Description
24α-ethyl Cholesterol is a naturally occurring plant sterol with antioxidant, anticancer, anti-
inflammatory, angiogenic, chemopreventive, and immunomodulatory activities. It inhibits the absorption of dietary and endogenously-
produced cholesterol from the small intestine, reducing blood cholesterol concentrations. Because of its nutraceutical benefits, 24α-ethyl cholesterol has been used as a food additive intended to lower LDL cholesterol. 24α-ethyl Cholesterol (0.1 -
100 μM) can dose-
dependently induce adipogenesis and lipolysis in rat primary preadipocytes as well as stimulate glucose uptake in differentiated adipocytes.
Chemical Properties
White powder
Uses
A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.This compound is a contaminant of emerging concern (CECs)
Uses
antiinflammatory, immunomodulator
Definition
ChEBI: A phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.
Definition
sterol: Any of a group of steroidbasedalcohols having a hydrocarbonside-chain of 8–10 carbon atoms.Sterols exist either as free sterols oras esters of fatty acids. Animal sterols(zoosterols) include cholesterol andlanosterol. The major plant sterol(phytosterol) is beta-sitosterol, whilefungal sterols (mycosterols) includeergosterol.
Definition
A steroid with long
aliphatic side chains (8–10 carbons) and at
least one hydroxyl group. They are lipidsoluble and often occur in membranes. Examples are cholesterol and ergosterol.
General Description
Sitosterol, also called as β-sitosterol, is synthesized through the mevalonate and deoxy xylulose pathways. Synthetically, it is synthesized from stigmasterol by Δ22–23 alkene group hydrogenation. Structurally sitosterol differ from cholesterol with ethyl (sitosterol) group in C24 position of side chain(65). Sitosterol is a lipid component of membranes. It corresponds to a molecular mass of 414.71 g/mol).
Biochem/physiol Actions
Sitosterol promotes the antioxidant levels and is used as an effective anti-inflammatory, antiapoptotic and anticancer agent in medicinal preparations. It acts as a neutralizing agent for the venom from viper and cobra. Sitosterol acts on protein kinase C (PKC) and in the sphingomyelin cycle to mediate tumor progression inhibition.
Purification Methods
Crystallise -sitosterol from EtOH, MeOH, Me2CO, Me2CO/EtOH or Me2CO/MeOH. It has also been purified by zone melting. The acetate crystallises from MeOH or EtOH as plates with m 127128o and [] D 20 -41o (c 2, CHCl3). The benzoate crystallises from EtOH as needles with m 146-147o and [] D 20 –13.8o (c 2, CHCl3). [Fujimoto & Jacobson J Org Chem 29 3377, 3381 1964, Shoppee J Chem Soc 10431948, Heilbron et al. J Chem Soc 344, 347 1941, Beilstein 6 III 2696.]
References
[1] X.C. WENG W. W. Antioxidant activity of compounds isolated from Salvia plebeia[J]. Food Chemistry, 2000, 71 4: Pages 489-493. DOI:
10.1016/s0308-8146(00)00191-6[2] JEN-WAI CHAI. Gene regulation in β-sitosterol-mediated stimulation of adipogenesis, glucose uptake, and lipid mobilization in rat primary adipocytes.[J]. Genes & Nutrition, 2011, 6 2: 181-188. DOI:
10.1007/s12263-010-0196-4[3] EVAN HADRIAN. Steroids from Atactodea striata and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines[J]. Indonesian Journal of Chemistry, 2022. DOI:
10.22146/ijc.76438[4] JIANFENG XU Tiantian L Lei Yang. β-sitosterol targets glucocorticoid receptor to reduce airway inflammation and remodeling in allergic asthma[J]. Pulmonary pharmacology & therapeutics, 2023, 78: Article 102183. DOI:
10.1016/j.pupt.2022.102183[5] I IKEDA. Antihypercholesterolemic activity of beta-sitostanol in rabbits.[J]. Journal of nutritional science and vitaminology, 1981, 27 3: 243-251. DOI:
10.3177/jnsv.27.243[6] AYOUB MEDJMEDJ. In Cellulo and In Vivo Comparison of Cholesterol, Beta-Sitosterol and Dioleylphosphatidylethanolamine for Lipid Nanoparticle Formulation of mRNA.[J]. Nanomaterials, 2022. DOI:
10.3390/nano12142446
