A set of biogenetically interesting polyhalogenated acetogenins from Ptilonia magellanica

Abstract

Ptilonines A-F, pyranosylmagellanicus D-E and magellenediol are previously undescribed acetogenins isolated from the red alga Ptilonia magellanica. Their structures were determined from spectroscopic evidence. The absolute configuration of the known pyranosylmagellanicus A, was established by derivatization with (R)- and (S)-α-methoxy -α-phenylacetic acids (MPA). Ptilonines exhibit an unusual halogenation pattern, that may confer evolutionary advantages to Ptilonia magellanica, for which a biogenetic origin is proposed. The antimicrobial effect of some of these compounds was evaluated.

Keywords: Absolute configuration; Biogenesis; Bonnemaisoniaceae; Magellenediol; Ptilonia magellanica; Ptilonines; Pyranosylmagellanicus; Red algae; Strait of Magellan; Unusual halogenation pattern.