翠雀碱

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	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。

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）的变构调节剂（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。

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

^ 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.

[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）.

[pmid18201930-3] 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.

[Benn-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.

[Jacobs-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.

[pmid13747515-12] 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.

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