斯蒂醇巴戎宁，一种来自马钱科钩吻属植物的根的具有前所未有骨架的非对称双吲哚生物碱。

Strychnobaillonine, an unsymmetrical bisindole alkaloid with an unprecedented skeleton from Strychnos icaja roots.

机构信息

Center for Studies on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies (IMPM) , P.O. Box 6163, Yaoundé, Cameroon.

出版信息

J Nat Prod. 2014 Apr 25;77(4):1078-82. doi: 10.1021/np400908u. Epub 2014 Mar 4.

DOI:10.1021/np400908u

PMID:24593048

Abstract

A reinvestigation of the roots of Strychnos icaja resulted in the isolation of a new bisindole alkaloid named strychnobaillonine (1) with original C-17-N-1' and C-23-C-17' junctions, in addition to sungucine, bisnordihydrotoxiferine, and strychnohexamine (2). Compound 1 showed potent activity against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum in vitro with an IC50 value of 1.1 μM. The structures of the compounds were defined by detailed spectroscopic analyses, especially 1H and 13C NMR, DEPT, HSQC, COSY, NOESY, HMBC, and HRESIMS. The proposed absolute configuration was based on biosynthetic considerations and spectroscopic data (CD, NMR) supported by molecular modeling.

摘要

对 Strychnos icaja 的根部进行重新研究，分离得到一种新的双吲哚生物碱，命名为 strychnobaillonine（1），具有独特的 C-17-N-1' 和 C-23-C-17' 连接，此外还有 sungucine、bisnordihydrotoxiferine 和 strychnohexamine（2）。化合物 1 对体外氯喹敏感的 Plasmodium falciparum 3D7 株具有很强的活性，IC50 值为 1.1 μM。通过详细的光谱分析，特别是 1H 和 13C NMR、DEPT、HSQC、COSY、NOESY、HMBC 和 HRESIMS，确定了化合物的结构。根据生物合成考虑和光谱数据（CD、NMR）以及分子建模的支持，提出了绝对构型。