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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Phytochemical Study: Molecular Docking of Eugenol Derivatives as Antioxidant and Antimicrobial Agents

Author(s): Achraf Abdou*, Sabrine Idouaarame, Mohammed Salah, Nabil Nor, Soukaina Zahm, Abdelhakim El Makssoudi, Noureddine Mazoir, Ahmed Benharref, Abdelmjid Dari, Jamal Jamal Eddine, Mohamed Blaghen and Mohamed Dakir

Volume 19, Issue 9, 2022

Published on: 15 February, 2022

Page: [774 - 783] Pages: 10

DOI: 10.2174/1570178619666220111112125

Price: $65

Abstract

Eugenol (4-allyl-2-methoxyphenol) is a natural phenolic compound present in certain aromatic plants; however, it is generally extracted from the essential oil of Eugenia caryophyllata (Syzygiumaromaticum) (L.) Merr. and L.M. Perry. This bioactive natural compound has generated considerable biological interest with well-known antimicrobial and antioxidant actions. This study aimed at evaluating eugenol derivatives as antimicrobial and antioxidant agents with the aid of molecular dynamic simulation. The starting material was extracted from cloves using hydrodistillation. Two eugenol derivatives, acetyleugenol (4-allyl-2-methoxyphenylacetate) and epoxyeugenol 4-(2,3- Epoxypropyl)-2-methoxyphenol, were prepared and tested against two strains Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). The results have revealed that the three compounds (eugenol, acetyleugenol, and epoxyeugenol) possess important potentials for inhibition against E. coli and S. aureus. The antioxidant activity of eugenol derivatives was evaluated by reacting with DPPH (1,1- diphenyl-2-picrylhydrazyl), and it was reported that the epoxyeugenol was the most active compound. The molecular docking scores of three compounds and the amino acids in the active site pockets of the selected proteins of the two bacteria have approved and explained the biological experimental outcomes.

Keywords: Phytochemical study, eugenol, semisynthesis, antioxidant activity, antibacterial activity, molecular docking.

