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Org Lett. 2003 Nov 13;5(23):4393-6.

Unusual C25 steroids produced by a sponge-derived Penicillium citrinum.

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  • 1Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California Santa Cruz, Santa Cruz, California 95064, USA.


[structure: see text] Structurally unique steroids, isocyclocitrinol A (1) and 22-acetylisocyclocitrinol A (2), were isolated from the extract of a saltwater culture of sponge-derived Penicilliun citrinum. The structures were established by analysis of 1D and 2D NMR data. The absolute structures were determined on the basis of X-ray structure analysis and application of modified Mosher's method. Furthermore, the structure of cyclocitrinol (3a) previously isolated from a terrestrial P. citrinum was revised as 3b. Compounds 1 and 2 showed weak antibacterial activity against Staphylococcus epidermidis and Enterococcus durans.

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