fbpx
Wikipedia

Delsoline

April 12, 2024

Delsoline and delcosine are two closely related naturally occurring diterpene alkaloids first isolated from Delphinium consolida. They occur widely in the Ranunculaceae plant family. The polycyclic ring system containing nineteen carbon atoms and one nitrogen atom in these compounds is the same as in aconitine and this is reflected in their preferred IUPAC name.

Delcosine (R = H)

Delsoline (R = CH3)
Names
IUPAC name
(1α,6β,14α,16β)-20-Ethyl-6,16-dimethoxy-4-(methoxymethyl)aconitane-1,7,8,14-tetrol
Identifiers
  • Compounds
  • R = H: Delcosine
  • R = CH3: Delsoline
  • R = H: 545-56-2
  • R = CH3: 509-18-2
3D model (JSmol)
  • R = CH3: Interactive image
ChemSpider
  • R = H: 58804922
  • R = CH3: 22875325
  • R = H: 441725
  • R = CH3: 71454486
  • 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
    Key: JVBLTQQBEQQLEV-DIZROUMASA-N
  • R = CH3: CC[N@]1C[C@@]2(CC[C@@H]([C@@]34[C@@H]2[C@@H](C([C@H]31)([C@]5(C[C@@H]([C@H]6C[C@@H]4[C@@H]5[C@H]6OC)OC)O)O)OC)O)COC
Properties
C25H41NO7
Molar mass 467.603 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

History edit

 
Delsoline and delcosine were first isolated from Delphinium consolida

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 edit

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]

Natural occurrence edit

The compounds co-occur in Aconitum variegatum[7] and many species of Delphinium[8] including Delphinium ajacis[9] and other Consolida species in the Ranunculaceae plant family.[10]

Biochemistry edit

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 edit

  1. ^ 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. PMID 20255295.
  2. ^ Marion, L. (1963). "The highly-oxygenated diterpenoid alkaloids". Pure and Applied Chemistry. 6 (4): 621–634. doi:10.1351/pac196306040621. S2CID 96279513.
  3. ^ 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. ISBN 9780124695122.
  4. ^ 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. S2CID 98764332.
  5. ^ Sakai, S.; Shinma, N.; Hasegawa, S.; Okamoto, T. (1978). "On the Alkaloids of Aconitum gigas Lev. et Van. and the structure of a New Base, Gigactonine". Yakugaku Zasshi. 98 (10): 1376–1384. doi:10.1248/yakushi1947.98.10_1376.
  6. ^ Cherney, Emily C.; Baran, Phil S. (2011). "Terpenoid-Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis". Israel Journal of Chemistry. 51 (3–4): 391–405. doi:10.1002/ijch.201100005. PMC 4508874. PMID 26207071.
  7. ^ Díaz, Jesús G.; Ruiza, Juan García; Herz, Werner (April 2005). "Norditerpene and diterpene alkaloids from Aconitum variegatum". Phytochemistry. 66 (7): 837–46. doi:10.1016/j.phytochem.2005.01.019. PMID 15797610.
  8. ^ Yin, Tianpeng; Cai, Le; Ding, Zhongtao (2020). "An overview of the chemical constituents from the genus Delphinium reported in the last four decades". RSC Advances. 10 (23): 13669–13686. Bibcode:2020RSCAd..1013669Y. doi:10.1039/D0RA00813C. PMC 9051563. PMID 35492993.
  9. ^ 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.
  10. ^ a b Yin, Tianpeng; Cai, Le; Ding, Zhongtao (2020). "A systematic review on the chemical constituents of the genus Consolida (Ranunculaceae) and their biological activities". RSC Advances. 10 (58): 35072–35089. Bibcode:2020RSCAd..1035072Y. doi:10.1039/D0RA06811J. PMC 9056944. PMID 35515663.
  11. ^ 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. ISBN 9780124695320.

See also edit

April 12, 2024
delsoline, delcosine, closely, related, naturally, occurring, diterpene, alkaloids, first, isolated, from, delphinium, consolida, they, occur, widely, ranunculaceae, plant, family, polycyclic, ring, system, containing, nineteen, carbon, atoms, nitrogen, atom, . Delsoline and delcosine are two closely related naturally occurring diterpene alkaloids first isolated from Delphinium consolida They occur widely in the Ranunculaceae plant family The polycyclic ring system containing nineteen carbon atoms and one nitrogen atom in these compounds is the same as in aconitine and this is reflected in their preferred IUPAC name Delcosine R H Delsoline R CH3 NamesIUPAC name 1a 6b 14a 16b 20 Ethyl 6 16 dimethoxy 4 methoxymethyl aconitane 1 7 8 14 tetrolIdentifiersCompoundsR H DelcosineR CH3 DelsolineCAS Number R H 545 56 2R CH3 509 18 23D model JSmol R CH3 Interactive imageChemSpider R H 58804922R CH3 22875325PubChem CID R H 441725R CH3 71454486InChI 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 s1Key BMZNJVXOLCBDPZ FCXNFKKQSA NR 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 s1Key JVBLTQQBEQQLEV DIZROUMASA NSMILES R CH3 CC N 1C C 2 CC C H C 34 C H 2 C H C C H 31 C 5 C C H C H 6C C H 4 C H 5 C H 6OC OC O O OC O COCPropertiesChemical formula C 25H 41N O 7Molar mass 467 603 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 History 2 Synthesis 3 Natural occurrence 4 Biochemistry 5 References 6 See alsoHistory edit nbsp Delsoline and delcosine were first isolated from Delphinium consolidaDelsoline 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 editAlthough 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 Natural occurrence editThe compounds co occur in Aconitum variegatum 7 and many species of Delphinium 8 including Delphinium ajacis 9 and other Consolida species in the Ranunculaceae plant family 10 Biochemistry editCompounds 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 edit Marion Leo 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 PMID 20255295 Marion L 1963 The highly oxygenated diterpenoid alkaloids Pure and Applied Chemistry 6 4 621 634 doi 10 1351 pac196306040621 S2CID 96279513 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 ISBN 9780124695122 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 S2CID 98764332 Sakai S Shinma N Hasegawa S Okamoto T 1978 On the Alkaloids of Aconitum gigas Lev et Van and the structure of a New Base Gigactonine Yakugaku Zasshi 98 10 1376 1384 doi 10 1248 yakushi1947 98 10 1376 Cherney Emily C Baran Phil S 2011 Terpenoid Alkaloids Their Biosynthetic Twist of Fate and Total Synthesis Israel Journal of Chemistry 51 3 4 391 405 doi 10 1002 ijch 201100005 PMC 4508874 PMID 26207071 Diaz Jesus G Ruiza Juan Garcia Herz Werner April 2005 Norditerpene and diterpene alkaloids from Aconitum variegatum Phytochemistry 66 7 837 46 doi 10 1016 j phytochem 2005 01 019 PMID 15797610 Yin Tianpeng Cai Le Ding Zhongtao 2020 An overview of the chemical constituents from the genus Delphinium reported in the last four decades RSC Advances 10 23 13669 13686 Bibcode 2020RSCAd 1013669Y doi 10 1039 D0RA00813C PMC 9051563 PMID 35492993 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 a b Yin Tianpeng Cai Le Ding Zhongtao 2020 A systematic review on the chemical constituents of the genus Consolida Ranunculaceae and their biological activities RSC Advances 10 58 35072 35089 Bibcode 2020RSCAd 1035072Y doi 10 1039 D0RA06811J PMC 9056944 PMID 35515663 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 ISBN 9780124695320 See also editAconitine Retrieved from https en wikipedia org w index php title Delsoline amp oldid 1177962498, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.