嘉兰小檗中的三萜。天然和半合成的弗里烷的细胞毒性评价。

Triterpenes from Garcia parviflora. Cytotoxic evaluation of natural and semisynthetic friedelanes.

机构信息

Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México DF.

出版信息

J Nat Prod. 2010 Nov 29;73(11):1839-45. doi: 10.1021/np100440p. Epub 2010 Oct 19.

DOI:10.1021/np100440p

PMID:20958014

Abstract

Three new friedelane-type triterpenes, 1,2-dehydro-2,3-secofriedelan-3-oic acid (1), 1β-hydroxyfriedelin (2), and 3β-hydroxyfriedelan-23-oic acid (3), and the known compounds friedelin-3,4-lactone (4), acetyl aleuritolic acid (5), 4-hydroxy-5-propionyl-1,3-di-O-methylpyrogallol, elemicin, and (-)-syringaresinol were isolated from the leaves of Garcia parviflora. The structures of 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR, HREIMS, X-ray, and CD analysis. Some derivatives of 2 (6-14) were prepared via oxidation, reduction, and esterification. The natural triterpenes and the semisynthetic friedelane derivatives were tested for cytotoxic activity against human cancer cell lines U251, PC-3, K562, HCT-15, MCF-7, and SKLU-1. Compound 5 was cytotoxic against U251 cells.

摘要

从 Garcia parviflora 的叶子中分离得到三种新的 friedelane 型三萜，分别为 1,2-去氢-2,3-二氢 friedelan-3-酸（1）、1β-羟基friedelin（2）和 3β-羟基friedelan-23-酸（3），以及已知化合物 friedelin-3,4-内酯（4）、乙酰 aleuritolic 酸（5）、4-羟基-5-丙酰基-1,3-二-O-甲基焦儿茶酚、elemicin 和 (-)-丁香树脂醇。通过光谱方法，包括 1D 和 2D NMR、HREIMS、X 射线和 CD 分析，确定了 1-3 的结构。通过氧化、还原和酯化制备了 2 的一些衍生物（6-14）。对天然三萜和半合成 friedelane 衍生物进行了人癌细胞系 U251、PC-3、K562、HCT-15、MCF-7 和 SKLU-1 的细胞毒性测试。化合物 5 对 U251 细胞具有细胞毒性。