Cholestenone

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)