterol stand out

Tetraterpenes. These are constituted by 40 carbon atoms and eight units of isoprene, many of them are dyes like carotenes, among these the most important are

Essential oils are common secondary metabolites in vegetables. From 10 to 200 compounds can be found in an essential oil, and their main characteristic is their ability to evaporate at room temperature. The chemical variability in an oil is significant; however, its components can be classified into three large groups

Terpenes are the majority group, being monoterpenes and sesquiterpenes the most abundant. These can be present as hydrocarbons, consisting of carbon and

Polyterpenes. These are composed of more than 40 carbon atoms; they are often

among the terpenes containing 30 carbon atoms or six units of isoprene.

**14**

**Figure 1.**

*Main molecules of essential oils.*

hydrogen, or can have various functional groups such as alcohols, thiols, aldehydes, ketones, and ethers.

The second group of importance is aromatic compounds, many of them with an important biological activity such as derivatives of cinnamaldehyde, thymol, anethole or carvacrol.

There is a third miscellaneous group in a lower proportion that groups various molecules such as hydrocarbons, aldehydes, ketones, esters, etc. Examples of these substances are isovaleraldehyde or dodecanal.

Essential oils are usually found in low concentrations in plant organisms, ranging from 0.1 to 1%. They can exceed this value as is the case of clove oil with up to 10%, and are present in all plant organs and leaves: *Mentha piperita*, *Origanum majorana*, *Thymus vulgaris*; flowers: *Rosa damascena*, *Matricaria chamomilla*, *Lavandula officinale*; stems: *Cinnamomum verum*, *Ocotea quixos*, *Santalum álbum*; roots: *Valeriana officinale*; fruits: *Citrus bergamia*; rhizomes: *Zingiber officinale, Curcuma longa*; and seeds: *Pimpinella anisum*, *Syzygium aromaticum* and *Cuminum cyminum*.

The extraction processes are diverse, depending on the part of the plant used; the simplest and most widespread is the extraction by distillation with steam current, which does not require expensive equipment. Other methods are mechanical extraction used mainly to obtain oil from citrus pericarps, extraction using solvents which is useful when components can be affected by high temperatures and extraction using a supercritical CO2 current, which does not need high temperatures while maintaining the chemistry of molecules, but it is very expensive to implement.

About 4000 species have been investigated by their ability to produce essential oils, but only about 30 are marketed massively globally; their main use is intended for the cosmetic industry and aromatherapy, although several of the compounds from essences could be valuable to the pharmaceutical industry. There are certainly still species whose essential oils have not been analyzed in their chemical composition or in their bioactivity, which could be interesting as a source of new secondary metabolites.

#### **3. Chemical analysis**

Since they are volatile metabolites, their low boiling points make it possible to have them as steam in a remarkably simple way; for this reason the ideal analysis is gas chromatography with GC/MS mass spectrometry.

The use of capillary columns has made it possible to have defined separations in essential oils that exceed 100 compounds, usually chromatographic separation is made in nonpolar columns with 95% dimethylpolysiloxane, due to the fact that several components of an essential oil contain polar groups such as hydroxyl (OH); the realization of these components using columns of intermediate polarity has been made. Both assays result in a complete chemical inquiry of molecules and are complementary. The correct structural elucidation is performed by combining several analyses such as comparison with spectrum databases and the theoretical and experimental determination of the retention rates of the compounds. For this purpose, there are databases, being the most used the "Identification of essential oil components by gas chomatography/mass spectrometry," with approximately 4000 compounds from essential oils [4].

The GC/MS technique is limited in the fact that it is ineffective in evaluating stereoisomers, in such cases it is necessary to use chiral columns or techniques such as nuclear magnetic resonance imaging.

A more thorough investigation of the chemical identity of the molecules of an essential oil can be done with an equipment that couples gas chromatography with spectrophotometric techniques, such as nuclear magnetic resonance imaging and infrared spectroscopy. It is also possible to analyze NMR or IR spectra in previously isolated molecules by column or thin layer chromatography [5].

#### **4. Monoterpenes with therapeutic importance**

Several monoterpenes have a diverse and useful biological activity for treating diseases and ailments; some have valuable aromatic characteristics in cosmetics and perfumery. Those molecules that have relevant information and studies are analyzed to verify their use as phytotherapeutic elements (**Figure 2**).

Pinenes. These have alpha and beta isomers; their formula is C10H10 and they are common in essential oils from conifers, although they can be found in many other species such as rosemary and lavender [6–8]; oils with high concentrations of pinenes generally have antimicrobial activity [8, 9]. Traditionally many plants containing pinene-rich essential oils are used in respiratory system disease [9].

1–8 cineol (Eucalyptol). Oxygenated monoterpene has a C10H18O formula whose functional group is an ether that is present in many varieties of eucalyptus. Among its most noteworthy properties are analgesic, anti-inflammatory and antimicrobial [10]. Plants with eucalyptol-rich essential oils are used for expectorant and decongestant properties of the respiratory system [11].

Limonene. It is a monoterpene whose formula is C10H16; it has two optical isomers R-limonene or D- limonene and S-limonene or L-limonene, which stand out by the insecticide [12, 13] and antimicrobial properties [14].

Myrcene. It is a monoterpene whose formula is C10H16; it is the main component of *Cannabis sativa* essential oil [15]. Several studies highlight its analgesic-sedative [16, 17] and anti-inflammatory activity [18].

Linalool. It is a hydroxylated monoterpene with C10H18O formula, its pleasant aroma makes it widely used in perfumery. Its action on the central nervous system is evidenced by its sedative, anxiolytic, analgesic and anti-inflammatory

**17**

anticancer [48].

inflammatory [53].

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

ated with good results [21, 22].

is noteworthy [26].

level [31, 32].

and sedative [33, 35].

[39], and antioxidant [40].

**5. Sesquiterpenes with therapeutic importance**

widely used in the cosmetic industry [44].

properties [19, 20]. Its antimicrobial and antioxidant properties have been evalu-

Citral. It is an oxygenated monoterpene containing a group of aldehyde; its formula is C10H16O. There are two isomers known as neral (cis isomer) and geranial (trans isomer) [23], which are abundant in species such as *Backhousia citriodora* [24] and *Cymbopogon citratus* [25]. Its antimicrobial [25] and insect repellent action

Camphor. It is an oxygenated monoterpene whose functional group is a ketone; its formula is C10H16O and it is present in two optical isomers R and S, which are abundant in the species *Cinnamomum camphora* [27]. Traditionally camphor has been used in traditional Asian medicine, and it is known to have digestive effects, but its most important use is related to its analgesic and antiseptic effect, being very popular its inclusion in topical formulations such as liniments and creams [28, 29]. Menthol. It is a hydroxylated monoterpene, with a C10H20O formula, which has seven isomers that are very common in mint varieties such as Peppermint. It is one of the most used compounds in the food, cosmetic, pharmaceutical industries, and pesticides, among others. Its aromatic properties are very well known [30]; however, its most noticeable and known effect is that of analgesia at the topical

Terpineol. It is a hydroxylated monoterpene with a C10H18O formula. It is known by having five isomers (α, β, γ, δ and 4-terpineol) [33], which are abundant in the essential oil of tea tree (*Malaleuca alternifolia*) [34]. The outstanding properties are antihypertensive, anticancer, antioxidant, antimicrobial, antifungal

Citronellol. It is a hydroxylated monoterpene with a C10H20O formula. There are two enantiomers (+)-citronellol and (−)-citronellol [36]. The first is quite common in citronella oil, and the second is abundant in rose oil [37], which is used in perfumery. Its properties are insecticide [38], analgesic and anti-inflammatory

Several molecules with interesting properties can be found in C15 sesquiterpene (**Figure 3**). From a therapeutic view, there is evidence that validates its biological

Bisabolol. These are isomers, out of which stand (−)-α-Bisabolol, (−)-epi-α-Bisabolol, (+)-α-Bisabolol and (+)-epi-α-Bisabolol which are abundant in the species *Matricaria camomilla* [41], and in other species such as *Salvia runcinata* [42]. The most well-known effects in the molecule are analgesic and anti-inflammatory [43], antimicrobial and antioxidant properties; for this reason, the molecule is

β-Caryophyllene. It has a C15H24 formula. It is one of the most abundant sesquiterpenes in essential oils. Various bioactivity studies have been carried out in this molecule with good results, such as analgesic [45, 46], anti-inflammatory [47] and

Chamazulene. With a C14H16 formula, it is a molecule derived from the sesquiterpene matricina, which is one of the few aromatic molecules that have a blue coloration. It is found in *Matricaria camomilla*, being its most known property the anti-inflammatory [49, 50]. Several studies highlight its antioxidant effects [51, 52]. Caryophyllene oxide. It is an oxygenated sesquiterpene with a C15H24O formula;

it has properties similar to those of caryophyllene, such as analgesic and anti-

activity, highlighting anti-inflammatory, analgesic and anticancer trials.

**Figure 2.** *Monoterpene molecules with therapeutic importance.*

#### *Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

*Terpenes and Terpenoids-Recent Advances*

A more thorough investigation of the chemical identity of the molecules of an essential oil can be done with an equipment that couples gas chromatography with spectrophotometric techniques, such as nuclear magnetic resonance imaging and infrared spectroscopy. It is also possible to analyze NMR or IR spectra in previously

Several monoterpenes have a diverse and useful biological activity for treating diseases and ailments; some have valuable aromatic characteristics in cosmetics and perfumery. Those molecules that have relevant information and studies are

Pinenes. These have alpha and beta isomers; their formula is C10H10 and they are common in essential oils from conifers, although they can be found in many other species such as rosemary and lavender [6–8]; oils with high concentrations of pinenes generally have antimicrobial activity [8, 9]. Traditionally many plants containing pinene-rich essential oils are used in respiratory system disease [9].

1–8 cineol (Eucalyptol). Oxygenated monoterpene has a C10H18O formula whose functional group is an ether that is present in many varieties of eucalyptus. Among its most noteworthy properties are analgesic, anti-inflammatory and antimicrobial [10]. Plants with eucalyptol-rich essential oils are used for expectorant and decon-

Myrcene. It is a monoterpene whose formula is C10H16; it is the main component of *Cannabis sativa* essential oil [15]. Several studies highlight its analgesic-sedative

Linalool. It is a hydroxylated monoterpene with C10H18O formula, its pleasant aroma makes it widely used in perfumery. Its action on the central nervous system is evidenced by its sedative, anxiolytic, analgesic and anti-inflammatory

Limonene. It is a monoterpene whose formula is C10H16; it has two optical isomers R-limonene or D- limonene and S-limonene or L-limonene, which stand

out by the insecticide [12, 13] and antimicrobial properties [14].

isolated molecules by column or thin layer chromatography [5].

analyzed to verify their use as phytotherapeutic elements (**Figure 2**).

**4. Monoterpenes with therapeutic importance**

gestant properties of the respiratory system [11].

[16, 17] and anti-inflammatory activity [18].

*Monoterpene molecules with therapeutic importance.*

**16**

**Figure 2.**

properties [19, 20]. Its antimicrobial and antioxidant properties have been evaluated with good results [21, 22].

Citral. It is an oxygenated monoterpene containing a group of aldehyde; its formula is C10H16O. There are two isomers known as neral (cis isomer) and geranial (trans isomer) [23], which are abundant in species such as *Backhousia citriodora* [24] and *Cymbopogon citratus* [25]. Its antimicrobial [25] and insect repellent action is noteworthy [26].

Camphor. It is an oxygenated monoterpene whose functional group is a ketone; its formula is C10H16O and it is present in two optical isomers R and S, which are abundant in the species *Cinnamomum camphora* [27]. Traditionally camphor has been used in traditional Asian medicine, and it is known to have digestive effects, but its most important use is related to its analgesic and antiseptic effect, being very popular its inclusion in topical formulations such as liniments and creams [28, 29].

Menthol. It is a hydroxylated monoterpene, with a C10H20O formula, which has seven isomers that are very common in mint varieties such as Peppermint. It is one of the most used compounds in the food, cosmetic, pharmaceutical industries, and pesticides, among others. Its aromatic properties are very well known [30]; however, its most noticeable and known effect is that of analgesia at the topical level [31, 32].

Terpineol. It is a hydroxylated monoterpene with a C10H18O formula. It is known by having five isomers (α, β, γ, δ and 4-terpineol) [33], which are abundant in the essential oil of tea tree (*Malaleuca alternifolia*) [34]. The outstanding properties are antihypertensive, anticancer, antioxidant, antimicrobial, antifungal and sedative [33, 35].

Citronellol. It is a hydroxylated monoterpene with a C10H20O formula. There are two enantiomers (+)-citronellol and (−)-citronellol [36]. The first is quite common in citronella oil, and the second is abundant in rose oil [37], which is used in perfumery. Its properties are insecticide [38], analgesic and anti-inflammatory [39], and antioxidant [40].

#### **5. Sesquiterpenes with therapeutic importance**

Several molecules with interesting properties can be found in C15 sesquiterpene (**Figure 3**). From a therapeutic view, there is evidence that validates its biological activity, highlighting anti-inflammatory, analgesic and anticancer trials.

Bisabolol. These are isomers, out of which stand (−)-α-Bisabolol, (−)-epi-α-Bisabolol, (+)-α-Bisabolol and (+)-epi-α-Bisabolol which are abundant in the species *Matricaria camomilla* [41], and in other species such as *Salvia runcinata* [42]. The most well-known effects in the molecule are analgesic and anti-inflammatory [43], antimicrobial and antioxidant properties; for this reason, the molecule is widely used in the cosmetic industry [44].

β-Caryophyllene. It has a C15H24 formula. It is one of the most abundant sesquiterpenes in essential oils. Various bioactivity studies have been carried out in this molecule with good results, such as analgesic [45, 46], anti-inflammatory [47] and anticancer [48].

Chamazulene. With a C14H16 formula, it is a molecule derived from the sesquiterpene matricina, which is one of the few aromatic molecules that have a blue coloration. It is found in *Matricaria camomilla*, being its most known property the anti-inflammatory [49, 50]. Several studies highlight its antioxidant effects [51, 52].

Caryophyllene oxide. It is an oxygenated sesquiterpene with a C15H24O formula; it has properties similar to those of caryophyllene, such as analgesic and antiinflammatory [53].

#### **Figure 3.**

*Sesquiterpene molecules with therapeutic purposes.*

Germacrene. It belongs to the sesquiterpenes family, and it has three double links in its structure. There are five types of germacrenes: A, B, C, D, E. Recent studies mention its antioxidant potential [5, 54].

Artemisinic acid. It has a C15H22O2 formula, and it is one of the most interesting sesquiterpenes for health due to its antimalarial properties [55]. It is abundant in the species *Artemisia annua*, and it is generally found as a sesquiterpenic lactone [56].

Patchoulene. It is a sesquiterpene with a C15H24 formula. It is common to find its isomers α, β, α, and δ in essential oils. It is attributed to various types of bioactivity, the most relevant being those found in β-patchoulene as anti-inflammatory [57], antigastritis [58, 59], and cosmetic [60].

Humulene. Also known as α-caryophyllene, its formula is C15H24. It is named after the essential oil of the species *Humulus lupulus* [61]. It has anti-inflammatory [62, 63] and anticancer properties [64].

