Antimicrobial Properties of 6-Bromoeugenol and Eugenol

Article Preview

Abstract:

We have studied the antimicrobial properties of 6-bromoeugenol and eugenol by three strains: Pseudomonas aeruginosa (S1), Escherichia coli (S2) and Staphylococcus aureus (S3). We have determined the minimum inhibitory concentration (MIC) for a range of concentrations using the disc diffusion method. We note that all samples present an antimicrobial activity toward the tested bacterial strains at different concentrations (1, 0.5 and 0.25 mg/ml). The 6-bromoeugenol gives modest activity with (S1) and (S3). Eugenol reacts positively with the Pseudomonas aeruginosa (S1) at all concentrations and with the Escherichia coli (S2) at 0.5 mg/ml. We remark that the Pseudomonas aeruginosa (S1) is the more sensitive strain than Escherichia coli (S2) and Staphylococcus aureus (S3). We have estimated the activity coefficient which has confirmed the antimicrobial activity of the different samples. So, 6-bromoeugenol has shown his efficiency as antimicrobial agent.

Info:

Pages:

57-64

Citation:

Online since:

April 2016

Export:

Share:

Citation:

* - Corresponding Author

[1] S. Burt, Essential oils: Their antimicrobial properties and potential applications in foods: A review, International Journal of Food Microbiology. 94 (2004) 223-253.

DOI: 10.1016/j.ijfoodmicro.2004.03.022

Google Scholar

[2] P.J. Delaquis, K. Stanich, B. Girard, G. Mazza, Antimicrobial activity of individual and mixed fractions of dill, cilantro, coriander and eucalyptus essential oils, International Journal of Food Microbiology. 74 (2002) 101-109.

DOI: 10.1016/s0168-1605(01)00734-6

Google Scholar

[3] P.M. Davidson, M.E. Parish, Methods for testing the efficacy of food antimicrobials, Food Technology. 43 (1989) 148-155.

Google Scholar

[4] A.O. Gill, P. Delaquis, P. Russo, R.A. Holley, Evaluation of antilisterial action of cilantro oil on vacuum packed ham, International Journal of Food Microbiology. 3 (2002) 83-92.

DOI: 10.1016/s0168-1605(01)00712-7

Google Scholar

[5] A. Mourey, N. Canillac, Anti-Listeria monocytogenes activity of essential oils components of conifers, Food Control. 13 (2002) 289-292.

DOI: 10.1016/s0956-7135(02)00026-9

Google Scholar

[6] J. Reichling, P. Schnitzler, U. Suschke, R. Saller, Essential oils of aromatic plants with antibacterial, antifungal, antiviral, and cytotoxic properties-an overview, Forsch Komplementmed. 16 (2009) 79-90.

DOI: 10.1159/000207196

Google Scholar

[7] A. Koroch, H.R. Juliani, J.A. Zygadlo, Flavours and Fragrances. Chemistry, Bioprocessing and Sustainability. Berger RG. Ed. Springer Verlag: Berlin, Germany, 2007, pp.87-115.

DOI: 10.1007/978-3-540-49339-6_5

Google Scholar

[8] D. Nayak, A.P. Minz, A. Ashe, P.R. Rauta, M. Kumari, P. Chopra, B. Nayak, Synergistic combination of antioxidant, silver nanoparticles and chitosan in a nanoparticle based formulation: Characterization and cytotoxic effect on MCF-7 breas cancer cell lines. Journal of Colloid and Interface Science, (2016) In Press.

DOI: 10.1016/j.jcis.2016.02.043

Google Scholar

[9] J. Yi, Y. Fan, W. Yokoyama, Y. Zhang, L. Zhao, Thermal degradation and isomerization of beta-carotene in oil-in-water nanoemulsions supplemented with natural antioxidants, Journal of Agricultural and Food Chemistry, (2016) In Press.

