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 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.
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California Santa Cruz, Santa Cruz, California 95064, USA.
Taro
T
Amagata
Akiko
A
Amagata
Karen
K
Tenney
Frederick A
FA
Valeriote
Emil
E
Lobkovsky
Jon
J
Clardy
Phillip
P
Crews
D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium / Q000378:metabolism*; D011161:Porifera / Q000382:microbiology*; D013256:Steroids / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology
D000890:Anti-Infective Agents; D013256:Steroids