Bergamotene. It is a sesquiterpene with a C15H24 formula. It has four isomers α-cis, β-cis, α-trans and β-trans. It is found in several citric species such as *Citrus bergamia* [65]. One of the properties of this molecule is to act as a pheromone [66, 67].

Farnesene. It has a C15H24 formula. It is a molecule found in several essential oils, and it is a precursor to many other sesquiterpenes since its open-chain structure and its 4-double bonds contribute to this action, as well as in the possibility of having a wide variety of isomers between geometrics and stereoisomers. Its cytotoxic and genotoxic [68], insecticide [69] and neuroprotective effects [70, 71] have been evaluated.

Eudesmol. Hydroxylated sesquiterpene with a C15H26O formula is a very interesting molecule by the multiple positive bioactivity assays, highlighting antimicrobial and antifungal [72], anticancer [73, 74] and antiangiogenic [75].

#### **6. Toxicity**

Most of the terpenes present in essential oils have some degree of toxicity, which is not detected when consuming aromatic species directly because in most cases

**19**

**Author details**

Salesian Polytechnic University, Quito, Ecuador

provided the original work is properly cited.

\*Address all correspondence to: pnoriega@ups.edu.ec

© 2020 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium,

Paco Noriega

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

being neurotoxic [79].

**7. Conclusion**

the oil yield is low. Many commonly used essential oil components are potentially dermal irritating with restrictions on application concentrations [76, 77]. There are also some terpenes whose toxicity is much more dangerous, such as pulegone which causes liver damage and seizures [78], and thujone that can cause dementia by

This brief review has shown the chemical and biological importance of low molecular weight and volatile terpenes. For this reason, components of secondary metabolites are known as essential oils. The abundance of these molecules is much higher than the one presented in this chapter, since the information presented covers those whose scientific evidence and industrial importance are references in this family of metabolites. There is still much research to be carried out on the hundreds of molecules from which there is still little or no information. There are still aromatic species whose essential oils have not yet been described and that could be a source of

new monoterpenes and sesquiterpenes that are beneficial to humans.

the oil yield is low. Many commonly used essential oil components are potentially dermal irritating with restrictions on application concentrations [76, 77]. There are also some terpenes whose toxicity is much more dangerous, such as pulegone which causes liver damage and seizures [78], and thujone that can cause dementia by being neurotoxic [79].

### **7. Conclusion**

*Terpenes and Terpenoids-Recent Advances*

Germacrene. It belongs to the sesquiterpenes family, and it has three double links in its structure. There are five types of germacrenes: A, B, C, D, E. Recent

the species *Artemisia annua*, and it is generally found as a sesquiterpenic

Artemisinic acid. It has a C15H22O2 formula, and it is one of the most interesting sesquiterpenes for health due to its antimalarial properties [55]. It is abundant in

Patchoulene. It is a sesquiterpene with a C15H24 formula. It is common to find its isomers α, β, α, and δ in essential oils. It is attributed to various types of bioactivity, the most relevant being those found in β-patchoulene as anti-inflammatory [57],

Humulene. Also known as α-caryophyllene, its formula is C15H24. It is named after the essential oil of the species *Humulus lupulus* [61]. It has anti-inflammatory

Bergamotene. It is a sesquiterpene with a C15H24 formula. It has four isomers

Farnesene. It has a C15H24 formula. It is a molecule found in several essential oils, and it is a precursor to many other sesquiterpenes since its open-chain structure and its 4-double bonds contribute to this action, as well as in the possibility of having a wide variety of isomers between geometrics and stereoisomers. Its cytotoxic and genotoxic [68], insecticide [69] and neuroprotective effects [70, 71] have been

Most of the terpenes present in essential oils have some degree of toxicity, which is not detected when consuming aromatic species directly because in most cases

α-cis, β-cis, α-trans and β-trans. It is found in several citric species such as *Citrus bergamia* [65]. One of the properties of this molecule is to act as a phero-

Eudesmol. Hydroxylated sesquiterpene with a C15H26O formula is a very interesting molecule by the multiple positive bioactivity assays, highlighting antimicrobial and antifungal [72], anticancer [73, 74] and antiangiogenic [75].

studies mention its antioxidant potential [5, 54].

*Sesquiterpene molecules with therapeutic purposes.*

antigastritis [58, 59], and cosmetic [60].

[62, 63] and anticancer properties [64].

lactone [56].

**Figure 3.**

mone [66, 67].

evaluated.

**6. Toxicity**

**18**

This brief review has shown the chemical and biological importance of low molecular weight and volatile terpenes. For this reason, components of secondary metabolites are known as essential oils. The abundance of these molecules is much higher than the one presented in this chapter, since the information presented covers those whose scientific evidence and industrial importance are references in this family of metabolites. There is still much research to be carried out on the hundreds of molecules from which there is still little or no information. There are still aromatic species whose essential oils have not yet been described and that could be a source of new monoterpenes and sesquiterpenes that are beneficial to humans.

### **Author details**

Paco Noriega Salesian Polytechnic University, Quito, Ecuador

\*Address all correspondence to: pnoriega@ups.edu.ec

© 2020 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

### **References**

[1] Natanya C. Natural Products in Chemical Biology. Hoboken, New Jersey: John Wiley & Sons; 2012. pp. 127-129

[2] Guimarães AG, Serafini MR, Quintans-Júnior LJ. Terpenes and derivatives as a new perspective for pain treatment: A patent review. Expert Opinion on Therapeutic Patents. 2014;**24**(3):243-265

[3] Perveen S, Al-Taweel A. Introductory chapter: Terpenes and terpenoids. In: Terpenes and Terpenoids. London: IntechOpen; 2018. pp. 1-7

[4] Adams RP. Identification of Essential Oils by Ion Trap Mass Spectroscopy. San Diego, California: Academic Press; 2012

[5] Noriega P, Guerrini A, Sacchetti G, Grandini A, Ankuash E, Manfredini S. Chemical composition and biological activity of five essential oils from the Ecuadorian Amazon rain forest. Molecules. 2019;**24**(8):1637

[6] Jiang Y, Wu N, Fu YJ, Wang W, Luo M, Zhao CJ, et al. Chemical composition and antimicrobial activity of the essential oil of rosemary. Environmental Toxicology and Pharmacology. 2011;**32**(1):63-68

[7] Zheljazkov VD, Astatkie T, Hristov AN. Lavender and hyssop productivity, oil content, and bioactivity as a function of harvest time and drying. Industrial Crops and Products. 2012;**36**(1):222-228

[8] Silva ACRD, Lopes PM, Azevedo MMBD, Costa DCM, Alviano CS, Alviano DS. Biological activities of a-pinene and β-pinene enantiomers. Molecules. 2012;**17**(6):6305-6316

[9] Rivera PFN, Paredes EA, Gómez ED, Lueckhoff A, Almeida GA, Suarez SE.

Composición química y actividad antimicrobiana del aceite esencial de los rizomas de *Renealmia thyrsoidea* (Ruiz & Pav) Poepp. & Eddl (shiwanku muyu). Revista Cubana de Plantas Medicinales. 2017;**22**(2)

[10] Bhowal M, Gopal M. Eucalyptol: Safety and pharmacological profile. Journal of Pharmaceutical Sciences. 2015;**5**:125-131

[11] Adnan M. Bioactive potential of essential oil extracted from the leaves of *Eucalyptus globulus* (Myrtaceae). Journal of Pharmacognosy and Phytochemistry. 2019;**8**(1):213-216

[12] Karr LL, Costas JR. Insecticidal properties of d-limonene. Journal of Pesticide Science. 1988;**13**(2):287-290

[13] Malacrinò A, Campolo O, Laudani F, Palmeri V. Fumigant and repellent activity of limonene enantiomers against *Tribolium confusum* du Val. Neotropical Entomology. 2016;**45**(5):597-603

[14] Espina L, Gelaw TK, de Lamo-Castellví S, Pagán R, García-Gonzalo D. Mechanism of bacterial inactivation by (+)-limonene and its potential use in food preservation combined processes. PLoS One. 2013;**8**(2):e56769

[15] Gulluni N, Re T, Loiacono I, Lanzo G, Gori L, Macchi C, et al. Cannabis essential oil: A preliminary study for the evaluation of the brain effects. Evidence-Based Complementary and Alternative Medicine. 2018;(1):1-11

[16] Mirghaed AT, Ghelichpour M, Hoseini SM. Myrcene and linalool as new anesthetic and sedative agents in common carp, *Cyprinus carpio* - Comparison with eugenol. Aquaculture. 2016;**464**:165-170

**21**

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

> constituents in the essential oil of *Cymbopogon citratus* (DC.) Stapf. Journal of Ethnopharmacology.

[26] Hao H, Wei J, Dai J, Du J. Hostseeking and blood-feeding behavior of *Aedes albopictus* (Diptera: Culicidae) exposed to vapors of geraniol, citral, citronellal, eugenol, or anisaldehyde. Journal of Medical Entomology.

1984;**12**(3):279-286

2014;**45**(3):533-539

[27] Pragadheesh VS, Saroj A, Yadav A, Chanotiya CS, Alam M, Samad A. Chemical characterization and antifungal activity of *Cinnamomum camphora* essential oil. Industrial Crops

and Products. 2013;**49**:628-633

Nature Reviews. Neuroscience.

[30] Kamatou GP, Vermaak I,

[31] Galeotti N, Mannelli LDC,

Neuroscience Letters. 2002;**322**(3):145-148

2005;**6**(11):826-826

2013;**96**:15-25

[28] Green BG. Sensory characteristics of camphor. The Journal of Investigative Dermatology. 1990;*94*(5):662-666

[29] Craven R. The comfort of camphor.

Viljoen AM, Lawrence BM. Menthol: A simple monoterpene with remarkable biological properties. Phytochemistry.

Mazzanti G, Bartolini A, Ghelardini C. Menthol: A natural analgesic compound.

[32] Pan R, Tian Y, Gao R, Li H, Zhao X, Barrett JE, et al. Central mechanisms of menthol-induced analgesia. The Journal of Pharmacology and Experimental Therapeutics. 2012;**343**(3):661-672

[33] Khaleel C, Tabanca N, Buchbauer G. α-Terpineol, a natural monoterpene: A review of its biological properties. Open

Chemistry. 2018;**16**(1):349-361

[34] Papadopoulos CJ, Carson CF, Chang BJ, Riley TV. Role of the

[17] Rao VSN, Menezes AMS, Viana GSB. Effect of myrcene on nociception in mice. The Journal of Pharmacy and Pharmacology. 1990;**42**(12):877-878

[18] Rufino AT, Ribeiro M, Sousa C, Judas F, Salgueiro L, Cavaleiro C, et al. Evaluation of the anti-inflammatory, anti-catabolic and pro-anabolic effects of E-caryophyllene, myrcene and limonene in a cell model of osteoarthritis. European Journal of Pharmacology. 2015;**750**:141-150

[19] Aprotosoaie AC, Hăncianu M, Costache II, Miron A. Linalool: A review on a key odorant molecule with valuable biological properties. Flavour and Fragrance Journal. 2014;**29**(4):193-219

[20] Pereira I, Severino P, Santos AC, Silva AM, Souto EB. Linalool bioactive properties and potential applicability in drug delivery systems. Colloids and Surfaces, B: Biointerfaces.

[21] Herman A, Tambor K, Herman A. Linalool affects the antimicrobial efficacy of essential oils. Current Microbiology.

responsive linalool capsules with high loading ratio for excellent antioxidant and antibacterial efficiency. Colloids and Surfaces, B: Biointerfaces.

[23] Sacks J, Greenley E, Leo G, Willey P, Gallis D, Mangravite JA. Separation and analysis of citral isomers: An undergraduate organic laboratory experiment. Journal of Chemical Education. 1983;**60**(5):434

[24] Southwell IA, Russell M, Smith RL, Archer DW. *Backhousia citriodora* F. Muell. (Myrtaceae), a superior source of citral. Journal of Essential Oil Research.

2018;**171**:566-578

2016;**72**(2):165-172

2020;**190**:110978

2000;**12**(6):735-741

[25] Onawunmi GO, Yisak WA, Ogunlana EO. Antibacterial

[22] Hu J, Liu S, Deng W. Dual

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

[17] Rao VSN, Menezes AMS, Viana GSB. Effect of myrcene on nociception in mice. The Journal of Pharmacy and Pharmacology. 1990;**42**(12):877-878

[18] Rufino AT, Ribeiro M, Sousa C, Judas F, Salgueiro L, Cavaleiro C, et al. Evaluation of the anti-inflammatory, anti-catabolic and pro-anabolic effects of E-caryophyllene, myrcene and limonene in a cell model of osteoarthritis. European Journal of Pharmacology. 2015;**750**:141-150

[19] Aprotosoaie AC, Hăncianu M, Costache II, Miron A. Linalool: A review on a key odorant molecule with valuable biological properties. Flavour and Fragrance Journal. 2014;**29**(4):193-219

[20] Pereira I, Severino P, Santos AC, Silva AM, Souto EB. Linalool bioactive properties and potential applicability in drug delivery systems. Colloids and Surfaces, B: Biointerfaces. 2018;**171**:566-578

[21] Herman A, Tambor K, Herman A. Linalool affects the antimicrobial efficacy of essential oils. Current Microbiology. 2016;**72**(2):165-172

[22] Hu J, Liu S, Deng W. Dual responsive linalool capsules with high loading ratio for excellent antioxidant and antibacterial efficiency. Colloids and Surfaces, B: Biointerfaces. 2020;**190**:110978

[23] Sacks J, Greenley E, Leo G, Willey P, Gallis D, Mangravite JA. Separation and analysis of citral isomers: An undergraduate organic laboratory experiment. Journal of Chemical Education. 1983;**60**(5):434

[24] Southwell IA, Russell M, Smith RL, Archer DW. *Backhousia citriodora* F. Muell. (Myrtaceae), a superior source of citral. Journal of Essential Oil Research. 2000;**12**(6):735-741

[25] Onawunmi GO, Yisak WA, Ogunlana EO. Antibacterial

constituents in the essential oil of *Cymbopogon citratus* (DC.) Stapf. Journal of Ethnopharmacology. 1984;**12**(3):279-286

[26] Hao H, Wei J, Dai J, Du J. Hostseeking and blood-feeding behavior of *Aedes albopictus* (Diptera: Culicidae) exposed to vapors of geraniol, citral, citronellal, eugenol, or anisaldehyde. Journal of Medical Entomology. 2014;**45**(3):533-539

[27] Pragadheesh VS, Saroj A, Yadav A, Chanotiya CS, Alam M, Samad A. Chemical characterization and antifungal activity of *Cinnamomum camphora* essential oil. Industrial Crops and Products. 2013;**49**:628-633

[28] Green BG. Sensory characteristics of camphor. The Journal of Investigative Dermatology. 1990;*94*(5):662-666

[29] Craven R. The comfort of camphor. Nature Reviews. Neuroscience. 2005;**6**(11):826-826

[30] Kamatou GP, Vermaak I, Viljoen AM, Lawrence BM. Menthol: A simple monoterpene with remarkable biological properties. Phytochemistry. 2013;**96**:15-25

[31] Galeotti N, Mannelli LDC, Mazzanti G, Bartolini A, Ghelardini C. Menthol: A natural analgesic compound. Neuroscience Letters. 2002;**322**(3):145-148

[32] Pan R, Tian Y, Gao R, Li H, Zhao X, Barrett JE, et al. Central mechanisms of menthol-induced analgesia. The Journal of Pharmacology and Experimental Therapeutics. 2012;**343**(3):661-672

[33] Khaleel C, Tabanca N, Buchbauer G. α-Terpineol, a natural monoterpene: A review of its biological properties. Open Chemistry. 2018;**16**(1):349-361

[34] Papadopoulos CJ, Carson CF, Chang BJ, Riley TV. Role of the

**20**

*Terpenes and Terpenoids-Recent Advances*

[1] Natanya C. Natural Products in Chemical Biology. Hoboken, New Jersey: John Wiley & Sons; 2012.

