Unusual C25 steroids produced by a sponge-derived Penicillium citrinum

[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 wer...

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Bibliographic Details
Published in:Organic letters 2003-11, Vol.5 (23), p.4393-4396
Main Authors: Amagata, Taro, Amagata, Akiko, Tenney, Karen, Valeriote, Frederick A, Lobkovsky, Emil, Clardy, Jon, Crews, Phillip
Format: Article
Language:English
Subjects:
Animals
Anti-Infective Agents - chemistry
Anti-Infective Agents - pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Penicillium - metabolism
Porifera - microbiology
Steroids - biosynthesis
Steroids - chemistry
Steroids - pharmacology
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Summary:[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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0356800