Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Jacaranone and Related Compounds from the Fresh Fruits of Ternstroemia japonica and their Antioxidative Activity

  • Jo Youngmi (College of Pharmacy, Pusan National University) ;
  • Suh Jiyoung (College of Pharmacy, Pusan National University) ;
  • Shin Myoung Hee (College of Pharmacy, Pusan National University) ;
  • Jung Jee H. (College of Pharmacy, Pusan National University) ;
  • Im Kwang Sik (College of Pharmacy, Pusan National University)
  • Published : 2005.08.01
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Abstract

Jacaranone and related compounds (1-3) were isolated, along with three triterpenes (4-6), from the fresh fruits of Ternstroemia japonica. The compounds were identified as jacaranone (1), 3-hydroxy-2,3-dihydrojacaranone (2), 3-methoxy-2,3-dihydrojacaranone (3), 3-O-acetyl­oleanolic acid (4), 3-O-acetylursolic acid (5), and ursolic acid (6). Jacaranone and its derivatives were isolated for the first time from Theaceae. Of the isolated compounds, compound 3 is a new compound. Jacaranone (1) exhibited weak antioxidative effect on 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) radical.

Keywords

References

  1. Akamatsu, K., Wakanyaku. Ishiyaku Shuppan, Tokyo, p.234 (1970)
  2. Bohlmann, F., Zdero, C., King, R. M., and Robinson, H., The first acetylenic monoterpene and other constituents from Senecio clevelandii. Phytochemistry, 20, 2425-2427 (1981) https://doi.org/10.1016/S0031-9422(00)82681-3
  3. Cabezas, J. A., Ciccio, J. F., Hidalgo, G., and Echandi, G., Synthesis and antibacterial activity of jacaranone and ester side chain analogs. Rev. Latinoam. Quim., 22, 49-52 (1991)
  4. Fujita, R., Duan, H., and Takaishi, Y., Terpenoid from Tripterigyum hypoglaucum. Phytochemistry, 53, 715-722 (2000) https://doi.org/10.1016/S0031-9422(99)00557-9
  5. Jakupovic, J., Chau-Thi, T. V., and Castro, V., Cyclohexene derivatives from Pseudogynoxys cunninghammii. Fitoterapia, 58, 187-188 (1987)
  6. Kikuchi, K. and Yamaguchi, M., Structure of ternstroemiaxanthin, a new aldehydic $C_{40}$-carotenoid. Bull. Chem. Soc. Jpn., 47, 885-887 (1974) https://doi.org/10.1246/bcsj.47.885
  7. Kim, T. J., Korean Resources Plants Vol. 3, Seoul Nat'l Univ. Press, Seoul, p. 107, 1996
  8. Mericli, A. H., Mericli, F., Jakupovic, J., Bohlmann, F., Dominguez, X. A., Vega, and H. S., Eremophilane derivatives and other constituents from Mexican Senecio species. Phytochemistry, 28, 1149-1153 (1989) https://doi.org/10.1016/0031-9422(89)80199-2
  9. Muhammad, P., Ahmad, S., Nawaz, H. R., Ullah, N., and Malik, A., New acetylated quinols from Ajuga parviflora. Fitoterapia, 70, 229-232 (1999) https://doi.org/10.1016/S0367-326X(99)00019-2
  10. Mukoda, T., Sun, B., and Ishiguro, A., Antioxidant activities of buckwheat hull extract toward various oxidative stress in vitro and in vivo. Biol. Pharm. Bull., 24, 209-213 (2001) https://doi.org/10.1248/bpb.24.209
  11. Ogura, M., Cordell, G. A., and Farnsworth, N. R., Potential anticancer agents III. Jacaranone, a novel phytoquinoid from Jacaranda caucana. Lloydia, 39, 255-257 (1976)
  12. Olafsdottir, E. S., Omarsdottir, S., and Jaroszewski, J. W., Constituents of three Icelandic Alchemilla species. Biochemical Systematics and Ecology, 29, 959-962 (2001) https://doi.org/10.1016/S0305-1978(01)00038-2
  13. Perez-Castorena, A. L., Arciniegas, A., Martinez, F., Marquez, C., and Villasenor, J. L., Chemical constituents of Packera coahuilensis and Packera bellidifolia. Biochemical Systematics and Ecology, 29, 203-206 (2001) https://doi.org/10.1016/S0305-1978(00)00043-0
  14. Santos, G. G., Alves, J. C. N., Rodilla, J. M. L., Duarte, A. P., Lithgow, A. M., and Urones, J. G., Terpenoids and other constituents of Eucalyptus globulus. Phytochemistry, 44, 1309-1312 (1997) https://doi.org/10.1016/S0031-9422(96)00680-2
  15. Shin, M. H., Wang, W., Nam, K. I., Jo, Y., Jung, J. H., and Im, K. S., Triterpenoid saponins from the fruits of Ternstroemia japonica. J. Nat. Prod., 66, 1351-1355 (2003) https://doi.org/10.1021/np0301644
  16. Tan, G. T., Miller, J. F., Kinghorn, A. D., Hughes, S. H., and Pezzuto, J. M., HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. Biochem. Biophys. Res. Commun., 185, 370-378 (1992) https://doi.org/10.1016/S0006-291X(05)80995-7
  17. Yoshida, T., Mori, K., Hatano, T., Okumura, T., Uehara, I., Komagoe, K., and Okuda, T., Studies on inhibition mechanism of autooxidation by tannins and flavonoids. Chem. Pharm. Bull., 37, 1919-1921 (1989) https://doi.org/10.1248/cpb.37.1919
  18. Yoshioka, I., Takeda, R., Matsuda, A., and Kitagawa, I., Saponin and sapogenol. V. Sapogenol constituents of seeds of Camellia sasanqua and leaves of Ternstroemia japonica. Chem. Pharm. Bull., 20, 1237-1242 (1972) https://doi.org/10.1248/cpb.20.1237