(+)-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 conclus...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-01, Vol.3 (1), p.118-122
Main Authors: Capon, Robert J, Vuong, Dat, McNally, Michelle, Peterle, Torsten, Trotter, Nicholas, Lacey, Ernest, Gill, Jennifer H
Format: Article
Language:English
Subjects:
Animals
Antinematodal Agents - chemistry
Antinematodal Agents - isolation & purification
Antinematodal Agents - pharmacology
Australia
Betaine - analogs & derivatives
Betaine - chemistry
Betaine - isolation & purification
Betaine - pharmacology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Porifera - chemistry
Species Specificity
Stereoisomerism
Structure-Activity Relationship
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b414839h