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

  • Published : 2007.08.20

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

References

  1. Kim, T. J. In Korean Resources Plants Seoul National University Press: Seoul, 1996; Vol. 4, p 172
  2. 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
  3. Iwabuchi, M.; Murase, J. K.; Imamura, J. J. Biol. Chem. 2003, 278, 4603 https://doi.org/10.1074/jbc.M210748200
  4. Igarashi, M.; Miyazawa, T. Cancer Lett. 2000, 148, 173 https://doi.org/10.1016/S0304-3835(99)00332-8
  5. Suzuki, R.; Noguchi, R.; Ota, T.; Abe, M.; Miyashita, K.; Kawada, T. J. Am. Oil Chem. Soc. 2001, 36, 477
  6. 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
  7. Zhao, S.; Wang, Y.; Wei, H. Cell. Mol. Immunol. 2006, 3, 297
  8. Shaw, P.-C.; Lee, K.-M.; Wong, K.-B. Toxicon 2005, 45, 683 https://doi.org/10.1016/j.toxicon.2004.12.024
  9. Chan, S.-H.; Hung, F. S.-J.; Chan, D. S.-B.; Shaw, P.-C. Eur. J. Biochem. 2001, 268, 2107
  10. Li, M.-X.; Yeung, H.-W.; Pan, L.-P.; Chan, S. I. Nucleic Acids Res. 1991, 19, 6309
  11. 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 https://doi.org/10.1016/j.abb.2004.11.009
  12. Narayanan, P.; Mak, N. K.; Luong, P. B.; Wong, R. N. S. Plant Sci. 2002, 162, 79 https://doi.org/10.1016/S0168-9452(01)00533-7
  13. Hikino, H.; Yoshizawa, M.; Suzuki, Y.; Oshima, Y.; Konno, C. Planta Med. 1989, 55, 349 https://doi.org/10.1055/s-2006-962025
  14. Shidoji, Y.; Ogawa H. J. Lipid Res. 2004, 45, 1092 https://doi.org/10.1194/jlr.M300502-JLR200
  15. Akihisa, T.; Tokuda, H.; Ichiishi, E.; Mukainaka, T.; Toriumi, M.; Ukiya, M.; Yasukawa, K.; Nishino, H. Cancer Lett. 2001, 173, 9 https://doi.org/10.1016/S0304-3835(01)00689-9
  16. Akihisa, T.; Yasukawa, K.; Kimura, Y.; Takido, M.; Kokke, W. C. M. C.; Tamura, T. Phytochemistry 1994, 36, 153 https://doi.org/10.1016/S0031-9422(00)97029-8
  17. Homberg, E. E.; Seher, A. Phytochemistry 1977, 16, 288 https://doi.org/10.1016/S0031-9422(00)86810-7
  18. Yoshizaki, M.; Fujino, H.; Masuyama, M.; Arisawa, M.; Morita, N. Phytochemistry 1987, 26, 2557 https://doi.org/10.1016/S0031-9422(00)83876-5
  19. 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
  20. 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 https://doi.org/10.1093/jnci/82.13.1107
  21. Pauli, G. F.; Junior, P. Phytochemistry 1995, 38, 1245 https://doi.org/10.1016/0031-9422(94)00635-7
  22. Voirin, B.; Jay, M.; Hauteville, M. Phytochemistry 1975, 14, 257 https://doi.org/10.1016/0031-9422(75)85050-3
  23. Leu, Y.-L.; Shi, L.-S.; Damu, A. G. Chem. Pharm. Bull. 2003, 51, 599 https://doi.org/10.1248/cpb.51.599
  24. Harborne, J. B. Phytochemistry 1978, 17, 915 https://doi.org/10.1016/S0031-9422(00)88646-X
  25. Yu, D.; Chen, C.-H.; Brossi, A.; Lee, K.-H. J. Med. Chem. 2004, 47, 4072 https://doi.org/10.1021/jm0400505
  26. Stochmal, A.; Simonet, A. M.; Macias, F. A.; Oleszek, W. J. Agric. Food Chem. 2001, 49, 5310 https://doi.org/10.1021/jf010600x
  27. Kuwabara, H.; Mouri, K.; Otsuka, H.; Kasai, R.; Yamasaki, K. J. Nat. Prod. 2003, 66, 1273 https://doi.org/10.1021/np030020p
  28. Gantimur, D.; Semenov, A. A. Chem. Nat. Compd. (Engl. Transl.) 1984, 20, 362 https://doi.org/10.1007/BF00575771
  29. 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
  30. Fiasson, K. G.; Bonvin, J. F.; Fiasson, J. L. Phytochemistry 1991, 30, 1673 https://doi.org/10.1016/0031-9422(91)84231-G

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