**4. Chemical composition of essential oils of the genus** *Pimenta*

Essential oils, also called essences, volatile oils, or etheric oils [13, 61], are from a chemical point of view complex mixtures of volatile substances that comprise between 20 and 100 or more components at various concentrations; in general, there are two or three major compounds, which are in concentrations between 20 and 70% in comparison with the other components of the oil that may be present in lower amounts or even in traces [14]. They are described frequently only as a product of "vegetable raw materials" [61, 62]; this oils are lipophilic, usually odoriferous, yellow pale, or colorless when recently extracted and liquid at room temperature [61]; they are oxidized by exposure to air, light, and heat [13] and produced by the plants as defense mechanism, signaling, or as part of their secondary metabolism [61, 63, 64]; they can be biosynthesized in different parts of the plant anatomy (in the leaves, in the flowers, in the fruits, in the pericarp of the fruit, in the seeds, in the bark, and in the rhizomes, whether stored in glands of oils, glandular hairs, or dissolved in resins) [13, 14], and almost always, they are endowed with aromas pleasant as the case of species from genus *Pimenta* with aromas at lemon, anise, or clove [60].


(Gomes) Landrum LR, which is endemic from Brazil [39, 40, 44, 45]. In Venezuela, it is only represented by *P. racemosa* (Mill.) JW Moore (*P. acris* Kostel) and is distributed in Falcón,

The species of this genus are used in several countries including Barbados, Brazil, China, Cuba, Dominican Republic, England, Haití, India, Kerala, Mangalore, Mexico, Middle East, Taiwan, USA, and Venezuela [45–56], in various areas, whether to build agricultural tools, houses, or living fences because of the resistance of its wood against termites, industrially for the production of condiments, flavors, perfumes, and cosmetics, or in the treatment of various pathologies of traditional medicine such as fever, rheumatism, toothache, abdominal pain, pneumonia, colds, pectoral angina, diarrhea, incontinence, stroke, anti-inflammatory, and analgesic properties [10, 12, 15, 57–59]. Among pharmacological effects reported for different *Pimenta* species include anticancer, antidermatophytic, antihemorrhagic bleeding, anti-inflammatory, antimicrobial, antimutagenic, antinociceptive, antioxidant, antipyretic, central nervous system depressant, cobra venom, hypoglycemic, hypotensive, inhibitor of histone acetyl transferase

Federal District, Lara, Mérida, Nueva Esparta, Táchira, Sucre, and Zulia states [35].

24 Potential of Essential Oils

enzyme, inhibitor of enzyme histidine carboxylase, and insect repellent [10, 12, 15, 59].

and clove odor due to the presence of chavicol/eugenol (73%) [60].

with aromas at lemon, anise, or clove [60].

Chemistry studies of *Pimenta* species have led to the identification of a variety of secondary metabolites of the type: tannins, phenolic compounds, flavonoids, and a structural variety of volatile substances such as monoterpenes, sesquiterpenes, and phenylpropenes (present in essential oils), which could generate a content of volatile essences from fresh leaves between 1 and 5% [12, 13]. Essential oils of *P. racemosa* can present characteristic, aromatic, and pleasant odors, due to their major components; for example, a lemon smell due to the neral/geranial content (72%), an aniseed odor due to the presence of methylchavicol/methyleugenol (81%),

Furthermore, the best-known species of this genus, due to its economic and pharmacological

Essential oils, also called essences, volatile oils, or etheric oils [13, 61], are from a chemical point of view complex mixtures of volatile substances that comprise between 20 and 100 or more components at various concentrations; in general, there are two or three major compounds, which are in concentrations between 20 and 70% in comparison with the other components of the oil that may be present in lower amounts or even in traces [14]. They are described frequently only as a product of "vegetable raw materials" [61, 62]; this oils are lipophilic, usually odoriferous, yellow pale, or colorless when recently extracted and liquid at room temperature [61]; they are oxidized by exposure to air, light, and heat [13] and produced by the plants as defense mechanism, signaling, or as part of their secondary metabolism [61, 63, 64]; they can be biosynthesized in different parts of the plant anatomy (in the leaves, in the flowers, in the fruits, in the pericarp of the fruit, in the seeds, in the bark, and in the rhizomes, whether stored in glands of oils, glandular hairs, or dissolved in resins) [13, 14], and almost always, they are endowed with aromas pleasant as the case of species from genus *Pimenta*

importance, are *P. dioica* (L.) Merrill and *P. racemosa* (Mill.) J. W. Moore [40, 41].

