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Lanosterol
From Wikipedia, the free encyclopedia
| Lanosterol | |
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| IUPAC name | lanosta-8,24-dien-3-ol |
| Identifiers | |
| CAS number | [] |
| MeSH | |
| Properties | |
| Molecular formula | C30H50O |
| Molar mass | 426.70 g/mol |
| Melting point |
138-140 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. Lanosterol is biochemically synthesized from farnesyl pyrophosphate. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide. Further elaboration under enzyme catalysis leads to the core structure of steroids. 14-demethylation of lanosterol by CYP51 eventually yields cholesterol.
Contents |
- Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene - by squalene synthase;
- Squalene is reduced by NADPH to 2,3-oxidosqualene (squalene epoxide) - by squalene monooxygenase;
- 2,3-oxidosqualene is converted to a protosterol cation and finally to lanosterol, catalyzed by the enzyme lanosterol synthase:
- Cycloartenol
- CYP51
- E. J. Corey, W. E. Russey, P. R. Ortiz de Montellano (1966). "2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene". Journal of the American Chemical Society 88 (20): 4750 - 4751. DOI:10.1021/ja00972a056.
- I. Abe, M. Rohmer, G. D. Prestwich (1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews 93 (6): 2189 - 2206. DOI:10.1021/cr00022a009.
Adosterol - Cholecalciferol/Ergocalciferols - Cholesterol - Dihydrotachysterol - Fusidic acid - Lanosterol - Phytosterols - Solanine