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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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Supplementary files

Article information


Submitted
13 Jan 2014
Accepted
14 Jan 2014
First published
15 Jan 2014

Org. Biomol. Chem., 2014,12, 1579-1584
Article type
Paper
Author version available

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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