**4. Chemical composition of essential oils of the genus** *Pimenta*


*P. pseudocaryophyllus* var. *pseudocaryophyllus* (Brazil)

*P. pseudocaryophyllus*

*P. pseudocaryophyllus*

(Brazil)

(Brazil)

*P. obscura* (Jamaica) Leaves Steam distillation 1,8-cineole (16.84–25.11),

Leaves Hydrodistillation Geranial (34.26),

Leaves Hydrodistillation Chavibetol (70.9), methyl-

*P. pseudocaryophyllus* (Brazil) Leaves (Cardoso isle) Hydrodistillation Eugenol (71.9) [91]

*P. pseudocaryophyllus* (Brazil) Leaves Hydrodistillation Eugenol (92.59) [92]

*P. pseudocaryophyllus* (Brazil) Leaves (Brazilian) Hydrodistillation (*E*)-methyl-isoeugenol

*P. pseudocaryophyllus* (Brazil) Leaves Hydrodistillation Chavibetol (50.2–70.9),

*P. pseudocaryophyllus* (Brazil) Leaves Hydrodistillation Geranial (37.3–46.6), neral

*P. pseudocaryophyllus* (Brazil) Leaves Hydrodistillation (*E*)-methyl-

*P. pseudocaryophyllus* (Brazil) Leaves (citral) Hydrodistillation Geranial (36.49), neral

Leaves (Paranapiacaba)

do Abaeté)

*P. pseudocaryophyllus* (Brazil) Leaves (São Gonçalo

**(area %)**

Chemical Composition of Essential Oil of Genus *Pimenta* (Myrtaceae): Review

(7.64)

Hydrodistillation Methyl-eugenol (94.6) [91]

(2.8)

Hydrodistillation Geranial (36.5–47.2),

ρ-cymene (10.97–11.33), α-terpineol (6.71–8.13), limonene (5.31), β-eudesmol (5.29), 4-terpineol (4.92–9.80), α-phellandrene (6.33), Ledol (13.47), palustrol

http://dx.doi.org/10.5772/intechopen.78004

neral (27.85), linalol (5.18), geraniol (4.82), β-caryophyllene (4.40)

eugenol (20.7), o-cymene

(78.0–93.6), methyleugenol (3.1–18.1)

neral (21.4–33.6), β-caryophyllene (0–6.1), caryophyllene oxide

methyl-eugenol (15.4–20.7)

(25.8–28.7), spathulenol (0–6.1), caryophyllene oxide (0–5.5),

β-caryophyllene (0–8.0), Bicyclogermacrene (0–5.7)

isoeugenol (5.0–94.3), (β-caryophyllene (8.5–26.6), elemicin (5.8–11.7), δ-cadinene (0–9.2), α-copaene (0–5.7), (*E*)-asarone (0–65.5)

caryophyllene oxide

(27.59),

(8.88)

(0–13.5)

**Reference**

27

[89]

[90]

[93]

[11]

[11]

[94]

[95]

[95]

[96]


*P. dioica* (Brazil) Fruits Hydrodistillation Eugenol (76.98), β-pinene

*P. dioica* (Mexico) Fruits Hydrodistillation Methyl-eugenol (48.7),

*P. dioica* (USA) Leaves Hydrodistillation Eugenol (62.1), methyl-

*P. dioica* (India) Leaves Hydrodistillation Eugenol (68.4), chavicol

*P. dioica* (México) Leaves Hydrodistillation Eugenol (94.86),

*P. dioica* (Sri Lanka) Leaves Hydrodistillation Eugenol (85.33),

*P. guatemalensis* (Costa Rica) Leaf Hydrodistillation Eugenol (72.8),

*P. guatemalensis* (Costa Rica) Fruits Hydrodistillation Eugenol (74.7),

*P. jamaicensis* (Jamaica) Leaves Steam distillation Eugenol (61.79),

*P. dioica* (India) Fruits Commercial (Plant

*P. haitiensis* (Dominican

26 Potential of Essential Oils

*P. haitiensis* (Dominican

Republic)

