Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 10, Pages 1579-1584Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00091a
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Funding
- IMB Postgraduate Awards
- University of Queensland
- Institute for Molecular Bioscience, The University of Queensland
- Australian Research Council [ARC LP0775547, LP0989954]
- Noscira (Madrid, Spain)
- Australian Research Council [LP0989954] Funding Source: Australian Research Council
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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 (GSK3 beta). 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.
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