Composición química y actividad antimicrobiana del aceite esencial de los rizomas de *Renealmia thyrsoidea* (Ruiz & Pav) Poepp. & Eddl (shiwanku muyu). Revista Cubana de Plantas Medicinales.

[10] Bhowal M, Gopal M. Eucalyptol: Safety and pharmacological profile. Journal of Pharmaceutical Sciences.

[11] Adnan M. Bioactive potential of essential oil extracted from the leaves of *Eucalyptus globulus* (Myrtaceae). Journal of Pharmacognosy and Phytochemistry.

[12] Karr LL, Costas JR. Insecticidal properties of d-limonene. Journal of Pesticide Science. 1988;**13**(2):287-290

enantiomers against *Tribolium confusum* du Val. Neotropical Entomology.

preservation combined processes. PLoS

[13] Malacrinò A, Campolo O, Laudani F, Palmeri V. Fumigant and repellent activity of limonene

2017;**22**(2)

2015;**5**:125-131

2019;**8**(1):213-216

2016;**45**(5):597-603

[14] Espina L, Gelaw TK, de Lamo-Castellví S, Pagán R, García-Gonzalo D. Mechanism of bacterial inactivation by (+)-limonene

and its potential use in food

[15] Gulluni N, Re T, Loiacono I, Lanzo G, Gori L, Macchi C, et al. Cannabis essential oil: A preliminary study for the evaluation of the brain effects. Evidence-Based Complementary and Alternative Medicine. 2018;(1):1-11

[16] Mirghaed AT, Ghelichpour M, Hoseini SM. Myrcene and linalool as new anesthetic and sedative agents in common carp, *Cyprinus carpio* - Comparison with eugenol. Aquaculture.

One. 2013;**8**(2):e56769

2016;**464**:165-170

[2] Guimarães AG, Serafini MR, Quintans-Júnior LJ. Terpenes and derivatives as a new perspective for pain treatment: A patent review. Expert Opinion on Therapeutic Patents.

[3] Perveen S, Al-Taweel A. Introductory chapter: Terpenes and terpenoids. In: Terpenes and Terpenoids. London:

[4] Adams RP. Identification of Essential Oils by Ion Trap Mass Spectroscopy. San Diego, California: Academic Press; 2012

[5] Noriega P, Guerrini A, Sacchetti G, Grandini A, Ankuash E, Manfredini S. Chemical composition and biological activity of five essential oils from the Ecuadorian Amazon rain forest.

antimicrobial activity of the essential oil of rosemary. Environmental Toxicology and Pharmacology. 2011;**32**(1):63-68

pp. 127-129

**References**

2014;**24**(3):243-265

IntechOpen; 2018. pp. 1-7

Molecules. 2019;**24**(8):1637

[7] Zheljazkov VD, Astatkie T, Hristov AN. Lavender and hyssop productivity, oil content, and bioactivity as a function of harvest time and drying. Industrial Crops and

Products. 2012;**36**(1):222-228

[8] Silva ACRD, Lopes PM, Azevedo MMBD, Costa DCM, Alviano CS, Alviano DS. Biological

activities of a-pinene and

2012;**17**(6):6305-6316

β-pinene enantiomers. Molecules.

[9] Rivera PFN, Paredes EA, Gómez ED, Lueckhoff A, Almeida GA, Suarez SE.

[6] Jiang Y, Wu N, Fu YJ, Wang W, Luo M, Zhao CJ, et al. Chemical composition and MexAB-OprM efflux pump of Pseudomonas aeruginosa in tolerance to tea tree (*Melaleuca alternifolia*) oil and its monoterpene components terpinen-4-ol, 1, 8-cineole, and α-terpineol. Applied and Environmental Microbiology. 2008;**74**(6):1932-1935

[35] Kong Q, Zhang L, An P, Qi J, Yu X, Lu J, et al. Antifungal mechanisms of α-terpineol and terpene-4-alcohol as the critical components of *Melaleuca alternifolia* oil in the inhibition of rot disease caused by *Aspergillus ochraceus* in postharvest grapes. Journal of Applied Microbiology. 2019;**126**(4):1161-1174

[36] Ravid U, Putievsky E, Katzir I, Ikan R, Weinstein V. Determination of the enantiomeric composition of citronellol in essential oils by chiral GC analysis on a modified γ-cyclodextrin phase. Flavour and Fragrance Journal. 1992;**7**(4):235-238

[37] Katsukawa M, Nakata R, Koeji S, Hori K, Takahashi S, Inoue H. Citronellol and geraniol, components of rose oil, activate peroxisome proliferator-activated receptor α and γ and suppress cyclooxygenase-2 expression. Bioscience, Biotechnology, and Biochemistry. 2011;**75**(5):1010-1012

[38] Brari J, Thakur DR. Insecticidal potential properties of citronellol derived ionic liquid against two major stored grain insect pests. Journal of Entomology and Zoology Studies. 2016;**4**(3):365-370

[39] Brito RG, Guimarães AG, Quintans JS, Santos MR, De Sousa DP, Badaue-Passos D, et al. Citronellol, a monoterpene alcohol, reduces nociceptive and inflammatory activities in rodents. Journal of Natural Medicines. 2012;**66**(4):637-644

[40] Jagdale AD, Kamble SP, Nalawade ML, Arvindekar AU. Citronellol: A potential antioxidant and aldose reductase inhibitor from *Cymbopogon citratus*.

International Journal of Pharmacy and Pharmaceutical Sciences. 2015;**7**(3):203-209

[41] Isaac O, Thiemer K. Biochemical studies on camomile components/III. In vitro studies about the antipeptic activity of (−)-alpha-bisabolol (author's transl). Arzneimittel-Forschung. 1975;**25**:1352-1354

[42] Viljoen AM, Gono-Bwalya AB, Kamatou GPP, Baser KHC, Demirci B. The essential oil composition and chemotaxonomy of *Salvia stenophylla* and its allies *S. repens* and *S.runcinata*. Journal of Essential Oil Research. 2006;**18**:37-45

[43] Rocha NFM, Rios ERV, Carvalho AMR, Cerqueira GS, de Araújo LA, Leal LKAM, et al. Antinociceptive and anti-inflammatory activities of (−)-α-bisabolol in rodents. Naunyn-Schmiedeberg's Archives of Pharmacology. 2011;**384**(6):525-533

[44] Kamatou GP, Viljoen AM. A review of the application and pharmacological properties of α-bisabolol and α-bisabolol-rich oils. Journal of the American Oil Chemists' Society. 2010;**87**(1):1-7

[45] Ghelardini C, Galeotti N, Mannelli LDC, Mazzanti G, Bartolini A. Local anaesthetic activity of β-caryophyllene. Il Fármaco. 2001;**56**(5-7):387-389

[46] Fidyt K, Fiedorowicz A, Strządała L, Szumny A. β-Caryophyllene and β-caryophyllene oxide—Natural compounds of anticancer and analgesic properties. Cancer Medicine. 2016;**5**(10):3007-3017

[47] Tambe Y, Tsujiuchi H, Honda G, Ikeshiro Y, Tanaka S. Gastric cytoprotection of the non-steroidal anti-inflammatory sesquiterpene, β-caryophyllene. Planta Medica. 1996;**62**(05):469-470

**23**

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

> to produce an increased level of antimalarial drug precursor, artemisinic acid. BMC Biotechnology. 2008;**8**(1):83

[56] Ram M, Gupta MM, Naqvi AA, Kumar S. Effect of planting time on the yield of essential oil and artemisinin in *Artemisia annua* under subtropical conditions. Journal of Essential Oil Research. 1997;**9**(2):193-197

[57] Zhang Z, Chen X, Chen H, Wang L, Liang J, Luo D, et al. Anti-inflammatory activity of β-patchoulene isolated from patchouli oil in mice. European Journal of Pharmacology. 2016;**781**:229-238

[58] Liu Y, Liang J, Wu J, Chen H, Zhang Z, Yang H, et al. Transformation of patchouli alcohol to β-patchoulene by gastric juice: β-patchoulene is more effective in preventing ethanol-induced gastric injury. Scientific Reports.

[59] Liang J, Dou Y, Wu X, Li H, Wu J, Huang Q, et al. Prophylactic efficacy of patchoulene epoxide against ethanolinduced gastric ulcer in rats: Influence on oxidative stress, inflammation and apoptosis. Chemico-Biological Interactions. 2018;**283**:30-37

[60] Api AM, Belsito D, Botelho D, Browne D, Bruze M, Burton GA, et al. RIFM fragrance ingredient safety assessment β-Patchoulene, CAS Registry Number 514-51-2. Food and Chemical Toxicology. 2018;**115**:S256-S263

[61] Nance MR, Setzer WN. Volatile components of aroma hops (*Humulus lupulus* L.) commonly used in beer brewing. Journal of Brewing and Distilling. 2011;**2**(2):16-22

[62] Rogerio AP, Andrade EL, Leite DF, Figueiredo CP, Calixto JB. Preventive and therapeutic anti-inflammatory properties of the sesquiterpene α-humulene in experimental airways allergic inflammation. British Journal of Pharmacology. 2009;**158**(4):1074-1087

2017;**7**(1):1-13

[48] Legault J, Pichette A. Potentiating

[49] Ma D, He J, He D. Chamazulene reverses osteoarthritic inflammation

[50] Flemming M, Kraus B, Rascle A, Jürgenliemk G, Fuchs S, Fürst R, et al. Revisited anti-inflammatory activity of matricine in vitro: Comparison with chamazulene. Fitoterapia.

[51] Rekka EA, Kourounakis AP, Kourounakis PN. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Research Communications in Molecular

Pathology and Pharmacology.

[52] Capuzzo A, Occhipinti A, Maffei ME. Antioxidant and radical scavenging activities of chamazulene.

[53] Chavan MJ, Wakte PS, Shinde DB. Analgesic and anti-inflammatory activity of caryophyllene oxide from *Annona squamosa* L. bark. Phytomedicine. 2010;**17**(2):149-151

[54] Casiglia S, Bruno M, Bramucci M, Quassinti L, Lupidi G, Fiorini D, et al. *Kundmannia sicula* (L.) DC: A rich source of germacrene D. Journal of Essential Oil Research.

[55] Ro DK, Ouellet M, Paradise EM, Burd H, Eng D, Paddon CJ, et al. Induction of multiple pleiotropic drug resistance genes in yeast engineered

Natural Product Research. 2014;**28**(24):2321-2323

through regulation of matrix metalloproteinases (MMPs) and NF-kβ pathway in in-vitro and in-vivo models. Bioscience, Biotechnology, and Biochemistry. 2020;**84**(2):402-410

effect of β-caryophyllene on anticancer activity of α-humulene, isocaryophyllene and paclitaxel. The Journal of Pharmacy and Pharmacology.

2007;**59**(12):1643-1647

2015;**106**:122-128

1996;**92**(3):361-364

2017;**29**(6):437-442

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

[48] Legault J, Pichette A. Potentiating effect of β-caryophyllene on anticancer activity of α-humulene, isocaryophyllene and paclitaxel. The Journal of Pharmacy and Pharmacology. 2007;**59**(12):1643-1647

*Terpenes and Terpenoids-Recent Advances*

α-terpineol. Applied and Environmental Microbiology. 2008;**74**(6):1932-1935

International Journal of Pharmacy and Pharmaceutical Sciences.

[41] Isaac O, Thiemer K. Biochemical studies on camomile components/III. In vitro studies about the antipeptic activity of (−)-alpha-bisabolol (author's transl). Arzneimittel-Forschung.

Bwalya AB, Kamatou GPP, Baser KHC, Demirci B. The essential oil composition

[44] Kamatou GP, Viljoen AM. A review of the application and pharmacological

properties of α-bisabolol and α-bisabolol-rich oils. Journal of the American Oil Chemists' Society.

[45] Ghelardini C, Galeotti N, Mannelli LDC, Mazzanti G,

[46] Fidyt K, Fiedorowicz A,

2001;**56**(5-7):387-389

2016;**5**(10):3007-3017

1996;**62**(05):469-470

[47] Tambe Y, Tsujiuchi H,

Bartolini A. Local anaesthetic activity of β-caryophyllene. Il Fármaco.

Strządała L, Szumny A. β-Caryophyllene and β-caryophyllene oxide—Natural compounds of anticancer and

analgesic properties. Cancer Medicine.

Honda G, Ikeshiro Y, Tanaka S. Gastric cytoprotection of the non-steroidal anti-inflammatory sesquiterpene, β-caryophyllene. Planta Medica.

2010;**87**(1):1-7

and chemotaxonomy of *Salvia stenophylla* and its allies *S. repens* and *S.runcinata*. Journal of Essential Oil

2015;**7**(3):203-209

1975;**25**:1352-1354

[42] Viljoen AM, Gono-

Research. 2006;**18**:37-45

[43] Rocha NFM, Rios ERV, Carvalho AMR, Cerqueira GS, de Araújo LA, Leal LKAM, et al. Antinociceptive and anti-inflammatory activities of (−)-α-bisabolol in rodents. Naunyn-Schmiedeberg's Archives of Pharmacology. 2011;**384**(6):525-533

[35] Kong Q, Zhang L, An P, Qi J, Yu X, Lu J, et al. Antifungal mechanisms of α-terpineol and terpene-4-alcohol as the critical components of *Melaleuca alternifolia* oil in the inhibition of rot disease caused by *Aspergillus ochraceus* in postharvest grapes. Journal of Applied Microbiology. 2019;**126**(4):1161-1174

[36] Ravid U, Putievsky E, Katzir I, Ikan R, Weinstein V. Determination of the enantiomeric composition of citronellol in essential oils by chiral GC analysis on a modified γ-cyclodextrin phase. Flavour and Fragrance Journal.

[37] Katsukawa M, Nakata R, Koeji S, Hori K, Takahashi S, Inoue H.

Citronellol and geraniol, components of rose oil, activate peroxisome proliferator-activated receptor α and γ and suppress cyclooxygenase-2 expression. Bioscience, Biotechnology, and Biochemistry. 2011;**75**(5):1010-1012

[38] Brari J, Thakur DR. Insecticidal potential properties of citronellol derived ionic liquid against two major stored grain insect pests. Journal of Entomology and Zoology Studies.

1992;**7**(4):235-238

2016;**4**(3):365-370

[39] Brito RG, Guimarães AG,

Medicines. 2012;**66**(4):637-644

Quintans JS, Santos MR, De Sousa DP, Badaue-Passos D, et al. Citronellol, a monoterpene alcohol, reduces nociceptive and inflammatory

activities in rodents. Journal of Natural

[40] Jagdale AD, Kamble SP, Nalawade ML, Arvindekar AU. Citronellol: A potential antioxidant and aldose reductase inhibitor from *Cymbopogon citratus*.

