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

Mohamed El-Naggar; Melissa Conte; Robert J. Capon

doi:10.1039/B915624K

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Organic & Biomolecular Chemistry

Issue 2, 2010

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

Mohamed El-Naggar , Melissa Conte and Robert J. Capon

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

DOI: 10.1039/B915624K
Received 30 Jul 2009, Accepted 16 Oct 2009
First published on the web 30 Oct 2009

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Abstract
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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.

Abstract from Natural Product Updates 2010

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Supplementary Info

¹H NMR spectra, and tabulated 1D and 2D NMR data, for mirabilins C ( 3) and F–J ( 16–17, 22–24)
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Organic & Biomolecular Chemistry

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

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