Semi-synthesis of new antimicrobial esters from the natural oleanolic and maslinic acids

被引：46

作者：

Chouaib, Karim ^{[1
]}

Hichri, Faycal ^{[1
]}

Nguir, Asma ^{[1
]}

Daami-Remadi, Majda ^{[2
]}

Elie, Nicolas ^{[3
]}

Touboul, David ^{[3
]}

Ben Jannet, Hichem ^{[1
]}

Hamza, M'hamed Ali ^{[1
]}

机构：

[1] Univ Monastir, Fac Sci Monastir, Equipe Chim Med & Prod Nat, Lab Chim Heterocycl Prod Nat & React,Dept Chim, Monastir 5019, Tunisia

[2] Univ Sousse, Ctr Reg Rech Hort & Agr Biol Chott Mariem, Prod Horticole Integree Ctr Est Tunisien, UR13AGR09, Chott Mariem 4042, Tunisia

[3] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

来源：

FOOD CHEMISTRY | 2015年 / 183卷

关键词：

Olea europaea; Oleanolic acid; Maslinic acid; Pentacyclic triterpenoids esters; Antibacterial activity; Antifungal activity; ULTRASOUND-ASSISTED EXTRACTION; PENTACYCLIC TRITERPENOIDS; ANTIBACTERIAL ACTIVITIES; ANTIBIOTIC-RESISTANCE; DERIVATIVES; OPTIMIZATION; ANTIOXIDANT;

D O I：

10.1016/j.foodchem.2015.03.018

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

In this article, we report an effective procedure for the selective isolation of oleanolic acid 1 and maslinic acid 2(3.4 and 8.5 mg/g DW, respectively) from pomace olive (Olea europaea L.) using an ultrasonic bath, and the synthesis of a series of new triterpenic acid esters. The compounds were characterized by their spectral data and were evaluated for their antimicrobial activity. Among the compounds tested, those having sulfur and chlorine atoms were found to be antibacterial. They showed activity against two Gram-positive bacteria Staphylococcus aureus and Entero coccus faecalis and two Gram-negative bacteria Escherichia colt and Pseudomonas aeruginosa (MICs within a range of 5-25 mu g/mL). The fungus Penicillium italicum was found to be the most sensitive to both sulfur derivatives: (3 beta)-3-((thiophene-2-carbonyl)oxy)-olean-12-en-28-oic acid (1a) (IZ = 22 mm) and (2 alpha,3 beta-2,3-bis((thiophene-2-carbonyl)oxy)olean-12-en-28-oic acid (2a) (IZ = 24 mm). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8 / 17

页数：10

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