Alkaloidal Constituents from Aconitum jaluense

  • Shim, Sang-Hee (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Son, Kun-Ho (Department of Food and Nutrition, Andong National University) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Published : 2003.09.01

Abstract

Aconitum jaluense Komar. (Ranunculaceae) is one of the Aconitum plants growing in Korean peninsula. An investigation of the alkaloidal constituents of this species led to the isolation of seven $C_{19}$-norditerpenoid and a $C_{20}$-diterpenoid alkaloid. Three of them have been identified as neoline, mesaconitine, and hypaconitine, which were isolated from this plant collected from Mt. Bultasan in the north part. The other five alkaloids were determined as lipomesaconitine, lipohypaconitine, 15$\alpha$-hydroxyneoline, hokbusine A, and napelline, which have not been found in this plant. Structures of those alkaloids were determined on the basis of their spectral data. It is of interest to note that a comparison of the present work and the previous report showed some differences in the alkaloidal contents.

Keywords

References

  1. Chen, S.-Y., Liu, Y.-Q., and Wang, J.-C., The Alkaloidal Constituents of Cultivated Chuan-wu of Yunnan. Acta Bot. Yun., 4, 73-75 (1982)
  2. Chung, B. S. and Lee, H. K., Studies on Korean Aconitum Species (II). Alkaloids of Aconitum napiforme. Kor. J. Pharmacogn., 18, 103-106 (1987)
  3. Chung, B. S. and Lee, H. K., Studies on Korean Aconitum Species (IV). Alkaloids of Aconitum pseudolaeve var. erectum. Kor. J. Pharmacogn., 19, 181-187 (1988a)
  4. Chung, B. S., Lee, H. K., and Lee, H. S., Studies on Korean Aconitum Species (III). Alkaloids of Aconitum uchiyamai. Kor. J. Pharmacogn., 19, 177-180 (1988b)
  5. Chung, B. S., Lee, H. K., Pelletier, S. W., and Badawi, M. M., Rearrangement of the Structure of Tuguaconitine from Aconitum sibiricum. J. Nat. Prod., 49, 1074-1077 (1986) https://doi.org/10.1021/np50048a017
  6. Desai, H. K. and Pelletier, S. W., Falconericine and falconeridine: Two new alkaloids from Aconitum falconeri Stdpf. Heterocycles, 29, 225-230 (1989) https://doi.org/10.3987/COM-89-4795
  7. Hang, G.-Y., Cai, P., Wang, J.-Z., and Snyder, J. K., Correction of the spectroscopic data of hokbusine A: Confirmation of the C-8 methoxyl group. J. Nat. Prod., 51, 364-366 (1988) https://doi.org/10.1021/np50056a035
  8. Hanuman, J. B. and Katz, A., $^1H$-NMR Spectra of Norditerpenoid Alkaloids. A Review. J. Nat. Prod., 57, 1473-1483 (1994a) https://doi.org/10.1021/np50113a001
  9. Hanuman, J. B. and Katz, A., New Lipo Norditerpenoid Alkaloids from root tubers of Aconitum ferox. J. Nat. Prod., 57, 105-115 (1994b) https://doi.org/10.1021/np50103a015
  10. Hikino, H., Shiota S., Takahashi, M., and Murakami, M., Structure of Hokbusine A and B, Diterpenoid Alkaloids of Aconitum carmichaeli Roots from Japan. J. Nat. Prod., 46, 178-182 (1983a) https://doi.org/10.1021/np50026a006
  11. Hikino, H., Shiota, S., Takahashi, M., and Murakami, M., Seasonal Dynamics of the Accumulation of Aconitine Alkaloids in Aconitum carmichaeli Roots. Shoyakugaku Zasshi, 37, 68-72 (1983b)
