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.
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Authors | Mohamed El-Naggar, Melissa Conte, Robert J Capon |
Journal | Organic & biomolecular chemistry
(Org Biomol Chem)
Vol. 8
Issue 2
Pg. 407-12
(Jan 21 2010)
ISSN: 1477-0539 [Electronic] England |
PMID | 20066277
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Alkaloids
- Macrolides
- Saponins
- mirabilin
- Oleanolic Acid
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Topics |
- Alkaloids
(chemistry, isolation & purification, pharmacology)
- Animals
- Australia
- Cell Line, Tumor
- Humans
- Inhibitory Concentration 50
- Macrolides
(chemistry)
- Oleanolic Acid
(analogs & derivatives, chemistry, isolation & purification, pharmacology)
- Porifera
(chemistry)
- Saponins
(chemistry, isolation & purification, pharmacology)
- Spectrum Analysis
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