MexAB-OprM efflux pump of Pseudomonas aeruginosa in tolerance to tea tree (*Melaleuca alternifolia*) oil and its monoterpene components terpinen-4-ol, 1, 8-cineole, and

**22**

[49] Ma D, He J, He D. Chamazulene reverses osteoarthritic inflammation through regulation of matrix metalloproteinases (MMPs) and NF-kβ pathway in in-vitro and in-vivo models. Bioscience, Biotechnology, and Biochemistry. 2020;**84**(2):402-410

[50] Flemming M, Kraus B, Rascle A, Jürgenliemk G, Fuchs S, Fürst R, et al. Revisited anti-inflammatory activity of matricine in vitro: Comparison with chamazulene. Fitoterapia. 2015;**106**:122-128

[51] Rekka EA, Kourounakis AP, Kourounakis PN. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Research Communications in Molecular Pathology and Pharmacology. 1996;**92**(3):361-364

[52] Capuzzo A, Occhipinti A, Maffei ME. Antioxidant and radical scavenging activities of chamazulene. Natural Product Research. 2014;**28**(24):2321-2323

[53] Chavan MJ, Wakte PS, Shinde DB. Analgesic and anti-inflammatory activity of caryophyllene oxide from *Annona squamosa* L. bark. Phytomedicine. 2010;**17**(2):149-151

[54] Casiglia S, Bruno M, Bramucci M, Quassinti L, Lupidi G, Fiorini D, et al. *Kundmannia sicula* (L.) DC: A rich source of germacrene D. Journal of Essential Oil Research. 2017;**29**(6):437-442

[55] Ro DK, Ouellet M, Paradise EM, Burd H, Eng D, Paddon CJ, et al. Induction of multiple pleiotropic drug resistance genes in yeast engineered

to produce an increased level of antimalarial drug precursor, artemisinic acid. BMC Biotechnology. 2008;**8**(1):83

[56] Ram M, Gupta MM, Naqvi AA, Kumar S. Effect of planting time on the yield of essential oil and artemisinin in *Artemisia annua* under subtropical conditions. Journal of Essential Oil Research. 1997;**9**(2):193-197

[57] Zhang Z, Chen X, Chen H, Wang L, Liang J, Luo D, et al. Anti-inflammatory activity of β-patchoulene isolated from patchouli oil in mice. European Journal of Pharmacology. 2016;**781**:229-238

[58] Liu Y, Liang J, Wu J, Chen H, Zhang Z, Yang H, et al. Transformation of patchouli alcohol to β-patchoulene by gastric juice: β-patchoulene is more effective in preventing ethanol-induced gastric injury. Scientific Reports. 2017;**7**(1):1-13

[59] Liang J, Dou Y, Wu X, Li H, Wu J, Huang Q, et al. Prophylactic efficacy of patchoulene epoxide against ethanolinduced gastric ulcer in rats: Influence on oxidative stress, inflammation and apoptosis. Chemico-Biological Interactions. 2018;**283**:30-37

[60] Api AM, Belsito D, Botelho D, Browne D, Bruze M, Burton GA, et al. RIFM fragrance ingredient safety assessment β-Patchoulene, CAS Registry Number 514-51-2. Food and Chemical Toxicology. 2018;**115**:S256-S263

[61] Nance MR, Setzer WN. Volatile components of aroma hops (*Humulus lupulus* L.) commonly used in beer brewing. Journal of Brewing and Distilling. 2011;**2**(2):16-22

[62] Rogerio AP, Andrade EL, Leite DF, Figueiredo CP, Calixto JB. Preventive and therapeutic anti-inflammatory properties of the sesquiterpene α-humulene in experimental airways allergic inflammation. British Journal of Pharmacology. 2009;**158**(4):1074-1087

[63] Fernandes ES, Passos GF, Medeiros R, da Cunha FM, Ferreira J, Campos MM, et al. Anti-inflammatory effects of compounds alpha-humulene and (−)-trans-caryophyllene isolated from the essential oil of *Cordia verbenacea*. European Journal of Pharmacology. 2007;**569**(3):228-236

[64] El Hadri A, del Rio MG, Sanz J, Coloma AG, Idaomar M, Ozonas BR, et al. Cytotoxic activity of α-humulene and transcaryophyllene from *Salvia officinalis* in animal and human tumor cells. Anales de la Real Academia Nacional de Farmacia. 2010;**76**(3):343-356

[65] Navarra M, Mannucci C, Delbò M, Calapai G. *Citrus bergamia* essential oil: From basic research to clinical application. Frontiers in Pharmacology. 2015;**6**:36

[66] Cônsoli FL, Williams HJ, Vinson SB, Matthews RW, Cooperband MF. Transbergamotenes—Male pheromone of the ectoparasitoid *Melittobia digitata*. Journal of Chemical Ecology. 2002;**28**(8):1675-1689

[67] Haber AI, Sims JW, Mescher MC, De Moraes CM, Carr DE. A key floral scent component (β-trans-bergamotene) drives pollinator preferences independently of pollen rewards in seep monkeyflower. Functional Ecology. 2019;**33**(2):218-228

[68] Çelik K, Toğar B, Türkez H, Taşpinar N. In vitro cytotoxic, genotoxic, and oxidative effects of acyclic sesquiterpene farnesene. Turkish Journal of Biology. 2014;**38**(2):253-259

[69] Sun Y, Qiao H, Ling Y, Yang S, Rui C, Pelosi P, et al. New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins. Journal of Agricultural and Food Chemistry. 2011;**59**(6):2456-2461

[70] Arslan ME, Türkez H, Mardinoğlu A. In vitro neuroprotective effects of farnesene sesquiterpene on alzheimer's disease model of differentiated neuroblastoma cell line. The International Journal of Neuroscience. 2020;**130**:1-10

[71] Turkez H, Sozio P, Geyikoglu F, Tatar A, Hacimuftuoglu A, Di Stefano A. Neuroprotective effects of farnesene against hydrogen peroxideinduced neurotoxicity in vitro. Cellular and Molecular Neurobiology. 2014;**34**(1):101-111

[72] Noriega P, Ballesteros J, De la Cruz A, Veloz T. Chemical composition and preliminary antimicrobial activity of the hydroxylated sesquiterpenes in the essential oil from Piper barbatum Kunth leaves. Plants. 2020;**9**(2):211

[73] Plengsuriyakarn T, Karbwang J, Na-Bangchang K. Anticancer activity using positron emission tomographycomputed tomography and pharmacokinetics of β-eudesmol in human cholangiocarcinoma xenografted nude mouse model. Clinical and Experimental Pharmacology and Physiology. 2015;**42**(3):293-304

[74] Miyazawa M, Shimamura H, Nakamura SI, Kameoka H. Antimutagenic activity of (+)-β-eudesmol and paeonol from *Dioscorea japonica*. Journal of Agricultural and Food Chemistry. 1996;**44**(7):1647-1650

[75] Tsuneki H, Ma EL, Kobayashi S, Sekizaki N, Maekawa K, Sasaoka T, et al. Antiangiogenic activity of β-eudesmol in vitro and in vivo. European Journal of Pharmacology. 2005;**512**(2-3):105-115

[76] Mekonnen A, Tesfaye S, Christos SG, Dires K, Zenebe T, Zegeye N, et al. Evaluation of skin irritation and acute and subacute oral toxicity of *Lavandula angustifolia* essential oils in rabbit and mice. Journal of Toxicology. 2019;(1):1-8

**25**

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

[77] Lee CJ, Chen LW, Chen LG, Chang TL, Huang CW, Huang MC, et al. Correlations of the components of tea tree oil with its antibacterial effects and skin irritation. Journal of Food and Drug Analysis. 2013;**21**(2):169-176

[78] Gordon WP, Forte AJ, McMurtry RJ, Gal J, Nelson SD. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology. 1982;**65**(3):413-424

[79] Pelkonen O, Abass K, Wiesner J. Thujone and thujone-containing herbal medicinal and botanical products: Toxicological assessment. Regulatory Toxicology and Pharmacology.

2013;**65**(1):100-107

*Terpenes in Essential Oils: Bioactivity and Applications DOI: http://dx.doi.org/10.5772/intechopen.93792*

[77] Lee CJ, Chen LW, Chen LG, Chang TL, Huang CW, Huang MC, et al. Correlations of the components of tea tree oil with its antibacterial effects and skin irritation. Journal of Food and Drug Analysis. 2013;**21**(2):169-176

*Terpenes and Terpenoids-Recent Advances*

Medeiros R, da Cunha FM, Ferreira J, Campos MM, et al. Anti-inflammatory effects of compounds alpha-humulene and (−)-trans-caryophyllene isolated from the essential oil of *Cordia verbenacea*. European Journal of Pharmacology. 2007;**569**(3):228-236

[70] Arslan ME, Türkez H,

2014;**34**(1):101-111

Mardinoğlu A. In vitro neuroprotective effects of farnesene sesquiterpene on alzheimer's disease model of differentiated neuroblastoma cell line. The International Journal of Neuroscience. 2020;**130**:1-10

[71] Turkez H, Sozio P, Geyikoglu F, Tatar A, Hacimuftuoglu A, Di Stefano A. Neuroprotective effects of farnesene against hydrogen peroxideinduced neurotoxicity in vitro. Cellular and Molecular Neurobiology.

[72] Noriega P, Ballesteros J, De la Cruz A, Veloz T. Chemical composition and preliminary antimicrobial activity of the hydroxylated sesquiterpenes in the essential oil from Piper barbatum Kunth leaves. Plants. 2020;**9**(2):211

[73] Plengsuriyakarn T, Karbwang J, Na-Bangchang K. Anticancer activity using positron emission tomography-

xenografted nude mouse model. Clinical and Experimental Pharmacology and Physiology. 2015;**42**(3):293-304

Nakamura SI, Kameoka H. Antimutagenic activity of (+)-β-eudesmol and paeonol from *Dioscorea japonica*. Journal of Agricultural and Food Chemistry.

[75] Tsuneki H, Ma EL, Kobayashi S, Sekizaki N, Maekawa K, Sasaoka T, et al. Antiangiogenic activity of β-eudesmol in vitro and in vivo. European Journal of Pharmacology. 2005;**512**(2-3):105-115

[76] Mekonnen A, Tesfaye S, Christos SG, Dires K, Zenebe T, Zegeye N, et al. Evaluation of skin irritation and acute and subacute oral toxicity of *Lavandula angustifolia* essential oils in rabbit and mice. Journal

of Toxicology. 2019;(1):1-8

[74] Miyazawa M, Shimamura H,

1996;**44**(7):1647-1650

computed tomography and pharmacokinetics of β-eudesmol in human cholangiocarcinoma

[64] El Hadri A, del Rio MG, Sanz J, Coloma AG, Idaomar M, Ozonas BR, et al. Cytotoxic activity of α-humulene and transcaryophyllene from *Salvia officinalis* in animal and human tumor cells. Anales de la Real Academia Nacional de Farmacia.

[65] Navarra M, Mannucci C, Delbò M, Calapai G. *Citrus bergamia* essential oil: From basic research to clinical application. Frontiers in Pharmacology.

[66] Cônsoli FL, Williams HJ, Vinson SB, Matthews RW, Cooperband MF. Transbergamotenes—Male pheromone of the ectoparasitoid *Melittobia digitata*. Journal of Chemical Ecology.

[67] Haber AI, Sims JW, Mescher MC, De Moraes CM, Carr DE. A key floral scent component (β-trans-bergamotene) drives pollinator preferences

independently of pollen rewards in seep monkeyflower. Functional Ecology.

[68] Çelik K, Toğar B, Türkez H, Taşpinar N. In vitro cytotoxic, genotoxic, and oxidative effects of acyclic sesquiterpene farnesene. Turkish Journal of Biology.

[69] Sun Y, Qiao H, Ling Y, Yang S, Rui C, Pelosi P, et al. New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins. Journal of Agricultural and Food Chemistry.

2010;**76**(3):343-356

2002;**28**(8):1675-1689

2019;**33**(2):218-228

2014;**38**(2):253-259

2011;**59**(6):2456-2461

2015;**6**:36

[63] Fernandes ES, Passos GF,

**24**

[78] Gordon WP, Forte AJ, McMurtry RJ, Gal J, Nelson SD. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology. 1982;**65**(3):413-424

[79] Pelkonen O, Abass K, Wiesner J. Thujone and thujone-containing herbal medicinal and botanical products: Toxicological assessment. Regulatory Toxicology and Pharmacology. 2013;**65**(1):100-107

**27**

**Chapter 3**

**Abstract**

volatile compounds, terpenes

and certain types of cancer [3].

the bitter and pungent sensory notes [4].

**1. Introduction**

Terpene Compounds of New

different ripeness stage was strictly connected with the ripeness stage.

**Keywords:** virgin olive oil, headspace-solid-phase microextraction (HS-SPME),

after olive fruits are crushed during industrial oil production. Extra virgin olive oil (EVOO) is unique for its high monounsaturated fatty acids levels and the existence of a wide range of minor components responsible for their organoleptic characteristics and health properties [1]. EVOO attract the interest of the scientific community for its health properties; is an indispensable element of the Mediterranean diet [2]. Its consumption is correlated with a lower incidence of a number of diseases correlated to inflammatory processes such as cardiovascular diseases, diabetes, arthritis, Alzheimer

Virgin olive oil is characterized through its distinctive perfume, which is synthesized

A potential interacting impact of phenolic compounds on EVOO aroma release and perception has been recently described. Volatile minor components are consequently responsible for the aroma of EVOO whereas phenolics are closely related to

Aldehydes and alcohols of six straight-chain carbons (C6), as well as their corresponding esters, are the most important compounds in EVOO volatile compounds, also quantitatively or qualitatively. Linolenic (LnA) and Linoleic (LA) acids are the main substrates for this synthesis. Lastly, terpenes found in the volatile fraction of EVOO seem not to be important contributors to EVOO aroma

Baccouri et al. [6] revealed that Solid-phase microextraction (SPME) of the head space (HS) in combination with mass spectrometry (GC–MS) and gas

due to their low concentration and high odor threshold [1, 5].

Effect of Ripening Stage

*Bechir Baccouri and Imene Rajhi*

Tunisian Extra-Virgin Olive Oil:

The volatile profiles of Tunisian virgin olive oils were established by solid phase micro-extraction (SPME) and gas chromatography (GC), using flame ionisation and mass spectrometer detectors. Terpenes compounds were identified and characterized. Limonene, the main terpene compound extracted by SPME, characterized the studied olive oil. Significant differences in the proportions of terpenes constituents from oils of different maturity index were detected. The results demonstrated that the accumulation of the terpenes compounds in the studied oils obtained from

#### **Chapter 3**

## Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage

*Bechir Baccouri and Imene Rajhi*

#### **Abstract**

The volatile profiles of Tunisian virgin olive oils were established by solid phase micro-extraction (SPME) and gas chromatography (GC), using flame ionisation and mass spectrometer detectors. Terpenes compounds were identified and characterized. Limonene, the main terpene compound extracted by SPME, characterized the studied olive oil. Significant differences in the proportions of terpenes constituents from oils of different maturity index were detected. The results demonstrated that the accumulation of the terpenes compounds in the studied oils obtained from different ripeness stage was strictly connected with the ripeness stage.

