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Título

Muriceanol, A 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols

AutorLorenzo, Manuel; Cueto, Mercedes ; D'Croz, Luis; Maté, Juan L.; San Martín, Aurelio; Darias, José
Palabras claveOctocoral
Non-zooxanthellate gorgonia
Muricea spp
24(28)-Epoxisterol
Side-chain dealkylation
Pregnanes
Biogenesis
Fecha de publicaciónfeb-2006
EditorJohn Wiley & Sons
CitaciónEuropean Journal of Organic Chemistry 2006(3): 582-585 (2006)
ResumenSide-chain-oxidized C-28-sterol 1 and one new pregnane metabolite 2 were isolated from eastern Pacific Muricea spp. The C-24(28)-epoxide functionality is a key intermediate in the C-24-dealkylation mechanism of the conversion of phytosterol to cholesterol by phytophagous insects. Certain marine invertebrates share this dealkylation pathway; however, such a key epoxide feature has not yet been found in a naturally occurring sterol from marine invertebrates. The unusual oxidation pattern of the side chain of 1 encourages speculation about its biogenesis and converts this non-zooxanthellate gorgonia into an interesting candidate organism for biosynthetic studies on C-24-dealkylation of phytosterols in octocorals. The (22S)-22-hydroxy group, after 24-dealkylation of 1, may be an advantageous functionalization in the side-chain cleavage to C-21-pregnane steroids in Muricea spp.
Descripción4 pages, 2 figures, 1 table, 1 scheme.-- Available online Dec 12, 2005.-- Supporting information (10 pages) available at: http://www.wiley-vch.de/contents/jc_2046/2006/o200500775_s.pdf
Versión del editorhttp://dx.doi.org/10.1002/ejoc.200500775
URIhttp://hdl.handle.net/10261/13456
DOI10.1002/ejoc.200500775
ISSN1434-193X
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