Fu Liwei, Zhang Shujun, Li Na, Wang Jinlan, Zhao Ming, Sakai Junichi, Hasegawa Toshiaki, Mitsui Tomokazu, Kataoka Takao, Oka Seiko, Kiuchi Miwa, Hirose Katutoshi, Ando Masayoshi
Graduate School of Science and Technology, Department of Chemistry and Chemical Engineering, Niigata University, 2-8050 Ikarashi, Niigata 950-2181, Japan.
J Nat Prod. 2005 Feb;68(2):198-206. doi: 10.1021/np040072u.
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-3beta,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-dihydroxyoleanan-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.
从夹竹桃叶子中分离得到新型乌苏烷型三萜1、齐墩果烷型三萜2和达玛烷型三萜15，以及12种已知的三萜，即3β - 羟基 - 12 - 乌苏烯 - 28 - 酸（熊果酸，3）、3β,27 - 二羟基 - 12 - 乌苏烯 - 28 - 酸（4）、3β,13β - 二羟基乌苏 - 11 - 烯 - 28 - 酸（5）、3β - 羟基乌苏 - 12 - 烯 - 28 - 醛（6）、28 - 降乌苏 - 12 - 烯 - 3β - 醇（7）、乌苏 - 12 - 烯 - 3β -醇（8）、乌苏 - 12 - 烯 - 3β,28 - 二醇（9）、3β - 羟基 - 12 - 齐墩果烯 - 28 - 酸（齐墩果酸，10）、3β,27 - 二羟基 - 12 - 齐墩果烯 - 28 - 酸（11）、3β - 羟基 - 20(29) - 羽扇烯 - 28 - 酸（桦木酸，12）、20(29) - 羽扇烯 - 3β,28 - 二醇（桦木醇，13）和(20S,24R) - 环氧达玛烷 - 3β,25 - 二醇（14）。根据它们的光谱数据，确定新化合物1、2和15的结构分别为3β,20α - 二羟基乌苏 - 21 - 烯 - 28 - 酸、3β,12α - 二羟基齐墩果烷 - 28,13β - 内酯和(20S,24S) - 环氧达玛烷 - 3β,25 - 二醇。基于对细胞间黏附分子 - 1（ICAM - 1）诱导的抑制活性，检测了七种分离得到的化合物以及熊果酸和齐墩果酸甲酯的体外抗炎活性。基于对三种人类细胞系的细胞生长抑制活性，检测了14种分离得到的化合物（包括1、2、15以及熊果酸和齐墩果酸甲酯）的体外抗癌活性。
