New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica.
In this first report on the chemistry of the sponge Stylissa caribica, two known bromopyrrole metabolites and a new compound, N-methyldibromoisophakellin (1), were isolated and identified. The structure of 1 was determined using spectroscopic methods and the computer program COCON. N-Methyldibromoisophakellin (1) was shown to be the only secondary metabolite in Stylissa caribica that, at its natural concentration, is active as a feeding deterrent against a common omnivorous reef fish.
Assmann
M
M
Alfred-Wegener-Institut für Polar- und Meeresforschung, Sektion Chemie Mariner Spuren- und Naturstoffe, Am Handelshafen 12, D-27570 Bremerhaven, Germany.
van Soest
R W
RW
Köck
M
M
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001444:Bahamas; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D005247:Feeding Behavior / Q000187:drug effects; D005399:Fishes; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
D000470:Alkaloids; C440686:N-methyldibromoisophakellin; D011758:Pyrroles