**Keywords:** virgin olive oil, headspace-solid-phase microextraction (HS-SPME), volatile compounds, terpenes

#### **1. Introduction**

Virgin olive oil is characterized through its distinctive perfume, which is synthesized after olive fruits are crushed during industrial oil production. Extra virgin olive oil (EVOO) is unique for its high monounsaturated fatty acids levels and the existence of a wide range of minor components responsible for their organoleptic characteristics and health properties [1]. EVOO attract the interest of the scientific community for its health properties; is an indispensable element of the Mediterranean diet [2]. Its consumption is correlated with a lower incidence of a number of diseases correlated to inflammatory processes such as cardiovascular diseases, diabetes, arthritis, Alzheimer and certain types of cancer [3].

A potential interacting impact of phenolic compounds on EVOO aroma release and perception has been recently described. Volatile minor components are consequently responsible for the aroma of EVOO whereas phenolics are closely related to the bitter and pungent sensory notes [4].

Aldehydes and alcohols of six straight-chain carbons (C6), as well as their corresponding esters, are the most important compounds in EVOO volatile compounds, also quantitatively or qualitatively. Linolenic (LnA) and Linoleic (LA) acids are the main substrates for this synthesis. Lastly, terpenes found in the volatile fraction of EVOO seem not to be important contributors to EVOO aroma due to their low concentration and high odor threshold [1, 5].

Baccouri et al. [6] revealed that Solid-phase microextraction (SPME) of the head space (HS) in combination with mass spectrometry (GC–MS) and gas

chromatography is a very powerful technique that is used quite regularly for the analysis of aroma compounds in foods. HS-SPME–GG–MS has been applied to study the volatile of products derived from the olive fruit, such as oil or table olives [7]. Actually, SPME-GC–MS is the technique of reference to validate the discriminating power of new e-sensing technologies such as the electronic nose for olive oil [8–10].

The main triterpenes present in EVOO are two hydroxyl pentacyclic triterpene acids (oleanolic and maslinic acid) and two dialcohols (uvaol and erythrodiol) [2]. These compounds are mostly found in the epicarp of drupes, therefore, pomace olive oil extracted from olive pomace after the first press with the use of solvents or other chemical processes generally contains 10-fold higher concentrations than EVOO [11].

In in vitro studies, EVOO triterpenes have been described as potent inhibitors of LDL oxidation [12] and to possess antiatherogenic properties via preventing LDL-supporting thrombin generation [3]. A role of these compounds in atherosclerosis protection has been further suggested in a feed work with apolipoprotein (apo) E knockout (KO) mice developing a spontaneous atherosclerosis that mimics most of the features of human atherogenesis [11].

EVOO triterpenes together with hydrocarbons and lignans inhibited cell proliferation and DNA synthesis in Caco-2 colon cancer cell cultures induced through oleic acid, as oleic acid in deficiency of growth factors was capable to induce Caco-2 propagation [13]. In addition, pentacyclic triterpenes from olives established an antiproliferative, and proapoptotic action on on HT-29 colon cancer cells and MCF-7 human breast cancer cells [14].

#### **2. Material and methods**

#### **2.1 Sampling**

This work was carried out on the study of Effect of ripening period on Terpene compounds of new Tunisian extra-virgin olive oil obtained through controlled crossings on Meski variety. Preliminary work evaluating the oil fatty acid composition of the oil of 50 hybrids showed the performance of these cultivars (9d) among the studied descendants. This new cultivars have an improved oil composition compared to that of Chemlali, the most abundant variety in Tunisia. Samples, obtained from homogeneous olive have picked by hand at a known ripening degree during the crop season 2018/2019. Healthy fruits, without any infection or physical damage, were processed. The olives were washed, deleafed and crushed with a hammer crusher, and the paste mixed at 25 °C for 30 min, centrifuged without addition of warm water and then transferred into dark glass bottles.

#### **2.2 Analysis of volatile compounds: HS–SPME analysis**

Before use, the fibre was conditioned; the fibre used for the extraction of the volatile components was divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/ PDMS) 50/30 mm.

5 g olive oil was placed in a 20 ml vial closed by PTFE/silicone septum. Before extraction, the stabilization of the headspace in the vial was accomplished by equilibration for 60 min at 25 °C. The extraction was carried out at room temperature, with magnetic stirring (900 trs/min). To determine the optimal adsorption time of the fibre with the sample headspace, the fibre DVB/CAR/PDMS was exposed for time periods of 10, 30, 60, 90 and 120 min [5].

**29**

*Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage*

The injections were performed using a SPME autosampler. The fibre was thermally desorbed into a GC and left in the injection port for 4 min. The injector was set at 250 °C and operated in the splitless mode for 2 min unless otherwise stated. The fibre was reconditioned for 5 min in a washing port at 250 °C and blank runs

Each oil was analysed by GC–MS using an Agilent 6890N/5973N system, with fused-silica capillary columns HP-1 (50 m X 0.20 mm; film thickness: 0.5 mm). The identification of the constituents was based on comparison of the retention times with those of authentic samples. Several structures were also confirmed by standard compounds injection. All chemicals were purchased from Fluka or Sigma–Aldrich

Sesquiterpene hydrocarbons were a major class of compounds identified in the EVOOs samples. Monoterpenes and sesquiterpenes are the lower molecular weight representatives of the terpenoid compounds; they are produced by two and three

Studied EVOOs made during ripeness process were exposed. Ten sesquiterpenes (**Table 1**), acyclic, monocyclic, bicyclic and tricyclic, were studieded. The variables which were more decisive to discriminate among ripeness stages were sesquiterpenes and aldehydes, such as limonene, α-agarofuran, α-muurolene, *trans*-α-bergamotene, α-farnesene, α-copaene, β-selinene, β-elemene, β-dihydroagarofuran, β-caryophyllene, (Z)-β-farnesene, δ-cadinene, (*E,E*)- (*E*)-β-ocimene, (*Z*)-3-hexenal and nonanal. This finding is in very good agreement with previous studies on other varieties [2, 8].

Several terpene hydrocarbons (mono- and sesquiterpenes) were often detected, and they totally accounted for 2.9–13.5% of the whole volatiles (**Table 1**). (E,E) α-farnesene (0.1–0.7%), a mono-unsaturated sesquiterpene, was the main one. Besides (E,E)- α-farnesene, other important sesquiterpenes were cyclosativene and α-muurolene, a tetra-unsaturated sesquiterpene that has already been detected in Spanish oils, mainly in those obtained from olives of the Hojiblanca variety [15]. Sesquiterpene hydrocarbons, tended to increase during the maturation process. The highest value (1.3%) was registered in EVOOs obtained from fruits at MI = 6,

During maturation process, α-copaene remained almost constant during the two maturation stages followed the general trend described above, varying from 0.2% (MI = 2) to 0.4% (MI = 6). further sesquiterpene, such as β-slinene, γ-muurolene, cyclosativene, α-ylangene and α-cubebene, appeared in small amounts only at the

Monoterpene hydrocarbons, represented by limonene, p-cymene and (E)-βocimene, showed a constant increment of its levels during the three maturation stages. Limonene showed a constant increment of its levels passing from 2.2 to 9.4%. This strong dependence on maturity process, makes terpenes good candidates suitable for the discrimination of oils with different ripeness index. Vichi et al. [15] demonstrated that the amounts of α-muurolene, α-copaeneand and α-farnesene may be used to construct a decisional tree that successfully classifies Western-Liguria extra-virgin olive oils from further Mediterranean oils. Vichi et al. [15] confirmed also for the first time that the enhance of sesquiterpene is Maturationdependent in olive, and consequently that ripening must be taken carefully into

and the lowest (0.1%) in EVOOs from fruits at MI = 2.

*DOI: http://dx.doi.org/10.5772/intechopen.96254*

were done periodically during the study [5].

**2.3 GC–MS analyses**

(Saint Quentin Fallavier, France).

**3. Result and discussion**

isoprene units, respectively.

highest MI value (**Table 1**).

#### *Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage DOI: http://dx.doi.org/10.5772/intechopen.96254*

The injections were performed using a SPME autosampler. The fibre was thermally desorbed into a GC and left in the injection port for 4 min. The injector was set at 250 °C and operated in the splitless mode for 2 min unless otherwise stated. The fibre was reconditioned for 5 min in a washing port at 250 °C and blank runs were done periodically during the study [5].

#### **2.3 GC–MS analyses**

*Terpenes and Terpenoids-Recent Advances*

most of the features of human atherogenesis [11].

MCF-7 human breast cancer cells [14].

**2. Material and methods**

**2.1 Sampling**

PDMS) 50/30 mm.

for olive oil [8–10].

EVOO [11].

chromatography is a very powerful technique that is used quite regularly for the analysis of aroma compounds in foods. HS-SPME–GG–MS has been applied to study the volatile of products derived from the olive fruit, such as oil or table olives [7]. Actually, SPME-GC–MS is the technique of reference to validate the discriminating power of new e-sensing technologies such as the electronic nose

The main triterpenes present in EVOO are two hydroxyl pentacyclic triterpene acids (oleanolic and maslinic acid) and two dialcohols (uvaol and erythrodiol) [2]. These compounds are mostly found in the epicarp of drupes, therefore, pomace olive oil extracted from olive pomace after the first press with the use of solvents or other chemical processes generally contains 10-fold higher concentrations than

In in vitro studies, EVOO triterpenes have been described as potent inhibitors of LDL oxidation [12] and to possess antiatherogenic properties via preventing LDL-supporting thrombin generation [3]. A role of these compounds in atherosclerosis protection has been further suggested in a feed work with apolipoprotein (apo) E knockout (KO) mice developing a spontaneous atherosclerosis that mimics

EVOO triterpenes together with hydrocarbons and lignans inhibited cell proliferation and DNA synthesis in Caco-2 colon cancer cell cultures induced through oleic acid, as oleic acid in deficiency of growth factors was capable to induce Caco-2 propagation [13]. In addition, pentacyclic triterpenes from olives established an antiproliferative, and proapoptotic action on on HT-29 colon cancer cells and

This work was carried out on the study of Effect of ripening period on Terpene compounds of new Tunisian extra-virgin olive oil obtained through controlled crossings on Meski variety. Preliminary work evaluating the oil fatty acid composition of the oil of 50 hybrids showed the performance of these cultivars (9d) among the studied descendants. This new cultivars have an improved oil composition compared to that of Chemlali, the most abundant variety in Tunisia. Samples, obtained from homogeneous olive have picked by hand at a known ripening degree during the crop season 2018/2019. Healthy fruits, without any infection or physical damage, were processed. The olives were washed, deleafed and crushed with a hammer crusher, and the paste mixed at 25 °C for 30 min, centrifuged without

addition of warm water and then transferred into dark glass bottles.

Before use, the fibre was conditioned; the fibre used for the extraction of the volatile components was divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/

5 g olive oil was placed in a 20 ml vial closed by PTFE/silicone septum. Before extraction, the stabilization of the headspace in the vial was accomplished by equilibration for 60 min at 25 °C. The extraction was carried out at room temperature, with magnetic stirring (900 trs/min). To determine the optimal adsorption time of the fibre with the sample headspace, the fibre DVB/CAR/PDMS was

**2.2 Analysis of volatile compounds: HS–SPME analysis**

exposed for time periods of 10, 30, 60, 90 and 120 min [5].

**28**

Each oil was analysed by GC–MS using an Agilent 6890N/5973N system, with fused-silica capillary columns HP-1 (50 m X 0.20 mm; film thickness: 0.5 mm). The identification of the constituents was based on comparison of the retention times with those of authentic samples. Several structures were also confirmed by standard compounds injection. All chemicals were purchased from Fluka or Sigma–Aldrich (Saint Quentin Fallavier, France).

#### **3. Result and discussion**

Sesquiterpene hydrocarbons were a major class of compounds identified in the EVOOs samples. Monoterpenes and sesquiterpenes are the lower molecular weight representatives of the terpenoid compounds; they are produced by two and three isoprene units, respectively.

Studied EVOOs made during ripeness process were exposed. Ten sesquiterpenes (**Table 1**), acyclic, monocyclic, bicyclic and tricyclic, were studieded. The variables which were more decisive to discriminate among ripeness stages were sesquiterpenes and aldehydes, such as limonene, α-agarofuran, α-muurolene, *trans*-α-bergamotene, α-farnesene, α-copaene, β-selinene, β-elemene, β-dihydroagarofuran, β-caryophyllene, (Z)-β-farnesene, δ-cadinene, (*E,E*)- (*E*)-β-ocimene, (*Z*)-3-hexenal and nonanal. This finding is in very good agreement with previous studies on other varieties [2, 8].

Several terpene hydrocarbons (mono- and sesquiterpenes) were often detected, and they totally accounted for 2.9–13.5% of the whole volatiles (**Table 1**). (E,E) α-farnesene (0.1–0.7%), a mono-unsaturated sesquiterpene, was the main one. Besides (E,E)- α-farnesene, other important sesquiterpenes were cyclosativene and α-muurolene, a tetra-unsaturated sesquiterpene that has already been detected in Spanish oils, mainly in those obtained from olives of the Hojiblanca variety [15].

Sesquiterpene hydrocarbons, tended to increase during the maturation process. The highest value (1.3%) was registered in EVOOs obtained from fruits at MI = 6, and the lowest (0.1%) in EVOOs from fruits at MI = 2.

During maturation process, α-copaene remained almost constant during the two maturation stages followed the general trend described above, varying from 0.2% (MI = 2) to 0.4% (MI = 6). further sesquiterpene, such as β-slinene, γ-muurolene, cyclosativene, α-ylangene and α-cubebene, appeared in small amounts only at the highest MI value (**Table 1**).

Monoterpene hydrocarbons, represented by limonene, p-cymene and (E)-βocimene, showed a constant increment of its levels during the three maturation stages. Limonene showed a constant increment of its levels passing from 2.2 to 9.4%.

This strong dependence on maturity process, makes terpenes good candidates suitable for the discrimination of oils with different ripeness index. Vichi et al. [15] demonstrated that the amounts of α-muurolene, α-copaeneand and α-farnesene may be used to construct a decisional tree that successfully classifies Western-Liguria extra-virgin olive oils from further Mediterranean oils. Vichi et al. [15] confirmed also for the first time that the enhance of sesquiterpene is Maturationdependent in olive, and consequently that ripening must be taken carefully into


#### **Table 1.**

*Terpene composition of the studied olive oil at different stage of maturity.*

account when analyzing terpenes [16]. Our results are in agreement with the study of Vichi et al. [15]. These hydrocarbons may be used as markers to distinguish EVOO of different geographical origins [10].

The volatile fraction of the oil from Sfax (South of Tunisia) was characterized by the pre-eminence of α-copaene (24.5%) that may be used as markers to differentiate EVOO of different sites. The other main compounds detected were (E,E)- α -farnesene (6.8%), α -muurolene (4.8%), cyclosativene (3.0%), aromadendrene (1.8%) and longicyclene (1.7%).

