翠雀碱

化合物

翠雀碱delphinine)是一种有毒的二萜生物碱,存在于翠雀属除虱草属铁线莲属植物中[1]。翠雀碱是在除虱草种子中发现的主要生物碱之一。[2]它在结构与作用上与乌头碱相似,作为电压门控钠通道英语voltage gated sodium channels变构调节剂英语allosteric modulator[3]并产生低血压心动过缓心律失常。这些影响使其具有剧毒(LD50 1.5–3.0 mg/kg兔子和狗;青蛙的易感性约为10倍)[4]。虽然它已被用于一些替代药物(例如草药[5][6]),大多数医学界不建议使用它,因为它具有极高的毒性。

翠雀碱
别名 8-(Acetyloxy)-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-20-methylaconitan-14-yl benzoate
识别
CAS号 561-07-9  checkY
PubChem 441726
ChemSpider 390329
SMILES
 
  • CC(=O)O[C@]12C[C@@H]([C@]3(C[C@H]([C@@H]1[C@H]3OC(=O)C4=CC=CC=C4)[C@]56[C@H](CC[C@@]7([C@H]5[C@H]([C@H]2C6N(C7)C)OC)COC)OC)O)OC
InChI
 
  • 1/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1
InChIKey REVYTWNGZDPRKE-UWZYQZSNBH
性质
化学式 C33H45NO9
摩尔质量 599.712 g·mol⁻¹
外观 colorless solid
熔点 199 °C(472 K)
危险性
主要危害 Toxic
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

Isolation

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One of the earliest reports of the isolation of delphinine, from D. staphisagria, was that of the French chemists Lassaigne and Feneulle, in 1819.[7] A less antique and more accessible report is that of the USDA chemist L. N. Markwood, who also briefly reviewed the earlier isolation work.[8] Notably, these early isolations were carried out without the aid of chromatography, since delphinine crystallizes readily from a petroleum ether extract after the typical acid-base cycling used in traditional plant alkaloid-extraction methods.[9]

化学

尽管翠雀碱相对容易分离,但直到 1970 年代初,它的分子结构才以目前公认形式确立。当时,威斯纳的研究小组将C-1处的甲氧基的立体化学从β-修正为α-分子构型[10][11]因此,任何出现在 1971-1972 年之前的翠雀碱分子图都可能在 C-1 处显示不正确的立体化学。

药理

由于它的早期发现和结晶形式的分离(当时被认为是纯度标准),尽管事实上其分子结构未知,但在19世纪,翠雀碱药理特性得到广泛研究。其中一些调查很可能是用不纯的药物进行的,应该谨慎解释。在Benn和Jacyno的评论中可以找到对这些早期研究的参考和评论。[4] 最近的研究集中在翠雀碱的心血管毒性上。[12][13]

一般来说,翠雀碱的药理学似乎类似于乌头碱,尽管翠雀碱的急性毒性似乎低于乌头碱在试验动物中的毒性。[4]

参考文献

  1. ^ Harbourne JB, Baxter H (编). Phytochemical Dictionary. London: Taylor & Francis. 1993: 148. 
  2. ^ A Modern Herbal | Stavesacre. [2022-07-26]. (原始内容存档于2022-07-26). 
  3. ^ Turabekova MA, Rasulev BF, Levkovich MG, Abdullaev ND, Leszczynski J. Aconitum and Delphinium sp. alkaloids as antagonist modulators of voltage-gated Na+ channels. AM1/DFT electronic structure investigations and QSAR studies. Computational Biology and Chemistry. April 2008, 32 (2): 88–101. PMC 5001567 . PMID 18201930. doi:10.1016/j.compbiolchem.2007.10.003. 
  4. ^ 4.0 4.1 4.2 Benn MH, Jacyno JM. Pelletier SW , 编. Chapter 4. The Alkaloids: Chemical and Biological Perspectives (New York: Wiley). 1983, 1: 153–210. 
  5. ^ Desai HK, Hart BP, Caldwell RW, Jianzhong-Huang JH, Pelletier SW. Certain norditerpenoid alkaloids and their cardiovascular action. Journal of Natural Products. June 1998, 61 (6): 743–8. PMID 9644057. doi:10.1021/np970499j. 
  6. ^ Díaz JG, Ruiz JG, de La Fuente G. Alkaloids from Delphinium staphisagria. Journal of Natural Products. August 2000, 63 (8): 1136–9. PMID 10978212. doi:10.1021/np990453l. 
  7. ^ Lassaigne JL, Feneulle H. Analyse de la staphisaigre.. Ann. Chim. Phys. Série 2. 1819, 12: 358–71. 
  8. ^ Markwood LN. Isolation of the oil and alkaloids of stavesacre seed.(Delphinium staphisagria).. Journal of the American Pharmaceutical Association. October 1927, 16 (10): 928–32. doi:10.1002/jps.3080161006. 
  9. ^ Jacobs WA, Craig LC. DELPHININE. Journal of Biological Chemistry. February 1939, 127 (2): 361–6. doi:10.1016/S0021-9258(18)73787-3 . 
  10. ^ Aneja R, Locke DM, Pelletier SW. The diterpene alkaloids: the structure and stereochemistry of heteratisine.. Tetrahedron. January 1973, 29 (21): 3297–308. doi:10.1016/S0040-4020(01)93482-9. 
  11. ^ Pelletier SW, Wright LH. Recent developments in diterpenoid alkaloids chemistry. Alkaloids 2. London: The Chemical Society. January 1972: 247–258 (254–255). ISBN 978-0-85186-267-5. doi:10.1039/9781847555588-00247. 
  12. ^ Scherf D, Blumenfeld S, Tander D, Yildiz M. The effect of diphenylhydantoin (Dilantin) sodium on atrial flutter and fibrillation provoked by focal application of a conitine or delphinine. American Heart Journal. December 1960, 60 (6): 936–47. PMID 13747515. doi:10.1016/0002-8703(60)90125-3. 
  13. ^ Scherf D, Schott A. Extrasystoles and Allied Arrhythmias 2nd. London: Heinemann. 1973.