Republic)

*P. dioica* (India) Leaves Hydrodistillation Eugenol (47.80–55.35) [81]

Lipids Ltd. India)

Leaves Steam distillation Methyl-chavicol

Leaves Hydrodistillation Methyl-chavicol

**(area %)**

(17.1)

eugenol (22.9)

(6.52), limonene (4.09)

eugenol (16.3), myrcene

(10.4), methyl-eugenol (6.1), 1-octen-3-ol (2.7)

β-caryophyllene (4.36), 1,8-cineole (4.19)

β-caryophyllene (8.2), terpinolene (3.0).

caryophyllene oxide (3.3).

(11.65–41.10), 1,8-cineole (11.35–16.63), linalool (16.03–17.81), transanethol (6.76–8.70), methyl-eugenol (0.61–24.39),

(19.94–32.83), 1,8-cineole (17.62–33.14), linalool (15.97–16.32), methyleugenol (0–14.95), transanethole (4.66–8.50)

1,8-cineole (43.94–49.43), α-terpineol (0.34–18.02), limonene (10.33), 4-terpineol (6.37–7.17), p-cymene (2.25–10.25), β-caryophyllene (5.77)

α-terpineol (2.45)

Eugenol (35.42), methyl-eugenol (28.02), β-caryophyllene (8.66), β-Mirtsen (8.55), 1,8-cyneole (5.62)

**Reference**

[78]

[79]

[80]

[82]

[83]

[84]

[85]

[86]

[86]

[87]

[87]

[88]


*P. racemosa* (Benin) Leaves Hydrodistillation Eugenol (52.7), myrcene

*P. racemosa* (USA) Leaves Hydrodistillation Eugenol (64.0), myrcene

*P. racemosa* (India) Leaves Hydrodistillation Eugenol (72.9–92.9),

*P. racemosa* (Jamaica) Leaves Hydrodistillation Eugenol (64), myrcene

Leaves Steam distillation Eugenol (44.41–68.93),

Leaves (bay) Hydrodistillation Eugenol (56.1), chavicol

Leaves (lemon) Hydrodistillation Geranial (40.3), neral

Leaves (anise) Hydrodistillation Methyl-eugenol (48.1),

Leaves Hydrodistillation Eugenol (52.7), myrcene

Leaves Hydrodistillation Eugenol (48.7), limonene

Leaves (light oil) Hydrodistillation Eugenol (60.4) myrcene

Leaves (heavy oil) Hydrodistillation Eugenol (82.9), chavicol

Leaves Steam distillation Trans-methyl-isoeugenol

Leaves Hydrodistillation 4-metoxi-isoeugenol

Leaves Steam distillation Methyl-eugenol

*P. racemosa* var. *racemosa* (Dominican Republic)

*P. racemosa* var. *racemosa* (Guadeloupe)

*P. racemosa* var. *racemosa* (Guadeloupe)

*P. racemosa* var. *racemosa* (Guadeloupe)

*P. racemosa* var. *racemosa*

*P. racemosa* var. *racemosa*

*P. racemosa* var. *racemosa*

*P. racemosa* var. *racemosa*

*P. racemosa* var. *grisea* (Dominican Republic)

*P. racemosa* var. *grisea* (Dominican Republic)

*P. racemosa* var. *hispaniolensis* (Dominican Republic)

(Benin)

(Venezuela)

(Venezuela)

(Venezuela)

**(area %)**

Chemical Composition of Essential Oil of Genus *Pimenta* (Myrtaceae): Review

(14.6)

(0–7.7)

(29.4), chavicol (9.3)

myrcene (0–9.6), chavicol

http://dx.doi.org/10.5772/intechopen.78004

(14.6), chavicol (7.7), β-caryophyllene (4.9)

myrcene (0–16.17), chavicol (0–15.51), methyl-eugenol (0–11.88), β-caryophyllene (0–7.24)

(17.1), myrcene (6.4), linalool (6.0)

(31.7), limonene (5.3), myrcene (4.6)

methyl-chavicol (32.8), myrcene (12.8), linalol

(26.6), chavicol (6.3)

(13.6), 1,8-cineole (12.7)

