Biomaterial Database

15-Oxygenated sterols with the unnatural cis-C-D ring junction. Studies of the metabolism of 5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol and 5 alpha,14 beta-cholest-7-ene-3 beta,15 beta-diol. 1980

R A Pascal, and G J Schroepfer

Four 15-oxygenated sterols with the "unnatural" cis-C-D ring juncture have recently been shown to be potent inhibitors of sterol synthesis in animal cells in culture (Schroepfer, G.J., Jr., Parish, E.J., Chen, H.W., and Kandutsch, A.A. (1977) J. Biol. Chem. 252, 8975-8980; Schroepfer, G.J., Jr., Pascal, R.A., Jr., and Kandutsch, A.A. (1979) Biochem. Pharmacol. 28, 249-252). In the present study we have prepared two of these sterols, [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol and [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 beta-diol, in labeled form, 5 alpha,14 beta-Cholest-7-ene-3 beta, 15 alpha-diol, but not its 15 beta-hydroxy epimer, was shown to be efficiently converted to cholesterol in 10,000 x g supernatant fractions of liver homogenate preparations from both male and female rats. After incubation of [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol with these enzyme preparations a number of labeled products, in addition to cholesterol, were isolated and characterized. These included 5 alpha-cholesta-8,14-dien-3 beta-ol, cholesta-5,7-dien-3 beta-ol, 5 alpha-cholest-8-en-3 beta-ol, and 5 alpha-cholest-7-en-3 beta-ol. A scheme to account for the enzymatic formation of cholesterol and the other sterol precursors of cholesterol is presented.

UI	MeSH Term	Description	Entries
D007553	Isotope Labeling	Techniques for labeling a substance with a stable or radioactive isotope. It is not used for articles involving labeled substances unless the methods of labeling are substantively discussed. Tracers that may be labeled include chemical substances, cells, or microorganisms.	Isotope Labeling, Stable,Isotope-Coded Affinity Tagging,Isotopically-Coded Affinity Tagging,Affinity Tagging, Isotope-Coded,Affinity Tagging, Isotopically-Coded,Isotope Coded Affinity Tagging,Labeling, Isotope,Labeling, Stable Isotope,Stable Isotope Labeling,Tagging, Isotope-Coded Affinity,Tagging, Isotopically-Coded Affinity
D008099	Liver	A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances.	Livers
D002784	Cholesterol	The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.	Epicholesterol
D002845	Chromatography	Techniques used to separate mixtures of substances based on differences in the relative affinities of the substances for mobile and stationary phases. A mobile phase (fluid or gas) passes through a column containing a stationary phase of porous solid or liquid coated on a solid support. Usage is both analytical for small amounts and preparative for bulk amounts.	Chromatographies
D006888	Hydroxycholesterols	Cholesterol which is substituted by a hydroxy group in any position.
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D014316	Tritium	The radioactive isotope of hydrogen also known as hydrogen-3. It contains two NEUTRONS and one PROTON in its nucleus and decays to produce low energy BETA PARTICLES.	Hydrogen-3,Hydrogen 3
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus