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从天然齐墩果酸和马栗树皮酸合成新的抗菌酯。

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

机构信息

Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité. Equipe: Chimie Médicinale et Produits Naturels, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisia.

UR13AGR09, Production Horticole Intégrée au Centre Est Tunisien, Centre Régional des Recherches en Horticulture et Agriculture Biologique de Chott-Mariem, Université de Sousse, 4042 Chott-Mariem, Tunisia.

出版信息

Food Chem. 2015 Sep 15;183:8-17. doi: 10.1016/j.foodchem.2015.03.018. Epub 2015 Mar 14.

DOI:10.1016/j.foodchem.2015.03.018
PMID:25863603
Abstract

In this article, we report an effective procedure for the selective isolation of oleanolic acid 1 and maslinic acid 2 (3.4 and 8.5mg/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 Enterococcus faecalis and two Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa (MICs within a range of 5-25μg/mL). The fungus Penicillium italicum was found to be the most sensitive to both sulfur derivatives: (3β)-3-((thiophene-2-carbonyl)oxy)-olean-12-en-28-oic acid (1a) (IZ=22mm) and (2α,3β-2,3-bis((thiophene-2-carbonyl)oxy)olean-12-en-28-oic acid (2a) (IZ=24mm).

摘要

在本文中,我们报告了一种从橄榄渣(Olea europaea L.)中通过超声浴选择性分离齐墩果酸 1 和马司里酸 2(分别为 3.4 和 8.5mg/g DW)的有效方法,以及一系列新型三萜酸酯的合成。这些化合物通过其光谱数据进行了表征,并评估了它们的抗菌活性。在所测试的化合物中,含有硫和氯原子的化合物具有抗菌活性。它们对两种革兰氏阳性菌金黄色葡萄球菌和粪肠球菌以及两种革兰氏阴性菌大肠杆菌和铜绿假单胞菌表现出活性(MIC 范围在 5-25μg/mL 之间)。真菌 Penicillium italicum 对两种硫衍生物均表现出最高的敏感性:(3β)-3-(噻吩-2-羰基)氧基-齐墩-12-烯-28-酸(1a)(IZ=22mm)和(2α,3β-2,3-二(噻吩-2-羰基)氧基-齐墩-12-烯-28-酸(2a)(IZ=24mm)。

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