**1. Introduction**

Brazil has an extensive diversity of species in its flora, and great tradition in the use of medicinal plants linked to the popular medicine [1]. Medicinal plants are characterized by common sense within communities as an alternative for

nutritional and therapeutic purposes in the prevention and cure of diseases since ancient times. Their therapeutic use has aroused scientific interest, awakening new ways to control several diseases [2].

These species are commonly employed in the commercial sector, such as the food industry. Condiments or spices are used in the preparation of food in order to improve sensory characteristics and as a preservative agent due to its antioxidant and antimicrobial attributes [3]. These types of preservatives are more accepted by the population, mainly due to the search of the industries for healthier products [4].

The antimicrobial and antioxidant activities of various spices, such as *Rosmarinus officinalis* (rosemary) [5, 6], *Cinnamomum verum* (cinnamon) [7]*Curcuma longa* (saffron) [8], *Ocimum basilicum* (basil) [9, 10], *Zingiber officinale* (ginger) [11] and *Origanum vulgare* (oregano) [12, 13] that are widely used in the food industry have such proven biological properties.

The chemical constituents responsible for the antibacterial power of these condiments are named as phenolic compounds, such as carvacrol, linalool, thymol, menthol, limonene and eugenol [14], also including terpene derivatives, such as mono- and sesquiterpenes and phenylpropanoids [15].

These spices are mainly used through the essential oils obtained from these plants. Many of these oils are composed of substances such as those mentioned above and these are related to the permeability of the bacterial cell membrane and through this can act in the control of microbiological growth [16].

A very important factor is the yield of these oils, which are based on the method and extraction time [17] and thus add a higher commercial value associated with cost-benefit. Usually, they are synthesized by extraction techniques, such as distillation [18, 19] that separate it from the water by differences in density and polarity.

Essential oils are composed of a complex mixture of volatile chemicals present in various parts of medicinal plants. They provide the essence of the plant, being responsible for the flavor and aroma of spices [20]. They act in protection against pathogens, in the attraction of pollinators and can be found in leaves, flowers, fruits and even in roots of aromatic plants [21]. These compounds have specific odoriferous and lipophilic characteristics [22] and have received much attention in the last decades due to the antimicrobial activity that they present [23].

These natural products have proven antioxidant and antimicrobial potential and several studies describe the application of these products to prolong the shelf life of food products without risks to the consumer or interference in the natural characteristics of the food [19, 24].

The search for decrease in the use of antioxidants and synthetic antimicrobial agents intensifies studies to demonstrate the promising potential of these compounds [19, 25, 26]. These searches are based on the great risk of contamination through food, and the great resistance of bacteria to antibiotics, appearing the interest of adding natural antimicrobial agents in food as a way to mitigate cases of foodborne diseases [27].

Foodborne diseases can be identified when one or more individuals exhibit similar symptoms after ingestion of food contaminated with pathogenic microorganisms, their toxins, toxic chemicals or objects which constitute a common source. In the case of highly virulent pathogens, such as *Clostridium (C.) botulinum* and *Escherichia (E.) coli* O157: H7, only one case can be considered an outbreak [28]. Bacteria like *Staphylococcus aureus*, *Salmonella*, *Campylobacter* and *Escherichia coli* are important food pathogens, and are among the biggest cause of outbreaks in the word [29].

A polymerase chain reaction (PCR) analysis with samples of beef, sheep and processed chicken showed the presence of *Clostridium perfringens*, *Enterococcus faecalis* and *S. aureus* in 79, 86 and 94%, respectively. In meat samples, *E. coli* and enteric *Salmonella* were also found in respective concentrations of 90 and 91% [30].

**149**

Maranhão.

