Lanosterol
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| Names | |
|---|---|
| IUPAC name
lanosta-8,24-dien-3-ol | |
| Identifiers | |
79-63-0  | |
| ChEBI | CHEBI:16521  |
| ChEMBL | ChEMBL225111 |
| ChemSpider | 216175 |
| 2746 | |
| Jmol interactive 3D | Image |
| MeSH | Lanosterol |
| PubChem | 246983 |
| UNII | 1J05Z83K3M |
| |
| |
| Properties | |
| C30H50O | |
| Molar mass | 426.71 g/mol |
| Melting point | 138 to 140 °C (280 to 284 °F; 411 to 413 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungi steroids are derived. By contrast plant steroids are produced via cycloartenol.[1]
Role in creation of steroids
Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.
Simplified version of the lanosterol synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP), and squalene shown. Some intermediates are omitted.
Recent research suggests that lanosterol might be instrumental in prevention of formation of cataracts in mammals.[2]
Biosynthesis
| Description | Illustration | Enzyme |
| Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene |  | squalene synthase |
| Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) |  | squalene monooxygenase |
| 2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol |  | lanosterol synthase |
| (step 2) |  | (step 2) |
Clinical significance
Preliminary studies in dogs and rabbits have shown that lanosterol can prevent and even reverse cataract formation.[2][3] However, an attempt to replicate these results in age-related cataractous human lens nuclei removed during manual small incision cataract surgery by immersing them in lanosterol solution and incubating them for 6 days according to the method of Zhao et al.,[2] failed to reverse nuclear opacity.[4]
See also
References
- ↑ Schaller, Hubert (May 2003). "The role of sterols in plant growth and development". Progress in Lipid Research 42 (3): 163–175. doi:10.1016/S0163-7827(02)00047-4.
- 1 2 3 Ling Zhao, Xiang-Jun Chen, Jie Zhu, Yi-Bo Xi, Xu Yang, Li-Dan Hu, Hong Ouyang, Sherrina H. Patel, Xin Jin, Danni Lin, Frances Wu, Ken Flagg, Huimin Cai, Gen Li, Guiqun Cao, Ying Lin, Daniel Chen, Cindy Wen, Christopher Chung, Yandong Wang, Austin Qiu, Emily Yeh, Wenqiu Wang, Xun Hu, Seanna Grob; et al. (July 2015). "Lanosterol reverses protein aggregation in cataracts". Nature. doi:10.1038/nature14650.
- ↑ Groß, M. (2015), Aggregate aufgelöst. Chemie in unserer Zeit. doi:10.1002/ciuz.201580036
- ↑ Shanmugam, P. M., Barigali, A., Kadaskar, J., Borgohain, S., Mishra, D. K. C., Ramanjulu, R., & Minija, C. K. (2015). Effect of lanosterol on human cataract nucleus. Indian journal of ophthalmology, 63(12), 888-890 doi:10.4103/0301-4738.176040
- 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. PMID 5918046.
- 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.
- A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen". Helvetica Chimica Acta 38 (7): 1890–1904. doi:10.1002/hlca.19550380728.
External links
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