来自巴西药用植物多穗破布木的达玛烷型三萜类化合物。

Dammarane-type triterpenes from the Brazilian medicinal plant Cordia multispicata.

作者信息

Kuroyanagi Masanori, Kawahara Nobuo, Sekita Setsuko, Satake Motoyoshi, Hayashi Tatsuo, Takase Yoichi, Masuda Kazuo

机构信息

School of Bioresources, Hiroshima Prefectural University, 562 Nanatsuka, Shobara-shi, Hiroshima 727-0023, Japan.

出版信息

J Nat Prod. 2003 Oct;66(10):1307-12. doi: 10.1021/np020483f.

DOI:10.1021/np020483f

PMID:14575428

Abstract

From the Brazilian medicinal plant Carucaá (Cordia multispicata), oleanane- and ursane-type triterpenoids were previously reported as anti-androgenic constituents of the plant. In this study, purification of the polar elements of the EtOAc-soluble fraction of the plant revealed nine novel dammarane-type triterpenes, named cordianols A-I (1-9) along with the known compound cordialin A (10). The structures of these new compounds were elucidated by means of spectral methods including HRFABMS, (1)H NMR, (13)C NMR, and 2D NMR (HMQC, HMBC, NOESY). Absolute configuration at C-23 of compound 7 was determined by an excitone chirality method. Some of these new compounds revealed a hemiketal structure on the A ring and a hydroxylated or epoxidated 20(22)-(E)-ene side chain and showed weak anti-androgenic activity.

摘要

来自巴西药用植物卡鲁卡阿（多穗破布木）的齐墩果烷型和乌苏烷型三萜类化合物先前被报道为该植物的抗雄激素成分。在本研究中，对该植物乙酸乙酯可溶部分的极性成分进行纯化，得到了9种新的达玛烷型三萜，命名为破布木醇A - I（1 - 9）以及已知化合物破布木苷A（10）。这些新化合物的结构通过高分辨快原子轰击质谱（HRFABMS）、核磁共振氢谱（¹H NMR）、核磁共振碳谱（¹³C NMR）和二维核磁共振谱（HMQC、HMBC、NOESY）等光谱方法得以阐明。化合物7在C - 23位的绝对构型通过激子手性法确定。其中一些新化合物在A环上具有半缩酮结构，在20(22)-(E)-烯侧链上有羟基化或环氧化修饰，并显示出较弱的抗雄激素活性。