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麥角鈣化醇

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麥角鈣化醇
麥角鈣化醇結構
麥角鈣化醇球棍模型
臨床資料
商品名英語Drug nomenclatureDrisdol、Calcidol…
其他名稱viosterol
AHFS/Drugs.comMonograph
ATC碼
法律規範狀態
法律規範
識別資訊
  • (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
CAS號50-14-6 checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.000.014 編輯維基數據鏈接
化學資訊
化學式C28H44O
摩爾質量396.65 g/mol
3D模型(JSmol英語JSmol
熔點114至118 °C(237至244 °F)
  • 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
  • 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 checkY
  • Key:MECHNRXZTMCUDQ-RKHKHRCZSA-N

麥角鈣化醇(英語:Ergocalciferol)是維生素D2的化學名,為麥角固醇紫外線作用下產生的開環甾體英語secosteroid。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,含光固醇英語Lumisterol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]

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英語tissue calcification[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,為健保系統英語health system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麥淇淋等食物中加入麥角鈣化醇。[10][11]

用途

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]

機理

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英語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]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結合蛋白英語vitamin D-binding protein的親和力較低。麥角骨化三醇對骨化三醇受體英語vitamin D receptor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]

來源

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]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]

參考文獻

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