DOI: 10.1021/acs.jafc.5b05478

Google Scholar

[10] F. Frantianni, M.N.N. Ombra, A. Cozzolino, R. Riccardi, P. Spigno, P. Tremonte, R. Cppola, F. Nazzaro, Phenolic constituents, antioxidant, antimicrobial and anti-proliferaive activities of different endemic Italian varieties o garlic (Allium sativum L.), Journal of Functional Foods. 21 (2016) 240-248.

DOI: 10.1016/j.jff.2015.12.019

Google Scholar

[11] G. Huang, J. Jiang, D. Dai, Antioxidative and antibacterial activity of the methanol extract of Artemisia anomala S. Moore, African Journal of Biotechnology. 7 (2008) 1335-1338.

Google Scholar

[12] M.R.C. Raja, V. Srinivasan, S. Selvaraj, S.K. Mahapatra, Versatile and Synergistic potential of eugenol: a review, Pharmaceutica Analytica Acta. 6(5) 2015 367-372.

Google Scholar

[13] F.G. Li, J.Chen, W.M. Cheng, M.F. Ji, Embrotoxicity of eugenol based on a model of embryonic stem cell test, Chinese Journal of Tissuse Engineering Research, 19(19) (2015) 3017-3021.

Google Scholar

[14] M. He, M. Du, M. Fa, Z. Bian, In vivo activity of eugenol against Candida albicans biofilm, Mycopathologia. 163 (2007)137-143.

DOI: 10.1007/s11046-007-0097-2

Google Scholar

[15] D. Huang, B. Ou, R.L. Prior, The chemistry behind antioxidant capacity assays, Journal of Agricultural and Food Chemistry. 53 (2005) 1841-1856.

DOI: 10.1021/jf030723c

Google Scholar

[16] R. Mahboub, F. Memmou, Antioxidant activity and kinetics studies of eugenol and 6-bromoeugenol, Natural Product Research. 29 (2015) 966-971.

DOI: 10.1080/14786419.2014.958738

Google Scholar

[17] M. Pisano, G. Pagnan, M. Loi, M. E. Mura, M. G. Tilocca, G. Palmieri, D. Fabbri, M. A. Dettori, G. Delogu, M. Ponzoni, C. Rozzo, Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells, Molecular Cancer. 6 (2007) 1-12.

DOI: 10.1186/1476-4598-6-8

Google Scholar

[18] M.E Hidalgo, C. De la Rosa, Antioxydant capcity of eugenol derivatives, Quimica Nova. 32 (2009) 1467-1470.

Google Scholar

[19] G. Eyambe, L. Canale, B.K. Banik, Antimicrobial activity of eugenol derivatives, Heterocyclic Letters. 1 (2011) 154-157.

Google Scholar

[20] S. Lamy, M. Blanchette, J. Michaud-Levesque, R. Lafleur, Y. Durocher, A. Moghrabi, S. Barrette, D. Gingras, R. Béliveau, Carcinogenesis. 27 (2006) 989-996.

DOI: 10.1093/carcin/bgi279

Google Scholar

[21] Y.M. Choi, D.O. Noh, S.Y. Cho, H.J. Suh, K.M. Kim, J.M. Kim, Antioxidant and antimicrobial activities of propolis from several regions of Korea, LWT-Food Science and Technology. 39 (2006) 756-761.

DOI: 10.1016/j.lwt.2005.05.015

Google Scholar

[22] S. Athamena, Etude quantitative des flavonoïdes des graines de Cuminum cyminum et les feuilles de Rosmarinus officinalis et l'évaluation de l'activité biologique. Thèse de Magister; Université de Batna, 2009.

Google Scholar

[23] M.C. Pibiri, Assainissement microbiologique de l'air et des systèmes de ventilation au moyen d'huiles essentielles. Thèse N° 3311, Ecole Polytechnique Fédérale de Lausanne, 2006.

DOI: 10.3940/rina.innovsail.2010.14

Google Scholar

[24] F. Haddouchi, H.A. Lazouni, A. Meziane, A. Benmansour, Etude physicochimique et microbilogique de l'huile essentielle de Thymus fontanesii Boiss et Reut, Afrique Science. 5 (2009) 246-259.