*Comparative Analysis of the Chemical Composition, Antimicrobial and Antioxidant Activity…*

Food-borne illness is a real problem in the present scenario as the consumerism of packaged food. Pathogens entering the packaged foods may survive longer. Therefore, antimicrobial agents either alone or in combination are added to the food

Treatment in these cases leads to the indiscriminate use of antibiotics. These have provided a growing multidrug resistance of microorganisms, generating public health problems due to the residues in foods [2]. The antibiotics act as an important selective pressure for the emergence and persistence of resistant strains [32].

Exploiting the antimicrobial property, essential oils are considered as a "natural" remedy to this problem. Alternatives to the use of synthetic antimicrobial agents have been proposed in recent years, and some approaches include herbal products [28]. This promising determination of the action of these essential oils on microorganisms using Gram-positive and Gram-negative bacteria should be performed due to its low cost of acquisition, use and therapeutic action, such as the viability of medicinal potential and its use in the food industry, cosmetics and pharmaceuticals, whereas bacterial resistance is one of the most significant challenges to human health [33]. Thus, the objective of this chapter was to provide the antimicrobial and antioxidant activity of *Cinnamomum zeylanicum* (cinnamon), *O. vulgare* (oregano), *Z. officinale* (ginger), *R. officinalis* (rosemary), *C. longa L.* (saffron) and *C. latifolia* (tahiti lemon) essential oils as well as to determine its chemical composition.

*C. zeylanicum* leaves*, C. latifolia* barks*, O. vulgare* and *R. officinalis* aerial parts and *Z. officinale* and *C. longa L.* rhizome were collected in the city of São Luis Maranhão, Brazil (latitude: −2.53073, longitude: −44.3068 2° 31′ 51″ South, 44° 18′ 24″ West). The taxonomic identification was performed by Ana Zelia Silva in the Seabra Attic Herbarium of the Department of Botany of the Federal University of Maranhão. All five plants were dried for 48 h and sprayed in an electric knife mill at the Food and Water Quality Control Laboratory of the Federal University of

The essential oil was extracted by hydrodistillation using Clevenger system. A quantity of 300 g of dry plant material diluted in water at a ratio of 1:10 was boiled at 100°C for 3 h. The oil was dried with anhydrous sodium sulfate and kept in an amber bottle under refrigeration. For in vitro biological assay, the essential oils and reference drugs were dissolved in dimethylsulfoxide (DMSO) at 100 times the highest concentration of use, and subsequently diluted in an appropriate medium to

Chemical characterization of the essential oils was performed by gas chromatography coupled to mass spectrometry (GC-MS). The essential oils under study were dissolved in 1 mg/mL ethyl acetate and analyzed on Shimadzu QP 5000 gas chromatograph with ZB-5 ms capillary column (5% phenyl arylene 95% dimethylpolysiloxane) coupled at 70 eV (40–500 Da) electronic impact detector HP 5MS with a transfer temperature of 280°C. The chromatographic conditions were injection of 0.3 μL of ethyl acetate; helium carrier gas (99.99%); injector temperature: 280°C; split mode (1:10); then an initial temperature of 40°C and a final temperature of 300°C; initial time of 5 min and final time of 7.58min. The results obtained for *C.* 

A total of 15 compounds were identified and their main constituents such as cinnamic aldehyde (46.30%), α-copaene (16.35%) and trans-β-caryophyllene (8.26%) were identified and quantified. Various researchers have identified and quantified different chemical compounds of *C. zeylanicum* essential oil. A study identified nine

*DOI: http://dx.doi.org/10.5772/intechopen.86576*

**2. Essential oils chemical profile**

a final concentration of DMSO less than 1%.

*zeylanicum* leaves are shown in **Table 1**.

or packaging materials to eliminate these agents [31].

*Comparative Analysis of the Chemical Composition, Antimicrobial and Antioxidant Activity… DOI: http://dx.doi.org/10.5772/intechopen.86576*

Food-borne illness is a real problem in the present scenario as the consumerism of packaged food. Pathogens entering the packaged foods may survive longer. Therefore, antimicrobial agents either alone or in combination are added to the food or packaging materials to eliminate these agents [31].

