Methanol adduct of puupehenone, a biologically active derivative from the marine sponge Hyrtios species.

Abstract

A methanol adduct of puupehenone (1), 15alpha-methoxypuupehenol (2), an artifact resulting from the action of MeOH on puupehenone, was isolated during purification of the CH(2)Cl(2) extract of the New Caledonian marine sponge Hyrtios sp., as the major constituent. Its chemical structure was elucidated by 2D NMR experiments. Compound 2 displayed similar antimicrobial and antifungal activity as puupehenone and a lower cytotoxic activity toward KB cells with ED(50) values of 6 and 0.5 microg/mL, respectively. Compound 2 was slightly more active against three strains of Plasmodium falciparum than puupehenone.