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

Lipids in Health and Disease

Youssef Gargouri²  Sami Sayadi¹  Dhafer Laouini³  Mohamed Bouaziz¹  Rabiaa Manel Sghair³  Imen Aissa¹ 

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

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

Others  :  1160371
DOI  :  10.1186/1476-511X-11-13

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

【 摘 要 】

Background

Preparation of tyrosyl lipophilic derivatives was carried out as a response to the food, cosmetic and pharmaceutical industries' increasing demand for new lipophilic antioxidants.

Results

A large series of tyrosyl esters (TyC₂ to TyC_18:1) 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.

Conclusion

These 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】

   
2012 Aissa et al; licensee BioMed Central Ltd.

【 图 表 】

Figure 1.

Figure 2.

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