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Issue 10, 2014
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Callyspongisines A–D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

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Abstract

An extract of the Great Australian Bight marine sponge Callyspongia sp. (CMB-01152) displayed inhibitory activity against the neurodegenerative disease kinase targets casein kinase 1 (CK1), cyclin-dependent kinase 5 (CDK5) and glycogen synthase kinase 3 (GSK3β). Chemical investigation, employing HPLC-DAD-MS single ion extraction protocols, facilitated identification of the new bromopyrrole alkaloids, callyspongisines A–D (1–4), and two known co-metabolites, hymenialdisine (5) and 2-bromoaldisine (6). Structure elucidation of 1–6 was supported by detailed spectroscopic analysis and chemical interconversion, as well as biosynthetic and synthetic considerations. Callyspongisine A (1) is only the second reported example of a natural imino-oxazoline, and the first to feature a spiro heterocyclic framework, while callyspongisines B–D (2–4) were speculated to be storage and handling artefacts of 1. The kinase inhibitory activity detected in Callyspongia sp. (CMB-01152) was attributed to 5.

Graphical abstract: Callyspongisines A–D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

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Publication details

The article was received on 13 Jan 2014, accepted on 14 Jan 2014 and first published on 15 Jan 2014


Article type: Paper
DOI: 10.1039/C4OB00091A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 1579-1584
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    Callyspongisines A–D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

    F. Plisson, P. Prasad, X. Xiao, A. M. Piggott, X. Huang, Z. Khalil and R. J. Capon, Org. Biomol. Chem., 2014, 12, 1579
    DOI: 10.1039/C4OB00091A

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