A comparison with literature data on the chemical composition of olive oils is complicated because of the big variability of the volatile profiles. In fact, it has been reported that the concentrations of compounds depend on the enzymatic activity though external parameters (soil, climate, harvesting and extraction conditions) may alter the inherent olive oil sensory profile. The variation in levels of C6 aldehydes and alcohols for oil samples from different soils implies that pedologic conditions may influence the activity of alcohol dehydrogenase (ADH).

The triterpenic dialcohols (erythrodiol and uvaol), which are also part of the unsaponifiable fraction of the olive oil, are usually analysed together with the sterol fraction [1]. The erythrodiol and uvaol content of the studied olive oils varied according to maturity, ranging from 0.5 to 2.22% and from 0.1 to 0.92%, respectively (**Table 1**). The sum of erythrodiol and uvaol in all ripeness index was below the established limit of 4.5% for the "extra virgin" olive oil category. These results are consistent with the findings of other authors [15].

#### **4. Conclusions**

In conclusion, results demonstrated that the studied olive oils presents a elevated level of variability in terms of the volatile fraction. This aroma variability and the

**31**

**Author details**

maturity stage.

**Conflict of interest**

Bechir Baccouri1

Tunisia

\* and Imene Rajhi2

\*Address all correspondence to: bechirbaccouri@yahoo.fr

provided the original work is properly cited.

1 Laboratory of Olive Biotechnology, Centre of Biotechnology of Borj-Cédria,

© 2021 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium,

2 Laboratory of Legumes Centre of Biotechnology of Borj-Cédria, Tunisia

*Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage*

high genetic diversity of the cultivar germplasm collection suggest that it is possible both to identify old olive cultivars that give rise to oils with a high organoleptic quality and to select optimal parents for olive breeding programs with the aim of finding new cultivars with improved oil aroma. The application of SPME to the analysis of virgin olive oil headspace allowed the detection of significant differences in the proportion of volatile constituents from oils of different maturity index. The results indicate that the ripeness time influence the quali-quantitative production of volatiles. These results permit to use the volatile composition as an indicator of each

*DOI: http://dx.doi.org/10.5772/intechopen.96254*

The authors declare no conflicts of interest.

*Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage DOI: http://dx.doi.org/10.5772/intechopen.96254*

high genetic diversity of the cultivar germplasm collection suggest that it is possible both to identify old olive cultivars that give rise to oils with a high organoleptic quality and to select optimal parents for olive breeding programs with the aim of finding new cultivars with improved oil aroma. The application of SPME to the analysis of virgin olive oil headspace allowed the detection of significant differences in the proportion of volatile constituents from oils of different maturity index. The results indicate that the ripeness time influence the quali-quantitative production of volatiles. These results permit to use the volatile composition as an indicator of each maturity stage.

### **Conflict of interest**

*Terpenes and Terpenoids-Recent Advances*

account when analyzing terpenes [16]. Our results are in agreement with the study of Vichi et al. [15]. These hydrocarbons may be used as markers to distinguish

**Constituents RI 9d Im2 9d Im4 9d Im6** *p*-cymene 028 0,2 1,7 2,6 limonene 032 2,2 3,9 9,4 *(E)*-β-ocimene 052 0,2 0,2 0,2 α-cubebene 352 0,1 cyclosativene 370 0.2 α-ylangene 371 0,1 α-copaene 377 0,2 0,2 0,4 β-selinene 487 0,2 α-muurolene 499 0,2 *(E,E)*-α-farnesene 507 0,1 0,2 0,5 Monoterpene hydrocarbons 2,6 4,3 12,2 Sesquiterpene hydrocarbons 0,3 0,4 1,5 Total terpene hydrocarbons 2,9 4,7 13,7 erythrodiol 0,5 0,8 2,2 uvaol 0,1 0,4 0,9 erythrodiol +uvaol 0,57 1,2 3,14

The volatile fraction of the oil from Sfax (South of Tunisia) was characterized

A comparison with literature data on the chemical composition of olive oils is complicated because of the big variability of the volatile profiles. In fact, it has been reported that the concentrations of compounds depend on the enzymatic activity though external parameters (soil, climate, harvesting and extraction conditions) may alter the inherent olive oil sensory profile. The variation in levels of C6 aldehydes and alcohols for oil samples from different soils implies that pedologic conditions may influence the activity of alcohol dehydrogenase (ADH). The triterpenic dialcohols (erythrodiol and uvaol), which are also part of the unsaponifiable fraction of the olive oil, are usually analysed together with the sterol fraction [1]. The erythrodiol and uvaol content of the studied olive oils varied according to maturity, ranging from 0.5 to 2.22% and from 0.1 to 0.92%, respectively (**Table 1**). The sum of erythrodiol and uvaol in all ripeness index was below the established limit of 4.5% for the "extra virgin" olive oil category. These results

In conclusion, results demonstrated that the studied olive oils presents a elevated level of variability in terms of the volatile fraction. This aroma variability and the

by the pre-eminence of α-copaene (24.5%) that may be used as markers to differentiate EVOO of different sites. The other main compounds detected were (E,E)- α -farnesene (6.8%), α -muurolene (4.8%), cyclosativene (3.0%),

EVOO of different geographical origins [10].

*Terpene composition of the studied olive oil at different stage of maturity.*

aromadendrene (1.8%) and longicyclene (1.7%).

are consistent with the findings of other authors [15].

**30**

**Table 1.**

**4. Conclusions**

The authors declare no conflicts of interest.

### **Author details**

Bechir Baccouri1 \* and Imene Rajhi2

1 Laboratory of Olive Biotechnology, Centre of Biotechnology of Borj-Cédria, Tunisia

2 Laboratory of Legumes Centre of Biotechnology of Borj-Cédria, Tunisia

\*Address all correspondence to: bechirbaccouri@yahoo.fr

© 2021 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/ by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

### **References**

[1] Baccouri B., Ben Temime S., Daoud D., M'sallem M. and Zarrouk M. (2007). Analytical characteristics of virgin olive oils from two new varieties obtained by controlled crossing on Meski variety. Journal of Food Lipids *14,* 19-34

[2] Ben Temime S, Manai H, Methenni K, Baccouri B, Abaza L, Daoud D, (2008), Sterolic composition of Chetoui virgin olive oil: Influence of geographical origin. Food Chem 110:368-374.

[3] R. K. Manoharan, J. Lee, and J. Lee, (2017). "Antibiofilm and antihyphal activities of cedar leaf essential oil, camphor, and fenchone derivatives against Candida albicans," Front. Microbiol. 8, 1476.

[4] Mills, J.J.; Chari, R.S.; Boyer, I.J.; Gould, M.N.; Jirtle, R.L. (1995). Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. Cancer Res., *53*, 955-979.

[5] Baccouri B, Zarrouk W, Khichene D, Nouari I, Ben Youssef N, Daoud D, (2007). Influence of fruit ripening and crop yield on chemical properties of virgin olive oils from seven selected oleasters (*Olea europea* L.). J Agron 6:388-396.

[6] Baccouri, B., Zarrouk, W., Krichene, D., Nouairi, I., Ben youssef, N., Daoud, D., Zarrouk, M., (2007b). Influence of fruit ripening and crop yield on chemical properties of virgin olive oils from seven selected oleasters (Olea Europea L.). J. Agron. 6 (3), 388-396.

[7] Baccouri, B., Guerfel, M., Zarrouk, W., Taamalli, W., Daoud, D., Zarrouk, M., (2011). Wild olive (olea europea L.) selection for quality oil production. J. Food Biochem. 35, 161-176.

[8] Baccouri, B., Ben Temime, S., Campeol, E., Cioni, P.L., Daoud, D., Zarrouk, M., (2007a). Application of solid-phase microextraction to the analysis of volatile compounds in virgin olive oils from five new cultivars. Food Chem. 102, 850-856.

[9] Baccouri, B., Zarrouk, W., Guerfel, M., Baccouri, O., Nouairi, I., Krichene, D., Daoud, D., Zarrouk, M., (2008). Composition, quality and oxidative stability of virgin olive oils from some selected wild olives (Olea europaea L. subsp. Oleaster). Grasas Aceites 59 (4), 346-351.

[10] Ben Temime, S., Baccouri, B., Taamalli, W., Abaza, L., Daoud, D., Zarrouk, M., (2006). Location effects on Chetoui virgin olive oil stability. J. Food Biochem. 30, 659-670.

[11] Beltran G, Aguilera MP, Del Rio C(2005), Sanchez S and Martinez L, Influence of fruit ripening process on the natural antioxidant content of Hojiblanca virgin olive oils. Food Chem 89:207-215.

[12] H. Sebai, S. Selmi, K. Rtibi, A. Souli, N. Gharbi, and M. Sakly, (2013). "Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats," Lipids Health Dis. 12, 189.

[13] M. Božović and R. Ragno, (2017). "Calamintha nepeta (L.) Savi and its main essential oil constituent pulegone: Biological activities and chemistry," Molecules 22, 290.

[14] Urbina A., Martin M., Montero M., Carron R., Sevilla M., and L. Roman, (1990). "Antihistaminic activity of pulegone on the guinea-pig ileum," J. Pharm. Pharmacol. 42, 295-296.

[15] Vichi, S., Castellote, A.I., Pizzale, L., Conte, L.S., Buxaderas, S. & Lopez-Tamames, E. (2003). Analysis of

**33**

*Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage*

*DOI: http://dx.doi.org/10.5772/intechopen.96254*

[16] Heuberger, E.; Ilmberger, J.; Hartter, E.; Buchbauer, G. (2008) Physiological and behavioral effects of 1,8 cineol and (±)-linalool: A comparison of inhalation and massage aromatherapy. Nat. Prod.

virgin olive oil volatile compounds by headspace solid-phase microextraction

coupled to gas chromatography with mass spectrometric and flame ionization detection. Journal of Chromatography A, 983, 19-33.

Commun., , *3*, 1103-1110.

*Terpene Compounds of New Tunisian Extra-Virgin Olive Oil: Effect of Ripening Stage DOI: http://dx.doi.org/10.5772/intechopen.96254*

virgin olive oil volatile compounds by headspace solid-phase microextraction coupled to gas chromatography with mass spectrometric and flame ionization detection. Journal of Chromatography A, 983, 19-33.

[16] Heuberger, E.; Ilmberger, J.; Hartter, E.; Buchbauer, G. (2008) Physiological and behavioral effects of 1,8 cineol and (±)-linalool: A comparison of inhalation and massage aromatherapy. Nat. Prod. Commun., , *3*, 1103-1110.

**32**

*Terpenes and Terpenoids-Recent Advances*

[1] Baccouri B., Ben Temime S.,

[2] Ben Temime S, Manai H, Methenni K, Baccouri B, Abaza L, Daoud D, (2008), Sterolic composition of Chetoui virgin olive oil: Influence of geographical origin. Food Chem

110:368-374.

**References**

Microbiol. 8, 1476.

Cancer Res., *53*, 955-979.

6:388-396.

Daoud D., M'sallem M. and Zarrouk M. (2007). Analytical characteristics of virgin olive oils from two new varieties obtained by controlled crossing on Meski variety. Journal of Food Lipids *14,* 19-34

Zarrouk, M., (2007a). Application of solid-phase microextraction to the analysis of volatile compounds in virgin olive oils from five new cultivars. Food

[9] Baccouri, B., Zarrouk, W., Guerfel, M., Baccouri, O., Nouairi, I., Krichene, D., Daoud, D., Zarrouk, M., (2008). Composition, quality and oxidative stability of virgin olive oils from some selected wild olives (Olea europaea L. subsp. Oleaster). Grasas Aceites 59 (4),

[10] Ben Temime, S., Baccouri, B., Taamalli, W., Abaza, L., Daoud, D., Zarrouk, M., (2006). Location effects on Chetoui virgin olive oil stability. J.

[11] Beltran G, Aguilera MP, Del Rio C(2005), Sanchez S and Martinez L, Influence of fruit ripening process on the natural antioxidant content of Hojiblanca virgin olive oils. Food Chem

[12] H. Sebai, S. Selmi, K. Rtibi, A. Souli, N. Gharbi, and M. Sakly, (2013). "Lavender (Lavandula stoechas L.) essential oils attenuate hyperglycemia and protect against oxidative stress in alloxan-induced diabetic rats," Lipids

[13] M. Božović and R. Ragno, (2017). "Calamintha nepeta (L.) Savi and its main essential oil constituent pulegone: Biological activities and chemistry,"

[14] Urbina A., Martin M., Montero M., Carron R., Sevilla M., and L. Roman, (1990). "Antihistaminic activity of pulegone on the guinea-pig ileum," J. Pharm. Pharmacol. 42, 295-296.

[15] Vichi, S., Castellote, A.I., Pizzale, L., Conte, L.S., Buxaderas, S. & Lopez-Tamames, E. (2003). Analysis of

Food Biochem. 30, 659-670.

Chem. 102, 850-856.

346-351.

89:207-215.

Health Dis. 12, 189.

Molecules 22, 290.

[3] R. K. Manoharan, J. Lee, and J. Lee, (2017). "Antibiofilm and antihyphal activities of cedar leaf essential oil, camphor, and fenchone derivatives against Candida albicans," Front.

[4] Mills, J.J.; Chari, R.S.; Boyer, I.J.; Gould, M.N.; Jirtle, R.L. (1995). Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol.

[5] Baccouri B, Zarrouk W, Khichene D, Nouari I, Ben Youssef N, Daoud D, (2007). Influence of fruit ripening and crop yield on chemical properties of virgin olive oils from seven selected oleasters (*Olea europea* L.). J Agron

[6] Baccouri, B., Zarrouk, W., Krichene, D., Nouairi, I., Ben youssef, N., Daoud, D., Zarrouk, M., (2007b). Influence of fruit ripening and crop yield on chemical properties of virgin olive oils from seven selected oleasters (Olea Europea L.). J. Agron. 6 (3), 388-396.

[7] Baccouri, B., Guerfel, M., Zarrouk, W., Taamalli, W., Daoud, D., Zarrouk, M., (2011). Wild olive (olea europea L.) selection for quality oil production. J.

Food Biochem. 35, 161-176.

[8] Baccouri, B., Ben Temime, S., Campeol, E., Cioni, P.L., Daoud, D.,

**35**

**Chapter 4**

**Abstract**

chromatographic analysis

Japan, Canada and France [5].

**1. Introduction**

Sacha Inchi Seed (*Plukenetia* 

*Adriana Viñas-Ospino, Dayana Barriga-Rodriguez,* 

Sacha inchi oil is a product obtained from oilseed (*Plukenetia volubilis* L.) and is an excellent source of bioactive compounds, especially in polyunsaturated fatty acids, tocopherols, and sterols. These compounds are causally related to their positive impact on human health. In this study summarizes some monoterpenes, sesquiterpenes, and triterpenes reported in Sacha inchi oil seeds and reviews their sensory properties. The terpenoids that characterize Sacha inchi seed oil are: α-pinene, sabinene, limonene, aristolene, cycloartenol, 24-methylene cycloartenol, lanosterol, β-sitosterol, stigmasterol, campesterol and phytol. The sensory properties of this oil are due to a set of volatile compounds including terpenoids, the odor descriptors of monoterpenes, sesquiterpenes and diterpenes are: flower, pine, turpentine, pepper, wood, lemon, orange, and sweet. These compounds were

*Ana María Muñoz and Fernando Ramos-Escudero*

*volubilis* L.) Oil: Terpenoids

*Alexandra Valencia, Frank L. Romero-Orejon,* 

characterized by gas chromatography with different detectors.

