山道年

化合物

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,可用作驱虫药英语Anthelmintic。过去被美英等国药典列为蛔虫药英语Ascaricide,在中国也曾用于宝塔糖。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  checkY
PubChem 221071
ChemSpider 191779
SMILES
 
  • C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C
InChI
 
  • 1/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1
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
蒸气压 1*10−7mmHg
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

水解可成为山道年酸英语santonic acid (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。山道年使虫体麻痹;服药后,还应吃泻药以排出蛔虫。

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。

参考文献

  1. ^ Modern Drug Encyclopedia and Therapeutic Index, Sixth Edition, Drug Publications Inc, 1955
  2. ^ Base-catalyzed rearrangements 互联网档案馆存档,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,存于互联网档案馆) (this work is now in the public domain)
  6. ^ Botanical.com页面存档备份,存于互联网档案馆) (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.

  本条目包含来自公有领域出版物的文本: Chisholm, Hugh (编). Santonin. Encyclopædia Britannica 24 (第11版). London: Cambridge University Press: 195. 1911.