翠雀鹼
翠雀鹼（delphinine）是一種有毒的二萜生物鹼，存在於翠雀屬、除虱草屬、鐵線蓮屬植物中[1]。翠雀鹼是在除虱草種子中發現的主要生物鹼之一。[2]它在結構與作用上與烏頭鹼相似，作為電壓門控鈉通道的變構調節劑[3]並產生低血壓、心動過緩、心律失常。這些影響使其具有劇毒（LD50 1.5–3.0 mg/kg兔子和狗；青蛙的易感性約為10倍）[4]。雖然它已被用於一些替代藥物（例如草藥[5][6]），大多數醫學界不建議使用它，因為它具有極高的毒性。
| 翠雀鹼 | |
|---|---|
| |
| |
| 別名 | 8-(Acetyloxy)-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-20-methylaconitan-14-yl benzoate |
| 識別 | |
| CAS號 | 561-07-9 
|
| PubChem | 441726 |
| ChemSpider | 390329 |
| SMILES |
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| InChI |
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| InChIKey | REVYTWNGZDPRKE-UWZYQZSNBH |
| 性質 | |
| 化學式 | C33H45NO9 |
| 摩爾質量 | 599.712 g·mol⁻¹ |
| 外觀 | colorless solid |
| 熔點 | 199 °C（472 K） |
| 危險性 | |
| 主要危害 | Toxic |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
Isolation
編輯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]
化學
編輯儘管翠雀鹼相對容易分離，但直到 1970 年代初，它的分子結構才以目前公認形式確立。當時，威斯納的研究小組將C-1處的甲氧基的立體化學從β-修正為α-分子構型。[10][11]因此，任何出現在 1971-1972 年之前的翠雀鹼分子圖都可能在 C-1 處顯示不正確的立體化學。
藥理
編輯由於它的早期發現和結晶形式的分離（當時被認為是純度標準），儘管事實上其分子結構未知，但在19世紀，翠雀鹼藥理特性得到廣泛研究。其中一些調查很可能是用不純的藥物進行的，應該謹慎解釋。在Benn和Jacyno的評論中可以找到對這些早期研究的參考和評論。[4] 最近的研究集中在翠雀鹼的心血管毒性上。[12][13]
一般來說，翠雀鹼的藥理學似乎類似於烏頭鹼，儘管翠雀鹼的急性毒性似乎低於烏頭鹼在試驗動物中的毒性。[4]
參考文獻
編輯- ^ Harbourne JB, Baxter H (編). Phytochemical Dictionary. London: Taylor & Francis. 1993: 148.
- ^ A Modern Herbal | Stavesacre. [2022-07-26]. （原始內容存檔於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 , 編. 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.
