Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
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来自三叶草的三个新的具有四个羟基的相邻双四氢呋喃乙酰基。
DOI：
10.1021/np9605145
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发表时间：
1996
期刊：
影响因子：
--
通讯作者：
McLaughlin,JL
中科院分区：
文献类型：
--
作者：
He,K;Shi,G;Zhao,GX;Zeng,L;Ye,Q;Schwedler,JT;Wood,KV;McLaughlin,JL
从番荔枝属植物Asiminatriloba的茎皮中分离得到3个新的含4个羟基的邻双四氢呋喃环番荔枝内酯类化合物：bullatetrocin（1）、10-hydroxyasimicin（2）和10-hydroxytrilobacin（3），根据化学和光谱数据确定了它们的结构。通过将2和3分别转化为它们的酮内酯异构体2，4-cis/trans 10-hydroxyasimicinones和2，4-cis/trans 10-hydroxytrilobacinones，确定了C-10羟基位置的绝对立体化学。新化合物对盐水虾幼虫和六个人的实体瘤细胞系的生物活性的报告，和三羟基化和四羟基化的acetogenins之间的结构-活性关系进行了讨论。除1 −3外，还首次从该物种中分离到了阿替曲辛A、2，4-cis/trans-Aetrocin A-ones、annonacin和annonacin A。
Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark ofAsiminatriloba.Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting2and3to their ketolactone isomers, 2,4-cis/trans10-hydroxyasimicinones and 2,4-cis/trans10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure−activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to1−3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.