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[1]
Yeum, K.J.; Aldini, G.; Chung, H.Y.; Krinsky, N.I.; Russell, R.M. J. Nutr., 2003, 133(8), 2688-2691.
[http://dx.doi.org/10.1093/jn/133.8.2688] [PMID: 12888659]
[2]
Singh, R.S.G.; Negi, P.S.; Radha, C. J. Funct. Foods, 2013, 5, 1883-1891.
[http://dx.doi.org/10.1016/j.jff.2013.09.009]
[3]
Leong, L.P.; Shui, G. Food Chem., 2002, 76, 69-75.
[http://dx.doi.org/10.1016/S0308-8146(01)00251-5]
[4]
Benmeddour, Z.; Mehinagic, E.; Le Meurlay, D.; Louaileche, H. J. Funct. Foods, 2013, 5, 346-354.
[http://dx.doi.org/10.1016/j.jff.2012.11.005]
[5]
Seneviratne, K.N.; Kotuwegedara, R.T. Food Sci. Technol. Int., 2009, 15, 419-425.
[http://dx.doi.org/10.1177/1082013209352718]
[6]
Zhishen, J.; Mengcheng, T.; Jianming, W. Food Chem., 1999, 64, 555-559.
[http://dx.doi.org/10.1016/S0308-8146(98)00102-2]
[7]
Bendary, E.; Francis, R.R.; Ali, H.M.G.; Sarwat, M.I.; El Hady, S. Ann. Agric. Sci., 2013, 58, 173-181.
[http://dx.doi.org/10.1016/j.aoas.2013.07.002]
[8]
Zhang, Y.; Wang, Y.; Zhu, X.; Cao, P.; Wei, S.; Lu, Y. Microb. Pathog., 2017, 113, 396-402.
[http://dx.doi.org/10.1016/j.micpath.2017.10.054] [PMID: 29101062]
[9]
Pramod, K.; Ansari, S.H. Ali. J. Nat. Prod. Commun., 2010, 5(12), 1999-2006.
[http://dx.doi.org/10.1177/1934578X1000501236] [PMID: 21299140]
[10]
Gülçin İ. J. Med. Food, 2011, 14(9), 975-985.
[http://dx.doi.org/10.1089/jmf.2010.0197] [PMID: 21554120]
[11]
Daniel, A.N.; Sartoretto, S.M.; Schmidt, G.; Caparroz-Assef, S.M.; Bersani-Amado, C.A.; Cuman, R.K.N. Brazilian J. Pharmacogn., 2009, 19, 212-217.
[http://dx.doi.org/10.1590/S0102-695X2009000200006]
[12]
Pinto, E.; Vale-Silva, L.; Cavaleiro, C.; Salgueiro, L. J. Med. Microbiol., 2009, 58(Pt 11), 1454-1462.
[http://dx.doi.org/10.1099/jmm.0.010538-0] [PMID: 19589904]
[13]
Lahlou, S.; Figueiredo, A.F.; Magalhães, P.J.C.; Leal-Cardoso, J.H.; Gloria, P.D. Life Sci., 2004, 74(19), 2401-2412.
[http://dx.doi.org/10.1016/j.lfs.2003.09.063] [PMID: 14998717]
[14]
Wang, C.; Fan, Y. J. Sci. Food Agric., 2014, 94(4), 677-682.
[http://dx.doi.org/10.1002/jsfa.6304] [PMID: 23852671]
[15]
Guenette, S.A.; Beaudry, F.; Marier, J.F.; Vachon, P. J. Vet. Pharmacol. Ther., 2006, 29(4), 265-270.
[http://dx.doi.org/10.1111/j.1365-2885.2006.00740.x] [PMID: 16846463]
[16]
Machado, M.; Dinis, A.M.; Salgueiro, L.; Custódio, J.B.A.; Cavaleiro, C.; Sousa, M.C. Exp. Parasitol., 2011, 127(4), 732-739.
[http://dx.doi.org/10.1016/j.exppara.2011.01.011] [PMID: 21272580]
[17]
Zheng, G.Q.; Kenney, P.M.; Lam, L.K.T. J. Nat. Prod., 1992, 55(7), 999-1003.
[http://dx.doi.org/10.1021/np50085a029] [PMID: 1402962]
[18]
Abdou, A.; Elmakssoudi, A.; El Amrani, A.; Jamal Eddine, J.; Dakir, M. Med. Chem. Res., 2021, 30, 1011-1030.
[http://dx.doi.org/10.1007/s00044-021-02712-x]
[19]
Ginting, M.; Surbakti, D.; Triana, N. J. Chem. Nat. Resour., 2019, 01, 1-9.
[20]
Chaieb, K.; Hajlaoui, H.; Zmantar, T.; Kahla-Nakbi, A.B.; Rouabhia, M.; Mahdouani, K.; Bakhrouf, A. Phytother. Res., 2007, 21(6), 501-506.
[http://dx.doi.org/10.1002/ptr.2124] [PMID: 17380552]
[21]
Da Silva, F.F.M.; Monte, F.J.Q.; De Lemos, T.L.G.; Do Nascimento, P.G.G.; De Medeiros Costa, A.K.; De Paiva, L.M.M. Chem. Cent. J., 2018, 12, 1-9.
[http://dx.doi.org/10.1186/s13065-017-0364-3] [PMID: 29318401]
[22]
Marchese, A.; Barbieri, R.; Coppo, E.; Orhan, I.E.; Daglia, M.; Nabavi, S.M.; Ajami, M. Crit. Rev. Microbiol., 2017, 43, 668-689.
[http://dx.doi.org/10.1080/1040841X.2017.1295225] [PMID: 28346030]
[23]
Abdulhamid, A.; Awad, T.A.; Ahmed, A.E. Koua; Ismail, A.M. Microbiol. Res. (Pavia), 2021, 12, 1-15.
[http://dx.doi.org/10.3390/microbiolres12010001]
[24]
Bezerra, D.P.; Militão, G.C.G.; De Morais, M.C.; De Sousa, D.P. Nutrients, 2017, 12, 1-15.
[25]
Lipinski, B. Oxid. Med. Cell. Longev., 2011, 2011
[26]
Blakeley, D.; Sykes, D.A.; Ensor, P.; Bertran, E.; Aston, P.J.; Charlton, S.J. Br. J. Pharmacol., 2015, 172(21), 5037-5049.
[http://dx.doi.org/10.1111/bph.13263] [PMID: 26211929]
[27]
Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Lebensm. Wiss. Technol., 1995, 28, 25-30.
[http://dx.doi.org/10.1016/S0023-6438(95)80008-5]
[28]
