Study of chemical structure, antimicrobial, cytotoxic and mechanism of action of Syzygium aromaticum essential oil on foodborne pathogens
DOI:
https://doi.org/10.5219/1226Keywords:
Syzygium aromaticum, Scanning electron microscopy, Cytotoxic effect, Antimicrobial activity, HT29 cell lineAbstract
In this study, chemical composition (gas chromatography-mass spectroscopy), chemical structure (fourier transform infrared spectroscopy) and antioxidant potential (β-carotene bleaching assay and DPPH/ABTS-radical scavenging activity tests) of Syzygium aromaticum essential oil (SAEO) were evaluated. Eugenol (75.11%) was found to be the major compound of SAEO. Eugenol, as the main chemical constituent of SAEO, showed its signature peaks in the wavenumber range of 720 – 1250 cm-1, ascribing to the C=C region. The antimicrobial activity of SAEO on Escherichia coli, Staphylococcus aureus, Listeria innocua and Pseudomonas aeruginosa were evaluated. The scanning electron microscopy (SEM) was then applied to unravel the antibacterial mechanism of SAEO on E. coli as the most resistant strain and L. innocua as the most sensitive strain. The MTT assay was also used to investigate the cytotoxicity effect of SAEO on human colonic cancer cell lines (HT29 cell line) and the highest cytotoxic effect was observed at 200 mg.mL-1 concentration of SAEO. The SEM micrographs revealed that the SAEO treatment was able to manifestly increase the cell permeabilization and membrane integrity disruption. This means that the entirety of the cell membranes was remarkably affected by the essential oil, which could lead to cytoplasm secretion and subsequent cell death. The data strongly suggest that SAEO had a potential antioxidant, antimicrobial and cytotoxicity activity.
Downloads
Metrics
References
Alghooneh, A., Behbahani, B. A., Noorbakhsh, H., Yazdi, F. T. 2015. Application of intelligent modeling to predict the population dynamics of Pseudomonas aeruginosa in Frankfurter sausage containing Satureja bachtiarica extracts. Microbial pathogenesis, vol. 85, p. 58-65. https://doi.org/10.1016/j.micpath.2015.06.003 DOI: https://doi.org/10.1016/j.micpath.2015.06.003
Alizadeh Behbahani, B., Shahidi, F. 2019. Melissa officinalis essential oil: Chemical compositions, antioxidant potential, total phenolic content and antimicrobial activity. Nutrition and Food Sciences Research, vol. 6, no. 1, p. 17-25. https://doi.org/10.29252/nfsr.6.1.17 DOI: https://doi.org/10.29252/nfsr.6.1.17
Bakkali, F., Averbeck, S., Averbeck, D., Idaomar, M. 2008. Biological effects of essential oils–a review. Food and chemical toxicology, vol. 46, no. 2, p. 446-475. https://doi.org/10.1016/j.fct.2007.09.106 DOI: https://doi.org/10.1016/j.fct.2007.09.106
Barros, L., Ferreira, M. J., Queiros, B., Ferreira, I. C., Baptista, P. 2007. Total phenols, ascorbic acid, β-carotene and lycopene in Portuguese wild edible mushrooms and their antioxidant activities. Food chemistry, vol. 103, no. 2, p. 413-419. https://doi.org/10.1016/j.foodchem.2006.07.038 DOI: https://doi.org/10.1016/j.foodchem.2006.07.038
Behbahani, A. B., Imani Fooladi, A. A. 2018. Development of a novel edible coating made by Balangu seed mucilage and Feverfew essential oil and investigation of its effect on the shelf life of beef slices during refrigerated storage through intelligent modeling. Journal of food safety, vol. 38, no. 3, p. 1-16. https://doi.org/10.1111/jfs.12443 DOI: https://doi.org/10.1111/jfs.12443
Behbahani, B. A., Fooladi, A. A. I. 2018. Evaluation of phytochemical analysis and antimicrobial activities Allium essential oil against the growth of some microbial pathogens. Microbial pathogenesis, vol. 114, p. 299-303. https://doi.org/10.1016/j.micpath.2017.11.055 DOI: https://doi.org/10.1016/j.micpath.2017.11.055
Behbahani, B. A., Noshad, M., Falah, F. 2019. Cumin essential oil: Phytochemical analysis, antimicrobial activity and investigation of its mechanism of action through scanning electron microscopy. Microbial pathogenesis, vol. 136, p. 103716. https://doi.org/10.1016/j.micpath.2019.103716 DOI: https://doi.org/10.1016/j.micpath.2019.103716