**Keywords:** sacha inchi seed oil, terpenoids, sensory properties,

The Sacha inchi (*Plukenetia volubilis* L.) plant is a crop that has expanded rapidly in recent decades. This endemic crop of the South American Amazon is found mainly in Peru, Colombia, Ecuador, and Brazil. Other geographical regions of the world where Sacha inchi cultivation has flourished include China, Thailand, Vietnam, and Malaysia [1–4]. Its oleaginous plant has become a crop of economic importance for the food, pharmaceutical and cosmetic industries. Exports in Peru have grown notably for the year 2017, especially for its main products such as oil, roasted seed, and powder, having as main destinations, South Korea, United States,

Kodahl [6] mentioned that Sacha inchi seed has an unusual chemical composition as it contains remarkably high amounts of polyunsaturated fatty acids. According to the NTP [7] indicates that the requirements for the polyunsaturated fatty acids (PUFAs) profile is as follows: α-linolenic acid (ω-3, greater than 42%), linoleic acid (ω-6, greater than 32%) and polyunsaturated fatty acids (greater than 80%) of the total lipid fraction. Other main representatives of the unsaponifiable fraction are tocopherols, which are distributed in the oil as follows: α-tocopherol

#### **Chapter 4**

## Sacha Inchi Seed (*Plukenetia volubilis* L.) Oil: Terpenoids

*Alexandra Valencia, Frank L. Romero-Orejon, Adriana Viñas-Ospino, Dayana Barriga-Rodriguez, Ana María Muñoz and Fernando Ramos-Escudero*

#### **Abstract**

Sacha inchi oil is a product obtained from oilseed (*Plukenetia volubilis* L.) and is an excellent source of bioactive compounds, especially in polyunsaturated fatty acids, tocopherols, and sterols. These compounds are causally related to their positive impact on human health. In this study summarizes some monoterpenes, sesquiterpenes, and triterpenes reported in Sacha inchi oil seeds and reviews their sensory properties. The terpenoids that characterize Sacha inchi seed oil are: α-pinene, sabinene, limonene, aristolene, cycloartenol, 24-methylene cycloartenol, lanosterol, β-sitosterol, stigmasterol, campesterol and phytol. The sensory properties of this oil are due to a set of volatile compounds including terpenoids, the odor descriptors of monoterpenes, sesquiterpenes and diterpenes are: flower, pine, turpentine, pepper, wood, lemon, orange, and sweet. These compounds were characterized by gas chromatography with different detectors.

**Keywords:** sacha inchi seed oil, terpenoids, sensory properties, chromatographic analysis

#### **1. Introduction**

The Sacha inchi (*Plukenetia volubilis* L.) plant is a crop that has expanded rapidly in recent decades. This endemic crop of the South American Amazon is found mainly in Peru, Colombia, Ecuador, and Brazil. Other geographical regions of the world where Sacha inchi cultivation has flourished include China, Thailand, Vietnam, and Malaysia [1–4]. Its oleaginous plant has become a crop of economic importance for the food, pharmaceutical and cosmetic industries. Exports in Peru have grown notably for the year 2017, especially for its main products such as oil, roasted seed, and powder, having as main destinations, South Korea, United States, Japan, Canada and France [5].

Kodahl [6] mentioned that Sacha inchi seed has an unusual chemical composition as it contains remarkably high amounts of polyunsaturated fatty acids. According to the NTP [7] indicates that the requirements for the polyunsaturated fatty acids (PUFAs) profile is as follows: α-linolenic acid (ω-3, greater than 42%), linoleic acid (ω-6, greater than 32%) and polyunsaturated fatty acids (greater than 80%) of the total lipid fraction. Other main representatives of the unsaponifiable fraction are tocopherols, which are distributed in the oil as follows: α-tocopherol

(60–70 mg/kg), β-tocopherol (18–29 mg/kg), γ-tocopherol (1108–1367 mg/kg), δ-tocopherol (641–856 mg/kg), and sterols fraction of commercial oils was 1130–3635 mg/kg, and the main sterols were β-sitosterol, stigmasterol, campesterol and ∆5-avenasterol [8, 9]. Other compounds of interest are phenolic compounds (the main classes of phenols found in sacha inchi seed oil (SISO) are phenyl alcohol, isocoumarin, flavonoid, secoiridoid, and lignan) [10], volatile organic compounds (while the classes of VOCs identified in commercial oil were aldehydes, hydrocarbons, alcohols, ketone, furan, and carboxylic acid), and terpenoids [11].

Terpenoids are a large family of chemical compounds which can be found in a large number of plants, many of which have characteristic odors, flavors, and colors, and are main components of essential oils (especially monoterpenes and sesquiterpenes) [12]. Terpenoids can be structurally decomposed into two or more isoprene units or 2-methyl-1,3-butadiene and classified as monoterpenes (C10H16), sesquiterpenes (C15H24), diterpenes (C20H32), triterpenes (C30H48), and tetraterpenes or carotenes (C40H64) [13]. In vegetable oils, several terpenoids have been identified, these compounds provide aromatic properties (monoterpenoids: myrcene, citral, linalool, thymol, menthol, carvone, eucalyptol, α- and β-pinene, etc.), and are natural fat-soluble pigments (tetraterpenoids: lycopene, γ-carotene, β-carotene, lutein, zeaxanthin, etc.) [14], this last group of chemical species are responsible for transmitting the chromatic characteristics in vegetable oils. A list of oils from conventional and non-conventional plant sources where terpenoids have


**37**

*Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids*

some of heightened interest are mentioned in this section.

been identified: soybean, olive, rapeseed, sunflowerseed, flaxseed, sesame, pumpkin, pistachio, almond, hazelnut, safflower, hempseed, sacha inchi oils [15–20]. Traditionally, plant-based terpenoids have been used by humans in the food (terpenoids as natural flavorings compounds, preservatives for dairy products, stability of edibles oils flavored with essential oils) [21–23], pharmaceutical (production of pharmaceutical terpenoids for the treatment of human diseases) [24, 25], and chemical industries (natural additives for food or fragrances in perfumery) [26]. Various studies have shown the efficacy of terpenoids due to their biological and medical properties [25, 27, 28]. **Table 1** summarizes most of the effects, however

This document summarizes some monoterpenes, sesquiterpenes, and triterpenes reported in Sacha inchi oil seeds and reviews their sensory properties.

The biosynthesis of these compounds occurs via the methylerythritol phosphate pathway (MEP) or mevalonate (MVA) pathway involves several reactions to isopentenyl diphosphate production from acetyl CoA. The isopentenyl diphosphate (IPP) combines with dimethyl-allyl diphosphate (DMAPP) to that subsequently converted to geranyl pyrophosphate (GPP) by enzymatic catalysis of isopentenyl diphosphate isomerase. Geranyl pyrophosphate is the substrate to produce monoterpenoids. The enzymatic reaction is mediated by monoterpene synthases [48]. The monoterpenes found in SISO were α-pinene, sabinene and limonene (**Figure 1**). α-Pinene (C10H16) is the main bicyclic monoterpene found in this oil, it is also widely distributed in nature. The sesquiterpenes are formed by the condensation of IPP with GPP to yield farnesyl pyrophosphate (FPP) [50]. The GPP to FPP reaction is mediated by farnesyl pyrophosphate synthase. The only sesquiterpene found in SISO is the aristolene (C15H24) [20]. On the other hand, this biochemical pathway may be used for triterpene (some triterpenes were found in SISO, namely cycloartenol, 24-methylene cycloartenol and lanosterol isomers) and probably sterols (individual sterols found in SISO, namely β-sitosterol, stigmasterol, campesterol, Δ5-avenasterol, Δ5,24- stigmastadienol, Δ7-stigmastenol, Δ7-avenasterol, etc.) [8, 9, 51], and brassinosteroids biosynthesis, whereas geranylgeranyl pyrophosphate (GGPP) is utilized for the biosynthesis of photosynthetic pigments such as carotenoids, chlorophylls and

In the scientific literature there are few reports on the volatile composition of sacha inchi oil [20, 49]. The terpenoid fractions in the Sacha inchi oil is observed in **Table 2**. The identification of the classes of terpenoids found in Sacha inchi seed oil and commercial Sacha inchi oil were monoterpenes, sesquiterpenes, diterpenes, triterpenes and sterols. The first terpenoids identified in this oil were sterols: β-sitosterol > stigmasterol > campesterol > Δ5-avenasterol [51]. The sterol composition of these main compounds is around ~96%. The sterol content in the Sacha inchi seed oil was reported as 2472 mg/kg. While the sterol contents in commercial oils

The sterol content in Sacha inchi seed oil is represented by the content of β-sitosterol, stigmasterol and campesterol (**Table 2**). The β-sitosterol, followed by stigmasterol or campesterol and other minor sterols (triterpenes) such as

**2. Overview of terpenoids biosynthesis in Sacha inchi seed oil**

*DOI: http://dx.doi.org/10.5772/intechopen.96690*

diterpenes (phytol) (**Figure 1**) [9, 52, 53].

**3. Terpenoids in Sacha inchi seed oil**

ranging from 1130 to 3635 mg/kg [8, 9].

#### **Table 1.**

*Summary of terpenoids of Sacha inchi seed oil and biological effects.*

#### *Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.96690*

*Terpenes and Terpenoids-Recent Advances*

(60–70 mg/kg), β-tocopherol (18–29 mg/kg), γ-tocopherol (1108–1367 mg/kg), δ-tocopherol (641–856 mg/kg), and sterols fraction of commercial oils was

alcohols, ketone, furan, and carboxylic acid), and terpenoids [11].

1130–3635 mg/kg, and the main sterols were β-sitosterol, stigmasterol, campesterol and ∆5-avenasterol [8, 9]. Other compounds of interest are phenolic compounds (the main classes of phenols found in sacha inchi seed oil (SISO) are phenyl alcohol, isocoumarin, flavonoid, secoiridoid, and lignan) [10], volatile organic compounds (while the classes of VOCs identified in commercial oil were aldehydes, hydrocarbons,

Terpenoids are a large family of chemical compounds which can be found in a large number of plants, many of which have characteristic odors, flavors, and colors, and are main components of essential oils (especially monoterpenes and sesquiterpenes) [12]. Terpenoids can be structurally decomposed into two or more isoprene units or 2-methyl-1,3-butadiene and classified as monoterpenes (C10H16), sesquiterpenes (C15H24), diterpenes (C20H32), triterpenes (C30H48), and tetraterpenes or carotenes (C40H64) [13]. In vegetable oils, several terpenoids have been identified, these compounds provide aromatic properties (monoterpenoids: myrcene, citral, linalool, thymol, menthol, carvone, eucalyptol, α- and β-pinene, etc.), and are natural fat-soluble pigments (tetraterpenoids: lycopene, γ-carotene, β-carotene, lutein, zeaxanthin, etc.) [14], this last group of chemical species are responsible for transmitting the chromatic characteristics in vegetable oils. A list of oils from conventional and non-conventional plant sources where terpenoids have

**Terpenoids Class Effects Reference**

neuroprotective

Limonene Monoterpene Gastroprotective, anti-inflammatory, bradycardic,

β-Sitosterol Sterol Anticancer, lipid-lowering, anti-inflammatory,

Phytol Diterpene Antitumoral, antimutagenic, antimicrobial,

Stigmasterol Sterol Lipid-lowering, antiasthmatic,

*Summary of terpenoids of Sacha inchi seed oil and biological effects.*

antibacterial

Sabinene Monoterpene Antioxidant, antibacterial and antifungal [29, 30]

Aristolene Sesquiterpene Antifungal, antioxidant, and anticancer [34, 35] Cycloartenol Triterpene Anticancer, and antidiabetic [36, 37]

Lanosterol Triterpene Cytotoxic and immunomodulatory [38, 39]

and antioxidant

anti-inflammatory

Campesterol Sterol Anti-inflammatory, and cytotoxic [45]

cytoprotective, anticonvulsant, and

antiarrhythmic, antitumor, antiviral, and

Triterpene Antidiabetic [37]

immunomodulatory, antioxidant, and

anxiolytic, metabolism-modulating, cytotoxic, antioxidant, autophagy- and apoptosis-inducing, antinociceptive, anti-inflammatory, immunemodulating, antidiabetic, anti-atherogenic, lipid-lowering, antispasmodic, antiepileptic, antidepressant and immunoadjuvant

[27]

[31–33]

[40–43]

[41, 44]

[46, 47]

α-Pinene Monoterpene Cytogenetic, gastroprotective, anxiolytic,

**36**

**Table 1.**

24-Methylene cycloartenol

been identified: soybean, olive, rapeseed, sunflowerseed, flaxseed, sesame, pumpkin, pistachio, almond, hazelnut, safflower, hempseed, sacha inchi oils [15–20].

Traditionally, plant-based terpenoids have been used by humans in the food (terpenoids as natural flavorings compounds, preservatives for dairy products, stability of edibles oils flavored with essential oils) [21–23], pharmaceutical (production of pharmaceutical terpenoids for the treatment of human diseases) [24, 25], and chemical industries (natural additives for food or fragrances in perfumery) [26]. Various studies have shown the efficacy of terpenoids due to their biological and medical properties [25, 27, 28]. **Table 1** summarizes most of the effects, however some of heightened interest are mentioned in this section.

This document summarizes some monoterpenes, sesquiterpenes, and triterpenes reported in Sacha inchi oil seeds and reviews their sensory properties.

#### **2. Overview of terpenoids biosynthesis in Sacha inchi seed oil**

The biosynthesis of these compounds occurs via the methylerythritol phosphate pathway (MEP) or mevalonate (MVA) pathway involves several reactions to isopentenyl diphosphate production from acetyl CoA. The isopentenyl diphosphate (IPP) combines with dimethyl-allyl diphosphate (DMAPP) to that subsequently converted to geranyl pyrophosphate (GPP) by enzymatic catalysis of isopentenyl diphosphate isomerase. Geranyl pyrophosphate is the substrate to produce monoterpenoids. The enzymatic reaction is mediated by monoterpene synthases [48]. The monoterpenes found in SISO were α-pinene, sabinene and limonene (**Figure 1**). α-Pinene (C10H16) is the main bicyclic monoterpene found in this oil, it is also widely distributed in nature. The sesquiterpenes are formed by the condensation of IPP with GPP to yield farnesyl pyrophosphate (FPP) [50]. The GPP to FPP reaction is mediated by farnesyl pyrophosphate synthase. The only sesquiterpene found in SISO is the aristolene (C15H24) [20]. On the other hand, this biochemical pathway may be used for triterpene (some triterpenes were found in SISO, namely cycloartenol, 24-methylene cycloartenol and lanosterol isomers) and probably sterols (individual sterols found in SISO, namely β-sitosterol, stigmasterol, campesterol, Δ5-avenasterol, Δ5,24- stigmastadienol, Δ7-stigmastenol, Δ7-avenasterol, etc.) [8, 9, 51], and brassinosteroids biosynthesis, whereas geranylgeranyl pyrophosphate (GGPP) is utilized for the biosynthesis of photosynthetic pigments such as carotenoids, chlorophylls and diterpenes (phytol) (**Figure 1**) [9, 52, 53].

