Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula.
The lipid extract from a Curaçao collection of the marine cyanobacterium Lyngbya majuscula was toxic to the mollusc Biomphalaria glabrata. Subsequent bioassay-guided fractionation of this extract yielded a novel lipopeptide, barbamide, as the active compound (LC100 = 10 micrograms/mL). The structure of barbamide was determined by spectroscopic methods and was found to contain several unique structural features, including a trichloromethyl group and the methyl enol ether of a beta-keto amide.
Orjala
J
J
College of Pharmacy, Oregon State University, Corvallis 97331, USA.
Gerwick
W H
WH
D000818:Animals; D001156:Artemia; D001700:Biomphalaria; D000458:Cyanobacteria / Q000737:chemistry*; D006054:Goldfish; D009682:Magnetic Resonance Spectroscopy; D008975:Molluscacides / Q000302:isolation & purification* / Q000494:pharmacology; D013844:Thiazoles / Q000302:isolation & purification* / Q000494:pharmacology
D008975:Molluscacides; D013844:Thiazoles; C100545:barbamide