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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)
Publication Information
Archives of Pharmacal Research / v.28, no.8, 2005 , pp. 885-888 More about this Journal
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
Ternstroemia japonica; Theaceae; Jacaranone; Triterpene; Antioxidative activity; DPPH radical;
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Times Cited By Web Of Science : 10  (Related Records In Web of Science)
Times Cited By SCOPUS : 7
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1 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)
2 Fujita, R., Duan, H., and Takaishi, Y., Terpenoid from Tripterigyum hypoglaucum. Phytochemistry, 53, 715-722 (2000)   DOI   ScienceOn
3 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)   DOI   ScienceOn
4 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)   DOI   ScienceOn
5 Jakupovic, J., Chau-Thi, T. V., and Castro, V., Cyclohexene derivatives from Pseudogynoxys cunninghammii. Fitoterapia, 58, 187-188 (1987)
6 Olafsdottir, E. S., Omarsdottir, S., and Jaroszewski, J. W., Constituents of three Icelandic Alchemilla species. Biochemical Systematics and Ecology, 29, 959-962 (2001)   DOI   ScienceOn
7 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)   DOI   ScienceOn
8 Akamatsu, K., Wakanyaku. Ishiyaku Shuppan, Tokyo, p.234 (1970)
9 Kim, T. J., Korean Resources Plants Vol. 3, Seoul Nat'l Univ. Press, Seoul, p. 107, 1996
10 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)   DOI
11 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)   DOI   ScienceOn
12 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)   DOI   ScienceOn
13 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)   DOI   ScienceOn
14 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)
15 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)   DOI
16 Kikuchi, K. and Yamaguchi, M., Structure of ternstroemiaxanthin, a new aldehydic $C_{40}$-carotenoid. Bull. Chem. Soc. Jpn., 47, 885-887 (1974)   DOI
17 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)   DOI   ScienceOn
18 Muhammad, P., Ahmad, S., Nawaz, H. R., Ullah, N., and Malik, A., New acetylated quinols from Ajuga parviflora. Fitoterapia, 70, 229-232 (1999)   DOI   ScienceOn