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从抑磷菌中分离甲基硫代巴豆苷。

Isolation of Methyl Troposulfenin from Phaeobacter inhibens.

机构信息

Department of Biotechnology and Biomedicine , Technical University of Denmark , Søltofts Plads 221 , Kongens Lyngby , 2800 , Denmark.

Department of Chemistry , Technical University of Denmark , Kemitorvet 207 , Kongens Lyngby , 2800 , Denmark.

出版信息

J Nat Prod. 2019 May 24;82(5):1387-1390. doi: 10.1021/acs.jnatprod.8b01097. Epub 2019 Apr 12.

DOI:10.1021/acs.jnatprod.8b01097
PMID:30978024
Abstract

An S-methylated analogue of tropodithietic acid (TDA, 1), methyl troposulfenin (2), was isolated from the marine alphaproteobacterium Phaeobacter inhibens. The structure was elucidated by NMR and HRMS. Its inhibitory effect against the fish pathogen Vibrio anguillarum was 4-fold to 100-fold lower than that of the known antibacterial compound TDA. Methyl troposulfenin lacks the acidic proton of TDA, indicating that the methylation turns the potent antibacterial TDA into an inactive compound, and thereby, this analysis supports the proposed mode of action of TDA.

摘要

从海洋α变形菌抑制噬纤维菌(Phaeobacter inhibens)中分离到硫代二丙酸(TDA,1)的 S-甲基类似物甲基硫代巴豆酸(2)。通过 NMR 和 HRMS 确定了其结构。其对鱼类病原体鳗弧菌的抑制作用比已知抗菌化合物 TDA 低 4 至 100 倍。甲基硫代巴豆酸缺乏 TDA 的酸性质子,这表明甲基化将强效抗菌 TDA 转化为无活性化合物,因此,该分析支持 TDA 的拟议作用模式。

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