DOI: 10.4314/afsci.v5i2.61738

Google Scholar

[25] J. El Amri, Kh. Elbadaoui, T. Zair, H. Bouharb, S. Chakir, T. Alaoui, Étude de l'activité antibactérienne des huiles essentielles de Teucrium capitatium L et l'extrait de Siléne vulgaris sur différentes souches testées, Jouranal of Applied Biosciences. 82 (2014) 7481-7492. DOI References

DOI: 10.4314/jab.v82i1.16

Google Scholar

[1] S. Burt, Essential oils: Their antimicrobial properties and potential applications in foods: A review, International Journal of Food Microbiology. 94(3) (2004) 223-253

Google Scholar

[2] P.J. Delaquis, K. Stanich, B. Girard, G. Mazza, Antimicrobial activity of individual and mixed fractions of dill, cilantro, coriander and eucalyptus essential oils, International Journal of Food Microbiology. 74(1) (2002) 101-109

DOI: 10.1016/S0168-1605(01)00734-6

Google Scholar

[3] P.M. Davidson, M.E. Parish, Methods for testing the efficacy of food antimicrobials, Food Technology. 43(1) (1989) 148-155.

Google Scholar

[4] A.O. Gill, P. Delaquis, P. Russo, R.A. Holley, Evaluation of antilisterial action of cilantro oil on vacuum packed ham, International Journal of Food Microbiology. 3(1) (2002) 83-92

DOI: 10.1016/S0168-1605(01)00712-7

Google Scholar

[5] A. Mourey, N. Canillac, Anti-Listeria monocytogenes activity of essential oils components of conifers, Food Control. 13(4) (2002) 289-292

DOI: 10.1016/S0956-7135(02)00026-9

Google Scholar

[6] J. Reichling, P. Schnitzler, U. Suschke, R. Saller, Essential oils of aromatic plants with antibacterial, antifungal, antiviral, and cytotoxic properties-an overview, Forsch Komplementmed. 16 (2) (2009) 79-90

DOI: 10.1159/000207196

Google Scholar

[7] A.R. Koroch, H.R. Juliani, J.A. Zygadlo, Bioactivity of essential oils and their components, Flavours and Fragrances. Chemistry, Bioprocessing and Sustainability. Berger RG. Ed. Springer Verlag: Berlin, Germany, 2007, pp.87-115

DOI: 10.1007/978-3-540-49339-6_5

Google Scholar

[8] D. Nayak, A.P. Minz, A. Ashe, P.R. Rauta, M. Kumari, P. Chopra, B. Nayak, Synergistic combination of antioxidant, silver nanoparticles and chitosan in a nanoparticle based formulation: Characterization and cytotoxic effect on MCF-7 breas cancer cell lines. Journal of colloid and interface science, (2016) In Press. 10.016/j.jcis.2016.02.043

DOI: 10.1016/j.jcis.2016.02.043

Google Scholar

[9] J. Yi, Y. Fan, W. Yokoyama, Y. Zhang, L. Zhao, Thermal degradation and isomerization of beta-carotene in oil-in-water nanoemulsions supplemented with natural antioxidants, Journal of Agricultural and Food Chemistry, (2016) In Press

DOI: 10.1021/acs.jafc.5b05478

Google Scholar

[10] F. Frantianni, M.N.N. Ombra, A. Cozzolino, R. Riccardi, P. Spigno, P. Tremonte, R. Cppola, F. Nazzaro, Phenolic constituents, antioxidant, antimicrobial and anti-proliferaive activities of different endemic Italian varieties o garlic (Allium sativum L.), Journal of Functional Foods. 21 (2016) 240-248

DOI: 10.1016/j.jff.2015.12.019

Google Scholar

[11] G. Huang, J. Jiang, D. Dai, Antioxidative and antibacterial activity of the methanol extract of Artemisia anomala S. Moore, African Journal of Biotechnology. 7(9) (2008) 1335-1338

