Isolation and Oxidation Characteristics of Alkaloids of Aconitum volubile

가는줄돌쩌기 알칼로이드 성분의 분리 및 산화적 특성

  • Published : 2008.06.30

Abstract

From the under ground part of Aconitum volubile Pall. (Ranunculaceae),seven nor- or di-terpenoid alkaloids were isolated and identified by NMR spectra and mass spectrum. The alkaloids were three $C_{19}$-norditerpenoid alkaloids such as isotalatizidine, altaconitine and vilmorrianine A, and four $C_{20}$-diterpenoid alkaloids such as 12-epidehydronapelline, 12-epinapelline, songoramine and songorine. Some of the isolated diterpenoid alkaloids were subjected to oxidation reaction with active $MnO_2$ and oxoammonium salt. The results were C-12 oxidation(ketone formation) and N-dealkylation in veatchin-type and decomposition to non-alkaloidal compounds in atisine-type ajaconine.

Keywords

References

  1. 이창복(1982): 대한식물도감, 향문사, 서울, p. 562
  2. Kulanthaivel, P. and Pelletier, S. W.(1987): Deoxygenation reactions of $C_{19}$-diterpenoid alkaloids, Tetrahedron Letters, 28(34), 3883-86 https://doi.org/10.1016/S0040-4039(00)96410-4
  3. Glinski, J. A., Joshi, B. S., Jiang, Q. P. and Pelletier, S. W.(1988): Hetisine derivatives, Part 1: Acetylation and oxidation of hetisine, Heterocycles, 27(1), 185-193 https://doi.org/10.3987/COM-87-4335
  4. Ross, S. A. and Pelletier, S. W.(1988): New synthetic esters of delphisine and neoline, Heterocycles, 27(6), 1381-90 https://doi.org/10.3987/COM-87-4472
  5. Pelletier, S. W. and Ross, S. A.(1990): Synthetic esters and ethers of delphinine and lycoctonine, Heterocycles, 31(4), 671-675 https://doi.org/10.3987/COM-90-5323
  6. Pelletier, S. W., Desai, H. K., Finer-Moore, J. and Mody, N. V.(1982): An unusual oxidation of an $N-CH_3$ group to an NCHO group by osmium tetroxide, Tetrahedron Letters, 23(41), 4229-32 https://doi.org/10.1016/S0040-4039(00)88711-0
  7. Desai, H. K., Chokshi, H. P. and Pelletier, S. W.(1989): Oxidation of norditerpenoid alkaloids with osmium tetroxide, J. Nat. Prod., 52(6), 1296-1302 https://doi.org/10.1021/np50066a016
  8. Pelletier, S. W., Glinski, J. A. and Mody, N. V.(1982): Origin of oxonitine: A potassium permanganate oxidation product of aconitine, J. Am. Chem. Soc., 104, 4676-77 https://doi.org/10.1021/ja00381a029
  9. Gao, L., Zheng, S. Hao, X., Wang, X. and Shen, X.(1997): Preparation of imine alkaloids from norditerpenoid alkaloids, Ind. J. Chem., 36B, 682-684
  10. Song, I. S., Kim, H., Heo, K. H. and Lee, C. K.(2006): Oxidative characteristics of norditerpene alkaloids, Kor. J. Pharmacogn., 37(1), 60-66
  11. Attenburrow, J., Cameron, A. F. B., Chapman, J. H., Evans, R. M., Hems, B. A., Jansen, A. B. A. and Walker, T.(1952): A synthesis of vitamine A from cyclohexanone, J. Chem. Soc., 1952, 1094
  12. Pelletier, S. W., Mody, N. V. and Bhattacharyya, J.(1978): Active manganese dioxide: A reagent for constructing the oxazolidine ring of $C_{20}-diterpenoid$ alkaloids, Tetrahed. Lett., 52, 5187-88
  13. Glinski, J. A., Joshi, B. S., Jiang, Q. P. and Pelletier, S. W.(1988): Hetisine derivatives, Part 1: Acetylation and oxidation of hetisine, Heterocycles, 27(1), 185-193 https://doi.org/10.3987/COM-87-4335
  14. Pelletier, S. W., Ateya, A.-M. M., Mody, N. V. and Schramm, L. C.(1980): Formation of oxazolidine ring in $C_{20}-diterpenoid$ alkaloids by oxidative cyclization with silver oxide, Heterocycles, 14(8), 1155-57 https://doi.org/10.3987/R-1980-08-1155
