Glycolipids from sponges. VII. Simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex

The new glycolipids simplexides (1) have been isolated from the marine spon ge Plakortis simplex, and their structure determined by spectroscopic data and microgram-scale chemical degradation. Simplexides are composed of long- chain secondary alcohols glycosylated by a disaccharide chain, and represen t a new structural kind of glycolipids. Simplexides strongly inhibit prolif eration of activated T-cells by a non-cytotoxic mechanism and can be regard ed as simple model molecules for designing immunosuppressive drugs. (C) 199 9 Elsevier Science Ltd. All rights reserved.