CAS 22348-64-7: (22S)-Hydroxycholesterol

22(S)-hydroxy Cholesterol is a synthetic oxysterol and a modulator of the liver X receptor (LXR). [1] t prevents monocyte chemoattractant protein 1 (MCP-1) expression induced by the LXR agonist GW 3965 in primary hepatocytes and downregulates mRNA expression of the LXR target genes CD36, ACSL1, and SCD-1 in human myotubes. It decreases triacylglycerol and diacylglycerol synthesis from labeled palmitate and acetate, respectively, in human myoblasts by 50% when used at a concentration of 10 uM. 22(S)-hydroxy Cholesterol also reduces fatty acid synthase (FAS) reporter activity through an LXR response element in the promoter region in COS-1 cells transfected with RXRα and LXRα and decreases the expression of MCP-1 and CCR2 in a mouse model of chronic ethanol consumption.[1] [2] Dietary supplementation of 22(S)-hydroxy cholesterol (30 mg/kg per day) leads to less body weight gain and lower liver triacylglycerol levels in rats when fed either a regular chow or high-fat diet as well as prevents an increase in plasma triacylglycerol levels resulting from a high-fat diet.[3]

22-Hydroxycholesterol is a product of cholesterol synthesis, which is formed by the side-chain cleavage of cholesterol. This compound has been shown to inhibit cholesterol acyltransferase and to be cytotoxic in vitro. 22-Hydroxycholesterol has also been shown to have an inhibitory effect on protein synthesis and on the activity of forskolin, an activator of adenylate cyclase that is involved in the regulation of cellular levels of cAMP. The antioxidant properties of 22-hydoxycholesterol may be due to its chemical structure, which includes a hydroxyl group. This compound also shows an insulin-sensitizing effect in mice fed a high fat diet.

Applications The 22S-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity. References Samson, M., et al.: J. Biol. Chem., 272, 24934 (1997), Mackay, C., et al.: Nature Immunol., 2, 95 (2001), Navenot, J., et al.: J. Mol. Biol., 313, 1181 (2001),