Behbahani, B. A., Shahidi, F., Yazdi, F. T., Mortazavi, S. A., Mohebbi, M. 2017a. Antioxidant activity and antimicrobial effect of tarragon (Artemisia dracunculus) extract and chemical composition of its essential oil. Journal of Food Measurement and Characterization, vol. 11, no. 2, p. 847-863. https://doi.org/10.1007/s11694-016-9456-3 DOI: https://doi.org/10.1007/s11694-016-9456-3
Behbahani, B. A., Yazdi, F. T., Shahidi, F., Mortazavi, S. A., Mohebbi, M. 2017b. Principle component analysis (PCA) for investigation of relationship between population dynamics of microbial pathogenesis, chemical and sensory characteristics in beef slices containing Tarragon essential oil. Microbial pathogenesis, vol. 105, p. 37-50. https://doi.org/10.1016/j.micpath.2017.02.013 DOI: https://doi.org/10.1016/j.micpath.2017.02.013
Braga, P. C., Dal Sasso, M., Culici, M., Alfieri, M. 2007. Eugenol and thymol, alone or in combination, induce morphological alterations in the envelope of Candida albicans. Fitoterapia, vol. 78, no. 6, p. 396-400. https://doi.org/10.1016/j.fitote.2007.02.022 DOI: https://doi.org/10.1016/j.fitote.2007.02.022
Ćavar, S., Maksimović, M., Vidic, D., Parić, A. 2012. Chemical composition and antioxidant and antimicrobial activity of essential oil of Artemisia annua L. from Bosnia. Industrial Crops and Products, vol. 37, no. 1, p. 479-485. https://doi.org/10.1016/j.indcrop.2011.07.024 DOI: https://doi.org/10.1016/j.indcrop.2011.07.024
Cortés-Rojas, D. F., de Souza, C. R. F., Oliveira, W. P. 2014. Clove (Syzygium aromaticum): a precious spice. Asian Pacific journal of tropical biomedicine, vol. 4, no. 2, p. 90-96. https://doi.org/10.1016/S2221-1691(14)60215-X DOI: https://doi.org/10.1016/S2221-1691(14)60215-X
Dapkevicius, A., Venskutonis, R., van Beek, T. A., Linssen, J. P. 1998. Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in Lithuania. Journal of the Science of Food and Agriculture, vol. 77, no. 1, p. 140-146. https://doi.org/10.1002/(SICI)1097-0010(199805)77:1<140::AID-JSFA18>3.0.CO;2-K DOI: https://doi.org/10.1002/(SICI)1097-0010(199805)77:1<140::AID-JSFA18>3.0.CO;2-K
Do, Q. D., Angkawijaya, A. E., Tran-Nguyen, P. L., Huynh, L. H., Soetaredjo, F. E., Ismadji, S., Ju, Y. H. 2014. Effect of extraction solvent on total phenol content, total flavonoid content, and antioxidant activity of Limnophila aromatica. Journal of food and drug analysis, vol. 22, no. 3, p. 296-302. https://doi.org/10.1016/j.jfda.2013.11.001 DOI: https://doi.org/10.1016/j.jfda.2013.11.001
Frolova, N., Uktainets, A., Korablova, O., Voitsekhivskyi, V. 2019. Plants of nepeta cataria var. Citriodora beck. And essential oils from them for food industry. Potravinarstvo Slovak Journal of Food Sciences, vol. 13, no. 1, p. 449-455. https://doi.org/10.5219/1109 DOI: https://doi.org/10.5219/1109
Goupy, P., Dufour, C., Loonis, M., Dangles, O. 2003. Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. Journal of Agricultural and Food Chemistry, vol. 51, no. 3, p. 615-622. https://doi.org/10.1021/jf025938l DOI: https://doi.org/10.1021/jf025938l
Jabbari, M., Jabbari, A. 2016. Antioxidant potential and DPPH radical scavenging kinetics of water-insoluble flavonoid naringenin in aqueous solution of micelles. Colloids and Surfaces A: Physicochemical and Engineering Aspects, vol. 489, p. 392-399. https://doi.org/10.1016/j.colsurfa.2015.11.022 DOI: https://doi.org/10.1016/j.colsurfa.2015.11.022
Jeyaratnam, N., Nour, A. H., Kanthasamy, R., Nour, A. H., Yuvaraj, A. R., Akindoyo, J. O. 2016. Essential oil from Cinnamomum cassia bark through hydrodistillation and advanced microwave assisted hydrodistillation. Industrial Crops and Products, vol. 92, p. 57-66. https://doi.org/10.1016/j.indcrop.2016.07.049 DOI: https://doi.org/10.1016/j.indcrop.2016.07.049
