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麦角钙化醇

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麦角钙化醇
麦角钙化醇结构
麦角钙化醇球棍模型
臨床資料
商品名（英语：Drug nomenclature）Drisdol、Calcidol…
其他名稱viosterol
AHFS/Drugs.comMonograph
ATC碼
法律規範狀態
法律規範
识别信息
  • (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号50-14-6（ checkY）
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)
ECHA InfoCard100.000.014 編輯維基數據鏈接
化学信息
化学式C28H44O
摩尔质量396.65 g/mol
3D模型（JSmol（英语：JSmol））
熔点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

麦角钙化醇（英語：Ergocalciferol）是维生素D2的化学名，为麦角固醇在紫外线作用下产生的开环甾体（英语：secosteroid）。早期制备的麦角钙化醇商品名为Viosterol[1]，由麦角固醇在紫外线光照下制成，含光固醇（英语：Lumisterol）杂质。麦角钙化醇是一种维生素D膳食补剂，[2]可以治疗吸收不良、肝病[3]造成的维生素D缺乏症。[4]此药还可用于甲状腺功能减退造成的低血钙症。[3]麦角钙化醇可口服、肌注，在一些蘑菇中天然产生。[5]

过量使用麦角钙化醇可造成多尿、高血压、肾结石、肾衰竭、乏力、便秘。[6]长期高剂量使用可造成组织钙化（英语：tissue calcification），[3]因此建议此类人群监测血钙含量。[4]孕妇可以安全使用正常剂量。[7]麦角钙化醇增加肠道、肾脏吸收的钙质。[6]

麦角钙化醇最早于1936年发现描述。[8]此物名列世界卫生组织基本药物标准清单，为健保系统（英语：health system）所需的有效、安全药物之一。[9]麦角钙化醇为非处方药，且有通用名药物版本。[6]在英国，此药对國民保健署的一般开支不足每处方每月10英镑。[4]有些国家会在早餐麦片和麦淇淋等食物中加入麦角钙化醇。[10][11]

用途

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和晒太阳产生的胆钙化醇（维生素D3）一样，维生素D2可以用于补充维生素D。[12]

之前一般认为两种维生素D效果类似，因其在改善佝偻病、[13]降低年长患者跌倒的概率上效果相似[14]。现在对于维生素D2和D3在体内行为是否相似，和生成骨化三醇这种激素的效率，有相互矛盾的一些研究。一些初期研究表明维生素维生素D3效率更高，[15][16]而其它的研究则表明两者效率类似。[12][17][18]维生素D2和D3的新陈代谢路径稍有不同；有研究指出维生素D结合蛋白对维生素D3所形成的骨化三醇有更大亲和力[15]。有汇总分析指出，D3更适合提高血浆25-(OH)D浓度[19]，但也有研究说明两者在维持浓度方面效果相当。[20][21]

有研究发现奥兹海默症患者体内的麦角钙化醇含量较低，但这项研究并未提及这一结果和食品中麦角钙化醇缺乏是否有关。[22]

机理

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麦角钙化醇和胆钙化醇（D3）的作用机理大致相类。麦角钙化醇本身不具活性，需经过两次羟化才可具有活性：第一步羟化在肝内经过CYP2R1（英语：CYP2R1）生成25-羟基麦角钙化醇（麦角骨化二醇，25-OH D2[23]），第二部在肾内经CYP27B1转化为1,25-二羟基麦角钙化醇（麦角骨化三醇，1,25-(OH)2D2）。[24]与胆钙化醇不同，麦角钙化醇不由CYP27A1羟化。[25]

与D3的对应物比较，麦角钙化醇和各种代谢产物对维生素D结合蛋白（英语：vitamin D-binding protein）的亲和力较低。麦角骨化三醇对骨化三醇受体（英语：vitamin D receptor）的亲和力与骨化三醇相类。[25]麦角钙化醇及其产物可经24-羟化失效。[26]

来源

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麦角钙化醇最早从麦角中提取，故而得名。现在使用苔藓[27]、真菌[28]和苜蓿[29]进行中波紫外线照射就可以提取麦角钙化醇。以下列出一些食品内的含量：

  • 真菌[28][30]
    • 雙孢蘑菇（D2 + D3）：
      • 褐熟（portabello），生：0.3 μg（10 IU）；光照后：11.2 µg（446 IU）
      • 幼褐（crimini），生：0.1 μg（3 IU）；光照后：31.9 µg（1276 IU）
    • 香菇：
      • 生：维生素 D (D2 + D3)：0.4 μg (18 IU)
      • 干货：维生素 D (D2 + D3)：3.9 μg (154 IU)

在真菌中，麦角钙化醇由麦角固醇受紫外光照射产生。[31]人类可以吸收利用高D2酵母制成的面包中的维生素D。[32]食用紫外光（UV-B）照过的双孢蘑菇可以改善维生素D缺乏，其作用与维生素D2补充剂效果相类。[33]此类光照处理不会将蘑菇漂白。[34]西方记者发新闻称，一份普通食量（6 g 干重，约合 60 g）[34]的双胞蘑菇经过短波紫外光照射5分钟后可以提供3,500 IU的维生素D，引来多方关注。[35]

工业上，麦角钙化醇由酵母中提取的麦角固醇经紫外光照射和提纯制成。[36]

参考文献

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  32. ^ Hohman, E. E.; Martin, B. R.; Lachcik, P. J.; Gordon, D. T.; Fleet, J. C.; Weaver, C. M. Bioavailability and Efficacy of Vitamin D2from UV-Irradiated Yeast in Growing, Vitamin D-Deficient Rats. Journal of Agricultural and Food Chemistry. 2011, 59 (6): 2341–2346. PMC 3235799 可免费查阅. PMID 21332187. doi:10.1021/jf104679c. 
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  35. ^ Bringing Mushrooms Out of the Dark. MSNBC. 2006-04-18 [2007-08-06]. （原始内容存档于2007-11-01）. 
  36. ^ Holick MF. The vitamin D epidemic and its health consequences (PDF). The Journal of Nutrition. November 2005, 135 (11): 2739S–48S [2018-04-21]. PMID 16251641. （原始内容存档 (PDF)于2017-11-18）. [Vitamin D3] is produced commercially by extracting 7-dehydrocholesterol from wool fat, followed by UVB irradiation and purification [...] [Vitamin D2] is commercially made by irradiating and then purifying the ergosterol extracted from yeast 
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