  15. Pelletier, S. W., Ross, S. A. and Desai, H. K.(1990): A norterpenoid alkaloid from Delphinium elatum, Phytochemistry, 29(7), 2381-83 https://doi.org/10.1016/0031-9422(90)83086-G
  16. Bobbitt, J. M.(1998): Oxoammonium Salts. 6. 4-Acetylamino- 2,2,6,6- tetramethylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis, J. Org. Chem., 63 (25), 9367-74 https://doi.org/10.1021/jo981322c
  17. Pelletier, S. W. and Djarmati, Z.(1976): Carbon-13 Nuclear magnetic resonance: Aconitine-type diterpenoid alkaloids from Aconitum and Delphinium species, J. Am. Chem. Soc., 98, 2626-36 https://doi.org/10.1021/ja00425a036
  18. Pelletier, S. W., Mody, N. V., Sawhney, R. S. and Bhattacharyya, J.(1977): Application of Carbon-13 NMR spectroscopy to the structural elucidation of $C_{19}-diterpenoid$ alkaloids from Aconitum and Delphinium species, Heterocycles, 7(1), 327-339 https://doi.org/10.3987/S-1977-01-0327
  19. Pelletier, S. W., Mody, N. V. and Sawhney, R. S.(1979): $^{13}C$ nuclear magnetic resonance spectra of some $C_{19}-diterpenoid$ alkaloids and their derivatives, Can. J. Chem., 57, 1652-55 https://doi.org/10.1139/v79-266
  20. Pelletier, S. W., Mody, N. V. and Dailey, O.(1980): $^{13}C$ nuclear magnetic resonance spectroscopy of methylenedioxy group-containing $C_{19}-diterpenoid$ alkaloids and their derivatives, Can. J. Chem., 58, 1875-79 https://doi.org/10.1139/v80-296
  21. Pelletier, S. W., Mody, N. V., Joshi, B. S. and Schramm, L. C.(1984):$^{13}C$ and proton NMR shift assignment and physical constants of $C_{19}-diterpene$ alkaloids, pp. 205-213, Alkaloids: Chemical and Biological Perspectives, vol. 2, Wiley-Science, New York, U. S. A
  22. Joshi, B. S., Wunderlich, J. K. and Pelletier, S. W.(1987): $^{13}C$ Nuclear magnetic resonance spectroscopy in the elucidation of structures of diterpene alkaloids, Can. J. Chem., 65, 99-103 https://doi.org/10.1139/v87-016
  23. Desai, H. K. and Pelletier, S. W.(1993): $^{13}C>-NMR $ assignment for lactone-type norditerpenoid alkaloids, J. Nat. Prod., 56(2), 2193-97 https://doi.org/10.1021/np50102a027
  24. Pelletier, S. W., Mody, N. V., Venkov, A. P. and Jones, Jr., S. B.(1979): Alkaloids of Delphinium virescens Nutt.: virescenine and 14-acetylvirescenine, Heterocycles, 12(6), 779-782 https://doi.org/10.3987/R-1979-06-0779
  25. Batbayar, N., Batsuren, D., Tashkhodzhaev, B., Yusupova, I. M. and Sultankhodzhaev(1993): Alkaloids of the Mongolian Flora III. Altaconitine - A new alkaloid from Aconitum altaicum, translated from Khim. Prir. Soedin., No. 1, 47-53, Plenum Publishing Co
  26. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 99
  27. Takayama, H. Ito, M., Koga, M. and Sakai, S.(1981) Structure of zochasmanine, ezochasmaconitine, anisoezochasmanitine and synthesis of vilmorrianine A, Heterocycles, 15: 403-408 https://doi.org/10.3987/S-1981-01-0403
  28. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 308
  29. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 311
  30. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 312
  31. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 306
  32. Atta-ur-Rahman(1990): Handbook of Natural Products Data, Vol. 1. Diterpenoids and Steroidal Alkaloids, Elsevier, New York, p. 309