  12. Kawata, Y., Ma, C.-M., Meselhy, M.R., Nakamura, N., Wang, H., Hattori, M., Namba, T., Satoh, K., and Kuraishi, Y., Conversion of aconitine to lipoaconitine by human intestinal bacteria and their antinociceptive effects in mice. J. Trad. Med., 16, 15-23 (1999)
  13. Kim, D. K., Kwak, J. H., Song, K. W., Kwon, H. C., Zee, O. P., and Lee, K. R., Phytochemical Constituents from Aconitum pseudolaeve var. erectum. Kor. J. Pharmacogn., 27, 75-79 (1996)
  14. Kim, D. K., Kwon, H. Y., Lee, K. R., Rhee, D. K., and Zee, O. P., Isolation of a Multidrug Resistance Inhibitor for Aconitum pseudolaeve var. erectum. Arch. Pharm. Res., 21, 344-347 (1998) https://doi.org/10.1007/BF02975299
  15. Kim, L. S., An, B. S., and Dutschewska, H., Alkaloides Diterpeniques DAconitum jaluense Komarov. Plant. Med. Phytother., 26, 1-6 (1990)
  16. Kitagawa, I., Yoshikawa, M., Chen, Z. L., and Kobayashi, K., Four new lipo-alkaloids from Aconiti tuber. Chem. Pharm. Bull., 30, 758-761 (1982) https://doi.org/10.1248/cpb.30.758
  17. Kitagawa, I., Chen, I. L., Yoshihara, M., and Yoshikawa, M., Chemical Studies on Crude Drug Processing. II. Aconiti Tuber (1). On the Constituents of Chuan-wu', the Dried Tuber of Aconitum carmichaeli Debx. Yakugaku Zasshi, 104, 848-857 (1984) https://doi.org/10.1248/yakushi1947.104.8_848
  18. Konno, C., Shirasaka, M., and Hikino, H., Structure of senbusine A, B and C, Diterpenic Alkaloids of Aconitum carmichaeli roots from China. J. Nat. Prod., 45, 128-133 (1982) https://doi.org/10.1021/np50020a003
  19. Lee, C. B., Illustrated Flora of Korea. Hyangmoonsa, Seoul, pp. 359-365 (1989)
  20. Lee, H. S. and Chung, B. S., Studies on Korean Aconitum Species (V). On the chemical constituents from Aconitum pseudolaeve var. erectum. Kor. J. Pharmacogn., 20, 6-9 (1989)
  21. Pelletier, S. W., Djarmati, Z., and De Camp, W. H., Alkaloids of Delphinium staphisagria. The Structure and Stereochemistry of Delphisine, Neoline, Chasmanine, and Homochasmanine. J. Am. Chem. Soc., 98, 2617-2625 (1976) https://doi.org/10.1021/ja00425a035
  22. Shim, S. H., Kim, J. S., and Kang, S. S., Norditerpenoid Alkaloids from the Processed Tubers of Aconitum carmichaeli. Chem. Pharm. Bull., 51, 999-1002 (2003) https://doi.org/10.1248/cpb.51.999
  23. Sun, W. X., Song, F. R., Cui, M., and Lin, S. Y., Simultaneous Determination of lipo-alkaloids extracted from Aconitum carmichaeli using Electrospray Ionization Mass Spectroscopy and Multiple Tandom Mass Spectroscopy. Planta Med., 65, 432-436 (1999) https://doi.org/10.1055/s-1999-14086
  24. Takayama, H., Tokita, A., Ito, M., Sakai, S.-I., Kurosaki, F., and Okamoto, T., On the Alkaloids of Aconitum yesoense Nakai. Yakugaku Zasshi, 102, 245-257 (1982a) https://doi.org/10.1248/yakushi1947.102.3_245
  25. Takayama, H., Hasegawa, S., Sakai, S.-I., Haginiwa, J., and Okamoto, T., On the Alkaloids of Aconitum japonicum Thunb. Collected at Mt. Mineoka (Chiba Pref.): Structure Elucidation and Partial Synthesis of a New Alkaloid, $15\alpha$-hydroxyneoline. Yakugaku Zasshi, 102, 525-532 (1982b) https://doi.org/10.1248/yakushi1947.102.6_525
  26. Wada, K., Bando, H., Amiya, T., and Kawahara, N., Studies on Aconitum Species. Xll. Two New Diterpenoid Alkaloid from Aconitum jesoense var. macroyesoense (Nakai) Tamura V. Heterocycles, 29, 2141-2148 (1989) https://doi.org/10.3987/COM-89-5139