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Lanosterol
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| Names |
| IUPAC name
lanosta-8,24-dien-3-ol
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| Identifiers |
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CAS Number
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3D model (Jmol)
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| ChEBI |
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| ChemSpider |
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| ECHA InfoCard |
100.001.105 |
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IUPHAR/BPS
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| MeSH |
Lanosterol |
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| UNII |
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InChI
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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 N
Key: CAHGCLMLTWQZNJ-BQNIITSRSA-N N
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InChI=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/s1
Key: CAHGCLMLTWQZNJ-BQNIITSRBP
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SMILES
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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@]34C
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| Properties |
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Chemical formula
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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).
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| N verify (what is YN ?) |
| Infobox references |
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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]
Contents
- 1 Role in creation of steroids
- 2 Biosynthesis
- 3 Clinical significance
- 4 See also
- 5 References
- 6 External links
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 |
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squalene synthase |
| Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) |
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squalene monooxygenase |
| 2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol |
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lanosterol synthase |
| (step 2) |
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(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.
- ^ a b c 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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Cholestanes, membrane lipids: sterols
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- Adosterol
- Cholecalciferol/Ergocalciferols
- Cholesterol
- Dihydrotachysterol
- Fusidic acid
- Lanosterol
- Phytosterols
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Cholesterol and steroid metabolic intermediates
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| Mevalonate pathway |
| to HMG-CoA |
- Acetyl-CoA
- Acetoacetyl-CoA
- HMB
- HMB-CoA
- HMG-CoA
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| Ketone bodies |
- Acetone
- Acetoacetic acid
- β-Hydroxybutyric acid
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| to DMAPP |
- Mevalonic acid
- Phosphomevalonic acid
- 5-Diphosphomevalonic acid
- Isopentenyl pyrophosphate
- Dimethylallyl pyrophosphate
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| Geranyl- |
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
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| Carotenoid |
- Prephytoene diphosphate
- Phytoene
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| Non-mevalonate pathway |
- DOXP
- MEP
- CDP-ME
- CDP-MEP
- MEcPP
- HMB-PP
- IPP
- DMAPP
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| To Cholesterol |
- Farnesyl pyrophosphate
- Squalene
- 2,3-Oxidosqualene
- Lanosterol
- Lanosterol
- Lathosterol
- 7-Dehydrocholesterol
- Cholesterol
- Lanosterol
- Zymosterol
- 7-Dehydrodesmosterol
- Desmosterol
- Cholesterol
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From Cholesterol
(to steroids) |
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
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| Steroid hormones |
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| Nonhuman |
| Phytosterols |
- Stigmasterol
- Brassicasterol
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| Ergosterols |
- Ergosterol
- Ergocalciferol
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UpToDate Contents
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English Journal
- Impediment of selenite-induced cataract in rats by combinatorial drug laden liposomal preparation.
- Huang C, Li C, Muhemaitia P.
- The Libyan journal of medicine. 2019 12;14(1)1548252.
- Cataract is the leading cause of blindness globally with surgery being the only form of treatment. But cataract surgery is accompanied by complications, chiefly intra-ocular infections. Hence, preventive nanoformulations may be extremely beneficial. In the present study, novel chitosan-coated liposo
- PMID 30460877
- The P5A ATPase Spf1p is stimulated by phosphatidylinositol 4-phosphate and influences cellular sterol homeostasis.
- Sørensen DM, Holen HW, Pedersen JT, Martens HJ, Silvestro D, Stanchev LD, Costa SR, Günther Pomorski T, López-Marqués RL, Palmgren M.
- Molecular biology of the cell. 2019 Apr;30(9)1069-1084.
- P5A ATPases are expressed in the endoplasmic reticulum (ER) of all eukaryotic cells, and their disruption results in severe ER stress. However, the function of these ubiquitous membrane proteins, which belong to the P-type ATPase superfamily, is unknown. We purified a functional tagged version of th
- PMID 30785834
- Separation and purification of lanosterol, dihydrolanosterol and cholesterol from lanolin by high-performance counter-current chromatography dual-mode elution method.
- Pei H, Ma X, Pan Y, Han T, Lu Z, Wu R, Cao X, Zheng J.
- Journal of separation science. 2019 Apr;().
- Lanosterol is a potential drug for cataracts treatment which can reverse the aggregation of intracrystalline proteins. The low concentration in lanolin calls for high-performance separation methods. In this study, a counter-current chromatography (CCC) dual-mode elution method was developed for the
- PMID 30950563
Japanese Journal
- A New Amino Acid Substitution at G150S in Lanosterol 14-α Demethylase (Erg11 protein) in Multi-azole-resistant <I>Trichosporon asahii</I>
- Stimulated production of steroids in Inonotus obliquus by host factors from birch(BIOMEDICAL ENGINEERING)
- De Novo Design of Non-coordinating Indolones as Potential Inhibitors for Lanosterol 14-α-Demethylase (CYP51)
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