5-Alkyl-1,2,3,4-tetrahydroquinolines, new membrane-interacting lipophilic metabolites produced by combined culture of Streptomyces nigrescens and Tsukamurella pulmonis.
5-Alkyl-1,2,3,4-tetrahydroquinolines, new membrane-interacting lipophilic metabolites produced by combined culture of Streptomyces nigrescens and Tsukamurella pulmonis.
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DOI：
10.1021/acs.orglett.5b00607
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发表时间：
2015-03
期刊：
影响因子：
5.2
通讯作者：
Ryosuke Sugiyama;S. Nishimura;T. Ozaki;Shumpei Asamizu;H. Onaka;H. Kakeya
中科院分区：
文献类型：
--
作者：
Ryosuke Sugiyama;S. Nishimura;T. Ozaki;Shumpei Asamizu;H. Onaka;H. Kakeya
从变黑链霉菌HEK 616和肺冢丘菌TP-B 0596的混合培养物中分离得到8个新的5-烷基-1，2，3，4-四氢喹啉（5aTHQs）。通过光谱分析和全合成方法确定了化合物的结构和绝对构型。5aTHQs抑制野生型裂殖酵母的生长，而仅微弱地抑制几种合成早熟麦角固醇的突变株的生长。这些结果表明5aTHQ是可能靶向细胞膜的新型抗真菌药物。
Eight novel 5-alkyl-1,2,3,4-tetrahydroquinolines (5aTHQs) bearing different side chains have been isolated from a combined culture of Streptomyces nigrescens HEK616 and Tsukamurella pulmonis TP-B0596. The chemical structures including the absolute configuration were elucidated by spectroscopic analysis and total synthesis. 5aTHQs inhibited the growth of wild-type fission yeast while only weakly inhibiting the growth of several mutant strains synthesizing premature ergosterol. These results demonstrate that 5aTHQs are novel antifungals that may target cell membranes.