Issue 2, 2010

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

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.

Supplementary files

Article information

Article type
Paper
Submitted
30 Jul 2009
Accepted
16 Oct 2009
First published
30 Oct 2009

Org. Biomol. Chem., 2010,8, 407-412

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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