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Tsaokoarylone, a Cytotoxic Diarylheptanoid from Amomum tsao-ko Fruits

  • Moon, Surk-Sik (Department of Chemistry, Kongju National University) ;
  • Cho, Soon-Chang (Department of Chemistry, Kongju National University) ;
  • Lee, Ji-Young (Department of Chemistry, Kongju National University)
  • Published : 2005.03.20

Abstract

The crude methanol extract of the fruits of Amomum tsao-ko (Zingiberaceae) showed cytotoxic activity. Bioactivity-guided separation led to the isolation of a diarylheptanoid, tsaokoarylone [7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hepta-4E,6E-dien-3-one] (2). 2 showed cytotoxicity at 4.9 and 11.4 $\mu$g/mL ($IC_{50}$) against human nonsmall cell lung cancer A549 and human melanoma SK-Mel-2, respectively, determined by SRB colorimetric method. During purification-(4-hydroxyphenyl)-4-hydroxyhexan-2-one (4) together with three known diarylheptanoids was also isolated. Their structures were determined from interpretation of spectroscopic data (IR, UV, MS, and NMR) and synthesis confirmed the structure of 2.

Keywords

References

  1. Sui, Z.; Salto, R.; Li, J.; Craik, C.; de Montellano, P. Bioorg. Med. Chem. 1993, 6, 415-422
  2. Kim, D. S. H. L.; Park, S.-Y.; Kim, J.-Y. Neuroscience Lett. 2001, 303, 57-61 https://doi.org/10.1016/S0304-3940(01)01677-9
  3. Roth, G. N.; Chandra, A. C.; Nair, M. G. J. Nat. Prod. 1998, 61, 542-545 https://doi.org/10.1021/np970459f
  4. Ohtsu, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H.-K.; Itogawa, H.; Su, C.-Y.; Shih, C.; Chiang, T.; Chang, E.; Lee, Y.; Tsai, M.-Y.; Chang, C.; Lee, K.-H. J. Med. Chem. 2002, 45, 5037-5042 https://doi.org/10.1021/jm020200g
  5. Ishida, J.; Ohtsu, H.; Tachibana, Y.; Nakanish, Y.; Bastow, K. F.; Nagai, M.; Wang, H.-K.; Itogawa, H.; Lee, K.-H. Bioorg. Med. Chem. 2002, 10, 3481-3487 https://doi.org/10.1016/S0968-0896(02)00249-3
  6. Ohtsu, H.; Itokawa, H.; Xiao, Z.; Su, C.-Y.; Shih, C. C.-Y.; Chiang, T.; Chang, E.; Lee, Y.; Chiu, S.-Y.; Chang, C.; Lee, K.-H. Bioorg. Med. Chem. 2003, 11, 5083-5090 https://doi.org/10.1016/j.bmc.2003.08.029
  7. Moon, S.-S.; Lee, J.-Y.; Cho, S.-C. J. Nat. Prod. 2004, 67, 889-891 https://doi.org/10.1021/np030464l
  8. 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, 1107-1112 https://doi.org/10.1093/jnci/82.13.1107
  9. Papazisis, K. T.; Geromichalos, G. D.; Dimitriadis, K. A.; Kortsaris, A. H. J. Immunol. Methods 1997, 208, 151-158 https://doi.org/10.1016/S0022-1759(97)00137-3
  10. Ali, M. S.; Tezuka, Y.; Awale, S.; Banskota, A. H.; Kadota, S. J. Nat. Prod. 2001, 64, 289-293 https://doi.org/10.1021/np000496y
  11. Martin, T. S.; Kikuzaki, H.; Hisamoto, M.; Nakatani, N. J. Am. Oil Chem. Soc. 2000, 77, 667-673 https://doi.org/10.1007/s11746-000-0107-4
  12. J. Am. Oil Chem. Soc. v.77 Martin, T. S.;Kikuzaki, H.;Hisamoto, M.;Nakatani, N. https://doi.org/10.1007/s11746-000-0107-4

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