Chemistry:Lumisterol
Lumisterol, more specifically lumisterol2 (L2), is a compound that is part of the vitamin D family of steroid compounds. It is the (9β,10α) stereoisomer of ergosterol and occurs as a photochemical by-product in the preparation of vitamin D1, a mixture of vitamin D2 and lumisterol.[1][2] Lumisterol has an analog based on 7-dehydrocholesterol, known as lumisterol 3 or lumisterol3 (L3).[3]
Formation
Lumisterol is produced when previtamin D, instead of isomerizing to vitamin D, receives an additional UVB photon to cause a disrotatory electrocyclic ring-closure. In vivo this happens under high-dose or prolonged UVB exposure.[4]
Reactions
Vitamin D2 can be formed from L2 by an electrocyclic ring opening (back to the previtamin) and subsequent sigmatropic [1,7] hydride shift. This conversion reaction can be stimulated by UV-B or heat. At very high doses in mice, this conversion can occur in the body.[5]
L2 is metabolized by CYP27A1, causing hydroxylation at the 24, 27, 28 positions.[6]
L3 is processed by CYP27A1 to form products hydroxylated at positions 25 and/or 27. CYP11A1 can 20S-hydroxylate L3. The resulting products are biologically active.[7] Many of these products activate UV-defense mechanisms in keratinocytes.[8]
References
- ↑ Dewick, Paul M. (2002). Medicinal Natural Products. A Biosynthetic Approach (Second ed.). New York: John Wiley & Sons. p. 259. ISBN 0-471-49640-5. http://nadjeeb.files.wordpress.com/2009/10/dewick-natural-prod.pdf.
- ↑ Friedmann, Ernst (1989). Neurath, Hans. ed. Vitamin D. Perspectives in Biochemistry. 1. Washington, DC: American Chemical Society. ISBN 978-0-8412-1621-1. https://books.google.com/books?id=q-Y8AAAAIAAJ&pg=PA247.
- ↑ "Lumisterol 3 (CID=111049)" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/lumisterol_3.
- ↑ Liu, Wuzhang; Shan, Yu; Liu, Songtao; Zhou, Ye; Wang, Yan; Li, Linwei; Xu, Shu; Chen, Yu et al. (July 2024). "Optimization of synthesis process and photocatalytic mechanism of tachysterol under ultraviolet irradiation". Journal of Chemical Research 48 (4). doi:10.1177/17475198241265931.
- ↑ Kotwan, Julia; Kühn, Julia; Baur, Anja C.; Stangl, Gabriele I. (July 2021). "Oral Intake of Lumisterol Affects the Metabolism of Vitamin D". Molecular Nutrition & Food Research 65 (14). doi:10.1002/mnfr.202001165.
- ↑ Wu, D; Nealon, G; Liu, Y; Kim, TK; Slominski, AT; Tuckey, RC (October 2023). "Metabolism of Lumisterol(2) by CYP27A1.". The Journal of steroid biochemistry and molecular biology 233. doi:10.1016/j.jsbmb.2023.106370. PMID 37499840.
- ↑ Slominski, Andrzej T.; Kim, Tae-Kang; Janjetovic, Zorica; Ravichandran, Senthilkumar; Song, Yuwei; Podgorska, Ewa; Slominski, Radomir M.; Ewendt, Franz et al. (April 2026). "Metabolic activation of lumisterol to biologically active metabolites and their mechanism of action". Biochemical Pharmacology 246. doi:10.1016/j.bcp.2026.117711.
- ↑ Chaiprasongsuk, A; Janjetovic, Z; Kim, TK; Jarrett, SG; D'Orazio, JA; Holick, MF; Tang, EKY; Tuckey, RC et al. (June 2019). "Protective effects of novel derivatives of vitamin D(3) and lumisterol against UVB-induced damage in human keratinocytes involve activation of Nrf2 and p53 defense mechanisms.". Redox biology 24. doi:10.1016/j.redox.2019.101206. PMID 31039479.
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