番荔枝科植物尖叶番荔枝茎皮中的对映贝壳杉烷二萜及其细胞毒性评价

ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.

作者信息

Dutra Lívia M, Bomfim Larissa M, Rocha Suellen L A, Nepel Angelita, Soares Milena B P, Barison Andersson, Costa Emmanoel V, Bezerra Daniel P

机构信息

Department of Chemistry, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.

Gonçalo Moniz Research Center, Oswaldo Cruz Foundation (Fiocruz), Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, Bahia, Brazil.

出版信息

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3315-20. doi: 10.1016/j.bmcl.2014.06.005. Epub 2014 Jun 11.

DOI:10.1016/j.bmcl.2014.06.005

PMID:24969014

Abstract

This work describes a novel ent-kaurane diterpene, ent-3β-hydroxy-kaur-16-en-19-al along with five known ent-kaurane diterpenes, ent-3β,19-dihydroxy-kaur-16-eno, ent-3β-hydroxy-kaur-16-eno, ent-3β-acetoxy-kaur-16-eno, ent-3β-hydroxy-kaurenoic acid and kaurenoic acid, as well as caryophyllene oxide, humulene epoxide II, β-sitosterol, stigmasterol and campesterol from the stem bark of Annona vepretorum Mart. (Annonaceae). Cytotoxic activities towards tumor B16-F10, HepG2, K562 and HL60 and non-tumor PBMC cell lines were evaluated for ent-kaurane diterpenes. Among them, ent-3β-hydroxy-kaur-16-en-19-al was the most active compound with higher cytotoxic effect over K562 cell line (IC50 of 2.49 μg/mL) and lower over B16-F10 cell line (IC50 of 21.02 μg/mL).

摘要

这项研究描述了一种新型对映-贝壳杉烷二萜，对映-3β-羟基-贝壳杉-16-烯-19-醛，以及五种已知的对映-贝壳杉烷二萜，对映-3β,19-二羟基-贝壳杉-16-烯、对映-3β-羟基-贝壳杉-16-烯、对映-3β-乙酰氧基-贝壳杉-16-烯、对映-3β-羟基-贝壳杉烯酸和贝壳杉烯酸，还有氧化石竹烯、环氧葎草烯II、β-谷甾醇、豆甾醇和菜油甾醇，它们都来自马氏番荔枝（番荔枝科）的茎皮。评估了对映-贝壳杉烷二萜对肿瘤B16-F10、HepG2、K562和HL60以及非肿瘤PBMC细胞系的细胞毒性活性。其中，对映-3β-羟基-贝壳杉-16-烯-19-醛是活性最高的化合物，对K562细胞系具有较高的细胞毒性作用（IC50为2.49μg/mL），对B16-F10细胞系的毒性较低（IC50为21.02μg/mL）。