474-69-1
Chemical Structure
Lumisterol
Synonym(s): 9β,10α-Ergosterol
- CAS No.: 474-69-1
- Formula:C28H44O
- Molecular Weight:396.65
IUPAC Name: (3S,9R,10S,13R,14R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChIKey: DNVPQKQSNYMLRS-YAPGYIAOSA-N
SMILES: C[C@H](C(C)C)/C=C/[C@@H](C)[C@H]1CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C
Biological Activity: Lumisterol (9β,10α-Ergosterol) is a photoproduct of 7-dehydrocholesterol, present in the skin, and acts as an orally active VDR non-genomic modulator and ROR inverse agonist. Lumisterol binds to the SARS-CoV-2 Mpro substrate-binding pocket and the RdRP active site, inhibiting enzyme activity. Lumisterol induces NRF2-regulated antioxidant responses, p53 phosphorylation and nuclear translocation, and intracellular free radical scavenging. Lumisterol inhibits the proliferation of epidermal keratinocytes and melanoma cells, modulates cell cycle progression, and suppresses basal and TNFα-induced NFκB transcriptional activity. Lumisterol inhibits RORγ transcriptional activity and IL-17 production. Lumisterol is used in research on UVB-induced skin damage, melanoma, psoriasis, vitamin D deficiency, and COVID-19[1][2][3][4][5][6][7].
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Lumisterol | Lumisterol (9β,10α-Ergosterol) is a photoproduct of 7-dehydrocholesterol, present in the skin, and acts as an orally active VDR non-genomic modulator and ROR inverse agonist. Lumisterol binds to the SARS-CoV-2 Mpro substrate-binding pocket and the RdRP active site, inhibiting enzyme activity. Lumisterol induces NRF2-regulated antioxidant responses, p53 phosphorylation and nuclear translocation, and intracellular free radical scavenging. Lumisterol inhibits the proliferation of epidermal keratinocytes and melanoma cells, modulates cell cycle progression, and suppresses basal and TNFα-induced NFκB transcriptional activity. Lumisterol inhibits RORγ transcriptional activity and IL-17 production. Lumisterol is used in research on UVB-induced skin damage, melanoma, psoriasis, vitamin D deficiency, and COVID-19. | |||||||||||||||||||||
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References
- [1]. Slominski AT, et al. Photoprotective Properties of Vitamin D and Lumisterol Hydroxyderivatives. Cell biochemistry and biophysics. 2020 Jun;78(2):165-180. [Content Brief]
- [2]. Slominski AT, et al. Characterization of a new pathway that activates lumisterol in vivo to biologically active hydroxylumisterols. Scientific reports. 2017 Sep 12;7(1):11434. [Content Brief]
- [3]. Slominski AT, et al. On the role of cholesterol, vitamin D, lumisterol, and tachysterol signaling in psoriasis. J Invest Dermatol. 2026 Apr;146(4):887-889. [Content Brief]
- [4]. Domżalski P, et al. Anticancer Activity of Vitamin D, Lumisterol and Selected Derivatives against Human Malignant Melanoma Cell Lines. International journal of molecular sciences. 2024 Oct 10;25(20):10914. [Content Brief]
- [5]. Kotwan J, et al. Oral Intake of Lumisterol Affects the Metabolism of Vitamin D. Molecular nutrition & food research. 2021 Jul;65(14):e2001165. [Content Brief]
- [6]. Tuckey RC, et al. Selective ability of rat 7-Dehydrocholesterol reductase (DHCR7) to act on some 7-Dehydrocholesterol metabolites but not on lumisterol metabolites. The Journal of steroid biochemistry and molecular biology. 2021 Sep;212:105929. [Content Brief]
- [7]. Qayyum S, et al. Vitamin D and lumisterol novel metabolites can inhibit SARS-CoV-2 replication machinery enzymes. American journal of physiology. Endocrinology and metabolism. 2021 Aug 01;321(2):E246-E251. [Content Brief]
