Department of Natural Products for Chemical Genetic Research, Key Laboratory of Brain Functional Genomics, East China Normal University, No 3663 Zhongshan Road N, Shanghai 200062, PR China.
Bioorg Med Chem Lett. 2011 Jan 1;21(1):366-72. doi: 10.1016/j.bmcl.2010.10.138. Epub 2010 Nov 5.
Four new (1-4) and 13 known (5-17) sesquiterpene lactones along with two known diterpenes (18, 19) were isolated from the whole plant of Carpesium faberi. The new structures were elucidated by means of spectroscopic techniques and some chemical transformations to be pseudoguaian-1α(H)-8α,12-olide-4β-O-β-d-glucopyranoside (1), 4β,10α-dihydroxy-5α(H)-1,11(13)-guaidien-8α,12-olide (2), 4β,10β-dihydroxy-5α(H)-1, 11(13)-guaidien-8β,12-olide (3), and (4S)-acetyloxyl-11(13)-carabren-8β,12-olide (4). All isolates were tested against MCF-7 human breast cancer cells using the MTT assay. Among them, the sesquiterpene lactones (except tomentosin 17) possessing an α-methylene-γ-lactone moiety were found to have in vitro antiproliferative activities, with IC(50) values of 3.0-38.8μg/mL. The effects of four selected sesquiterpene lactones (guaianolide 2, carabranolide 4, pseudoguaianolide 9, eudesmanolide 13) on the cell cycle were examined using flow cytometry (FCM).
从苍耳全草中分离得到了 4 个新的(1-4)和 13 个已知的(5-17)倍半萜内酯,以及 2 个已知的二萜(18、19)。通过光谱技术和一些化学转化,阐明了新结构为伪愈创木烷-1α(H)-8α,12-内酯-4β-O-β-D-吡喃葡萄糖苷(1)、4β,10α-二羟基-5α(H)-1,11(13)-愈创木烷-8α,12-内酯(2)、4β,10β-二羟基-5α(H)-1,11(13)-愈创木烷-8β,12-内酯(3)和(4S)-乙酰氧基-11(13)-卡布伦-8β,12-内酯(4)。所有分离物均通过 MTT 测定法针对 MCF-7 人乳腺癌细胞进行了测试。其中,具有α-亚甲基-γ-内酯部分的倍半萜内酯(除了千里光内酯 17 外)被发现具有体外增殖活性,IC50 值为 3.0-38.8μg/mL。使用流式细胞术(FCM)研究了 4 种选定的倍半萜内酯(愈创木烷内酯 2、卡布兰内酯 4、伪愈创木烷内酯 9、艾里莫芬内酯 13)对细胞周期的影响。