Abstract
There are many food-borne pathogens in the wild and they are considered the cause of serious public health problems in both developed and developing countries. The use of natural products, such as antimicrobial compounds, has been increasing, in an attempt to control bacteria present in foods, mainly pathogens resistant to conventional antibiotics. This chapter is intended to provide the antimicrobial and antioxidant activity of essential oils of Cinnamomum zeylanicum (cinnamon), Origanum vulgare (oregano), Zingiber officinale (ginger), Rosmarinus officinalis (rosemary), Citrus latifolia (tahiti lemon) and Curcuma longa (saffron) as well as to determinate its chemical composition. The oils had been extracted by hydrodistillation with a Clevenger type apparatus and the antimicrobial activity was performed against standard strains Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. The antioxidant activity was carried out using the ABTS [2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)] method. The essential oils presented a mixture of mono- and sesquiterpenes. The best minimum inhibitory concentration was determined to C. zeylanicum against S. aureus. O. vulgare antioxidant activity presented inhibition of 90.74% and EC50 of 14 μg mL−1. These results demonstrate that the essential oils analyzed presented efficient antibacterial activity and antioxidant action being able to satisfy the demand of use as control of microorganisms in the food.
Keywords
- essential oils
- biological properties
- antimicrobial activity
- antioxidant activity
- chemical composition
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
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
A polymerase chain reaction (PCR) analysis with samples of beef, sheep and processed chicken showed the presence of
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
2. Essential oils chemical profile
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
Peak | ||
---|---|---|
Compounds | (%) | |
1 | α-Pinene | 1.47 |
2 | Benzaldehyde | 4.16 |
3 | 3-Phenylpropionaldehyde | 2.95 |
4 | Borneol | 1.06 |
5 | α-Terpineol | 0.87 |
6 | Cinnamic aldehyde | |
7 | 3-Phenyl-1-propanol | 1.46 |
8 | α-Copaene | 16.35 |
9 | trans-β-Caryophyllene | |
10 | (e)-Cinnamyl acetate | 7.54 |
11 | α-Humulene | 2.16 |
12 | delta-Cadienene | 1.42 |
13 | (−)-Spathulenol | 2.09 |
14 | Caryophyllene oxide | 2.80 |
15 | Benzyl benzoate | 1.12 |
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
The chemical profile obtained for the aerial parts such as
Peak | ||||
---|---|---|---|---|
Compounds | (%) | Compounds | (%) | |
1 | β-Pineno | 2.29 | α-Pinene | 0.80 |
2 | β-Mirceno | 4.36 | Bicyclo[3.1.0]hexane | 1.73 |
3 | ρ-Cimeno | 1.41 | (+)-4-Carene | 3.08 |
4 | Limoneno | 2.02 | ||
5 | Cyclohexene | 1.23 | ||
6 | γ-Terpineno | 1.61 | β-Phellandrene | 2.73 |
7 | Linalol | 2.99 | p-Menth-2-en-1-ol | 4.62 |
8 | 1,4-Cyclohexadiene | 1.21 | ||
9 | Pinocarvona | 217 | cis-Sabinene hydrate | 1.29 |
10 | Borneol | 3.24 | Terpinolene | 3.11 |
11 | Terpinen-4-ol | 4.79 | 1,6-Octadien-3-ol | 5.69 |
12 | trans-Sabinene hydrate | 1.59 | ||
13 | Verbenona | 5.85 | ||