Treatment in these cases leads to the indiscriminate use of antibiotics. These have provided a growing multidrug resistance of microorganisms, generating public health problems due to the residues in foods [2]. The antibiotics act as an important selective pressure for the emergence and persistence of resistant strains [32].

Exploiting the antimicrobial property, essential oils are considered as a "natural" remedy to this problem. Alternatives to the use of synthetic antimicrobial agents have been proposed in recent years, and some approaches include herbal products [28]. This promising determination of the action of these essential oils on microorganisms using Gram-positive and Gram-negative bacteria should be performed due to its low cost of acquisition, use and therapeutic action, such as the viability of medicinal potential and its use in the food industry, cosmetics and pharmaceuticals, whereas bacterial resistance is one of the most significant challenges to human health [33].

Thus, the objective of this chapter was to provide the antimicrobial and antioxidant activity of *Cinnamomum zeylanicum* (cinnamon), *O. vulgare* (oregano), *Z. officinale* (ginger), *R. officinalis* (rosemary), *C. longa L.* (saffron) and *C. latifolia* (tahiti lemon) essential oils as well as to determine its chemical composition.

### **2. Essential oils chemical profile**

*Essential Oils - Oils of Nature*

ways to control several diseases [2].

food industry have such proven biological properties.

mono- and sesquiterpenes and phenylpropanoids [15].

through this can act in the control of microbiological growth [16].

decades due to the antimicrobial activity that they present [23].

teristics of the food [19, 24].

foodborne diseases [27].

nutritional and therapeutic purposes in the prevention and cure of diseases since ancient times. Their therapeutic use has aroused scientific interest, awakening new

These species are commonly employed in the commercial sector, such as the food industry. Condiments or spices are used in the preparation of food in order to improve sensory characteristics and as a preservative agent due to its antioxidant and antimicrobial attributes [3]. These types of preservatives are more accepted by the population, mainly due to the search of the industries for healthier products [4]. The antimicrobial and antioxidant activities of various spices, such as *Rosmarinus officinalis* (rosemary) [5, 6], *Cinnamomum verum* (cinnamon)

[7]*Curcuma longa* (saffron) [8], *Ocimum basilicum* (basil) [9, 10], *Zingiber officinale* (ginger) [11] and *Origanum vulgare* (oregano) [12, 13] that are widely used in the

The chemical constituents responsible for the antibacterial power of these condiments are named as phenolic compounds, such as carvacrol, linalool, thymol, menthol, limonene and eugenol [14], also including terpene derivatives, such as

These spices are mainly used through the essential oils obtained from these plants. Many of these oils are composed of substances such as those mentioned above and these are related to the permeability of the bacterial cell membrane and

A very important factor is the yield of these oils, which are based on the method and extraction time [17] and thus add a higher commercial value associated with cost-benefit. Usually, they are synthesized by extraction techniques, such as distillation [18, 19] that separate it from the water by differences in density and polarity. Essential oils are composed of a complex mixture of volatile chemicals present in various parts of medicinal plants. They provide the essence of the plant, being responsible for the flavor and aroma of spices [20]. They act in protection against pathogens, in the attraction of pollinators and can be found in leaves, flowers, fruits and even in roots of aromatic plants [21]. These compounds have specific odoriferous and lipophilic characteristics [22] and have received much attention in the last

These natural products have proven antioxidant and antimicrobial potential and several studies describe the application of these products to prolong the shelf life of food products without risks to the consumer or interference in the natural charac-

The search for decrease in the use of antioxidants and synthetic antimicrobial agents intensifies studies to demonstrate the promising potential of these compounds [19, 25, 26]. These searches are based on the great risk of contamination through food, and the great resistance of bacteria to antibiotics, appearing the interest of adding natural antimicrobial agents in food as a way to mitigate cases of

