莱菔硫烷 E-J，少环螺旋甾烷三萜类化合物，来自于益母草果实。

Leonurusoleanolides E-J, minor spirocyclic triterpenoids from Leonurus japonicus fruits.

机构信息

Department of Natural Products Chemistry, School of Pharmacy, Fudan University , Shanghai 201203, People's Republic of China.

出版信息

J Nat Prod. 2014 Jan 24;77(1):178-82. doi: 10.1021/np400838a. Epub 2013 Dec 13.

DOI:10.1021/np400838a

PMID:24328283

Abstract

Six new (leonurusoleanolides E-J, 1-6) and five known (7-11) nortriterpenoids were isolated and characterized from the dried fruits of Leonurus japonicus. They all contain a distinctive 19(18→17)-abeo-28-noroleanane-type spirocylclic skeleton with a trans or a cis acyl substituent at C-3 or C-23. Similar to the previously known leonurusoleanolides A/B (7/8) and C/D (9/10), compounds 1/2 and 3/4 were also found to exist as equilibrium mixtures of trans and cis isomers. The isolated pure compounds and mixtures were evaluated for their cytotoxicity against a small panel of human cancer cell lines (BGC-823 and KE-97 gastric carcinoma, Huh-7 hepatocarcinoma, Jurkat T cell lymphoblasts, and MCF-7 breast adenocarcinoma) using the CellTiter-Glo luminescent cell viability assay method. Among them, (2α,3β,17R*,18β)-3-O-(trans-caffeoyl)-19(18→17)-abeo-28-norolean-12-ene-2,18,23-triol (leonurusoleanolide J, 6) showed the most potent cytotoxic activity, with IC50 values less than 10 μM.

摘要

从益母草的干果实中分离得到了 6 个新的（leonurusoleanolides E-J，1-6）和 5 个已知的（7-11）三萜化合物。它们都含有独特的 19(18→17)-abeo-28-noroleanane 型螺环骨架，在 C-3 或 C-23 位具有反式或顺式酰基取代基。与先前已知的益母草醇内酯 A/B（7/8）和 C/D（9/10）相似，化合物 1/2 和 3/4 也被发现为反式和顺式异构体的平衡混合物。用 CellTiter-Glo 发光细胞活力测定法评估了分离得到的纯化合物和混合物对人癌细胞系（BGC-823 和 KE-97 胃癌、Huh-7 肝癌、Jurkat T 淋巴细胞白血病和 MCF-7 乳腺癌）的细胞毒性。其中，（2α,3β,17R*,18β）-3-O-（反式-咖啡酰基）-19(18→17)-abeo-28-norolean-12-ene-2,18,23-三醇（leonurusoleanolide J，6）表现出最强的细胞毒性活性，IC50 值小于 10 μM。