R = H: InChI=1S/C24H39NO7/c1-5-25-10-21(11-30-2)7-6-15(26)23-13-8-12-14(31-3)9-22(28,16(13)17(12)27)24(29,20(23)25)19(32-4)18(21)23/h12-20,26-29H,5-11H2,1-4H3/t12-,13-,14+,15+,16-,17+,18-,19+,20+,21+,22-,23+,24-/m1/s1
Key: BMZNJVXOLCBDPZ-FCXNFKKQSA-N
R = CH3: InChI=1S/C25H41NO7/c1-6-26-11-22(12-30-2)8-7-16(27)24-14-9-13-15(31-3)10-23(28,17(14)18(13)32-4)25(29,21(24)26)20(33-5)19(22)24/h13-21,27-29H,6-12H2,1-5H3/t13-,14-,15+,16+,17-,18+,19-,20+,21+,22+,23-,24+,25-/m1/s1
Delsoline and delcosine were named in 1924 by Markwood, who isolated these alkaloids from
Delphinium consolida, but their structures were in doubt[1] until established in 1963[2] and later confirmed by the
X-ray crystallography of delsoline.[3][4] There are many other known diterpene alkaloids, some of which differ from these in only minor ways. Thus while delsoline (R=CH3) is a
methylated derivative of delcosine (R=H), it is also an isomeric methyl derivative of
gigactonine.[5]
Synthesis
Although individual members of this class of alkaloids have been extensively studied, their chemical complexity has limited the number which have been individually synthesised. Similarly, their full biosynthetic pathway is only known in outline in most cases.[6]
Compounds related to aconitine are widely studied for their properties in biological systems and these have been reviewed.[10] For example, delsoline has been reported be one of the active components in traditional Chinese medicinal plants.[11]
References
^Marion, Léo; Edwards, O. E. (1947). "The Alkaloids of Delphinium Consolida L.1". Journal of the American Chemical Society. 69 (8): 2010–2014.
doi:
10.1021/ja01200a055.
PMID20255295.
^Pelletier, S.W.; Keith, L.H. (1970). Chapter 1 Diterpene Alkaloids from Aconitum, Delphinium, and Garry a Species: The C19-Diterpene Alkaloids. The Alkaloids: Chemistry and Physiology. Vol. 12. pp. 1–134.
doi:
10.1016/S1876-0813(08)60100-1.
ISBN9780124695122.
^Joshi, Balawant S.; Desai, Haridutt K.; Pelletier, S. William; Newton, M. Gary (1992). "Crystal and molecular structure of delsoline". Journal of Crystallographic and Spectroscopic Research. 22 (4): 477–483.
doi:
10.1007/BF01195410.
S2CID98764332.
^Pelletier, S. William; Bhandaru, Sudhakar; Desai, Haridutt K.; Ross, Samir A.; Sayed, Hanna M. (1992). "Two New Norditerpenoid Alkaloids from the Roots of Delphinium ajacis". Journal of Natural Products. 55 (6): 736–743.
doi:
10.1021/np50084a005.
^Han, Gui-Qiu; Chen, Ya-Yan; Liang, Xiao-Tian (1988). Chapter 3 Distribution of Alkaloids in Traditional Chinese Medicinal Plants. The Alkaloids: Chemistry and Pharmacology. Vol. 32. pp. 241–270.
doi:
10.1016/S0099-9598(08)60217-5.
ISBN9780124695320.