Muriceanol, a 24(28)‐Epoxide Sterol Link in the Carbon Flux Toward Side‐Chain Dealkylation of Sterols | Zendy

Lorenzo Manuel | Zendy; Cueto Mercedes | Zendy; D’Croz Luis | Zendy; Maté Juan L. | Zendy; SanMartín Aurelio | Zendy; Darias José | Zendy

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

Author(s) -

Lorenzo Manuel,

Cueto Mercedes,

D’Croz Luis,

Maté Juan L.,

SanMartín Aurelio,

Darias José

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500775

Subject(s) - sterol , chemistry , alkylation , phytosterol , side chain , stereochemistry , epoxide , metabolite , marine invertebrates , biogenesis , biochemistry , cholesterol , organic chemistry , biology , ecology , gene , catalysis , polymer

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 (22 S )‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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