Chemistry:25-Hydroxycholesterol
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| IUPAC name
Cholest-5-ene-3β,25-diol
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| Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R)-6-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
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| Properties | |
| C27H46O2 | |
| Molar mass | 402.7 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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25-Hydroxycholesterol is a derivative of cholesterol, which plays a role in various biological processes in humans and other species. It is involved in cholesterol metabolism, antiviral process, inflammatory and immune response, and survival signaling pathway. 25-hydroxycholesterol is biosynthesized from cholesterol by adding a hydroxyl group at the position 25-carbon of a steroid nucleus. This reaction is catalyzed by cholesterol 25-hydroxylase, a family of enzymes that use oxygen and a di-iron cofactor to catalyze hydroxylation reaction.[1][2]
The CYP3A4 enzyme, a member of the cytochrome P450 family, can catalyze the oxidation of 25-hydroxycholesterol to 7α,25-dihydroxycholesterol, whereas 25-hydroxycholesterol can inhibit CYP4F2 mRNA expression, so that members of the cytochrome P450 family are also involved in the metabolism of 25-hydroxycholesterol besides cholesterol 25-hydroxylase.[3]
25-hydroxycholesterol has been found in various organisms such as mice, rats, rabbits, and cows. As of 2023,[update] its presence in other species has not been extensively studied.[2][1]
See also
References
- ↑ 1.0 1.1 "25-hydroxycholesterol: an integrator of antiviral ability and signaling". Front Immunol 14. 2023. doi:10.3389/fimmu.2023.1268104. PMID 37781400.
- ↑ 2.0 2.1 "Multiple Roles of 25-Hydroxycholesterol in Lipid Metabolism, Antivirus Process, Inflammatory Response, and Cell Survival". Oxid Med Cell Longev 2020. 2020. doi:10.1155/2020/8893305. PMID 33274010.
- ↑ "Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin". J Biol Chem 282 (8): 5225–36. February 2007. doi:10.1074/jbc.M608176200. PMID 17142457.
Further reading
- Zu, Shulong; Deng, Yong-Qiang; Zhou, Chao; Li, Jie; Li, Lili; Chen, Qi; Li, Xiao-Feng; Zhao, Hui et al. (November 2020). "25-Hydroxycholesterol is a potent SARS-CoV-2 inhibitor" (in en). Cell Research 30 (11): 1043–1045. doi:10.1038/s41422-020-00398-1. ISSN 1748-7838. PMID 32811977.
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