A cholesterol metabolite
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Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol.1 It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 ?g/ml.2 Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland.3 It has been used as synthetic intermediate in the synthesis of steroids.4
1.Salen, G., Batta, A.K., Tint, G.S., et al.Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemiaJ. Lipid Res.35(10)1878-1887(1994) 2.Chen, C.-L., Wu, D.-C., Liu, M.-Y., et al.Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cellsJ. Recept. Signal Transduct. Res.37(2)189-199(2017) 3.Steinberg, D., Fredrickson, D.S., and Avigan, J.Effects of Δ4-cholestenone in animals and in manProc. Soc. Exp. Biol. Med.97(4)784-790(1958) 4.Wu, K., Li, W., Song, J., et al.Production, purification, and identification of cholest-4-en-3-one produced by cholesterol oxidase from Rhodococcus sp. in aqueous/organic biphasic systemBiochem. Insights8(Suppl 1)1-8(2015)
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