山道年

山道年,也称散道宁、蛔蒿素,是从菊科植物蛔蒿的花中提取的一种酮内酯化学物质,可用作驱虫药。过去被美英等国药典列为蛔虫药。现已被效力更强、毒性更低的药物所代替。[1]

山道年
IUPAC名
(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
识别
CAS号 481-06-1  
PubChem 221071
ChemSpider 191779
SMILES
InChI
InChIKey XJHDMGJURBVLLE-BOCCBSBMBZ
ChEBI 16363
性质
化学式 C15H18O3
摩尔质量 246.3 g·mol−1
熔点 172 °C(445 K)
沸点 423 °C(696 K)
溶解性 难溶
蒸氣壓 1*10−7mmHg
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

水解可成为山道年酸 (C15H20O4)。[2][3][4][5][6][7]

可能的生物合成

Figure 1. Proposed Mechanistic Biosynthesis of α-santonin

生物合成尚未得到充分阐释。[8][9]

药用

可处理蛔虫等线虫感染,对绦虫无效。

山道年中毒可造成黄视、绿视。服用之前与之后起码3天不能吃油脂,以免脂溶性的山道年摄入体内。 服药后,还应吃泻药以排出蛔虫。

参考文献

  1. Modern Drug Encyclopedia and Therapeutic Index, Sixth Edition, Drug Publications Inc, 1955
  2. Base-catalyzed rearrangements 存檔,存档日期2009-02-07.
  3. Per the Encyclopædia Britannica (1911 edition)
  4. Modern botanicals also list Artemisia cina or Levant wormwood as the definitive source; this is also backed up by statements in formularies published in the heyday of santonin use such as King's American Dispensatory.
  5. King's American Dispensatory, 1898 页面存档备份,存于 (this work is now in the public domain)
  6. Botanical.com 页面存档备份,存于 (article on Levant Wormseed, primary source of santonin)
  7. original source, US Pharmacopoeia, 1898
  8. 1. de Kraker, J.W.; Franssen, M.C.; Dalm M.C.; de Groot, A.; Bouwmeester, H.J.; “Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis”. (2001). Plant Physiol. 125(4): 1930-40.
  9. Barton, D.H.R.; Moss, G.P.; Whittle, J.A.; “Investigations on the Biosynthesis of Steroids and Terpenoids. Part I. A Preliminary Study of the Biosynthesis of Santonin”. (1968). J. Chem. Soc. 338(8): 1813-18.

 本條目出自公有领域Chisholm, Hugh (编). . 24 (11th ed.). 劍橋大學出版社: 195. 1911.

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