Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities

Lipids in Health and Disease

Research

Dhafer Laouini¹  Rabiaa Manel Sghair¹  Youssef Gargouri²  Imen Aissa³  Sami Sayadi⁴  Mohamed Bouaziz⁴ 

[1] Groupe Immunobiologie des Leishmanioses, Labratoire de Transmission, Contrôle et Immunobiologie des Infections (LTCII), Institut Pasteur de Tunis, 13, B.P 74, place Pasteur, 1002, Tunis-Belvédère, Tunisie;Laboratoire de Biochimie et de Génie Enzymatique des Lipases, Ecole Nationale d'Ingénieurs de Sfax (ENIS). Route de Soukra, Université de Sfax, BP 1173, 3038, Sfax, Tunisie;Laboratoire de Biochimie et de Génie Enzymatique des Lipases, Ecole Nationale d'Ingénieurs de Sfax (ENIS). Route de Soukra, Université de Sfax, BP 1173, 3038, Sfax, Tunisie;Laboratoire des Bioprocédés, Centre de Biotechnologie de Sfax (CBS), Université de Sfax, BP 1177, 3018, Sfax, Tunisie;Laboratoire des Bioprocédés, Centre de Biotechnologie de Sfax (CBS), Université de Sfax, BP 1177, 3018, Sfax, Tunisie;

关键词: Tyrosol;    antioxidant;    antimicrobial activity;    leishmanicidal activity;   

DOI  :  10.1186/1476-511X-11-13

 received in 2011-12-16, accepted in 2012-01-20,  发布年份 2012

来源: Springer

【 摘 要 】

BackgroundPreparation of tyrosyl lipophilic derivatives was carried out as a response to the food, cosmetic and pharmaceutical industries' increasing demand for new lipophilic antioxidants.ResultsA large series of tyrosyl esters (TyC2 to TyC18:1) with increasing lipophilicity was synthesized in a good yield using lipase from Candida antarctica (Novozyme 435). Spectroscopic analyses of purified esters showed that the tyrosol was esterified on the primary hydroxyl group. Synthetized compounds were evaluated for either their antimicrobial activity, by both diffusion well and minimal inhibition concentration (MIC) methods, or their antileishmanial activity against Leishmania major and Leishmania infantum parasite species.Among all the tested compounds, our results showed that only TyC8, TyC10 and TyC12 exhibited antibacterial and antileishmanial activities. When MIC and IC50 values were plotted against the acyl chain length of each tyrosyl derivative, TyC10 showed a parabolic shape with a minimum value. This nonlinear dependency with the increase of the chain length indicates that biological activities are probably associated to the surfactant effectiveness of lipophilic derivatives.ConclusionThese results open up potential applications to use medium tyrosyl derivatives surfactants, antioxidants, antimicrobial and antileishmanial compounds in cosmetic, food and pharmaceutical industries.

【 授权许可】

Unknown   
© Aissa et al; licensee BioMed Central Ltd. 2012. This article is published under license to BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.