(11.7), chavicol (6.0), limonene (5.4), linalool

(85.08–86.32), methyleugenol (0–92.60), geraniol (0–85.52)

(7.08–63.88), methylchavicol (5.13–22.61), 1,8-cineole (17.57–37.96), 4-terpineol (16.21–28.98), timol (0–44.02), γ-terpinene (0–16.67), ρ-cymene (0–8.59)

(6.0)

(4.4)

(9.3)

(75.23)

**Reference**

29

[23]

[80]

[104]

[105]

[106]

[60]

[60]

[60]

[107]

[108]

[12, 15, 59]

[12, 15, 59]

[106]

[50, 109]

[106]


*P. pseudocaryophyllus* (Brazil) Leaves Commercial (Lazlo

28 Potential of Essential Oils

*P. racemosa* (Jamaica) Leaves Commercial

*P. racemosa* (Jamaica) Leaves Commercial

*P. pseudocaryophyllus* (Brazil) Leaves Hydrodistillation (*E*)-methyl-isoeugenol

*P. racemosa* Leaves Steam distillation Contenido de fenol

*P. racemosa* Leaves Commercial Eugenol (33.8), myrcene

*P. racemosa* Leaves (Bay) Steam distillation Eugenol (56.2), chavicol

*P. racemosa* Leaves (anise) Steam distillation Methyl-eugenol (43.1),

*P. racemosa* Leaves (lemon) Steam distillation Geranial (53.2), neral

*P. racemosa* Leaves Hydrodistillation Eugenol (56.9), myrcene

*P. racemosa* Leaves Commercial Eugenol (45.5), myrcene

*P. racemosa* (Cuba) Leaves Hydrodistillation terpinen-4-ol (20.7),

*P. racemosa* (Benin) Leaves Hydrodistillation Eugenol (55.7–61.9),

*P. racemosa* (Nigeria) Aerial part Hydrodistillation Germacrene D (10.6),

(Kurt Kitzing Co., Wallerstein, Germany,

(Kurt Kitzing Co. Wallerstein, Germany,

800116)

800116)

Aromatologia Ltda.,

Brazil)

*P. racemosa* (Colombia) Leaves Steam distillation Eugenol (96) [100]

**(area %)**

(93.9)

(65–73)

(32.6)

Eugenol (88.6), β-caryophyllene (4.8)

(21.3), 1,8-cineole (9.7), chavicol (8.9)

(21.6), myrcene (13.9)

methyl-chavicol (31.6), myrcene (12.0)

(18.4), chavicol (12.2)

(29.1), chavicol (12.0)

1,8-cineole (20.4), eugenol (10.7), chavicol (10.1), α-terpineol (10.0), ρ-cymene (8.0)

myrcene (12.5–22.3), chavicol (8.0–15.3)

β-elemene (8.8), germacreno A (7.3), selin-11-en-4-α-ol (6.3), δ-cadinene (5.9), β-caryophyllene (5.8), germacreno B (5.3), α-copaene (5.2)

Eugenol (45.6) [76]

Eugenol (45.60), myrcene (24.97), chavicol (9.31)

**Reference**

[96]

[97]

[98]

[99]

[101]

[101]

[101]

[101]

[101]

[20]

[102]

[103]

[22]

ρ-cymene (0–8.59)


**5. Conclusions and future perspectives**

**Author details**

**References**

2005

Billmary Zuleyma Contreras-Moreno1,2,3\*

Los Andes (ULA), Mérida, Venezuela

\*Address all correspondence to: billmary.contreras@gmail.com

Bioanalysis, University of Los Andes (ULA), Mérida, Venezuela

(NURR), University of Los Andes (ULA), Trujillo, Venezuela

Puerto Rico: Universidad de Puerto Rico; 1982

Revista de Ciencia y Tecnología de América. 2005;**30**:453-459

According to the study, the analysis of the chemical composition of the essential oils of *Pimenta* species collected in 16 countries revealed a high content of phenolic compounds, highlighting eugenol and methyl-eugenol as the major constituents. When comparing the major compounds of the essential oils among the 12 analyzed species of genus *Pimenta*, it is evident that there are variations between different species and between the same species with different origin. In addition, taking into account that eugenol can be considered a chemotaxonomic marker for the species *P. dioica*, *P. haitiensis*, *P. jamaicensis*, *P. pseudocaryophyllus*, and *P. racemosa* and that essential oils with a high content of eugenol exhibit antimicrobial, antioxidant, and insecticide activities, it can be said that the essential oils of the genus *Pimenta* have a therapeutic potential for the treatment of many pathologies. Therefore, the economic

Chemical Composition of Essential Oil of Genus *Pimenta* (Myrtaceae): Review

http://dx.doi.org/10.5772/intechopen.78004

31

importance of essential oils from genus *Pimenta* around the world is unquestionable.