Google Scholar

[12] M.R.C. Raja, V. Srinivasan, S. Selvaraj, S.K. Mahapatra, Versatile and Synergistic potential of eugenol: a review, Pharmaceutica Analytica Acta. 6(5) 2015 367-372

DOI: 10.4172/2153-2435.1000367

Google Scholar

[13] F.G. Li, J.Chen, W.M. Cheng, M.F. Ji, Embrotoxicity of eugenol based on a model of embryonic stem cell test, Chinese Journal of Tissue Engineering Research, 19(19) (2015) 3017-3021

Google Scholar

[14] M. He, M. Du, M. Fa, Z. Bian, In vivo activity of eugenol against Candida albicans biofilm, Mycopathologia. 163 (2007)137-143

DOI: 10.1007/s11046-007-0097-2

Google Scholar

[15] D. Huang, B. Ou, R.L. Prior, The chemistry behind antioxidant capacity assays, Journal of Agricultural and Food Chemistry. 53(6) (2005) 1841-1856

Google Scholar

[16] R. Mahboub, F. Memmou, Antioxidant activity and kinetics studies of eugenol and 6-bromoeugenol, Natural Product Research. 29(10) (2015) 966-971

DOI: 10.1080/14786419.2014.958738

Google Scholar

[17] M. Pisano, G. Pagnan, M. Loi, M. E. Mura, M. G. Tilocca, G. Palmieri, D. Fabbri, M. A. Dettori, G. Delogu, M. Ponzoni, C. Rozzo, Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells, Molecular Cancer. 6 (2007) 1-12

DOI: 10.1186/1476-4598-6-8

Google Scholar

[18] M.E Hidalgo, C. De la Rosa, Antioxydant capcity of eugenol derivatives, Quimica Nova. 32 (2009) 1467-1470

Google Scholar

[19] G. Eyambe, L. CanaleS, B.K. Banik, Antimicrobial activity of eugenol derivatives, Heterocyclic Letters. 1(2) (2011) 154-157.

Google Scholar

[20] S. Lamy, M. Blanchette, J. Michaud-Levesque, R. Lafleur, Y. Durocher, A. Moghrabi, S. Barrette, D. Gingras, R. Béliveau, Delphinidin, a dietary anthocyanidin, inhibits vascular endothelial growth factor receptor-2 phosphorylation, Carcinogenesis. 27(5) (2006) 989-996

DOI: 10.1093/carcin/bgi279

Google Scholar

[21] Y.M. Choi, D.O. Noh, S.Y. Cho, H.J. Suh, K.M. Kim, J.M. Kim, Antioxidant and antimicrobial activities of propolis from several regions of Korea, LWT-Food Science and Technology. 39(9) (2006) 756-761

DOI: 10.1016/j.lwt.2005.05.015

Google Scholar

[22] S. Athamena, Etude quantitative des flavonoïdes des graines de Cuminum cyminum et les feuilles de Rosmarinus officinalis et l'évaluation de l'activité biologique. Thèse de Magister; Université de Batna, 2009.

Google Scholar

[23] M.C. Pibiri, Assainissement microbiologique de l'air et des systèmes de ventilation au moyen d'huiles essentielles. Thèse N° 3311, Ecole Polytechnique Fédérale de Lausanne, 2006.

DOI: 10.3940/rina.innovsail.2010.14

Google Scholar

[24] F. Haddouchi, H.A. Lazouni, A. Meziane, A. Benmansour, Etude physicochimique et microbilogique de l'huile essentielle de Thymus fontanesii Boiss et Reut, Afrique Science. 5 (2009) 246-259.

DOI: 10.4314/afsci.v5i2.61738

Google Scholar

[25] J. El Amri, Kh. Elbadaoui, T. Zair, H. Bouharb, S. Chakir, T. Alaoui, Étude de l'activité antibactérienne des huiles essentielles de Teucrium capitatium L et l'extrait de Siléne vulgaris sur différentes souches testées, Journal of Applied Biosciences. 82 (2014) 7481-7492

DOI: 10.4314/jab.v82i1.15

Google Scholar