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曼宋酮G的烯丙基醚和异戊烯基醚,新型潜在半合成抗菌剂。

Allyl and prenyl ethers of mansonone G, new potential semisynthetic antibacterial agents.

作者信息

Hairani Rita, Mongkol Rachsawan, Chavasiri Warinthorn

机构信息

Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.

Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.

出版信息

Bioorg Med Chem Lett. 2016 Nov 1;26(21):5300-5303. doi: 10.1016/j.bmcl.2016.09.044. Epub 2016 Sep 17.

Abstract

Four natural 1,2-naphthoquinones: mansonones C, E, G, and H were isolated from the dichloromethane extract of Mansonia gagei Drumm. heartwoods. Mansonone G was further converted to eight ether and four ester analogues. The structures of mansonones and the analogues were well-confirmed by spectroscopic techniques. All compounds were evaluated for their antibacterial activity against Gram-positive and negative bacteria. Further modification of mansonone G furnished certain analogues displaying better activity than natural mansonones. Particularly, allyl and prenyl ethers of mansonone G exhibited better activity against Staphylococcus aureus with MIC sixty-four times better than their natural compound.

摘要

从毛叶曼森树(Mansonia gagei Drumm.)心材的二氯甲烷提取物中分离出四种天然的1,2-萘醌:曼宋酮C、E、G和H。曼宋酮G进一步转化为八个醚类和四个酯类类似物。通过光谱技术对曼宋酮及其类似物的结构进行了充分确证。对所有化合物针对革兰氏阳性和阴性细菌的抗菌活性进行了评估。对曼宋酮G的进一步修饰得到了某些活性优于天然曼宋酮的类似物。特别是,曼宋酮G的烯丙基醚和异戊烯基醚对金黄色葡萄球菌表现出更好的活性,其最低抑菌浓度(MIC)比其天然化合物好64倍。

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