麦角钙化醇

麦角钙化醇(英语:Ergocalciferol)是维生素D2的化学名,为麦角固醇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]

麦角钙化醇
麦角钙化醇结构
麦角钙化醇球棍模型
临床资料
商品名英语Drug nomenclatureDrisdol、Calcidol…
其他名称viosterol
AHFS/Drugs.comMonograph
ATC码
法律规范状态
法律规范
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 编辑维基数据链接
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

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,此药对国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麦淇淋等食物中加入麦角钙化醇。[10][11]

用途

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

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]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

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]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]
    • 双孢蘑菇(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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