Synthesis and Evaluation of Cytotoxicity of Stilbene Analogues

  • Lee, Sang-Kook (College of Pharmacy, Ewha Womans University) ;
  • Nam, Kyung-Ae (College of Pharmacy, Ewha Womans University) ;
  • Hoe, Yeon-Hoi (College of Pharmacy, Ewha Womans University) ;
  • Min, Hye-Young (College of Pharmacy, Ewha Womans University) ;
  • Kim, Eun-Young (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Ko, Hyojin (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Song, Soyoung (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Lee, Taeho (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Kim, Sanghee (Natural Products Research Institute, College of Pharmacy, Seoul National University)
  • Published : 2003.04.01

Abstract

Resveratrol analogs were newly synthesized and evaluated for cytotoxicity in cultured human lung and colon cancer cells. 3,5,4-Trimethoxy-trans-stilbene and 3,5,2',4'-tetramethoxy-trans-stilbene were found to be more potent rather than resveratrol. 3,4,5-Trimethoxy-4'-bromo-cis-stilbene was the most active among the test compounds.

Keywords

References

  1. Alonso, E., Ramon, D. J., and Yus, M., Simple synthesis of 5- substituted resorcinols: A revisited family of interesting bioactive molecules. J. Org. Chem., 62, 417-421 (1997) https://doi.org/10.1021/jo9610624
  2. Bellucci, G., Chiappe, C., and Moro, G. L., Crown ether catalyzed stereospecific synthesis of Z- and E-stilbenes by wittig reaction in a solid-liquid two-phases system. Tetrahedron Lett., 37, 4225-4228 (1996) https://doi.org/10.1016/0040-4039(96)00802-7
  3. Fontecave, M., Lepoivre, M., Elleingand, E., Gerez, C., and Guittet, O., Resveratrol, a remarkable inhibitor of ribonucleo-tide reductase. FEBS Lett., 421, 277-279 (1998) https://doi.org/10.1016/S0014-5793(97)01572-X
  4. Frankel, E. N., Waterhouse, A. L., and Kinsella, J. E., Inhibition of human LDL oxidation by resveratrol. Lancet., 341, 1103-1104 (1993)
  5. Jang, D. O., Park, D. J., and Kim, J. A., Mild and efficient procedure for the preparation of acid chlorides from carboxylic acids. Tetrahedron Lett., 40, 5323-5326 (1999) https://doi.org/10.1016/S0040-4039(99)00967-3
  6. Jang, M., Cai, L, Udeani, G. O., Slowing, K. V., Thomas, C. F., Beecher, C. W. W., Fong, H. S. S., Farnsworth, N. R., Kinghorn, A. D., Mehta, R. G., Moon, R. C., and Pezzuto, J. M., Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science, 275, 218-220 (1997) https://doi.org/10.1126/science.275.5297.218
  7. Kucerovy, A., Li, T., Prasad, K., Repie, O., and Blacklock, T. J., An efficient large-scale synthesis of methyl 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoate. Org. Process Res. Dev., 1, 287-293 (1997).
  8. Lee, S. K., Cui, B., Mehta, R. R., Kinghorn, A. D., and Pezzuto, J. M., Cytostatic mechanism and antitumor potential of novel 1H-cyclopenta[b]benzofuran lignans isolated from Aglaia elliptica. Chem-Biol. Interact., 115, 215-228 (1998) https://doi.org/10.1016/S0009-2797(98)00073-8
  9. Mgbonyebi, O. P., Russo, J., and Russo, I. H., Antiproliferative effect of synthetic resveratrol on human breast epithelial cells. Int. J. Oncol., 12, 865-869 (1998)
  10. Ohsumi, K., Hatanaka, T., Fujita, K., Nakagawa, R., Fukuda, Y., Nihei, Y., Suga, Y., Morinaga, Y., Akiyama, Y., and Tsuji, T., Syntheses and antitumor activity of cis-restricted combre-tastatins: 5-membered heterocyclic analogues. Bioorg. Med. Chem. Lett., 8, 3153-3158 (1998) https://doi.org/10.1016/S0960-894X(98)00579-4
  11. Orsini, F., Pelizzoni, F., Bellini, B., and Miglierini, G., Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series). Carbohyd. Res., 301, 95-109 (1997) https://doi.org/10.1016/S0008-6215(97)00087-6
  12. Pace-Asciak, C. R., Hahn, S., Diamandis, E. P., Soleas, G., and Goldberg, D. M., The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin. Chim. Acta, 235, 207-219 (1995) https://doi.org/10.1016/0009-8981(95)06045-1
  13. Park, J., Choi, Y., Jang, M., Lee, Y., Jun, D., Suh, S., Baek, W., Suh, M., Jin, I., and Kwon, T. K., Chemopreventive agent resveratrol, a natural product derived from grapes, reversibly inhibits progression through S and G2 phases of the cell cycle in U937 cells. Cancer Lett., 163, 43-49 (2001) https://doi.org/10.1016/S0304-3835(00)00658-3
  14. Pettit, G. R., Singh, S. B., Boyd, M. R., Hamel, E., Pettit, R. K., Schmidt, J. M., and Hogan, F., Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. J. Med. Chem., 38, 1666-1672 (1995) https://doi.org/10.1021/jm00010a011
  15. Pettit, G. R., Lippert III, J. W., and Herald, D. L., A Pinacol Rearrangement/Oxidation Synthetic Route to Hydroxyphen-statin. J. Org. Chem., 65, 7438-444 (2000) https://doi.org/10.1021/jo000705j
  16. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, T. W., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  17. Uenobe, F., Nakamura, S., and Miyazawa, M., Antimutagenic effect of resveratrol against Trp-P-1. Mutat. Res., 373, 197-200 (1997) https://doi.org/10.1016/S0027-5107(96)00191-1
  18. Wilds, A. L. and MaCormack, W. B., Hexahydro derivatives of meso-hexestrol. J. Am. Chem. Soc., 70, 4127-4132 (1948) https://doi.org/10.1021/ja01192a044
  19. Zhang, J. T., Dai, W., and Harvey, R. G., Synthesis of higher oxidized metabolites of dibenz[a,j]anthracene implicated in the mechanism of carcinogenesis. J. Org. Chem., 63, 8125-8132 (1998) https://doi.org/10.1021/jo980416j