Glycolipids from Sponges. Part 8: Plakopolyprenoside from the Marine Sponge Plakortis simplex. An Improved Procedure for Isolation of Glycolipids as Peracetyl Derivatives

Plakopolyprenoside, a unique cytotoxic glycolipid composed of a C35 linear polyisoprenoid alcohol and a dixylosyl carbohydrate chain was isolated from the Caribbean sponge Plakortis simplex as its pentaacetate. Because the isolation of native plakopolyprenoside was unfeasible, acetylation with trideuteroacetic anhydride was used to ensure that no acetyl group was already present in the natural compound. The structure of plakopolyprenoside was established from spectral data. Plakopolyprenoside is cytotoxic against the J774 cell line.