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Issue 1, 2005
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(+)-Echinobetaine B: isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp.

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Abstract

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.

Graphical abstract: (+)-Echinobetaine B: isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp.

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Publication details

The article was received on 24 Sep 2004, accepted on 20 Oct 2004 and first published on 17 Nov 2004


Article type: Paper
DOI: 10.1039/B414839H
Citation: Org. Biomol. Chem., 2005,3, 118-122
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    (+)-Echinobetaine B: isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp.

    R. J. Capon, D. Vuong, M. McNally, T. Peterle, N. Trotter, E. Lacey and J. H. Gill, Org. Biomol. Chem., 2005, 3, 118
    DOI: 10.1039/B414839H

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