(+)-Echinobetaine B: isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp.
The principle nematocidal agent present in a southern Australian marine sponge of the genus Echinodictyum has been isolated and identified as the novel betaine (+)-echinobetaine B (6), and the structure assigned by spectroscopic analysis has been confirmed by total synthesis. Preliminary SAR conclusions are drawn from analysis of synthetic intermediates and the known marine metabolites zooanemonin (12) and norzooanemonin (13), and the new sponge metabolite norzooanemonin methyl ester (14). The latter compound is reported for the first time from a selection of Australian sponges, including an Axinyssa sp., a Niphates sp., an Axinella sp. and a Ptilocaulis sp.
Capon
Robert J
RJ
Centre for Molecular Biodiversity, Institute for Molecular Biosciences, University of Queensland, St. Lucia, Queensland, 4072, Australia. r.capon@imb.uq.edu.au
Vuong
Dat
D
McNally
Michelle
M
Peterle
Torsten
T
Trotter
Nicholas
N
Lacey
Ernest
E
Gill
Jennifer H
JH
D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001315:Australia; D001622:Betaine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013045:Species Specificity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000969:Antinematodal Agents; C511679:echinobetaine B; D001622:Betaine