来自法属波利尼西亚一种新的单锚海绵属海绵的细胞毒性胍生物碱。

Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge.

作者信息

El-Demerdash Amr, Moriou Céline, Martin Marie-Thérèse, Rodrigues-Stien Alice de Souza, Petek Sylvain, Demoy-Schneider Marina, Hall Kathryn, Hooper John N A, Debitus Cécile, Al-Mourabit Ali

机构信息

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

Organic Chemistry Division, Chemistry Department, Faculty of Science, Mansoura University , Mansoura 35516, Egypt.

出版信息

J Nat Prod. 2016 Aug 26;79(8):1929-37. doi: 10.1021/acs.jnatprod.6b00168. Epub 2016 Jul 15.

DOI:10.1021/acs.jnatprod.6b00168

PMID:27419263

Abstract

Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.

摘要

从法属波利尼西亚一种新的莫纳锚海绵（Monanchora n. sp.）中分离出了四种双环胍生物碱和三种五环胍生物碱（1 - 7），同时还分离出了已知生物碱莫纳利定A（8）、已知天然产物克拉贝辛的对映体9 - 11以及已知的克拉贝西定12 - 15。通过光谱数据解析确定了其结构。通过对¹H NMR和NOESY谱的分析以及圆二色性分析确定了生物碱的相对和绝对构型。新的降克拉贝西酸（7）对应于五环核心内有趣的生物合成变化。所有化合物对KB、HCT116、HL60、MRC5和B16F10癌细胞均表现出抗增殖和细胞毒性作用，IC50值范围为4 nM至10 μM。