Mololipids, a new series of anti-HIV bromotyramine-derived compounds from a sponge of the order verongida

Abstract

A new series of lipids called mololipids have been identified from an Hawaiian sponge of the order Verongida. The structures of these lipids was deduced from spectroscopic data of the lipid mixture combined with GC-MS analysis. The core of this novel series of lipids is a bromotyramine homoserine-derived moiety known as moloka'iamine (1) which is found in many Verongid sponge metabolites. Moloka'iamine forms bisamides with a diverse series of fatty acids and the mololipids mixture (2) was active against HIV-1 with an EC(50) of 52.2 microM without cytotoxicity in human lymphocytes (IC(50) > 100 microM).