Callyspongisines A-D: Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

Plisson,Fabien, Prasad, Pritesh, Xiao, Xue, Piggott, Andrew M., Huang, Xiao-cong, Khalil, Zeinab and Capon, Robert J. (2014) Callyspongisines A-D: Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.. Organic and Biomolecular Chemistry, 12 10: 1579-1584. doi:10.1039/c4ob00091a

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Author Plisson,Fabien
Prasad, Pritesh
Xiao, Xue
Piggott, Andrew M.
Huang, Xiao-cong
Khalil, Zeinab
Capon, Robert J.
Title Callyspongisines A-D: Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2014-03-14
Year available 2014
Sub-type Article (original research)
DOI 10.1039/c4ob00091a
Open Access Status File (Author Post-print)
Volume 12
Issue 10
Start page 1579
End page 1584
Total pages 6
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2015
Language eng
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. This journal is
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Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Institute for Molecular Bioscience - Publications
 
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