Biomaterial Database

Inhibition of cholesterol synthesis by oxygenated sterols. 1978

A A Kandutsch, and H W Chen

Sterols derived from cholesterol by introducing a ketone or hydroxyl function in the 6, 7, 15, 20, 22, 24, or 25 positions are known to be potent inhibitors of sterol synthesis in cell cultures. To gain more information regarding structural requirements for inhibitory activity, inhibitory potencies were determined for a series of 18 C27-steroids with various combinations of ketone and hydroxyl functions substituted in positions 3, 4, 5, 6, and 7, or with a single ketone or hydroxyl function in one of these positions. The effects of nuclear double bonds upon inhibitory activity were also examined. A ketone or hydroxyl function in position 3 and a second ketone or hydroxyl function in position 6 or 7 was required for inhibitory activity with two kinds of cell culture. A 3beta5alpha6beta-triol was not more inhibitory than a comparable 3beta,6beta-diol. Cholestane-3beta 5alpha-diol inhibited sterol synthesis in L cells but not in liver cell cultures. The inhibitory activities of 7-oxygenated sterols were not markedly affected by the presence of a double bond in position 4 or 5. Current knowledge of the mechanism through which the oxygenated sterols suppress cholesterol synthesis is reviewed.

UI	MeSH Term	Description	Entries
D007739	L Cells	A cultured line of C3H mouse FIBROBLASTS that do not adhere to one another and do not express CADHERINS.	Earle's Strain L Cells,L Cell Line,L Cells (Cell Line),L-Cell Line,L-Cells,L-Cells, Cell Line,L929 Cell Line,L929 Cells,NCTC Clone 929 Cells,NCTC Clone 929 of Strain L Cells,Strain L Cells,Cell Line L-Cell,Cell Line L-Cells,Cell Line, L,Cell Line, L929,Cell Lines, L,Cell, L,Cell, L (Cell Line),Cell, L929,Cell, Strain L,Cells, L,Cells, L (Cell Line),Cells, L929,Cells, Strain L,L Cell,L Cell (Cell Line),L Cell Lines,L Cell, Strain,L Cells, Cell Line,L Cells, Strain,L-Cell,L-Cell Lines,L-Cell, Cell Line,L929 Cell,Strain L Cell
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
D002478	Cells, Cultured	Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others.	Cultured Cells,Cell, Cultured,Cultured Cell
D002777	Cholestanols	Cholestanes substituted in any position with one or more hydroxy groups. They are found in feces and bile. In contrast to bile acids and salts, they are not reabsorbed.	Bile Alcohol,Bile Alcohols,Hydroxycholestane,Hydroxycholestanes,Alcohol, Bile,Alcohols, Bile
D002778	Cholestanones	CHOLESTANES substituted with any number of keto groups.
D002782	Cholestenes	Steroids with methyl groups at C-10 and C-13 and a branched 8-carbon chain at C-17. Members include compounds with any degree of unsaturation; however, CHOLESTADIENES is available for derivatives containing two double bonds.
D002783	Cholestenones	CHOLESTENES with one or more double bonds and substituted by any number of keto groups.
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
D006888	Hydroxycholesterols	Cholesterol which is substituted by a hydroxy group in any position.
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships