Tanikolide, a toxic and antifungal lactone from the marine cyanobacterium Lyngbya majuscula

Abstract

A new brine-shrimp toxic and antifungal compound, tanikolide 1, has been isolated from the lipid extract of a Madagascan collection of the marine cyanobacterium Lyngbya majuscula. The structure of tanikolide was determined by spectroscopic methods, relying heavily on 2D NMR spectroscopy. The absolute configuration at C-5 of tanikolide was established as R by oxidizing the primary alcohol to an acid and analyzing the corresponding (R)- and (S)-PGME amide derivatives by (1)H NMR.