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]
Chemistry
Despite the relative ease of isolation and early discovery of delphinine, its molecular structure was not established in its currently accepted form until the early 1970s. At that time, Wiesner's research group corrected the stereochemistry of the methoxy group at C-1 from the β- to the α- configuration.[10][11] Thus, any drawing of the delphinine molecule appearing before 1971–1972 is likely to show the incorrect stereochemistry at C-1.
Pharmacology
As a result of its early discovery and isolation in crystalline form (then considered a criterion of purity), the pharmacological properties of delphinine were extensively investigated in the 19th century, despite the fact that its molecular structure was unknown. It is likely that some of these investigations were carried out with impure drug and should be interpreted with caution. References to and commentary on these early studies may be found in the review by Benn and Jacyno.[4] More recent studies focused on the cardiovascular toxicity of delphinine.[12][13]
In general, the pharmacology of delphinine seems to resemble that of aconitine, although the acute toxicity of delphinine appears to be lower than that of aconitine in test animals.[4]
References
^Harbourne JB, Baxter H, eds. (1993). Phytochemical Dictionary. London: Taylor & Francis. p. 148.
^ abcBenn MH, Jacyno JM (1983). Pelletier SW (ed.). "Chapter 4". The Alkaloids: Chemical and Biological Perspectives. 1. New York: Wiley: 153–210.
^Desai HK, Hart BP, Caldwell RW, Jianzhong-Huang JH, Pelletier SW (June 1998). "Certain norditerpenoid alkaloids and their cardiovascular action". Journal of Natural Products. 61 (6): 743–8. doi:10.1021/np970499j. PMID9644057.
^Díaz JG, Ruiz JG, de La Fuente G (August 2000). "Alkaloids from Delphinium staphisagria". Journal of Natural Products. 63 (8): 1136–9. doi:10.1021/np990453l. PMID10978212.
^Lassaigne JL, Feneulle H (1819). "Analyse de la staphisaigre". Ann. Chim. Phys. Série 2. 12: 358–71.
^Markwood LN (October 1927). "Isolation of the oil and alkaloids of stavesacre seed.(Delphinium staphisagria)". Journal of the American Pharmaceutical Association. 16 (10): 928–32. doi:10.1002/jps.3080161006.
^Aneja R, Locke DM, Pelletier SW (January 1973). "The diterpene alkaloids: the structure and stereochemistry of heteratisine". Tetrahedron. 29 (21): 3297–308. doi:10.1016/S0040-4020(01)93482-9.
^Pelletier SW, Wright LH (January 1972). "Recent developments in diterpenoid alkaloids chemistry". Alkaloids. Vol. 2. London: The Chemical Society. pp. 247–258 (254–255). doi:10.1039/9781847555588-00247. ISBN978-0-85186-267-5.
^Scherf D, Blumenfeld S, Tander D, Yildiz M (December 1960). "The effect of diphenylhydantoin (Dilantin) sodium on atrial flutter and fibrillation provoked by focal application of a conitine or delphinine". American Heart Journal. 60 (6): 936–47. doi:10.1016/0002-8703(60)90125-3. PMID13747515.
^Scherf D, Schott A (1973). Extrasystoles and Allied Arrhythmias (2nd ed.). London: Heinemann.
