Oxidative demethylation of lanosterol in cholesterol biosynthesis: accumulation of sterol intermediates
With (/sup 3/H-24,25)-dihydrolanosterol as substrate, large-scale metabolic formation of intermediates of lanosterol demethylation was carried out to identify all compounds in the metabolic process. Utilizing knowledge of electron transport of lanosterol demethylation, we interrupted the demethylation reaction allowing accumulation and confirmation of the structure of the oxygenated intermediates lanost-8-en-3 beta,32-diol and 3 beta-hydroxylanost-8-en-32-al, as well as the demethylation product 4,4-dimethyl-cholesta-8,14-dien-3 beta-ol. Further metabolism of the delta 8.14-diene intermediate to a single product 4,4-dimethyl-cholest-8-en-3 beta-ol occurs under interruption conditions in the presence of 0.5 mM CN-1. With authentic compounds, each intermediate has been rigorously characterized by high performance liquid chromatography and gas-liquid chromatography plus mass spectral analysis of isolated and derivatized sterols. Intermediates that accumulated in greater abundance were further characterized by ultraviolet, /sup 1/H-NMR, and infrared spectroscopy of the isolated sterols.
- Research Organization:
- E. I. du Pont de Nemours and Co., Wilmington, DE
- OSTI ID:
- 5811132
- Journal Information:
- J. Lipid Res.; (United States), Vol. 1
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
CHOLESTEROL
BIOSYNTHESIS
STEROLS
METABOLISM
INFRARED SPECTRA
ISOTOPE DILUTION
LIQUID COLUMN CHROMATOGRAPHY
NUCLEAR MAGNETIC RESONANCE
RATS
STRUCTURE-ACTIVITY RELATIONSHIPS
TRITIUM COMPOUNDS
ULTRAVIOLET SPECTRA
ANIMALS
CHROMATOGRAPHY
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MAGNETIC RESONANCE
MAMMALS
ORGANIC COMPOUNDS
RESONANCE
RODENTS
SEPARATION PROCESSES
SPECTRA
STEROIDS
SYNTHESIS
TRACER TECHNIQUES
VERTEBRATES
550201* - Biochemistry- Tracer Techniques