14 | Acetato de bornila | 4.28 | 3-Cyclohexen-1-ol | 5.26 |
15 | β-Cariofileno | 6.43 | (+)-α-Terpineol | 2.61 |
16 | α-Humuleno | 1.47 | Carvacrol methyl ether | 0.94 |
17 | α-Bisabolol | 1.65 | ||
18 | — | Thymol | 2.41 | |
19 | — | trans-β-Caryophyllene | 2.46 | |
20 | — | 1H-Cycloprop(E)azulen-7-ol | 3.16 |
With respect to
The chemical composition of the essential oils of
Peak | ||||
---|---|---|---|---|
Compounds | (%) | Compounds | (%) | |
1 | α-Pinene | 1.15 | α-Pineno | 1.46 |
2 | Myrcene | 0.37 | Canfeno | 5.02 |
3 | Vinyl propionate | 0.20 | β-Mirceno | 1.29 |
4 | ρ-Cymene | 1.01 | Sabineno | 5.23 |
5 | Bisabolone | 0.55 | 1,8-Cineol | 4.35 |
6 | Linalol | 0.50 | ||
7 | 1,8-Cineole | 1.01 | 4,4-Dimetil-2-pentinal | 0.80 |
8 | Camphor | 1.24 | terc-Dodeciltiol | 0.71 |
9 | α-Terpineol | 4.13 | Neral | 9.64 |
10 | Terpinolene | 0.43 | Nerol | 1.07 |
11 | α-Zingiberene | 0.29 | ||
12 | β-Sesquiphellandrene | 2.67 | 2-Undecanona | 0.63 |
13 | β-Caryophyllene | 1.00 | Farnesol | 1.27 |
14 | 1,1-Diciclopropiletileno | 0.55 | ||
15 | ar-Curcumene | 1.58 | ar-Curcumeno | 3.33 |
16 | ||||
17 | β-Sesquiphellandrene | 1.10 | ||
18 | — | - | β-Sesquifelandreno | 9.45 |
In the essential oil of
The chemical composition obtained from
Peak | ||
---|---|---|
Compounds | (%) | |
1 | ρ-Cymene | |
2 | D-Limonene | 8.85 |
3 | Cyclooctanone | 1.54 |
4 | ρ-Mentha-E-2,8(9)-dien-1-ol | 2.47 |
5 | trans-Pinocarveol | 3.23 |
6 | 14.70 Pinocarvone | 2.02 |
7 | ρ-Cymen-8-ol | 3.02 |
8 | Bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde,6,6-dimethyl- | 5.34 |
9 | Myrtenol | 6.31 |
10 | trans-Carveol | 1.58 |
11 | cis-Carveol | |
12 | Carvone | 1.68 |
13 | 19.02 Carvone oxide | 3.69 |
14 | Limonene dioxide | |
15 | 1,2-Cyclohexanediol 1-methyl-4-(1-methyleth) | 8.10 |
16 | 7-Oxabicyclo[4.1.0]heptane,1-methyl-4-1-(1-methylethyl) | 1.24 |
17 | 2,7-Octadiene-1,6-diol,2,6-dimethyl | 2.56 |
3. Antimicrobial activity
The inoculum (100 μL) of each bacterium was seeded in Mueller-Hinton agar, with filter paper impregnated with 50 μL of essential oil placed on the surface. The plates were incubated at 35°C and after 24 h, the inhibition halo was measured with a millimeter ruler [51]. The minimum inhibitory concentration (MIC) was determined using the broth dilution methodology [52] and performed in triplicates with the same bacterium used in solid media diffusion techniques. Initially, an aliquot of the essential oil prepared in DMSO was transferred to a test tube containing BHI broth. Serial dilutions were then performed resulting in concentrations of 5–2000 μg/mL. Microbial suspensions containing 1.5 × 108 CFU/mL of the bacteria were added at each concentration and incubated at 35°C for 24 h. Tubes without bacteria were reserved for control of broth sterility and bacterial growth. After the incubation period, the minimum essential oil inhibitory concentration was defined as the lowest concentration which visibly inhibited bacterial growth observed by the absence of visible turbidity. To confirm growth inhibition, the BHI broth was subjected to the inoculum microbial seeding test on the surface of the plate-count agar.