Foodborne diseases can be identified when one or more individuals exhibit similar symptoms after ingestion of food contaminated with pathogenic microorganisms, their toxins, toxic chemicals or objects which constitute a common source. In the case of highly virulent pathogens, such as *Clostridium (C.) botulinum* and *Escherichia (E.) coli* O157: H7, only one case can be considered an outbreak [28]. Bacteria like *Staphylococcus aureus*, *Salmonella*, *Campylobacter* and *Escherichia coli* are important food pathogens, and are among the biggest cause of outbreaks in the word [29]. A polymerase chain reaction (PCR) analysis with samples of beef, sheep and processed chicken showed the presence of *Clostridium perfringens*, *Enterococcus faecalis* and *S. aureus* in 79, 86 and 94%, respectively. In meat samples, *E. coli* and enteric *Salmonella* were also found in respective concentrations of 90 and 91% [30].

**148**

*C. zeylanicum* leaves*, C. latifolia* barks*, O. vulgare* and *R. officinalis* aerial parts and *Z. officinale* and *C. longa L.* rhizome were collected in the city of São Luis Maranhão, Brazil (latitude: −2.53073, longitude: −44.3068 2° 31′ 51″ South, 44° 18′ 24″ West). The taxonomic identification was performed by Ana Zelia Silva in the Seabra Attic Herbarium of the Department of Botany of the Federal University of Maranhão. All five plants were dried for 48 h and sprayed in an electric knife mill at the Food and Water Quality Control Laboratory of the Federal University of Maranhão.

The essential oil was extracted by hydrodistillation using Clevenger system. A quantity of 300 g of dry plant material diluted in water at a ratio of 1:10 was boiled at 100°C for 3 h. The oil was dried with anhydrous sodium sulfate and kept in an amber bottle under refrigeration. For in vitro biological assay, the essential oils and reference drugs were dissolved in dimethylsulfoxide (DMSO) at 100 times the highest concentration of use, and subsequently diluted in an appropriate medium to a final concentration of DMSO less than 1%.

Chemical characterization of the essential oils was performed by gas chromatography coupled to mass spectrometry (GC-MS). The essential oils under study were dissolved in 1 mg/mL ethyl acetate and analyzed on Shimadzu QP 5000 gas chromatograph with ZB-5 ms capillary column (5% phenyl arylene 95% dimethylpolysiloxane) coupled at 70 eV (40–500 Da) electronic impact detector HP 5MS with a transfer temperature of 280°C. The chromatographic conditions were injection of 0.3 μL of ethyl acetate; helium carrier gas (99.99%); injector temperature: 280°C; split mode (1:10); then an initial temperature of 40°C and a final temperature of 300°C; initial time of 5 min and final time of 7.58min. The results obtained for *C. zeylanicum* leaves are shown in **Table 1**.

A total of 15 compounds were identified and their main constituents such as cinnamic aldehyde (46.30%), α-copaene (16.35%) and trans-β-caryophyllene (8.26%) were identified and quantified. Various researchers have identified and quantified different chemical compounds of *C. zeylanicum* essential oil. A study identified nine


**Table 1.**

*C. zeylanicum (cinnamon) essential oil chemical composition.*

compounds [34] with (E)-cinnamaldehyde as its major component [35, 36]. The essential oils of this plant generally have cinnamaldehyde [37], which corroborates the results obtained in this study. We already presented similar results to chemical composition of *C. zeylanicum* essential oil [38].

The chemical profile obtained for the aerial parts such as *R. officinalis* and *O. vulgare* is shown in **Table 2**. Its total composition presented 17 components with the major constituents being camphor (37.00%), 1,8-cineol (11.32%) and α-terpineol (7.12%). In *O. vulgare* essential oil, 20 compounds were found, represented by the main constituents cis-ρ-menth-2-en-1-ol (33.88%), linalyl acetate (13.90%) and p-cymene (8.29%). Probst also identified camphor as the major component of R. officinalis essential oil [39], being possible to observe similarity with the essential oil composition of this study, while other study obtained 1,8-cineol in a higher percentage, but camphor was present in the second place among the major components [40].

