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Muriceanol, a 24(28)-Epoxide Sterol Link in the Carbon Flux Toward Side-Chain Dealkylation of Sterols
- Source :
- Digital.CSIC. Repositorio Institucional del CSIC, instname
- Publication Year :
- 2006
- Publisher :
- Wiley, 2006.
-
Abstract
- 4 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<br />Side-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.<br />This work was supported by the Ministerio de Educación y Ciencia (PPQ2002-02494), and the DGUI of the Canary Islands Government (PI2002/044). M. L. acknowledges MECESUP MAG0002, Chile, for financial support. The STRI provided support and facilities.
- Subjects :
- Stereochemistry
Chemistry
Muricea spp
Organic Chemistry
Epoxide
General Medicine
Alkylation
Pregnanes
Non-zooxanthellate gorgonia
Sterol
24(28)-Epoxisterol
chemistry.chemical_compound
Octocoral
Side-chain dealkylation
Side chain
Organic chemistry
Physical and Theoretical Chemistry
Biogenesis
Carbon flux
Subjects
Details
- ISSN :
- 10990690 and 1434193X
- Volume :
- 2006
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....d38fdc42c0532123939debf27e0009b4