Brighente, I.M.C.; Dias, M.; Verdi, L.G.; Pizzolatti, M.G. Pharm. Biol., 2007, 45, 156-161.
[http://dx.doi.org/10.1080/13880200601113131]
[29]
De Almeida, A.L.; Caleffi-Ferracioli, K.R.; De Almeida, A.L.; Caleffi-Ferracioli, K.R.; De, L. Scodro, R.B.; Baldin, V.P.; Montaholi, D.C.; Spricigo, L.F.; Nakamura-Vasconcelos, S.S.; Hegeto, L.A.; Sampiron, E.G.; Costacurta, G.F.; Yamazaki, D.A.; Gauze, G.D.F.; Siqueira, V.L.; Cardoso, R. Future Microbiol., 2019, 14, 331-344.
[http://dx.doi.org/10.2217/fmb-2018-0333] [PMID: 30757916]
[30]
Eyambe, G.; Canales, L.; Banik, B.K. Heterocycl. Lett., 2011, 1, 2231-3087.
[31]
Absorption, distribution, metabolism and elimination and druglikeness preadmet. Available from: preadmet.bmdrc.kr/toxicity (Accessed on August 3, 2021).
[32]
Garwin, J.L.; Klages, A.L.; Cronan, J.E., Jr J. Biol. Chem., 1980, 255(8), 3263-3265.
[http://dx.doi.org/10.1016/S0021-9258(19)85692-2] [PMID: 6988423]
[33]
Price, A.C.; Choi, K.H.; Heath, R.J.; Li, Z.; White, S.W.; Rock, C.O. J. Biol. Chem., 2001, 276(9), 6551-6559.
[http://dx.doi.org/10.1074/jbc.M007101200] [PMID: 11050088]
[34]
Discovery Studio software 3ds. Available from: 3ds.com/products-services/biovia/ (Accessed August 1, 2021).
[35]
Huang, X.; Yang, J.; Zhu, Y. J. Mol. Model., 2013, 19(3), 1355-1367.
[http://dx.doi.org/10.1007/s00894-012-1695-6] [PMID: 23192355]
[36]
El-hachem, N.; Haibe-kains, B.; Khalil, A.; Kobeissy, F.H.; Nemer, G. Neuroproteomics Methods and Protocols; methods in molecular biology; Springer Science, B.M., Ed., 2017, 1598, p. 391-403.
[http://dx.doi.org/10.1007/978-1-4939-6952-4_20]
[37]
Lee, J.Y.; Jeong, K.W.; Lee, J.U.; Kang, D.I.; Kim, Y. Bioorg. Med. Chem., 2009, 17(4), 1506-1513.
[http://dx.doi.org/10.1016/j.bmc.2009.01.004] [PMID: 19185501]
[38]
Chhibber, M.; Kumar, G.; Parasuraman, P.; Ramya, T.N.C.; Surolia, N.; Surolia, A. Bioorg. Med. Chem., 2006, 14(23), 8086-8098.
[http://dx.doi.org/10.1016/j.bmc.2006.07.034] [PMID: 16893651]
[39]
Luirink, J.; ten Hagen-Jongman, C.M.; Van der Weijden, C.C.; Oudega, B.; High, S.; Dobberstein, B.; Kusters, R. EMBO J., 1994, 13, 2289-2296.
[40]
Kempf, G.; Stjepanovic, G.; Sloan, J.; Hendricks, A.; Lapouge, K.; Sinning, I. Structure, 2018, 26(11), 1440-1450.
[http://dx.doi.org/10.1016/j.str.2018.07.008] [PMID: 30146170]
[41]
Mireku, S.A.; Ruetz, M.; Zhou, T.; Korkhov, V.M.; Kräutler, B.; Locher, K.P. Sci. Rep., 2017, 7, 1-11.
[http://dx.doi.org/10.1038/s41598-016-0028-x] [PMID: 28127051]
[42]
Dennis, M.L.; Lee, M.D.; Harjani, J.R.; Ahmed, M.; DeBono, A.J.; Pitcher, N.P.; Wang, Z.C.; Chhabra, S.; Barlow, N.; Rahmani, R.; Cleary, B.; Dolezal, O.; Hattarki, M.; Aurelio, L.; Shonberg, J.; Graham, B.; Peat, T.S.; Baell, J.B.; Swarbrick, J.D. Chemistry, 2018, 24(8), 1922-1930.
[http://dx.doi.org/10.1002/chem.201704730] [PMID: 29171692]
[43]
Reyes-Lamothe, R.; Sherratt, D.J.; Leake, M.C. Science, 2010, 328(5977), 498-501.
[http://dx.doi.org/10.1126/science.1185757] [PMID: 20413500]
[44]
Banach-Orlowska, M.; Fijalkowska, I.J.; Schaaper, R.M.; Jonczyk, P. Mol. Microbiol., 2005, 58(1), 61-70.
[http://dx.doi.org/10.1111/j.1365-2958.2005.04805.x] [PMID: 16164549]
[45]
Jergic, S.; Horan, N.P.; Elshenawy, M.M.; Mason, C.E.; Urathamakul, T.; Ozawa, K.; Robinson, A.; Goudsmits, J.M.H.; Wang, Y.; Pan, X.; Beck, J.L.; van Oijen, A.M.; Huber, T.; Hamdan, S.M.; Dixon, N.E. EMBO J., 2013, 32(9), 1322-1333.
[http://dx.doi.org/10.1038/emboj.2012.347] [PMID: 23435564]
[46]
Cacciatore, G.; Petz, M.; Rachid, S.; Hakenbeck, R.; Bergwerff, A.A. Anal. Chim. Acta, 2004, 520, 105-115.
[http://dx.doi.org/10.1016/j.aca.2004.06.060]
[47]
Zoraghi, R.; Worrall, L.; See, R.H.; Strangman, W.; Popplewell, W.L.; Gong, H.; Samaai, T.; Swayze, R.D.; Kaur, S.; Vuckovic, M.; Finlay, B.B.; Brunham, R.C.; McMaster, W.R.; Davies-Coleman, M.T.; Strynadka, N.C.; Andersen, R.J.; Reiner, N.E.; Reiner, N.E. J. Biol. Chem., 2011, 286(52), 44716-44725.
[http://dx.doi.org/10.1074/jbc.M111.289033] [PMID: 22030393]
[48]
Walters, W.P. Expert Opin. Drug Discov., 2012, 7(2), 99-107.
[http://dx.doi.org/10.1517/17460441.2012.648612] [PMID: 22468912]

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