从马氏瓜馥木茎皮中提取的新型细胞毒性1-氮杂蒽醌和3-氨基萘醌。

New cytotoxic 1-azaanthraquinones and 3-aminonaphthoquinone from the stem bark of Goniothalamus marcanii.

作者信息

Soonthornchareonnon N, Suwanborirux K, Bavovada R, Patarapanich C, Cassady J M

机构信息

Departments of Pharmacognosy, Pharmaceutical Botany, and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand.

出版信息

J Nat Prod. 1999 Oct;62(10):1390-4. doi: 10.1021/np990197c.

DOI:10.1021/np990197c

PMID:10543899

Abstract

Guided by brine shrimp toxicity and human tumor cell toxicity, fractionation of the alcoholic extract from the stem bark of Goniothalamus marcanii led to the isolation of four new 1-azaanthraquinones: marcanines B (3), C (4), D (5), and E (6), along with two known derivatives: marcanine A and dielsiquinone. A new 5-hydroxy-3-amino-2-aceto-1,4-naphthoquinone (7), a possible 1-azaanthraquinone biosynthetic precursor, was also isolated. The structures of the compounds were elucidated by spectroscopic analyses, mainly 1D and 2D NMR techniques ((1)H, (13)C, NOEDS, COSY, HMQC, and HMBC), as well as comparison with literature data. All the compounds except 6 were evaluated for cytotoxic activity. They exhibited significant cytotoxicity against several human tumor cell lines, A-549, HT-29, MCF7, RPMI, and U251 with the ED(50) in the range of 0.04-3.03 microM.

摘要

以卤虫毒性和人肿瘤细胞毒性为导向，对马氏哥纳香茎皮乙醇提取物进行分馏，分离得到4个新的1-氮杂蒽醌：马氏醌B（3）、C（4）、D（5）和E（6），以及2个已知衍生物：马氏醌A和二烯西醌。还分离得到一种新的5-羟基-3-氨基-2-乙酰基-1,4-萘醌（7），它可能是1-氮杂蒽醌的生物合成前体。通过光谱分析，主要是一维和二维核磁共振技术（（1）H、（13）C、NOEDS、COSY、HMQC和HMBC）以及与文献数据比较，阐明了这些化合物的结构。除6外，所有化合物均进行了细胞毒性活性评价。它们对几种人肿瘤细胞系A-549、HT-29、MCF7、RPMI和U251表现出显著的细胞毒性，半数有效剂量（ED50）在0.04 - 3.03微摩尔范围内。