Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.[2]
Lanosterol has been identified as a key component in maintaining eye lens clarity.[3] Pre-clinical research has identified Lanosterol as a possible agent for the reversal and prevention of cataracts.[4] In vivo experiments on dogs showed significant reversal of cataracts within 6 weeks of lanosterol injection.[5] In 2018, Lanosterol was shown to improve lens clarity in cells with lens clouding due to aging or physical stressors.[6] A subsequent study in 2022 by Kehao Wang, Hoshino, Kentaro Uesugi, Naoto Yagi, Pierscionek and Andley found positive results on the optics of the lens in mice with cataracts.[7]
Useedit
Lanosterol is an ingredient in over-the-counter ophthalmic products to prevent cataracts. However, the solubility and bioavailability of lanosterol is not conducive to aqueous formulations.[8] Heliostatix Biotechnology claims to have a method of solubilizing lanosterol for use in aqueous products.[9]
^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. PMID 12689617.
^"Do Lanosterol eye drops work for dogs? - PetACS Pet Health Products". petacs.com. Retrieved 2023-06-06.
^Huff, M; Telford, D (July 2005). "Lord of the rings – the mechanism for oxidosqualene:lanosterol cyclase becomes crystal clear". Trends in Pharmacological Sciences. 26 (7): 335–340. doi:10.1016/j.tips.2005.05.004. PMID 15951028.
^Zhang, K.; Zhao, L.; Zhu, J.; Hou, R.; Wang, S.; Yan, Y. (2016). "Lanosterol reversal of protein aggregation in cataract". Acta Ophthalmologica. 94. doi:10.1111/j.1755-3768.2016.0033.
^Wang, Kehao; Hoshino, Masato; Uesugi, Kentaro; Yagi, Naoto; Pierscionek, Barbara K.; Andley, Usha P. (2022-05-16). "Oxysterol Compounds in Mouse Mutant αA- and αB-Crystallin Lenses Can Improve the Optical Properties of the Lens". Investigative Ophthalmology & Visual Science. 63 (5): 15. doi:10.1167/iovs.63.5.15. ISSN 1552-5783. PMC9123516. PMID 35575904.
^Daszynski, Damian M.; Santhoshkumar, Puttur; Phadte, Ashutosh S.; Sharma, K. Krishna; Zhong, Haizhen A.; Lou, Marjorie F.; Kador, Peter F. (2019). "Failure of Oxysterols Such as Lanosterol to Restore Lens Clarity from Cataracts". Scientific Reports. 9 (1): 8459. Bibcode:2019NatSR...9.8459D. doi:10.1038/s41598-019-44676-4. PMC6560215. PMID 31186457.
Corey, E. J.; Russey, William E.; de Montellano, Paul R. Ortiz (October 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.
Abe, Ikuro.; Rohmer, Michel.; Prestwich, Glenn D. (1 September 1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews. 93 (6): 2189–2206. doi:10.1021/cr00022a009.
Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen" [For knowledge of the triterpenes. Part 190. A stereochemical interpretation of the biogenetic isoprene rule in triterpenes]. Helvetica Chimica Acta (in German). 38 (7): 1890–1904. doi:10.1002/hlca.19550380728.
Wang, Kehao; Hoshino, Masato; Uesugi, Kentaro; Yagi, Naoto; Pierscionek, Barbara K.; Andley, Usha P. (2022-05-16). "Oxysterol Compounds in Mouse Mutant αA- and αB-Crystallin Lenses Can Improve the Optical Properties of the Lens". Investigative Ophthalmology & Visual Science. 63 (5): 15. doi:10.1167/iovs.63.5.15. ISSN 1552-5783. PMC9123516. PMID 35575904.
