Enzymatic synthesis of 1,3-dihydroxyphenylacetoyl-sn-glycerol: Optimization by response surface methodology and evaluation of its antioxidant and antibacterial activities

被引:6
作者
Kharrat, Nadia [1 ]
Aissa, Imen [1 ]
Dgachi, Youssef [2 ]
Aloui, Fatma [1 ]
Chabchoub, Fakher [2 ]
Bouaziz, Mohamed [3 ]
Gargouri, Youssef [1 ]
机构
[1] Univ Sfax, Lab Biochem & Enzymat Engn Lipases, ENIS, POB 1173, Sfax 3038, Tunisia
[2] Univ Sfax, Fac Sci Sfax, Lab Appl Chem Heterocycles Lipids & Polymers, POB 802, Sfax 3000, Tunisia
[3] Univ Sfax, ENIS, Electrochem Environm Lab, POB 1173, Sfax 3038, Tunisia
关键词
Biocatalysis; Esterification; 1,3-Dihydroxyphenylacetoyl-sn-glycerol; Structural identification; Antibacterial and antioxidant activities; OLIVE OIL WASTE; CATALYZED SYNTHESIS; FERULIC ACID; GLYCEROL; DIACYLGLYCEROLS; HYDROXYTYROSOL; DERIVATIVES; ESTERASE;
D O I
10.1016/j.bioorg.2017.10.011
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this study, the enzymatic synthesis of phenylacetoyl glycerol ester was carried out as a response to the increasing consumer demand for natural compounds. 1,3-dihydroxyphenylacetoyl-sn-Glycerol (1,3-di-HPA-Gly), labeled as "natural" compound with interesting biological properties, has been successfully synthesized for the first time in good yield by a direct esterification of glycerol (Gly) with p-hydroxyphenylacetic acid (p-HPA) using immobilized Candida antarctica lipase as a biocatalyst. Spectroscopic analyses of purified esters showed that the glycerol was mono-or di-esterified on the primary hydroxyl group. These compounds were evaluated for their antioxidant activity using two different tests. The glycerol di-esters (1,3-di-HPA-Gly) showed a higher antiradical capacity than that of the butyl hydroxytoluene. Furthermore, compared to the p-HPA, synthesized ester (1,3-di-HPA-Gly) exhibited the most antibacterial effect mainly against Gram + bacteria. Among synthesized esters the 1,3-di-HPA-Gly was most effective as antioxidant and antibacterial compound. These findings could be the basis for a further exploitation of the new compound, 1,3-di-HPA-Gly, as antioxidant and antibacterial active ingredient in the cosmetic and pharmaceutical fields. (C) 2017 Published by Elsevier Inc.
引用
收藏
页码:347 / 356
页数:10
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