Eugenol derivatives as potential anti-oxidants: is phenolic hydroxyl necessary to obtain an effect?

Journal of Pharmacy and Pharmacology - Tập 66 Số 5 - Trang 733-746 - 2014
Marília d' Avila Farias1, Pathise Souto Oliveira1, Filipe S. Pereira‐Dutra2, Thiely Jacobsen Fernandes2, Cláudio M. P. Pereira1, Simone Quintana de Oliveira3, Francieli Moro Stefanello1, Claiton Leoneti Lencina2, Alethéa Gatto Barschak4,1
1Programa de Pós-Graduação em Bioquímica e Bioprospecção, UFPel, Campus Universitário s/n, Porto Alegre, RS, Brazil
2Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Pelotas, RS, Brazil
3Centro de Ciências da Saúde, Departamento de Ciências Farmacêuticas, UFSC, Campus Universitário, Florianópolis, SC, Brazil
4Departamento de Ciências Básicas da Saúde, Universidade Federal de Ciências da Saúde de Porto Alegre, Porto Alegre, RS, Brazil

Tóm tắt

Abstract Objectives Eugenol, obtained from clove oil (Eugenia caryophyllata), possess several biological activities. It is anti-inflammatory, analgesic, anaesthesic, antipyretic, antiplatelet, anti-anaphylactic, anticonvulsant, anti-oxidant, antibacterial, antidepressant, antifungal and antiviral. The anti-oxidant activity of eugenol have already been proven. From this perspective testing, a series of planned structural derivatives of eugenol were screened to perform structural optimization and consequent increase of the potency of these biological activities. Methods In an attempt to increase structural variability, 16 compounds were synthesized by acylation and alkylation of the phenolic hydroxyl group. Anti-oxidant activity capacity was based on the capture of DPPH radical (2,2-diphenyl-1-picryl-hydrazyl), ABTS radical 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid), measure of TBARS (thiobarbituric acid-reactive species), total sulfhydryl and carbonyl content (eugenol derivatives final concentrations range from 50 to 200 μm). Key findings Four derivatives presented an efficient concentration to decrease 50% of the DPPH radical (EC50) < 100 μm, which has a good potential as a free-radical scavenger. Three of these compounds also showed reduction of ABTS radical. Eugenol derivatives presenting alkyl or aryl (alkylic or arylic) groups substituting hydroxyl 1 of eugenol were effective in reducing lipid peroxidation, protein oxidative damage by carbonyl formation and increase total thiol content in cerebral cortex homogenates. In liver, the eugenol derivatives evaluated had no effect. Conclusions Our results suggest that these molecules are promising anti-oxidants agents.

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Thông tin xuất bản

Journal of Pharmacy and Pharmacology

Tập 66 Số 5

733-746

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