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Chemical Compound Review:

Lanostenol (3S,10S,13R,14R,17R)- 4,4,10,13,14...

Synonyms: CHEMBL132906, SureCN288307, AC1Q1PAX, AC1L23JH, 79-62-9, ...

Buttke, T.M. et al., Itoh, T. et al., Tint, G.S. et al., Trzaskos, J.M. et al., Strömstedt, M. et al., et al.

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Disease relevance of Lanostenol

The metabolism of lanosterol and 24,25-dihydrolanosterol (DL) was examined in a patient with cerebrotendinous xanthomatosis after intravenous pulse labeling with a mixture of DL-2-14C and 3S,4S,3R,4R-(4-3H)mevalonate [1].

High impact information on Lanostenol

In A3.01 cells cultured in 1% FBS medium, lanosterol and 24,25-dihydrolanosterol accounted for 7 and 45%, respectively, of total cellular sterols [2].
A3.01 cells grown in the presence of 10% fetal bovine serum (FBS) contain primarily cholesterol in their membranes, but based on [14C]acetate labeling, synthesize only lanosterol and 24,25-dihydrolanosterol [2].
This enzyme removes the 14alpha-methyl group from lanosterol and 24,25-dihydrolanosterol producing intermediates in cholesterol biosynthesis, the oocyte meiosis-activating sterols FF-MAS and MAS-412 [3].
As in yeast and fungi, the activity is likely to be due to inhibition of the cytochrome P-450-dependent 14 alpha-demethylation of lanosterol and/or 24,25-dihydrolanosterol [4].
Occurrence of lanosterol and lanostenol in seeds of red pepper (Capsicum annuum) [5].

Anatomical context of Lanostenol

Metabolism of 24,25-dihydrolanosterol analogs by partially purified cytochrome P-450(14DM) from rat liver microsomes [6].

Gene context of Lanostenol

When reconstituted with NADPH-cytochrome P-450 reductase, the purified protein showed an activity of 14 alpha-demethylation of 24,25-dihydrolanosterol (3.20 nmol/min per mg protein) [7].

Analytical, diagnostic and therapeutic context of Lanostenol

Electron transfer to rat liver microsomal cytochrome P-450 of 14 alpha-methyl group demethylation of 24,25-dihydrolanosterol (C30-sterol) has been studied with a new radio-high-performance liquid chromatography assay [8].
Lanosterol and lanostenol, whose occurrence in higher plants has hitherto been known as extremely rare, are identified in the fraction by gas liquid chromatography, combined gas liquid chromatography-mass spectrometry, and isolation as their epoxides [5].

References

Evidence for the early reduction of the 24,25 double bond in the conversion of lanosterol to cholesterol in cerebrotendinous xanthomatosis. Tint, G.S., Salen, G. Metab. Clin. Exp. (1977) [Pubmed]
Complete replacement of membrane cholesterol with 4,4',14-trimethyl sterols in a human T cell line defective in lanosterol demethylation. Buttke, T.M., Folks, T.M. J. Biol. Chem. (1992) [Pubmed]
Elevated expression of lanosterol 14alpha-demethylase (CYP51) and the synthesis of oocyte meiosis-activating sterols in postmeiotic germ cells of male rats. Strömstedt, M., Waterman, M.R., Haugen, T.B., Taskén, K., Parvinen, M., Rozman, D. Endocrinology (1998) [Pubmed]
Perturbation of sterol biosynthesis by itraconazole and ketoconazole in Leishmania mexicana mexicana infected macrophages. Hart, D.T., Lauwers, W.J., Willemsens, G., Vanden Bossche, H., Opperdoes, F.R. Mol. Biochem. Parasitol. (1989) [Pubmed]
Occurrence of lanosterol and lanostenol in seeds of red pepper (Capsicum annuum). Itoh, T., Jeong, T.M., Hirano, Y., Tamura, T., Matsumoto, T. Steroids (1977) [Pubmed]
Metabolism of 24,25-dihydrolanosterol analogs by partially purified cytochrome P-450(14DM) from rat liver microsomes. Sonoda, Y., Sekigawa, Y., Sato, Y. Chem. Pharm. Bull. (1989) [Pubmed]
Purification of a human cytochrome P-450 isozyme catalyzing lanosterol 14 alpha-demethylation. Sonoda, Y., Endo, M., Ishida, K., Sato, Y., Fukusen, N., Fukuhara, M. Biochim. Biophys. Acta (1993) [Pubmed]
Cytochrome P-450-dependent oxidation of lanosterol in cholesterol biosynthesis. Microsomal electron transport and C-32 demethylation. Trzaskos, J.M., Bowen, W.D., Shafiee, A., Fischer, R.T., Gaylor, J.L. J. Biol. Chem. (1984) [Pubmed]

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