来自决明花的细胞毒性生物碱。

Cytotoxic alkaloids from the flowers of Senna spectabilis.

作者信息

Sriphong Lawan, Sotanaphun Uthai, Limsirichaikul Siripan, Wetwitayaklung Penpan, Chaichantipyuth Chaiyo, Pummangura Sunibhond

机构信息

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Silpakorn University, Nakorn Prathom, Thailand.

出版信息

Planta Med. 2003 Nov;69(11):1054-6. doi: 10.1055/s-2003-45156.

DOI:10.1055/s-2003-45156

PMID:14735447

Abstract

Three new alkaloids, 3(R)-benzoyloxy-2(R)-methyl-6(R)-(11'-oxododecyl)-piperidine (3), 5-hydroxy-2-methyl-6-(11'-oxododecyl)-pyridine (4) and 5-hydroxy-2-methyl-6-(11'-oxododecyl)-pyridine N-oxide (5), together with a known alkaloid, (-)-cassine (1), were isolated from the flowers of Senna spectabilis. A derivative, N,O-diacetylcassine (2), was semisynthesized. Their structures and stereochemistry were established on the basis of spectroscopic analysis. Cytotoxic activity and brine shrimp lethality of these compounds were evaluated. Compounds 2, 3 and 5 exhibited cytoxicity against KB cell lines with IC50 values of 5.2, 3.7 and 2.0 microg/mL, respectively.

摘要

从决明花中分离出三种新生物碱，3(R)-苯甲酰氧基-2(R)-甲基-6(R)-(11'-氧代十二烷基)-哌啶(3)、5-羟基-2-甲基-6-(11'-氧代十二烷基)-吡啶(4)和5-羟基-2-甲基-6-(11'-氧代十二烷基)-吡啶N-氧化物(5)，以及一种已知生物碱(-)-水黄皮碱(1)。半合成了一种衍生物N,O-二乙酰水黄皮碱(2)。通过光谱分析确定了它们的结构和立体化学。评估了这些化合物的细胞毒性活性和卤虫致死率。化合物2、3和5对KB细胞系表现出细胞毒性，IC50值分别为5.2、3.7和2.0μg/mL。