With respect to *O. vulgare* essential oil, while there is a description of similar chemical composition to our study [38, 41], another study found three different chemotypes in 25 samples of this essential oil: linalool/linalyl acetate chemotypes with predominant linalyl acetate; the second major chemotypes rich in carvacrol and c-terpinene; and a third rich chemotype in thymol [42].

The chemical composition of the essential oils of *C. longa* (saffron) and *Z. officinale* rhizomes is shown in **Table 3**. For essential oils obtained from *C. longa* rhizomes, 17 compounds were identified and the major chemical composition is represented by turmerone (55.43%), β-turmerone (12.02%) and γ-curcumene (6.96%). Similar results were described to *C. longa* essential oil [38, 43–45], with the main compounds turmerone and β-turmerone presenting the highest percentages.

In the essential oil of *Z. officinale*, 18 components were identified, constituting α-zingiberene (27.14%), geranial (14.06%) and nerolidol (13.51%) in greater percentage. Diemer studing essential oil of Z. officinale quantified the chemical profile in 12 constituents and concluded that α-zingiberene was the predominant

**151**

**Table 2.**

*(oregano).*

*Comparative Analysis of the Chemical Composition, Antimicrobial and Antioxidant Activity…*

**Peak** *R. officinalis* **(rosemary) E.O.** *O. vulgare* **(oregano) E.O.**

*Chemical composition of the essential oils of Rosmarinus officinalis (rosemary) and Origanum vulgare* 

**Peak** *C. longa* **(saffron) E.O.** *Z. officinale* **(ginger) E.O.**

 α-Pinene 1.15 α-Pineno 1.46 Myrcene 0.37 Canfeno 5.02 Vinyl propionate 0.20 β-Mirceno 1.29 ρ-Cymene 1.01 Sabineno 5.23 Bisabolone 0.55 1,8-Cineol 4.35 **β-Turmerone 12.02** Linalol 0.50 1,8-Cineole 1.01 4,4-Dimetil-2-pentinal 0.80 Camphor 1.24 terc-Dodeciltiol 0.71 α-Terpineol 4.13 Neral 9.64 Terpinolene 0.43 Nerol 1.07 α-Zingiberene 0.29 **Geranial 14.06** β-Sesquiphellandrene 2.67 2-Undecanona 0.63 β-Caryophyllene 1.00 Farnesol 1.27 **γ-Curcumene 6.96** 1,1-Diciclopropiletileno 0.55

**Compounds (%) Compounds (%)**

 β-Pineno 2.29 α-Pinene 0.80 β-Mirceno 4.36 Bicyclo[3.1.0]hexane 1.73 ρ-Cimeno 1.41 (+)-4-Carene 3.08 Limoneno 2.02 **p-Cymene 8.29 1,8-Cineol 11.32** Cyclohexene 1.23 γ-Terpineno 1.61 β-Phellandrene 2.73 Linalol 2.99 p-Menth-2-en-1-ol 4.62 **Cânfora 37.00** 1,4-Cyclohexadiene 1.21 Pinocarvona 217 cis-Sabinene hydrate 1.29 Borneol 3.24 Terpinolene 3.11 Terpinen-4-ol 4.79 1,6-Octadien-3-ol 5.69 **α-Terpineol 7.12** trans-Sabinene hydrate 1.59 Verbenona 5.85 **cis-p-Menth-2-en-1-ol 33.88** Acetato de bornila 4.28 3-Cyclohexen-1-ol 5.26 β-Cariofileno 6.43 (+)-α-Terpineol 2.61 α-Humuleno 1.47 Carvacrol methyl ether 0.94 α-Bisabolol 1.65 **Linalyl acetate 13.90** — Thymol 2.41 — trans-β-Caryophyllene 2.46 — 1H-Cycloprop(E)azulen-7-ol 3.16