Lesgards, J. F., Baldovini, N., Vidal, N., Pietri, S. 2014. Anticancer activities of essential oils constituents and synergy with conventional therapies: a review. Phytotherapy Research, vol. 28, no. 10, p. 1423-1446. https://doi.org/10.1002/ptr.5165 DOI: https://doi.org/10.1002/ptr.5165
Li, Y. Q., Kong, D. X., Wu, H. 2013. Analysis and evaluation of essential oil components of cinnamon barks using GC–MS and FTIR spectroscopy. Industrial Crops and Products, vol. 41, p. 269-278. https://doi.org/10.1016/j.indcrop.2012.04.056 DOI: https://doi.org/10.1016/j.indcrop.2012.04.056
López-Malo, A., Palou, E., León-Cruz, R., Alzamora, S. M. 2006. Mixtures of natural and synthetic antifungal agents. Advances in food mycology, vol. 571, p. 261-286. https://doi.org/10.1007/0-387-28391-9_18 DOI: https://doi.org/10.1007/0-387-28391-9_18
Lv, F., Liang, H., Yuan, Q., Li, C. 2011. In vitro antimicrobial effects and mechanism of action of selected plant essential oil combinations against four food-related microorganisms. Food Research International, vol. 44, no. 9, p. 3057-3064. https://doi.org/10.1016/j.foodres.2011.07.030 DOI: https://doi.org/10.1016/j.foodres.2011.07.030
Moghayedi, M., Ahmadzadeh, H., Ghazvini, K., Goharshadi, E. K. 2017. Neglected antibacterial activity of ethylene glycol as a common solvent. Microbial pathogenesis, vol. 107, p. 457-461. https://doi.org/10.1016/j.micpath.2017.04.022 DOI: https://doi.org/10.1016/j.micpath.2017.04.022
Mohammed, K. A. K., Abdulkadhim, H. M., Noori, S. I. 2016. Chemical composition and anti-bacterial effects of clove (Syzygium aromaticum) flowers. Int. J. Curr. Microbiol. App. Sci., vol. 5, no. 2, p. 483-489. https://doi.org/10.20546/ijcmas.2016.502.054 DOI: https://doi.org/10.20546/ijcmas.2016.502.054
Neaz, S. 2019. Phytochemical and biological investigation on syzygium aromaticum (Myrtaceae) : dissertation theses. Bangladesh : University of Dhaka.
Noshad, M., Hojjati, M., Behbahani, B. A. 2018. Black Zira essential oil: Chemical compositions and antimicrobial activity against the growth of some pathogenic strain causing infection. Microbial pathogenesis, vol. 116, p. 153-157. https://doi.org/10.1016/j.micpath.2018.01.026 DOI: https://doi.org/10.1016/j.micpath.2018.01.026
Ogbole, O. O., Segun, P. A., Adeniji, A. J. 2017. In vitro cytotoxic activity of medicinal plants from Nigeria ethnomedicine on Rhabdomyosarcoma cancer cell line and HPLC analysis of active extracts. BMC complementary and alternative medicine, vol. 17, no. 1, p. 494. https://doi.org/10.1186/s12906-017-2005-8 DOI: https://doi.org/10.1186/s12906-017-2005-8
Pramod, K., Suneesh, C. V., Shanavas, S., Ansari, S. H., Ali, J. 2015. Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies. Journal of Analytical Science and Technology, vol. 6, no. 1, p. 34. https://doi.org/10.1186/s40543-015-0073-2 DOI: https://doi.org/10.1186/s40543-015-0073-2
Prashar, A., Locke, I. C., Evans, C. S. 2006. Cytotoxicity of clove (Syzygium aromaticum) oil and its major components to human skin cells. Cell Proliferation, vol. 39, no. 4, p. 241-248. https://doi.org/10.1111/j.1365-2184.2006.00384.x DOI: https://doi.org/10.1111/j.1365-2184.2006.00384.x
Ramak, P., Talei, G. R. 2018. Chemical composition, cytotoxic effect and antimicrobial activity of Stachys koelzii Rech. f. essential oil against periodontal pathogen Prevotella intermedia. Microbial pathogenesis, vol. 124, p. 272-278. https://doi.org/10.1016/j.micpath.2018.08.010 DOI: https://doi.org/10.1016/j.micpath.2018.08.010
Ranasinghe, L., Jayawardena, B., Abeywickrama, K. 2002. Fungicidal activity of essential oils of Cinnamomum zeylanicum (L.) and Syzygium aromaticum (L.) Merr et LM Perry against crown rot and anthracnose pathogens isolated from banana. Letters in Applied Microbiology, vol. 35, no. 3, p. 208-211. https://doi.org/10.1046/j.1472-765X.2002.01165.x DOI: https://doi.org/10.1046/j.1472-765X.2002.01165.x
Ribeiro-Santos, R., Andrade, M., de Melo, N. R., Sanches-Silva, A. 2017. Use of essential oils in active food packaging: Recent advances and future trends. Trends in food science & technology, vol. 61, p. 132-140. https://doi.org/10.1016/j.tifs.2016.11.021 DOI: https://doi.org/10.1016/j.tifs.2016.11.021