#### **3. Terpenoids in Sacha inchi seed oil**

In the scientific literature there are few reports on the volatile composition of sacha inchi oil [20, 49]. The terpenoid fractions in the Sacha inchi oil is observed in **Table 2**. The identification of the classes of terpenoids found in Sacha inchi seed oil and commercial Sacha inchi oil were monoterpenes, sesquiterpenes, diterpenes, triterpenes and sterols. The first terpenoids identified in this oil were sterols: β-sitosterol > stigmasterol > campesterol > Δ5-avenasterol [51]. The sterol composition of these main compounds is around ~96%. The sterol content in the Sacha inchi seed oil was reported as 2472 mg/kg. While the sterol contents in commercial oils ranging from 1130 to 3635 mg/kg [8, 9].

The sterol content in Sacha inchi seed oil is represented by the content of β-sitosterol, stigmasterol and campesterol (**Table 2**). The β-sitosterol, followed by stigmasterol or campesterol and other minor sterols (triterpenes) such as

#### **Figure 1.**

*Biosynthetic pathway of terpenoids and chemical compounds found in Sacha inchi seed oil. The diagram was modified according to Feng et al. [49]. Isopentenyl diphosphate (IPP), dimethyl-allyl diphosphate (DMAPP), geranyl pyrophosphate synthase (GPPS), farnesyl pyrophosphate synthase (FPPS), geranylgeranyl pyrophosphate synthase (GGPPS).*

fucosterol, and Δ5-avenasterol are the most representative in vegetable oils. In addition, 50% to 80% of the plant sterols intake comes from oils, spreads, butters, breads, cereals, grains, pastes, and vegetables [55]. On the other hand, other triterpenoids such as cycloartenol, 24-Methylene cycloartenol, and lanosterol were detected in commercial Sacha inchi oil, the contents ranged from 0.10 to 47.44%, 2.59 to 24.15%, 0.80 to 11.79%, respectively. A sole example of diterpene such as phytol were found in the range of 0.10 to 43.51% [9]. The monoterpenoids and sesquiterpene in the sacha inchi oil were α-pinene, sabinene, limonene and aristolene these compounds were also identified by Monroy-Soto et al. [11]. In addition, it has been reported that this class of terpenoids are considered potentiators. In this context, the minimum inhibitory concentration of some monoterpenoids

**39**

*Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids*

(α-pinene and limonene) on bacteria such as *Escherichia coli*, *Salmonella enterica* and *Staphylococcus aureus* have been reported previously [56]. Furthermore, these monoterpenoids have shown a potent antioxidant activity, especially α-pinene followed by limonene, both presented a 50% inhibitory concentration values (IC50) equal to 12.57 and 13.35 mg/mL, respectively. In this regard, terpenoids have huge

**Terpenoids Sacha inchi seed oil Commercial Sacha inchi oil** α-Pinene (μg/kg) (3.35–1179.24) μg/kg Sabinene (μg/kg) (0.87–416.51) μg/kg Limonene (μg/kg) (0.93–187.83) μg/kg Aristolene (μg/kg) (3.99–34.82) μg/kg Cycloartenol (%) (2.59–34.54) % 24-Methylene cycloartenol (%) (0.80–11.79) % Lanosterol (%) (0.10–47.44) % β-Sitosterol (%) 127.4 mg/100 g (21.45–68.91) % Stigmasterol (%) 58.7 mg/100 g (10.4–27.4) % Campesterol (%) 15.3 mg/100 g (5.1–18.9) % Δ5-Avenasterol (%) (0.10–7.78) % Phytol (%) (0.10–43.51) % *References, for Sacha inchi seed oil: Chirinos et al. [54]. For commercial Sacha inchi oil: Chasquibol et al. [8];* 

The storage food products are subject to changes in the chemical composition and as a result the formation of undesirable volatile compounds. Therefore, terpenoids as natural preservatives can be used to slow down food spoilage. Some monoterpenoids such as limonene can be used as substitutes for synthetic antioxidants (TBHQ, BHA, BHT) and improves oxidative stability in edible oils [58]. Wang et al. [58] have mentioned that monoterpenoids can be used as a reference for the

Terpenoids are compounds responsible for the smell of most plants. Phytol, α-pinene, sabinene, limonene, and aristolene have been found in Sacha inchi oil (**Table 3**). These compounds provide some odor notes such as flower, pine, turpentine, pepper, wood, lemon, orange, and sweet. The content of monoterpenoids and sesquiterpenoids in Sacha inchi oil, fraction constituted about 9.0% of total volatile fraction. Ramos-Escudero et al. [20] have mentioned that these compounds are responsible for the floral aroma in this oil. However, the sensory characteristics of Sacha inchi oil not only correspond to the sensory notes of the terpenoids, but to a combination of sensory attributes such as herbal, green, nutty, seeds, butter, rancid, fruity, floral, and woody [20, 59]. Different volatile compounds including terpenoids have been identified in vegetable oils and each compound has different characteristics of key odorants. For example, in virgin sunflower oil the most preferred attributes were sweet and wood/vegetable resin, the latter possibly due

potential as natural food preservatives for use in the food industry [57].

**4. Terpenoids and sensory properties in Sacha inchi seed oil**

food manufacturing, lifestyle, and nutrition in the future.

*DOI: http://dx.doi.org/10.5772/intechopen.96690*

*Ramos-Escudero et al. [9].*

*Summary of terpenoids identified in Sacha inchi oil.*

**Table 2.**

*Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.96690*


*References, for Sacha inchi seed oil: Chirinos et al. [54]. For commercial Sacha inchi oil: Chasquibol et al. [8]; Ramos-Escudero et al. [9].*

#### **Table 2.**

*Terpenes and Terpenoids-Recent Advances*

**38**

**Figure 1.**

*pyrophosphate synthase (GGPPS).*

fucosterol, and Δ5-avenasterol are the most representative in vegetable oils. In addition, 50% to 80% of the plant sterols intake comes from oils, spreads, butters, breads, cereals, grains, pastes, and vegetables [55]. On the other hand, other triterpenoids such as cycloartenol, 24-Methylene cycloartenol, and lanosterol were detected in commercial Sacha inchi oil, the contents ranged from 0.10 to 47.44%, 2.59 to 24.15%, 0.80 to 11.79%, respectively. A sole example of diterpene such as phytol were found in the range of 0.10 to 43.51% [9]. The monoterpenoids and sesquiterpene in the sacha inchi oil were α-pinene, sabinene, limonene and aristolene these compounds were also identified by Monroy-Soto et al. [11]. In addition, it has been reported that this class of terpenoids are considered potentiators. In this context, the minimum inhibitory concentration of some monoterpenoids

*Biosynthetic pathway of terpenoids and chemical compounds found in Sacha inchi seed oil. The diagram was modified according to Feng et al. [49]. Isopentenyl diphosphate (IPP), dimethyl-allyl diphosphate (DMAPP), geranyl pyrophosphate synthase (GPPS), farnesyl pyrophosphate synthase (FPPS), geranylgeranyl*  *Summary of terpenoids identified in Sacha inchi oil.*

(α-pinene and limonene) on bacteria such as *Escherichia coli*, *Salmonella enterica* and *Staphylococcus aureus* have been reported previously [56]. Furthermore, these monoterpenoids have shown a potent antioxidant activity, especially α-pinene followed by limonene, both presented a 50% inhibitory concentration values (IC50) equal to 12.57 and 13.35 mg/mL, respectively. In this regard, terpenoids have huge potential as natural food preservatives for use in the food industry [57].

The storage food products are subject to changes in the chemical composition and as a result the formation of undesirable volatile compounds. Therefore, terpenoids as natural preservatives can be used to slow down food spoilage. Some monoterpenoids such as limonene can be used as substitutes for synthetic antioxidants (TBHQ, BHA, BHT) and improves oxidative stability in edible oils [58]. Wang et al. [58] have mentioned that monoterpenoids can be used as a reference for the food manufacturing, lifestyle, and nutrition in the future.

#### **4. Terpenoids and sensory properties in Sacha inchi seed oil**

Terpenoids are compounds responsible for the smell of most plants. Phytol, α-pinene, sabinene, limonene, and aristolene have been found in Sacha inchi oil (**Table 3**). These compounds provide some odor notes such as flower, pine, turpentine, pepper, wood, lemon, orange, and sweet. The content of monoterpenoids and sesquiterpenoids in Sacha inchi oil, fraction constituted about 9.0% of total volatile fraction. Ramos-Escudero et al. [20] have mentioned that these compounds are responsible for the floral aroma in this oil. However, the sensory characteristics of Sacha inchi oil not only correspond to the sensory notes of the terpenoids, but to a combination of sensory attributes such as herbal, green, nutty, seeds, butter, rancid, fruity, floral, and woody [20, 59]. Different volatile compounds including terpenoids have been identified in vegetable oils and each compound has different characteristics of key odorants. For example, in virgin sunflower oil the most preferred attributes were sweet and wood/vegetable resin, the latter possibly due

#### **Table 3.**

*Terpenoids, structures, and percepts of in Sacha inchi seed oil.*

to the presence of terpenes such as linalool and α- and β-pinene. Furthermore, the sensory profile of Niger seed oil showed positive attributes such as dried fruit, spicy and bitter, which could be related to the presence of some terpenes, specifically limonene and phellandrene. On the other hand, the sensory notes of pine perceived in the pine nut (*Pinus pinea*) oil were described under the wood/plant resin attribute, which could be attributable to the high contents of α-pinene as well as other terpenes such as β-pinene, β-myrcene and α- and γ-terpinene present in its volatile composition [15].

#### **5. Comparison of terpenoid contents in other vegetable oils**

Information about the volatile composition, including some terpenoids in vegetable oils can be found in published reports. Aguilar-Hernández et al. [60] reported the profile of terpenoids including monoterpenes and sesquiterpenes in lemon peel oil. In this oil around 23 terpenoids have been found, the most relevant being limonene, γ-terpinene, sabinene, α-pinene, β-pinene, α-thujene, terpinolene, α-terpineol, neral, geranial, and trans- α- bergamotene. Ivanova-Petropulos et al. [17] reported a higher content of terpenoids in sunflower seed oil and pumpkin seed oil. The most common monoterpenoids and sesquiterpenoids in both oils were: α-thujene, α-pinene, α-fenchene, camphene, verbenene, sabinene, 2-β-pinene, α-phellandrene, α-terpinene, DL-limonene, β-phellandrene, 1,8-cineole, *o*-cymene, *p*-cymene, γ-terpinene, α-terpinolene, α-campholenal,

**41**

**Compounds**

> 1

2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21

α-campholenal

X

α-terpinolene

X

γ-terpinene

X

X

p-cymene

X

X

X

X

X

X

X

o-cymene

1,8-cineole

X

X

β-phellandrene

X

X

X

X

X

X

X

X

X

X

X

X

X

limonene

β-ocimene

α-terpinene

X

X

X

X

X

X

X

X

4-carene

3-carene

X

α-phellandrene

X

X

X

2-β-pinene

X

X

sabinene

verbenene

X

X

camphene

X

X

α-fenchene

X

β-pinene

α-pinene

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

α-thujene

X

**Flaxseed oil**

**Rapeseed oil**

**Sesame seed oil**

**Sunflower seed oil**

**Pumpkin oil**

**Sacha inchi oil**

**Pistachio oils**

X

**Almond oil**

**Hazelnut oil**

X

X

X

X

X

X

*Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids*

*DOI: http://dx.doi.org/10.5772/intechopen.96690*


#### *Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.96690*

*Terpenes and Terpenoids-Recent Advances*

296.54 g/mol

136.23 g/mol

136.23 g/mol

136.23 g/mol

204.35 g/mol

*Terpenoids, structures, and percepts of in Sacha inchi seed oil.*

Phytol C20H40O

α-Pinene C10H16

Sabinene C10H16

Limonene C10H16

Aristolene C15H24

to the presence of terpenes such as linalool and α- and β-pinene. Furthermore, the sensory profile of Niger seed oil showed positive attributes such as dried fruit, spicy and bitter, which could be related to the presence of some terpenes, specifically limonene and phellandrene. On the other hand, the sensory notes of pine perceived in the pine nut (*Pinus pinea*) oil were described under the wood/plant resin attribute, which could be attributable to the high contents of α-pinene as well as other terpenes such as β-pinene, β-myrcene and α- and γ-terpinene present in its volatile

**Terpenoids MF/MW Structure Percepts**

flower

pine, turpentine

pepper, turpentine,

lemon, orange

flower, sweet

wood

Information about the volatile composition, including some terpenoids in vegetable oils can be found in published reports. Aguilar-Hernández et al. [60] reported the profile of terpenoids including monoterpenes and sesquiterpenes in lemon peel oil. In this oil around 23 terpenoids have been found, the most relevant being limonene, γ-terpinene, sabinene, α-pinene, β-pinene, α-thujene, terpinolene, α-terpineol, neral, geranial, and trans- α- bergamotene. Ivanova-Petropulos et al. [17] reported a higher content of terpenoids in sunflower seed oil and pumpkin seed oil. The most common monoterpenoids and sesquiterpenoids in both oils were: α-thujene, α-pinene, α-fenchene, camphene, verbenene, sabinene, 2-β-pinene, α-phellandrene, α-terpinene, DL-limonene, β-phellandrene, 1,8-cineole, *o*-cymene, *p*-cymene, γ-terpinene, α-terpinolene, α-campholenal,

**5. Comparison of terpenoid contents in other vegetable oils**

**40**

composition [15].

**Table 3.**


**43**

**Compounds**

> 42

43 44 45 **Table 4.**

*Chemical characterization of terpenoids detected in vegetable oils.*


longifolene

δ-cadinene

β-bisabolene

**Flaxseed oil**

**Rapeseed oil**

**Sesame seed oil**

**Sunflower seed oil**

**Pumpkin oil**

**Sacha inchi oil**

**Pistachio oils**

**Almond oil**

**Hazelnut oil**

X

X

X

X

X

X

X

X

X

X

*Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids*

*DOI: http://dx.doi.org/10.5772/intechopen.96690*

#### *Terpenes and Terpenoids-Recent Advances*

#### *Sacha Inchi Seed (*Plukenetia volubilis *L.) Oil: Terpenoids DOI: http://dx.doi.org/10.5772/intechopen.96690*

*Terpenes and Terpenoids-Recent Advances*

**42**

**Compounds**

> 22

23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41

α-amorphene

calarene

γ-cadinene

aristolen

2-norpinene

X

X

X

X

X

X

X

X

X

X

X

X

β-myrcene

β-selinene

β-bourbonene

β-elemene

α-copaene

camphor

X

α-cubebene

verbenone

myrtenal

2-pinen-10-ol

3-pinanone

4-terpineol

borneol

α-phellandren-8-ol

trans-pinocarveol

**Flaxseed** 

**Rapeseed** 

**Sesame seed** 

**Sunflower seed** 

**Pumpkin** 

**Sacha inchi** 

**Pistachio** 

**Almond** 

**Hazelnut oil**

**oils**

**oil**

**oil**

**oil**

**oil**

**oil**

**oil**

**oil**

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

X