**Compounds (%) Compounds (%)**

*DOI: http://dx.doi.org/10.5772/intechopen.86576*


*Comparative Analysis of the Chemical Composition, Antimicrobial and Antioxidant Activity… DOI: http://dx.doi.org/10.5772/intechopen.86576*

#### **Table 2.**

*Essential Oils - Oils of Nature*

**Peak** *C. zeylanicum* **E.O.**

 α-Pinene 1.47 Benzaldehyde 4.16 3-Phenylpropionaldehyde 2.95 Borneol 1.06 α-Terpineol 0.87 Cinnamic aldehyde **46.30** 3-Phenyl-1-propanol 1.46 α-Copaene 16.35 trans-β-Caryophyllene **8.26** (e)-Cinnamyl acetate 7.54 α-Humulene 2.16 delta-Cadienene 1.42 (−)-Spathulenol 2.09 Caryophyllene oxide 2.80 Benzyl benzoate 1.12

**Compounds (%)**

compounds [34] with (E)-cinnamaldehyde as its major component [35, 36]. The essential oils of this plant generally have cinnamaldehyde [37], which corroborates the results obtained in this study. We already presented similar results to chemical

The chemical profile obtained for the aerial parts such as *R. officinalis* and *O. vulgare* is shown in **Table 2**. Its total composition presented 17 components with the major constituents being camphor (37.00%), 1,8-cineol (11.32%) and α-terpineol (7.12%). In *O. vulgare* essential oil, 20 compounds were found, represented by the main constituents cis-ρ-menth-2-en-1-ol (33.88%), linalyl acetate (13.90%) and p-cymene (8.29%). Probst also identified camphor as the major component of R. officinalis essential oil [39], being possible to observe similarity with the essential oil composition of this study, while other study obtained 1,8-cineol in a higher percentage, but camphor was present in the second place among the major components [40].

With respect to *O. vulgare* essential oil, while there is a description of similar chemical composition to our study [38, 41], another study found three different chemotypes in 25 samples of this essential oil: linalool/linalyl acetate chemotypes with predominant linalyl acetate; the second major chemotypes rich in carvacrol

The chemical composition of the essential oils of *C. longa* (saffron) and *Z. officinale* rhizomes is shown in **Table 3**. For essential oils obtained from *C. longa* rhizomes, 17 compounds were identified and the major chemical composition is represented by turmerone (55.43%), β-turmerone (12.02%) and γ-curcumene (6.96%). Similar results were described to *C. longa* essential oil [38, 43–45], with the main compounds turmerone and β-turmerone presenting the highest percentages. In the essential oil of *Z. officinale*, 18 components were identified, constituting α-zingiberene (27.14%), geranial (14.06%) and nerolidol (13.51%) in greater percentage. Diemer studing essential oil of Z. officinale quantified the chemical profile in 12 constituents and concluded that α-zingiberene was the predominant

and c-terpinene; and a third rich chemotype in thymol [42].

composition of *C. zeylanicum* essential oil [38].

*C. zeylanicum (cinnamon) essential oil chemical composition.*

**150**

**Table 1.**

*Chemical composition of the essential oils of Rosmarinus officinalis (rosemary) and Origanum vulgare (oregano).*



**Table 3.**

*Chemical composition of Curcuma longa (saffron) and Zingiber officinale (ginger) essential oils.*


#### **Table 4.**

*Chemical composition of lemon tahiti essential oil.*

component [46]. Same results were observed by us in the present study. However, there are also descriptions of geranial as its major constituent in this oil [47].

The chemical composition obtained from *C. latifolia* leaves is presented in **Table 4**. The essential oil obtained presented from 17 components with the main constituents being limonene dioxide (25.92%), cis-carveol (11.59%) and ρ-cymene (10.86%). Similarly, it was found in the researches carried out in *C. latifolia* tanaka, identifying 17 compounds and limonene as the major compound with 46.3% [48] and 58.43% [49].
