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Muriceanol, a 24(28)-epoxide sterol link in the carbon flux toward side-chain dealkylation of sterols

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2006-01-30
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Lorenzo, Manuel
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Muriceanol, a 24(28)-epoxide sterol link in the carbon flux toward side-chain dealkylation of sterols
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Author
  • Lorenzo, Manuel;
  • Cueto, Mercedes;
  • D'Croz, Luis;
  • Maté, Juan L.;
  • San Martín Barrientos, Aurelio;
  • Darías, José;
Abstract
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 I 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.
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URI: https://repositorio.uchile.cl/handle/2250/118819
ISSN: 1434-193X
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Issue: 3 Pages: 582-585 Published: JAN 30 2006
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