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Issue 2, 2010
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Mirabilins revisited: polyketidealkaloids from a southern Australian marine sponge, Clathria sp.

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Abstract

Chemical investigation of a southern Australian marine sponge, Clathria sp., yielded the known mirabilins C, F and G, together with three new analogues, mirabilins H–J. For the first time mirabilins C and F are documented as the underivatized natural products, and a complete absolute stereochemistry is assigned to mirabilin F. Mirabilin I represents the first member of this structure class to incorporate a trans-fused ring junction. Structures for all mirabilins are assigned on the basis of detailed spectroscopic analysis. A plausible polyketide origin is proposed, linking all mirabilins and related sponge alkaloids. Mirabilin cytotoxicity against several human cancer cell lines is discussed.

Graphical abstract: Mirabilins revisited: polyketide alkaloids from a southern Australian marine sponge, Clathria sp.

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Supplementary files

Article information


Submitted
30 Jul 2009
Accepted
16 Oct 2009
First published
30 Oct 2009

Org. Biomol. Chem., 2010,8, 407-412
Article type
Paper

Mirabilins revisited: polyketide alkaloids from a southern Australian marine sponge, Clathria sp.

M. El-Naggar, M. Conte and R. J. Capon, Org. Biomol. Chem., 2010, 8, 407
DOI: 10.1039/B915624K

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