羊毛甾醇
Multi tool use
羊毛甾醇
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IUPAC名
lanosta-8,24-dien-3-ol
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识别
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CAS号
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79-63-0 
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PubChem
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246983
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ChemSpider
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216175
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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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InChI
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- 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
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InChIKey
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CAHGCLMLTWQZNJ-BQNIITSRBP
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ChEBI
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16521
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MeSH
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Lanosterol
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IUPHAR配体
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2746
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性质
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化学式
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C30H50O
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摩尔质量
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426.71 g/mol g·mol⁻¹
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熔点
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138-140 °C
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若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。
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羊毛甾醇（Lanosterol）是一种甾體化合物，分子式C30H50O，动物和真菌合成类固醇的过程中均经过此化合物。而植物的甾体合成则通过环阿屯醇。[1]
生物化学
类固醇合成中的角色
酶催化下，角鲨烯闭环形成羊毛甾醇，该过程形成甾体核心结构。 通过CYP51的14号位脱甲基化作用，最终产生胆固醇。
上图显示了羊毛甾醇合成过程的简化版本。中间体分别为
异戊烯焦磷酸（IPP），
二甲基烯丙基焦磷酸（DMAPP），
香叶基焦磷酸（GPP）和角鲨烯。其它一些中间体被省略。
生物合成
| 描述 |
图示 |
酶
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两分子法尼基焦磷酸被NADPH还原，生成角鲨烯
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鲨烯合酶
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| 角鲨烯被氧化成2,3-环氧角鲨烯 |
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鲨烯单加氧酶
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| 2,3-环氧角鲨烯关环 |
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羊毛甾醇合酶
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| （第二步） |
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（第二步）
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医学用途
一项2015年的研究推测羊毛甾醇可能有助于预防哺乳动物白内障的形成。[2]相关研究显示羊毛甾醇能防止甚至逆转狗与兔的白内障。[2][3]但是，一项验证实验中，将手术切除的患有白内障人眼球晶状体浸入含羊毛甾醇溶液培养，晶状体透明度并未得到逆转。[4]
参考资料
^ Schaller, Hubert. The role of sterols in plant growth and development. Progress in Lipid Research. May 2003, 42 (3): 163–175. doi:10.1016/S0163-7827(02)00047-4.
^ 2.02.1 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; 等. Lanosterol reverses protein aggregation in cataracts. Nature. July 2015. 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. 2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene. Journal of the American Chemical Society. 1966, 88 (20): 4750–4751. PMID 5918046. doi:10.1021/ja00972a056.
I. Abe; M. Rohmer; G. D. Prestwich. Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chemical Reviews. 1993, 93 (6): 2189–2206. doi:10.1021/cr00022a009.
Albert Eschenmoser|A. Eschenmoser, Lavoslav Ružička|L. Ruzicka, O. Jeger, D. Arigoni. Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helvetica Chimica Acta. 1955, 38 (7): 1890–1904. doi:10.1002/hlca.19550380728.
胆固醇与甾体代谢中间产物
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| 甲羟戊酸途径 |
到HMG-CoA
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乙酰辅酶A · 乙酰乙酰辅酶A · β-羟-β-甲戊二酸单酰辅酶A · Β-羥基β-甲基丁酸
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酮体 |
丙酮 · 乙酰乙酸 · β-羟丁酸
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到二甲基烯丙基焦磷酸
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甲羟戊酸 · 磷酸甲羟戊酸 · 5-二磷酸甲羟戊酸 · 异戊烯焦磷酸 · 二甲基丙烯酰焦磷酸
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牻牛儿基- |
牻牛儿基焦磷酸 · 牻牛儿基牻牛儿基焦磷酸
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类胡萝卜素 |
前植物烯二磷酸 · 八氢番茄红素
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| 非甲羟戊酸途径 |
DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP
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到胆固醇
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法尼基焦磷酸 · 鲨烯 · 2,3-氧鲨烯 · 羊毛甾醇
羊毛甾醇 · 7-烯胆甾烷醇 · 7-脱氢胆固醇 · 胆固醇
羊毛甾醇 · 酵母甾醇 · 7-脱氢胆甾醇 · 链甾醇 · 胆固醇
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| 甾体 |
皮质类固醇
（二十一碳孕烷）
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盐皮质激素 |
孕烯醇酮 · 孕酮 · 11-脱氧皮质酮 · 皮质酮 · 醛固酮
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糖皮质激素 |
孕烯醇酮 · 17-羟孕烯醇酮 · 17-羟孕酮 · 11-脱氧皮质醇 · 皮质醇
皮质醇 · 皮质酮
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性类固醇 |
雄激素
（十九碳雄固烷）
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DHEA · 雄烯二酮/5-雄烯二醇 · 睾酮 · 双氢睾酮
脱氢表雄酮硫酸盐 · 表睾酮
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雌激素
（十八碳雌烷）
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雌酮 · 雌二醇 · 雌三醇
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| 非人类 |
植物固醇类
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豆固醇 · 菜籽固醇
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麦角固醇类
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麦角固醇 · 钙化醇
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代谢、k,c/g/r/p/y/i,f/h/s/l/o/e,a/u,n,m
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k,cgrp/y/i,f/h/s/l/o/e,au,n,m,人名体征
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药物(A16/C10)、中间产物(k,c/g/r/p/y/i,f/h/s/o/e,a/u,n,m)
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內分泌系統索引
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| 描述 |
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| 疾病 |
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| 治療 |
- 程序
- 藥物
- 鈣平衡
- 皮质类固醇
- 口服降血糖藥物
- 腦下垂體及下視丘
- 甲狀腺
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生物化學物質種類索引
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| 糖类 |
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| 酯質 |
- 类花生酸类
脂肪酸
- 甘油酯
- 磷脂
- 鞘脂類
- 胆固醇与甾体中间产物
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| 核酸 |
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| 蛋白質 |
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| 其他 |
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IcO1wfffn7Kxi1uZKizamJT FKBr2Dk3TeJ4agbIb7fKBLk2Us
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