Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor
Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor
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Asperversiamides，来自海洋衍生真菌 Aspergillus versicolor 的线性融合异戊二烯化吲哚生物碱
DOI：
10.1021/acs.joc.8b01087
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发表时间：
2018-08-03
影响因子：
3.6
通讯作者：
Zhang, Yonghui
中科院分区：
文献类型：
--
作者：
Li, Huaqiang;Sun, Weiguang;Zhang, Yonghui
从海洋真菌杂色曲霉（Aspergillus versicolor）中分离得到8个异戊烯化吲哚生物碱，其中1个为吡喃并[3，2-f]吲哚结构单元。这些化合物的结构和绝对构型通过广泛的光谱分析，单晶X-射线衍射，电子圆二色性（ECD）计算，和旋光度（OR）计算阐明。对异三七酰胺B C-21位的相对构型进行了修正，并建立了一种新的方法来初步判断螺双环[2.2.2]二氮杂辛烷型吲哚生物碱的双环[2.2.2]二氮杂辛烷部分的相对构型是顺式还是反式。对分离的化合物的抗炎活性进行了测试，在这些化合物中，7个化合物显示出对iNOS的有效抑制作用，IC 50值为5.39 μ M。
Asperversiamides A-H (1-8), eight linearly fused prenylated indole alkaloids featuring an unusual pyrano[3,2-f]indole unit, were isolated from the marine-derived fungus Aspergillus versicolor. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and optical rotation (OR) calculations. The relative configuration of C-21 of iso-notoamide B was herein revised, and a new methodology for preliminarily determining if the relative configuration of the bicyclo[2.2.2] diazaoctane moiety of a spirobicyclo[2.2.2]diazaoctane-type indole alkaloid is syn or anti was developed. The anti-inflammatory activities of the isolated compounds were all tested, and of these compounds, 7 exhibited a potent inhibitory effect against iNOS with an IC50 value of 5.39 mu M.