山道年

化合物

山道年,也稱散道寧、蛔蒿素,是從菊科植物蛔蒿的花中提取的一種酮內酯化學物質,可用作驅蟲藥英語Anthelmintic。過去被美英等國藥典列為蛔蟲藥英語Ascaricide,在中國也曾用於寶塔糖。現已被效力更強、毒性更低的藥物所代替。[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
識別
CAS號 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
性質
化學式 C15H18O3
摩爾質量 246.3 g·mol−1
熔點 172 °C(445 K)
沸點 423 °C(696 K)
溶解性 難溶
蒸氣壓 1*10−7mmHg
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

水解可成為山道年酸英語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闡釋。[8][9]

藥用

可處理蛔蟲等線蟲感染,對絛蟲無效。山道年使蟲體麻痹;服藥後,還應吃瀉藥以排出蛔蟲。

山道年中毒可造成黃視、綠視。服用之前與之後起碼3天不能吃油脂,以免脂溶性的山道年攝入體內。

參考文獻

  1. ^ Modern Drug Encyclopedia and Therapeutic Index, Sixth Edition, Drug Publications Inc, 1955
  2. ^ Base-catalyzed rearrangements 互聯網檔案館存檔,存檔日期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頁面存檔備份,存於互聯網檔案館) (this work is now in the public domain)
  6. ^ Botanical.com頁面存檔備份,存於互聯網檔案館) (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.

  本條目包含來自公有領域出版物的文本: Chisholm, Hugh (編). Santonin. Encyclopædia Britannica 24 (第11版). London: Cambridge University Press: 195. 1911.