Three new Triterpenes from Nerium oleander and biological activity of the isolated compounds
Three new Triterpenes from Nerium oleander and biological activity of the isolated compounds
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DOI：
10.1021/np040072u
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发表时间：
2005-02-01
影响因子：
5.1
通讯作者：
Ando, M
中科院分区：
文献类型：
--
作者：
Fu, LW;Zhang, SJ;Ando, M
从夹竹桃（Nerium oleander）叶中分离得到新的熊烷型三萜1、齐墩果烷型三萜2和达玛烷型三萜15，并分离得到12个已知三萜3 β-羟基-12-熊烷-28-酸（熊果酸，3），3 β，27-二羟基-12-熊烯-28-酸（4），3 β，13 β-二羟基熊-11-烯-28-酸（5），3 β-羟基熊-12-烯-28-醛（6），28-norurs-12-en-3beta-ol（7），urs-12-en-3beta-ol（8），urs-12-ene-3beta，28-diol（9），3beta-hydroxy-12-oleanen-28-oic acid（油酸，10），3 β，27-二羟基-12-齐墩果烯-28-酸（11），3 β-羟基-20（29）-羽扇烯-28-酸（桦木酸，12）、20（29）-羽扇烯-3，28-二醇（桦木醇，13）和（20 S，24 R）-环氧达玛烷-3 β，25-二醇（14）。新化合物1、2和15的结构分别确定为3 β，20 α-二羟基乌苏-21-烯-28-酸、3 β，12 α-二羟基-齐墩果烷-28，13 β-内酯和（20 S，24 S）-环氧达玛烷-3beta，25-二醇。根据对细胞间粘附分子-1（ICAM-1）诱导的抑制活性，检查了七种分离的化合物和熊果酸和油酸甲酯的体外抗炎活性。对分离得到的14个化合物进行了体外抗肿瘤活性测定，包括熊果酸和油酸的1、2、15和甲酯。
New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxy-oleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.