Callyspongisines A-D

Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

Fabien Plisson, Pritesh Prasad, Xue Xiao, Andrew M. Piggott, Xiao Cong Huang, Zeinab Khalil, Robert J. Capon*

*Corresponding author for this work

Research output: Contribution to journalArticle

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1579-1584
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number10
DOIs
Publication statusPublished - 14 Mar 2014
Externally publishedYes

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