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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)