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http://dx.doi.org/10.5012/bkcs.2007.28.8.1261

Isoetin 5'-Methyl Ether, A Cytotoxic Flavone from Trichosanthes kirilowii  

Rahman, Md. Aziz Abdur (Department of Chemistry, Kongju National University)
Moon, Surk-Sik (Department of Chemistry, Kongju National University)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.8, 2007 , pp. 1261-1264 More about this Journal
Abstract
Bioassay-directed fractionations of the seed extracts of Trichosanthes kirilowii, have resulted in the isolation of two new compounds, 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol (2) and isoetin 5'-methyl ether (5,7,2',4'-tetrahydroxy-5'-methoxyflavone) (3), together with two known compounds, 7-hydroxychromone (1) and 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (tricin, 4). Their structures were characterized by spectroscopic analysis such as 2D-NMR, HRTOFMS, and UV. Compound 3 showed cytotoxicity against human lung cancer cell line A549, human skin melanoma SK-Mel-2, and mouse melanoma B16F1, with IC50 of 0.92, 8.0, and 7.23 μg/mL, respectively.
Keywords
Trichosanthes kirilowii; Isoetin 5'-methyl ether; Tricin; Cytotoxicity;
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1 Harborne, J. B. Phytochemistry 1978, 17, 915   DOI   ScienceOn
2 Yu, D.; Chen, C.-H.; Brossi, A.; Lee, K.-H. J. Med. Chem. 2004, 47, 4072   DOI   ScienceOn
3 Stochmal, A.; Simonet, A. M.; Macias, F. A.; Oleszek, W. J. Agric. Food Chem. 2001, 49, 5310   DOI   ScienceOn
4 Kuwabara, H.; Mouri, K.; Otsuka, H.; Kasai, R.; Yamasaki, K. J. Nat. Prod. 2003, 66, 1273   DOI   ScienceOn
5 Gantimur, D.; Semenov, A. A. Chem. Nat. Compd. (Engl. Transl.) 1984, 20, 362   DOI   ScienceOn
6 Lee, K.-H.; Tagahara, K.; Suzuki, H.; Wu, R.-Y.; Haruna, M.; Hall, I. H.; Huang, H.-C.; Ito, K.; Lida, T.; Lai, J.-S. J. Nat. Prod. 1981, 44, 530
7 Fiasson, K. G.; Bonvin, J. F.; Fiasson, J. L. Phytochemistry 1991, 30, 1673   DOI   ScienceOn
8 Suzuki, R.; Noguchi, R.; Ota, T.; Abe, M.; Miyashita, K.; Kawada, T. J. Am. Oil Chem. Soc. 2001, 36, 477
9 Chang, H.-M.; But, P. P.-H., editors; Yao, S.-C.; Wang, L.-L.; Yeung, S. C.-S. Translators. In Pharmacology and Applications of Chinese Material Medica, 1st ed.; World Scientific Publishing Co. Pte. Ltd.: Singapore, 1986; Vol. 1, pp 404-409
10 Chan, S.-H.; Hung, F. S.-J.; Chan, D. S.-B.; Shaw, P.-C. Eur. J. Biochem. 2001, 268, 2107
11 Li, M.-X.; Yeung, H.-W.; Pan, L.-P.; Chan, S. I. Nucleic Acids Res. 1991, 19, 6309
12 Akihisa, T.; Yasukawa, K.; Kimura, Y.; Takido, M.; Kokke, W. C. M. C.; Tamura, T. Phytochemistry 1994, 36, 153   DOI   ScienceOn
13 Homberg, E. E.; Seher, A. Phytochemistry 1977, 16, 288   DOI   ScienceOn
14 Yoshizaki, M.; Fujino, H.; Masuyama, M.; Arisawa, M.; Morita, N. Phytochemistry 1987, 26, 2557   DOI   ScienceOn
15 Hikino, H.; Yoshizawa, M.; Suzuki, Y.; Oshima, Y.; Konno, C. Planta Med. 1989, 55, 349   DOI   ScienceOn
16 Narayanan, P.; Mak, N. K.; Luong, P. B.; Wong, R. N. S. Plant Sci. 2002, 162, 79   DOI   ScienceOn
17 Pauli, G. F.; Junior, P. Phytochemistry 1995, 38, 1245   DOI   ScienceOn
18 Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107   DOI
19 Zhao, S.; Wang, Y.; Wei, H. Cell. Mol. Immunol. 2006, 3, 297
20 Shaw, P.-C.; Lee, K.-M.; Wong, K.-B. Toxicon 2005, 45, 683   DOI   ScienceOn
21 Leu, Y.-L.; Shi, L.-S.; Damu, A. G. Chem. Pharm. Bull. 2003, 51, 599   DOI   ScienceOn
22 Voirin, B.; Jay, M.; Hauteville, M. Phytochemistry 1975, 14, 257   DOI   ScienceOn
23 Mi, S.-L.; An, C.-C.; Wang, Y.; Chen, J.-Y.; Che, N.-Y.; Gao, Y.; Chen, Z.-L. Arch. Biochem. Biophys. 2005, 434, 258   DOI   ScienceOn
24 Kim, T. J. In Korean Resources Plants Seoul National University Press: Seoul, 1996; Vol. 4, p 172
25 Iwabuchi, M.; Murase, J. K.; Imamura, J. J. Biol. Chem. 2003, 278, 4603   DOI   ScienceOn
26 Igarashi, M.; Miyazawa, T. Cancer Lett. 2000, 148, 173   DOI   ScienceOn
27 Jang, K. C.; Lee, J. H.; Kim, S. C.; Song, E. Y.; Ro, N. Y.; Moon, D. Y.; Um, Y. C.; Park, K. H. J. Appl. Biol. Chem. 2007, 50, 17   과학기술학회마을
28 Shidoji, Y.; Ogawa H. J. Lipid Res. 2004, 45, 1092   DOI   ScienceOn
29 Akihisa, T.; Tokuda, H.; Ichiishi, E.; Mukainaka, T.; Toriumi, M.; Ukiya, M.; Yasukawa, K.; Nishino, H. Cancer Lett. 2001, 173, 9   DOI   ScienceOn
30 Koba, K.; Akahoshi, A.; Yamasaki, M.; Tanaka, K.; Yamada, K.; Iwata, T.; Kamegai, T.; Tsutsumi, K.; Sugano, M. J. Am. Oil Chem. Soc. 2002, 37, 343