麥角鈣化醇(英語:Ergocalciferol)是維生素D2的化學名,為麥角固醇在紫外線作用下產生的開環甾體。早期製備的麥角鈣化醇商品名為Viosterol[1],由麥角固醇在紫外線光照下製成,含光固醇雜質。麥角鈣化醇是一種維生素D膳食補劑,[2]可以治療吸收不良、肝病[3]造成的維生素D缺乏症。[4]此藥還可用於甲狀腺功能減退造成的低血鈣症。[3]麥角鈣化醇可口服、肌注,在一些蘑菇中天然產生。[5]
Quick Facts 臨床資料, 商品名(英語:Drug nomenclature) ...
麥角鈣化醇 |
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商品名 | Drisdol、Calcidol… |
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其他名稱 | viosterol |
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AHFS/Drugs.com | Monograph |
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ATC碼 | |
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法律規範 |
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(3β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol OR 3-[2-[7-((2E)-1,4,5-trimethylhex-2-enyl)-6-methylbicyclo[4.3.0]non-2-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
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CAS號 | 50-14-6( Y) |
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PubChem CID | |
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DrugBank | |
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ChemSpider | |
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UNII | |
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KEGG | |
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ChEBI | |
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ChEMBL | |
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CompTox Dashboard (EPA) | |
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ECHA InfoCard | 100.000.014 |
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化學式 | C28H44O |
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摩爾質量 | 396.65 g/mol |
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3D模型(JSmol) | |
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熔點 | 114至118 °C(237至244 °F) |
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O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C)C(C)C)C)C
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InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 YKey:MECHNRXZTMCUDQ-RKHKHRCZSA-N
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過量使用麥角鈣化醇可造成多尿、高血壓、腎結石、腎衰竭、乏力、便秘。[6]長期高劑量使用可造成組織鈣化,[3]因此建議此類人群監測血鈣含量。[4]孕婦可以安全使用正常劑量。[7]麥角鈣化醇增加腸道、腎臟吸收的鈣質。[6]
麥角鈣化醇最早於1936年發現描述。[8]此物名列世界衛生組織基本藥物標準清單,為健保系統所需的有效、安全藥物之一。[9]麥角鈣化醇為非處方藥,且有通用名藥物版本。[6]在英國,此藥對國民保健署的一般開支不足每處方每月10英鎊。[4]有些國家會在早餐麥片和麥淇淋等食物中加入麥角鈣化醇。[10][11]
和曬太陽產生的膽鈣化醇(維生素D3)一樣,維生素D2可以用於補充維生素D。[12]
之前一般認為兩種維生素D效果類似,因其在改善佝僂病、[13]降低年長患者跌倒的概率上效果相似[14]。現在對於維生素D2和D3在體內行為是否相似,和生成骨化三醇這種激素的效率,有相互矛盾的一些研究。一些初期研究表明維生素維生素D3效率更高,[15][16]而其它的研究則表明兩者效率類似。[12][17][18]維生素D2和D3的新陳代謝路徑稍有不同;有研究指出維生素D結合蛋白對維生素D3所形成的骨化三醇有更大親和力[15]。有匯總分析指出,D3更適合提高血漿25-(OH)D濃度[19],但也有研究說明兩者在維持濃度方面效果相當。[20][21]
有研究發現奧茲海默症患者體內的麥角鈣化醇含量較低,但這項研究並未提及這一結果和食品中麥角鈣化醇缺乏是否有關。[22]
麥角鈣化醇和膽鈣化醇(D3)的作用機理大致相類。麥角鈣化醇本身不具活性,需經過兩次羥化才可具有活性:第一步羥化在肝內經過CYP2R1生成25-羥基麥角鈣化醇(麥角骨化二醇,25-OH D2[23]),第二部在腎內經CYP27B1轉化為1,25-二羥基麥角鈣化醇(麥角骨化三醇,1,25-(OH)2D2)。[24]與膽鈣化醇不同,麥角鈣化醇不由CYP27A1羥化。[25]
與D3的對應物比較,麥角鈣化醇和各種代謝產物對維生素D結合蛋白的親和力較低。麥角骨化三醇對骨化三醇受體的親和力與骨化三醇相類。[25]麥角鈣化醇及其產物可經24-羥化失效。[26]
麥角鈣化醇最早從麥角中提取,故而得名。現在使用苔蘚[27]、真菌[28]和苜蓿[29]進行中波紫外線照射就可以提取麥角鈣化醇。以下列出一些食品內的含量:
- 真菌[28][30]
- 雙孢蘑菇(D2 + D3):
- 褐熟(portabello),生:0.3 μg(10 IU);光照後:11.2 µg(446 IU)
- 幼褐(crimini),生:0.1 μg(3 IU);光照後:31.9 µg(1276 IU)
- 香菇:
- 生:維生素 D (D2 + D3):0.4 μg (18 IU)
- 乾貨:維生素 D (D2 + D3):3.9 μg (154 IU)
在真菌中,麥角鈣化醇由麥角固醇受紫外光照射產生。[31]人類可以吸收利用高D2酵母製成的麵包中的維生素D。[32]食用紫外光(UV-B)照過的雙孢蘑菇可以改善維生素D缺乏,其作用與維生素D2補充劑效果相類。[33]此類光照處理不會將蘑菇漂白。[34]西方記者發新聞稱,一份普通食量(6 g 乾重,約合 60 g)[34]的雙胞蘑菇經過短波紫外光照射5分鐘後可以提供3,500 IU的維生素D,引來多方關注。[35]
工業上,麥角鈣化醇由酵母中提取的麥角固醇經紫外光照射和提純製成。[36]
Science Service (1930) Viosterol official name for irradiated ergosterol, J. Chem. Educ. 7(1) 166, DOI: 10.1021/ed007p166, see [pubs.acs.org/doi/abs/10.1021/ed007p166, accessed 10 July 2014.
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