LIPID MAPS

24α-ethyl Cholesterol is a phytosterol that has been found in S. plebia and has diverse biological activities.^1,2,3,4,5 It protects lard from thermal oxidation when used at concentrations of 0.02 and 0.04%.¹ 24α-ethyl Cholesterol (100 µM) induces glucose uptake and lipolysis in primary rat differentiated adipocytes and adipogenesis in primary rat preadipocytes.² It is cytotoxic to MCF-7 breast cancer cells (IC50 = 264.83 µM).³ 24α-ethyl Cholesterol increases protein levels of the glucocorticoid receptor in TGF-β1-induced human bronchial smooth muscle cells and prevents pulmonary fibrosis in a mouse model of allergic asthma induced by ovalbumin.⁴ Dietary administration of 24α-ethyl cholesterol (0.5%) reduces cholesterol-induced increases in liver weight and hepatic levels of cholesterol in rabbits.⁵ 24α-ethyl Cholesterol has also been used in the generation of lipid nanoparticles (LNPs) for the delivery of mRNA in vitro and in vivo.⁶ Formulations containing 24α-ethyl cholesterol have been used as dietary supplements.

This information has been provided by Cayman Chemical

References

1. Medjmedj, A., Ngalle-Loth, A., Clemençon, R., et al. In cellulo and in vivo comparison of cholesterol, beta-sitosterol and dioleylphosphatidylethanolamine for lipid nanoparticle formulation of mRNA. Nanomaterials (Basel) 12(14), 2446 (2022).

2. Xu, J., Yang, L., and Lin, T. β-sitosterol targets glucocorticoid receptor to reduce airway inflammation and remodeling in allergic asthma. Pulm. Pharmacol. Ther. 78, 102183 (2023).

3. Hadrian, E., Sari, A.P., Mayanti, T., et al. Steroids from Atactodea striata and their cytotoxic activity against MCF-7 breast cancer cell lines. Indones. J. Chem. 23(1), 200-209 (2023).

4. Ikeda, I., Kawasaki, A., Samezima, K., et al. Antihypercholesterolemic activity of β-sitostanol in rabbits. J. Nutr. Sci. Vitaminol. (Tokyo) 27(3), 243-251 (1981).

5. Weng, X.C., and Weng, W. Antioxidant activity of compounds isolated from Salvia plebia. Food Chem. 71(4), 489-493 (2000).

6. Chai, J.W., Lim, S.L., Kanthimathi, M.S., et al. Gene regulation in β-sitosterol-mediated stimulation of adipogenesis, glucose uptake, and lipid mobilization in rat primary adipocytes. Genes Nutr. 6(2), 181-188 (2011).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

InChiKey (Click to copy)

KZJWDPNRJALLNS-VJSFXXLFSA-N

InChi (Click to copy)

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CC[C@@H](CC)C(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Wikipedia

Sitosterol

KEGG ID

C01753

HMDB ID

HMDB0000852

CHEBI ID

27693

LIPIDBANK ID

SST9067