Concerning the role of 24,25-dihydrolanosterol and lanostanol in sterol biosynthesis by cultured cells

W. David Nes, Robert A. Norton, Edward J. Parish, Aniko Meenan, George Popják

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Abstract

Rat hepatoma cells (H4-II-E-C3) efficiently converted a dietary supplement of [2-3H]24,25-dihydrolanosterol (1) to [3H]cholesterol while [2-3H]lanostanol (4,4,14α-trimethyl-cholestanol(2) was recovered from the cells without apparent transformation, although it was esterified and induced an accumulation of lanosterol. A comparison of the Chromatographic (TLC, GLC and HPLC), spectral (MS and 1H-NMR) and physical properties of 1 and 2 is given for the first time. The inability to detect 2 in nature coupled with our findings that 1 but not 2 is metabolized to cholesterol by H4 cells is interpreted to imply that the biosynthetic inclusion of the Δ8(9)-bond during the cyclization process of squalene-oxide to a tetracyclic product is an evolutionary adaptation selected for because the olefinic linkage is structually important in the subsequent conversion of lanosterol and its stereoisomers, e.g., cycloartenol, to Δ5-sterols.

Original languageEnglish
Pages (from-to)461-475
Number of pages15
JournalSteroids
Volume53
Issue number3-5
DOIs
StatePublished - 1989

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