翠雀碱
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的变构调节剂[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 
|
| PubChem | 441726 |
| ChemSpider | 390329 |
| SMILES |
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| InChI |
|
| 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
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
- ^ Harbourne JB, Baxter H (编). Phytochemical Dictionary. London: Taylor & Francis. 1993: 148.
- ^ A Modern Herbal | Stavesacre. [2022-07-26]. （原始内容存档于2022-07-26）.
- ^ 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.
- ^ 4.0 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.
- ^ 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.
- ^ 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.
- ^ Lassaigne JL, Feneulle H. Analyse de la staphisaigre.. Ann. Chim. Phys. Série 2. 1819, 12: 358–71.
- ^ 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.
- ^ Jacobs WA, Craig LC. DELPHININE. Journal of Biological Chemistry. February 1939, 127 (2): 361–6. doi:10.1016/S0021-9258(18)73787-3 .
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Scherf D, Schott A. Extrasystoles and Allied Arrhythmias 2nd. London: Heinemann. 1973.
