来自马达加斯加海绵Biemna laboutei的五种新的三环胍生物碱——去甲胺类O-S及其抗疟活性。

Netamines O-S, Five New Tricyclic Guanidine Alkaloids from the Madagascar Sponge Biemna laboutei, and Their Antimalarial Activities.

作者信息

Gros Emmanuelle, Martin Marie-Thérèse, Sorres Jonathan, Moriou Céline, Vacelet Jean, Frederich Michel, Aknin Maurice, Kashman Yoel, Gauvin-Bialecki Anne, Al-Mourabit Ali

机构信息

Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, 15 Avenue René Cassin, CS 92003, FR-97744 Saint-Denis Cedex 9, La Réunion, (phone: +262-262-938197; fax: +262-262-938183).

Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, Avenue de la Terrasse, FR-91198 Gif-sur-Yvette.

出版信息

Chem Biodivers. 2015 Nov;12(11):1725-33. doi: 10.1002/cbdv.201400350.

DOI:10.1002/cbdv.201400350

PMID:26567950

Abstract

In our continuing program to isolate new compounds from the Madagascar sponge Biemna laboutei, five new tricyclic guanidine alkaloids, netamines O - S (1-5, resp.), have been identified together with the known compounds netamine E (6) and mirabilin J (7). The structures of all new netamines were assigned on the basis of spectroscopic analyses. Their relative configurations were established by analysis of ROESY data and comparison with literature data. Netamines O, P, and Q, which were isolated in sufficient quantities, were tested for their cytotoxic activities against KB cells and their activities against the malaria parasite Plasmodium falciparum. Netamines O and Q were found to be moderately cytotoxic. Netamines O, P, and Q exhibited antiplasmodial activities with IC₅₀ values of 16.99 ± 4.12, 32.62 ± 3.44, and 8.37 ± 1.35 μM, respectively.

摘要

在我们从马达加斯加海绵Biemna laboutei中分离新化合物的持续项目中，已鉴定出五种新的三环胍生物碱，即网胺O - S（分别为1 - 5），以及已知化合物网胺E（6）和奇灵碱J（7）。所有新网胺的结构均通过光谱分析确定。它们的相对构型通过ROESY数据的分析并与文献数据比较得以确定。分离得到足够量的网胺O、P和Q，测试了它们对KB细胞的细胞毒性活性以及对疟原虫恶性疟原虫的活性。发现网胺O和Q具有中等细胞毒性。网胺O、P和Q表现出抗疟活性，IC₅₀值分别为16.99 ± 4.12、32.62 ± 3.44和8.37 ± 1.35 μM。