The disc diffusion method evaluated the antibacterial activity of
IH (mm) | MIC (μg mL−1) | IH (mm) | MIC (μg mL−1) | IH (mm) | MIC (μg mL−1) | |
---|---|---|---|---|---|---|
12.67 (±1.00) | 216.67 (±14.43) | 15.33 (±0.58) | 9.33 (±0.58) | 383.33 (±0.01) | ||
15.33 (±0.58) | 14.67 (±0.58) | 216.67 (±28.87) | 10.33 (±0.58) | 550.00 (±28.87) | ||
14.33 (±0.58) | 266.67 (±28.87) | 166.67 (±14.43) | 12.00 (±0.58) | 483.33 (±57.74) | ||
10.70 (±0.58) | 1000.00 | 9.70 (±0.58) | 200.00 | 8.67 (±0.58) | 1500.0 | |
9.70 (±0.58) | 1700.00 | 10.70 (±0.58) | 1500.00 | 7.67 (±0.58) | 1700.0 | |
21 | 250 | 10 | 500 | 11 | 1000 |
The minimum inhibitory concentration (MIC) in μg mL−1, the lowest visible concentration that prevents visible microbial growth in the culture medium by the action of the natural product, is being reported in Table 5.
The bactericidal activity of
The MIC’s of
To the antimicrobial potential of
On the other hand,
Soković et al. [62] obtained MIC’s for
For
In relation to the bactericidal effect of the
4. Antioxidant activity
The antioxidant activity by the ABTS method [2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)] was adapted according to the methodology suggested by [70]. The ABTS˙+ radical was prepared by the reaction of 5.0 mL of a 3840 μg mL−1 of ABTS solution with 88 μL of the 37,840 μg mL−1 potassium persulfate solution. The mixture was left in the dark for 16 h. After formation of the radical, the mixture was diluted in ethanol (approximately 1:30 v/v) and absorbance was obtained at 734 nm. From the extracts and essential oils concentrations (5–150 μg mL−1), the reaction mixture was prepared with the ABTS radical cation. In a dark environment, a 30 μL aliquot of each extract and essential oil concentration was transferred into 23 test tubes containing 3.0 mL of the ABTS radical cation and homogenized on a tube shaker. After 6 min, absorbance of the reaction mixture was obtained in a spectrophotometer at 734 nm. The analyzes were performed in triplicate and the capture of the free radical was expressed as percent inhibition (% I) of the ABTS radical cation.
The ABTS method allowed the calculation of the 50% effective concentration of the essential oils, which express the minimum concentration required to reduce the initial concentration of ABTS by 50%, and these are expressed in Table 6. The lowest concentration and consequently the best antioxidant activity was observed to oregano, with an EC50 quantified in 14 μg mL−1 and consequently also the highest percentage of ABTS inhibition.
Essential oil | Effective concentration 50% EC50 (μg mL−1) | % ABTS inhibition (50 μg mL−1) |
---|---|---|
215.93 | 11.11 | |
308.16 | 25.9 | |
153.7 | 25.7 | |
173.43 | 14.8 | |
250 | 24.89 |
The antioxidant effect of
The result for
On the other hand [72], while evaluating the antioxidant capacity of rosemary essential oil using DPPH, it had a relatively higher concentration than this study
Regarding the antioxidant potential of oregano essential oil, the author [74] obtained a higher value of efficient concentration than presented in our study, which highlights the data obtained satisfactory in this research. However [75], while still evaluating the antioxidant activity of
When checking the antioxidant activity of
When studying the anti-inflammatory and anti-inflammatory activity of ginger essential oil [77], a much higher EC50 value is obtained which was presented in this study. These results are lower than that obtained in this study, and the authors attribute to this fact that the low concentration of phenolic compounds is mainly responsible for the antioxidant activity.
A relatively lower EC50 value was found for
5. Conclusions
These studies have shown that the essential oils of
Acknowledgments
The present study was funded by Coordenacão de Aperfeiçoamento de Pessoal de Nível Superior, Brazil (CAPES) [Finance Code 001]; Fundação de Amparo à Pesquisa do Estado do Rio de Janeiro (E-26/111.252/2014), for Kátia da Silva Calabrese; by the Fundação de Amparo à Pesquisa e Desenvolvimento Científico do Maranhão (APP-00844/09 and Pronex-241709/2014); Conselho Nacional de Desenvolvimento Científico e Tecnológico, (407831/2012.6 and 309885/2017-5) for Ana Lucia Abreu-Silva and by CNPq/SECTI/FAPEMA (DCR03438/16) for Fernando Almeida-Souza; as well as the IOC (article processing charges).
Conflict of interest
The authors declare that there are no conflicts of interest regarding the publication of this article.
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