Chemical Constituents from Aphanamixis grandifolia
Chemical Constituents from Aphanamixis grandifolia
复制标题
大叶丝豆藤的化学成分
DOI：
10.1248/cpb.58.1431
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发表时间：
2010-11-01
影响因子：
1.7
通讯作者：
Gao, Kun
中科院分区：
文献类型：
--
作者：
Liu, Quan;Chen, Chao-Jun;Gao, Kun
（23 E）-25-甲基环阿耳茨-23-烯-3 β-醇（1），一种具有31个碳原子的不寻常骨架的环阿耳茨烷型三萜，（17 E）-环阿耳茨-17，26-二烯-3 β-醇（2），一种新的环阿耳茨烷型三萜，另外两个新化合物4 R-羟基-4-（9 S-羟基-12-甲基己-6-基）-3-甲基环己-2-烯酮（6）和7-羟基-5-甲基环己-2-烯酮（6）。（2 ′-羟基-4 ′，5 ′-二甲氧基苯基）-2-甲氧基-6-甲基-1，4-萘醌（7）和3个已知的环阿替-3 β-醇三萜（3-5）从大叶星芹（Aphanamixis grandifolia）的地上部分中分离得到。化合物1的结构经X-射线单晶衍射证实。通过圆二色性（CD）和辅助手性α-甲氧基-α-三氟甲基苯乙酸（MTPA）衍生物，确定化合物6的两个碳立体中心的绝对构型为4 R，9 S。化合物3对HL-60、Hep G2和HeLa细胞有明显的细胞毒作用，化合物1、2、5、6和7对HL-60、Hep G2和HeLa细胞有一定的细胞毒作用。化合物4没有活性可能是由于在C-24处不存在羟基。
(23E)-25-Methylcycloart-23-en-3 beta-ol (1), a cycloartane-type triterpenoid featuring an unusual skeleton of 31 carbon atoms, (17E)-cycloart-17,26-dien-3 beta-ol (2), a new cycloartane-type triterpenoid, and the other two new compounds 4R-hydroxy-4-(9S-hydroxy-12-methylhexan-6-yl)-3-methylcyclopent-2-enone (6) and 7-hydroxy-5-(2'-hydroxy-4',5'-dimethoxyphenyl)-2-methoxy-6-methyl-1,4-naphthoquinone (7), together with three known cycloart-3 beta-ol triterpenoids (3-5) were isolated from aerial parts of Aphanamixis grandifolia. Their structures were elucidated by spectroscopic analysis, and that of 1 was confirmed by single-crystal X-ray diffraction. The absolute configuration of two carbon stereocenters of compound 6 was determined to be 4R,9S by means of circular dichroism (CD) and auxiliary chiral alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid (MTPA) derivatives, respectively. The compound 3 exhibited significant cytotoxicities against HL-60, Hep G2 and HeLa, and compounds 1, 2, 5, 6 and 7 exhibited modest cytotoxicities. No activity of compound 4 could be due to the absence of the hydroxyl group at C-24.