1 Laboratory of Polymers and Colloids (POLYCOL), Faculty of Engineering, University of

2 Laboratory "C" of Natural Products, Research Institute, Faculty of Pharmacy and

3 Natural Products Research Group (GIPRONA), Nucleus University Rafael Urdaneta

[1] Bermúdez A, Oliveira-Miranda MA, Velázquez D. La investigación etnobotánica sobre plantas medicinales: Una revisión de sus objetivos y enfoques actuales. Interciencia:

[2] Fonnegra RdeJ, Jiménez SL, Plantas medicinales aprobadas en Colombia. Colección

[3] Restrepo M, Romero P, Fraume NJ. Manual el milagro de las plantas, aplicaciones medicinales y orofaríngeas. Colombia: San Pablo: Fundación Hogares Juveniles Campesinos;

[4] Núñez E, Plantas medicinales de Puerto Rico: Folklore y fundamentos científicos. 1° ed.

Salud/Interés General. 2nd ed. Colombia: Universidad de Antioquia; 2007

**Table 1.** Main compounds of essential oils from genus *Pimenta* (L).

The composition of essential oils contributes significantly to the determination of the pharmacological potential attributed to the plant species (indicated mainly by the major compounds) and is constantly being transformed, due to factors external to the biology of the plants (edaphic or environmental) and/or intrinsic to the biology of plants (physiological and genetic) [14, 65, 66].

Essential oils of *Pimenta* are characterized by the presence of monoterpenes, sesquiterpenes, and phenylpropanoids, and due to medicinal and economic interest, many researchers in different latitudes of the planet have been dedicated to carrying out studies to their chemical composition (**Table 1**), using basically three methods of extraction: steam distillation, hydrodistillation, and supercritical CO<sup>2</sup> extraction, with gas chromatography coupled to mass spectrometry (GC-MS) as analysis technique.

The subsequent text is reflected in **Table 1**; the chemical composition for species of genus *Pimenta* is analyzed by GC-MS and reported in the study consulted from 1921 to the present. All the information collected was organized taking into account plant species, origin, part of plant used, extraction method, and main compounds (area %).

According to the data reported in **Table 1**, the important qualitative and quantitative differences in the chemical composition of the essential oils of genus *Pimenta* can be estimated; the leaves have been the most studied part of the plant, followed by fruits and aerial parts. The conventional technique and the most used was the hydrodistillation using Clevenger apparatus. Of all the known species from genus *Pimenta* in South America, only *P. pseudocaryophyllus*, *P. racemosa*, and *P. dioica* have been collected. GC/MS analysis demonstrated the presence of volatile compounds with a content higher than 20% (area peak), such as eugenol (*P. dioica*, *P. haitiensis*, *P. jamaicensis*, *P. pseudocaryophyllus*, and *P. racemosa*), methyleugenol (*P. dioica*, *P. haitiensis*, *P. pseudocaryophyllus*, *P. racemosa*, *P. racemosa* var. *grisea*, *P. racemosa* var. *hispaniolensis*, and *P. racemosa* var. *racemosa*), 1,8-cineole (*P. dioica*, *P. haitiensis*, *P. jamaicensis*, *P. obscura*, *P. pseudocaryophyllus*, *P. racemosa*, *P. racemosa* var. *hispaniolensis*, *P. racemosa* var. *ozua*, and *P. racemosa* var. *racemosa*), and myrcene (*P. dioica*, *P. racemosa*, *P. racemosa* var. *hispaniolensis*, and *P. racemosa* var. *Racemosa*). It can also be seen that these compounds are mainly derivatives of phenylpropanoids and monoterpenes.
