Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
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Oxidative Characteristics of Norditerpene Alkaloids

노르디테르펜 알칼로이드류의 산화적 특성

  • Published : 2006.03.30
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Abstract

Norditerpene alkaloids are the main toxic principles of traditional oriental herb 'chuawu(bu-shi),' which have been used in Chinese materia medica mainly for the treatment of musculoskeletal disorders. They are biosynthesized via cyclization of geranylgeranyl pyrophosphate, incoration of 2-aminoethanol and decarboxylation not via amino acid pathway, and the structural characteristics have tempted several oxidative reactions. In this study various norditerpene alkaloids were subjected to react active manganese dioxide and oxoammonium salt as oxidants. The oxidation was proceeded as dealkylation with aconitine type and dehydrogenations with lycoctonin and heteratisine type.

Keywords

References

  1. 보건복지부 (2002) 대한약전 제 8개정 제2부 (KP VIII-2) pp. 1323-25
  2. Pelletier, S. Wand Mody, N. V. (1979) The Alkaloids, Chapter 1, Academic Press, New York, U. S. A
  3. 보건복지부 (2004) 약전외 생약(한약) 규격집 (KHP 2004) p.311
  4. Kulanthaivel, P. and Pelletier, S. W. (1987) Deoxygenation reactions of $C_{19}$-diterpenoid alkaloids, Tetrahedron Letters, 28: 3883-86 https://doi.org/10.1016/S0040-4039(00)96410-4
  5. 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: 185-193 https://doi.org/10.3987/COM-87-4335
  6. Ross, S. A and Pelletier, S. W (1988) New synthetic esters of delphisine and neoline, Heterocycles, 27: 1381-90 https://doi.org/10.3987/COM-87-4472
  7. Pelletier, S. W and Ross, S. A (1990) Synthetic esters and ethers of delphinine and Iycoctdnine, Heterocycles, 31: 671-675 https://doi.org/10.3987/COM-90-5323
  8. 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 N-CHO group by osmium tetroxide, Tetrahedron Letters, 23: 4229-32 https://doi.org/10.1016/S0040-4039(00)88711-0
  9. Desai, H. K., Chokshi, H. P. and Pelletier, S. W (1989) Oxidation of norditerpenoid alkaloids with osmiwn tetroxide, J. Nat. Prod.. 52: 1296-1302 https://doi.org/10.1021/np50066a016
  10. Pelletier, S. W, Glinski, J. A. and Mody, N. V. (1982) Origin of oxonitine: A potassium pennanganate oxidation product of aconitine, J. Am. Chem. Soc., 104: 4676-77 https://doi.org/10.1021/ja00381a029
  11. 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
  12. Pelletier, S. W, Mody, N. V. and Bhattacharyya, J. (1978) Active manganese dioxide: A reagent for constructmg the oxazolidine ring of Tetrahedron Letters, 52: 5187-88
  13. Bobbitt, J. M. (1998) Oxoammoniwn Salts. 6. 4-Acetylamino- 2,2,6,6-tetra-methylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis, J. Org. Chem., 63: 9367-74 https://doi.org/10.1021/jo981322c
  14. 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
  15. Pelletier, S. W. and Djannati, 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
  16. 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: 327-339 https://doi.org/10.3987/S-1977-01-0327
  17. 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
  18. Pelletier, S. W, Mody, N. V and Dailey, O. (1980) $^{13}C$ nuclear magnetic resonance spectroscopy of methylenedioxy groupccontaining $C_{19}$-diterpenoid alkaloids and their derivatives, Can. J. Chem., 58: 1875-79 https://doi.org/10.1139/v80-296
  19. Pelletier, S. W, Mody, N. V, Joshi, B. S. and Schramm, L. C. (1984) $^{13}C$ and protonNMRshift 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
  20. 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
  21. Desai, H. K. and Pelletier, S. W (1993) $^{13}C$_NMR assignment for lactone-type norditerpenoid alkaloids, J. Nat. Prod., 56: 2193-97 https://doi.org/10.1021/np50102a027
  22. Pelletier, S. W (1992) Studies in the chemistry of natural products: Rearrangement reactions of diterpenoid and norditerpenoid alkaloids, J. Nat. Prod., 55: 1-24 https://doi.org/10.1021/np50079a001
  23. Pelletier, S. Wand Page, S. W. (1986) Diterpenoid alkaloids, Nat. Prod. Rep., 451-464
  24. Joshi, B. S., Srivastava, S. K., Barber, A D., Desai, H. K. and Pelletier, S. W (1997) Selective demethylation of some aconitine-type norditerpene alkaloids, J. Nat. Prod., 60: 439-443 https://doi.org/10.1021/np9606862
  25. Liang, X., Desai, H. K., Joshi, B. S. and Pelletier, S. W. (1990) Demethylation of norditerpenoid alkaloids, Heterocycles, 31: 1889-94 https://doi.org/10.3987/COM-90-5546
  26. 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
  27. Bai, Y, Desai, H. K. and Pelletier, S. W. (1995) N-Oxide of some norditerpene alakloids, J. Nat. Prod, 58: 929-33 https://doi.org/10.1021/np50120a018
  28. Pelletier, S. W., Lajsic, D. S. and De Camp, W. H. (1976) Alkaloids of Delphinium staphisagria. The structure and stereochemistry of delphisine, neoline, chasmanine and homochasmanine, J. Am. Chem. Soc., 98: 2617-25 https://doi.org/10.1021/ja00425a035
  29. Silverman, L. P.(1997) Studies on the Oxidation of some Norditerpene Alkaloids(M. S. Thesis), Dept. of Chem., Univ. of Georgia
  30. Pelletier, S. W. and Joshi, B. S. (1991) Carbon-13 and proton NMR shift assignment, in Alkaloids: Chemical and Biological Perspectives, Vol. 7, p. 425, Springer-Verlag
  31. Srivastava, S., Joshi, B. S., Newton. M. G, Lee, D. and Pelletier, S. W. (1995) Heterolytic fragmentation of deltaline, a nordietrpenoid alkaloid, Tetrahed Lett., 36: 519-522 https://doi.org/10.1016/0040-4039(94)02300-Z
  32. Pelletier, S. W. and Joshi, B. S. (1991) Carbon-13 and proton NMR shift assignment, in Alkaloids: Chemical and Biological Perspectives, Vol. 7, p. 370, Springer-Verlag