External linksedit
January 07, 2024
lanosterol, tetracyclic, triterpenoid, compound, from, which, animal, fungal, steroids, derived, contrast, plant, steroids, produced, cycloartenol, namesiupac, name, lanosta, dien, olsystematic, iupac, name, 11ar, pentamethyl, methylhept, tetradecahydro, cyclo. Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived By contrast plant steroids are produced via cycloartenol 1 Lanosterol NamesIUPAC name Lanosta 8 24 dien 3b olSystematic IUPAC name 1R 3aR 5aR 7S 9aS 11aR 3a 6 6 9a 11a Pentamethyl 1 2R 6 methylhept 5 en 2 yl 2 3 3a 4 5 5a 6 7 8 9 9a 10 11 11a tetradecahydro 1H cyclopenta a phenanthren 7 olIdentifiersCAS Number 79 63 0 Y3D model JSmol Interactive imageBeilstein Reference 2226449ChEBI CHEBI 16521 YChEMBL ChEMBL225111 YChemSpider 216175 YDrugBank DB03696ECHA InfoCard 100 001 105EC Number 201 214 9IUPHAR BPS 2746KEGG C01724MeSH LanosterolPubChem CID 246983UNII 1J05Z83K3M YCompTox Dashboard EPA DTXSID1040744InChI InChI 1S C30H50O c1 20 2 10 9 11 21 3 22 14 18 30 8 24 12 13 25 27 4 5 26 31 16 17 28 25 6 23 24 15 19 29 22 30 7 h10 21 22 25 26 31H 9 11 19H2 1 8H3 t21 22 25 26 28 29 30 m1 s1 YKey CAHGCLMLTWQZNJ BQNIITSRSA N YInChI 1 C30H50O c1 20 2 10 9 11 21 3 22 14 18 30 8 24 12 13 25 27 4 5 26 31 16 17 28 25 6 23 24 15 19 29 22 30 7 h10 21 22 25 26 31H 9 11 19H2 1 8H3 t21 22 25 26 28 29 30 m1 s1Key CAHGCLMLTWQZNJ BQNIITSRBPSMILES C C H CCC C C C C H 1CC C 2 C C1CCC3 C2CC C H 4C C C C H O CC C 34CPropertiesChemical formula C30H50OMolar mass 426 71 g molMelting 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 N verify what is Y N Infobox references Contents 1 Role in the biosynthesis of other steroids 2 Biosynthesis 3 Research 4 Use 5 See also 6 References 7 Further reading 8 External linksRole in the biosynthesis of other steroids editElaboration of lanosterol under enzyme catalysis leads to the core structure of steroids 14 Demethylation of lanosterol by CYP51 eventually yields cholesterol 2 nbsp 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 Biosynthesis editDescription Illustration EnzymeTwo molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene nbsp squalene synthaseSqualene is oxidized to 2 3 oxidosqualene squalene epoxide nbsp squalene monooxygenase2 3 Oxidosqualene is converted to a protosterol cation and finally to lanosterol nbsp lanosterol synthase step 2 nbsp step 2 Research editLanosterol has been identified as a key component in maintaining eye lens clarity 3 Pre clinical research has identified Lanosterol as a possible agent for the reversal and prevention of cataracts 4 In vivo experiments on dogs showed significant reversal of cataracts within 6 weeks of lanosterol injection 5 In 2018 Lanosterol was shown to improve lens clarity in cells with lens clouding due to aging or physical stressors 6 A subsequent study in 2022 by Kehao Wang Hoshino Kentaro Uesugi Naoto Yagi Pierscionek and Andley found positive results on the optics of the lens in mice with cataracts 7 Use editLanosterol is an ingredient in over the counter ophthalmic products to prevent cataracts However the solubility and bioavailability of lanosterol is not conducive to aqueous formulations 8 Heliostatix Biotechnology claims to have a method of solubilizing lanosterol for use in aqueous products 9 See also