Shan, B., Cai, Y. Z., Sun, M., Corke, H. 2005. Antioxidant capacity of 26 spice extracts and characterization of their phenolic constituents. Journal of agricultural and food chemistry, vol. 53, no. 20, p. 7749-7759. https://doi.org/10.1021/jf051513y DOI: https://doi.org/10.1021/jf051513y
Shokeen, P., Bala, M., Singh, M., Tandon, V. 2008. In vitro activity of eugenol, an active component from Ocimum sanctum, against multiresistant and susceptible strains of Neisseria gonorrhoeae. International journal of antimicrobial agents, vol. 32, no. 2, p. 174-179. https://doi.org/10.1016/j.ijantimicag.2008.03.018 DOI: https://doi.org/10.1016/j.ijantimicag.2008.03.018
Spickett, C. M., Forman, H. J. 2015. Lipid oxidation in health and disease. Boca Raton, USA : CRC Press., 404 p. ISBN 9781482202854. https://doi.org/10.1201/b18138 DOI: https://doi.org/10.1201/b18138
Srivastava, A. K., Srivastava, S. K., Syamsundar, K. V. 2005. Bud and leaf essential oil composition of Syzygium aromaticum from India and Madagascar. Flavour and Fragrance Journal, vol. 20, no. 1, p. 51-53. https://doi.org/10.1201/b18138 DOI: https://doi.org/10.1002/ffj.1364
Tohidi, B., Rahimmalek, M., Arzani, A. 2017. Essential oil composition, total phenolic, flavonoid contents, and antioxidant activity of Thymus species collected from different regions of Iran. Food Chemistry, vol. 220, p. 153-161. https://doi.org/10.1016/j.foodchem.2016.09.203 DOI: https://doi.org/10.1016/j.foodchem.2016.09.203
Turan, I., Demir, S., Kilinc, K., Yaman, S. O., Misir, S., Kara, H., Deger, O. 2018. Cytotoxic effect of Rosa canina extract on human colon cancer cells through repression of telomerase expression. Journal of Pharmaceutical Analysis, vol. 8, no. 6, p. 394-399. https://doi.org/10.1016/j.jpha.2017.12.005 DOI: https://doi.org/10.1016/j.jpha.2017.12.005
Wang, G., Huang, X., Pei, D., Duan, W., Quan, K., Li, X., Di, D. 2016. DPPH-HPLC-DAD analysis combined HSCCC for screening and identification of radical scavengers in Cynomorium songaricum Rupr. New Journal of Chemistry, vol. 40. no. 4, p. 3885-3891. https://doi.org/10.1039/C5NJ03233D DOI: https://doi.org/10.1039/C5NJ03233D
Wojdyło, A., Oszmiański, J., Czemerys, R. 2007. Antioxidant activity and phenolic compounds in 32 selected herbs. Food chemistry, vol. 105, no. 3, p. 940-949. https://doi.org/10.1016/j.foodchem.2007.04.038 DOI: https://doi.org/10.1016/j.foodchem.2007.04.038
Yeganegi, M., Yazdi, F. T., Mortazavi, S. A., Asili, J., Behbahani, B. A., Beigbabaei, A. 2018. Equisetum telmateia extracts: Chemical compositions, antioxidant activity and antimicrobial effect on the growth of some pathogenic strain causing poisoning and infection. Microbial pathogenesis, vol.. 116, p. 62-67. https://doi.org/10.1016/j.micpath.2018.01.014 DOI: https://doi.org/10.1016/j.micpath.2018.01.014
Zhang, L., Zhang, T., Chang, M., Lu, M., Liu, R., Jin, Q., Wang, X. 2019. Effects of interaction between α-tocopherol, oryzanol, and phytosterol on the antiradical activity against DPPH radical. LWT, vol. 112, p. 108206. https://doi.org/10.1016/j.lwt.2019.05.104 DOI: https://doi.org/10.1016/j.lwt.2019.05.104
Zhang, Y., Liu, X., Wang, Y., Jiang, P., Quek, S. 2016. Antibacterial activity and mechanism of cinnamon essential oil against Escherichia coli and Staphylococcus aureus. Food Control, vol. 59, p. 282-289. https://doi.org/10.1016/j.foodcont.2015.05.032 DOI: https://doi.org/10.1016/j.foodcont.2015.05.032
Zhong, N. J., Liu, G. Q., Zhao, X. H., Gao, Y. Q., Li, L., Li, B. 2015. Lipid Peroxidation Inhibitation Activity of Maillard Reaction Products Derived from Sugar-amino Acid Model Systems. Advance Journal of Food Science and Technology, vol. 9, no. 5, p. 393-397. https://doi.org/10.19026/ajfst.9.1922 DOI: https://doi.org/10.19026/ajfst.9.1922
Published
How to Cite
Issue
Section
License
This license permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited, and is not altered, transformed, or built upon in any way.