editCycloartenol CYP51References edit 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 PMID 12689617 Do Lanosterol eye drops work for dogs PetACS Pet Health Products petacs com Retrieved 2023 06 06 Huff M Telford D July 2005 Lord of the rings the mechanism for oxidosqualene lanosterol cyclase becomes crystal clear Trends in Pharmacological Sciences 26 7 335 340 doi 10 1016 j tips 2005 05 004 PMID 15951028 Zhang K Zhao L Zhu J Hou R Wang S Yan Y 2016 Lanosterol reversal of protein aggregation in cataract Acta Ophthalmologica 94 doi 10 1111 j 1755 3768 2016 0033 Zhao Ling Chen Xiang Jun Zhu Jie Xi Yi Bo Yang Xu Hu Li Dan Ouyang Hong Patel Sherrina H Jin Xin Lin Danni Wu Frances Flagg Ken Cai Huimin Li Gen Cao Guiqun Lin Ying Chen Daniel Wen Cindy Chung Christopher Wang Yandong Qiu Austin Yeh Emily Wang Wenqiu Hu Xun Grob Seanna Abagyan Ruben Su Zhiguang Tjondro Harry Christianto Zhao Xi Juan Luo Hongrong Hou Rui Jefferson J Perry P Gao Weiwei Kozak Igor Granet David Li Yingrui Sun Xiaodong Wang Jun Zhang Liangfang Liu Yizhi Yan Yong Bin Zhang Kang July 2015 Lanosterol reverses protein aggregation in cataracts Nature 523 7562 607 611 Bibcode 2015Natur 523 607Z doi 10 1038 nature14650 PMID 26200341 S2CID 4469138 Shen Xinyue Zhu Manhui Kang Lihua Tu Yuanyuan Li Lele Zhang Rutan Qin Bai Yang Mei Guan Huaijin 11 July 2018 Lanosterol Synthase Pathway Alleviates Lens Opacity in Age Related Cortical Cataract Journal of Ophthalmology 2018 1 9 doi 10 1155 2018 4125893 PMC 6079410 PMID 30116630 Wang Kehao Hoshino Masato Uesugi Kentaro Yagi Naoto Pierscionek Barbara K Andley Usha P 2022 05 16 Oxysterol Compounds in Mouse Mutant aA and aB Crystallin Lenses Can Improve the Optical Properties of the Lens Investigative Ophthalmology amp Visual Science 63 5 15 doi 10 1167 iovs 63 5 15 ISSN 1552 5783 PMC 9123516 PMID 35575904 Daszynski Damian M Santhoshkumar Puttur Phadte Ashutosh S Sharma K Krishna Zhong Haizhen A Lou Marjorie F Kador Peter F 2019 Failure of Oxysterols Such as Lanosterol to Restore Lens Clarity from Cataracts Scientific Reports 9 1 8459 Bibcode 2019NatSR 9 8459D doi 10 1038 s41598 019 44676 4 PMC 6560215 PMID 31186457 Heliostatix orgFurther reading editCorey E J Russey William E de Montellano Paul R Ortiz October 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 Abe Ikuro Rohmer Michel Prestwich Glenn D 1 September 1993 Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes Chemical Reviews 93 6 2189 2206 doi 10 1021 cr00022a009 Eschenmoser A Ruzicka L Jeger O Arigoni D 1955 Zur Kenntnis der Triterpene 190 Mitteilung Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen For knowledge of the triterpenes Part 190 A stereochemical interpretation of the biogenetic isoprene rule in triterpenes Helvetica Chimica Acta in German 38 7 1890 1904 doi 10 1002 hlca 19550380728 Wang Kehao Hoshino Masato Uesugi Kentaro Yagi Naoto Pierscionek Barbara K Andley Usha P 2022 05 16 Oxysterol Compounds in Mouse Mutant aA and aB Crystallin Lenses Can Improve the Optical Properties of the Lens Investigative Ophthalmology amp Visual Science 63 5 15 doi 10 1167 iovs 63 5 15 ISSN 1552 5783 PMC 9123516 PMID 35575904 External links edit Retrieved from https en wikipedia org w index php title Lanosterol amp oldid 1191068112, wikipedia, wiki, book, books, library,
