Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Syntheses of Resveratrol and its Hydroxylated Derivatives as Radical Scavenger and Tyrosinase Inhibitor

  • Lee, Hyun-Suck (Department of Chemistry and Institute of Applied Chemistry) ;
  • Lee, Byung-Won (Institute of Natural Medicine, Hallym University) ;
  • Kim, Mi-Ran (Department of Chemistry and Institute of Applied Chemistry) ;
  • Jun, Jong-Gab (Department of Chemistry and Institute of Applied Chemistry)
  • Published : 2010.04.20
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Abstract

Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with $IC_{50}$ values of 4.1 and $8.6\;{\mu}M$, respectively.

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References

  1. Howitz, K. T.; Bitterman, K. J.; Cohen, H. Y.; Lamming, D. W.;Lavu, S.; Wood, J. G.; Zipkin, R. E.; Chung, P.; Kisielewski, A.Nature 2003, 425, 191. https://doi.org/10.1038/nature01960
  2. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.;Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Kinghorn,A. D.; Mehta, R. C.; Moon, R. C.; Pezzuto, J. M. Science 1997,275, 218. https://doi.org/10.1126/science.275.5297.218
  3. Wu, C.-P.; Calcagno, A. M.; Hladky, S. B.; Ambudkar, S. V.; Barrand, M. A. FEBS J. 2005, 272, 4725. https://doi.org/10.1111/j.1742-4658.2005.04888.x
  4. Gledhill, J. R.; Montgomery, M. G.; Leslie, A. G. W.; Walker, J. E. Proc. Natl. Acad. Sci. U.S.A. 2007, 272, 4725.
  5. Song, S.; Lee, H.; Jin, Y.; Ha, Y. M.; Bae, S.; Chung, H. Y.; Suh, H.Bioorg. Med. Chem. Lett. 2007, 17, 461. https://doi.org/10.1016/j.bmcl.2006.10.025
  6. Robb. D. A. Tyrosinase In Copper Proteins and Copper Enzymes; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 2, pp 207-240.
  7. Kim, Y. M.; Yun, J.; Lee, C. K.; Lee, H.; Min, K. R.; Kim, Y. J. Biol. Chem. 2002, 277, 16340. https://doi.org/10.1074/jbc.M200678200
  8. Meier, H.; Dullweber, U. Tetrahedron Lett. 1996, 37, 1191. https://doi.org/10.1016/0040-4039(95)02414-X
  9. Kim, S.; Ko, H.; Park, J. E.; Jung, S.; Lee, S. K.; Chun, Y.-J. J. Med. Chem. 2002, 45, 160. https://doi.org/10.1021/jm010298j
  10. Guiso, M.; Marra, C.; Farina, A. Tetrahedron Lett. 2002, 43, 597. https://doi.org/10.1016/S0040-4039(01)02227-4
  11. Murias, M.; Handler, N.; Erker, T.; Pleban, K.; Ecker, G.; Saiko, P.; Szekeres, T.; Jager, W. Bioorg. Med. Chem. 2004, 12, 5571. https://doi.org/10.1016/j.bmc.2004.08.008
  12. Han, S. Y.; Lee, H. S.; Choi, D. H.; Hwang J. W.; Yang, D. M.;Jun, J.-G. Synth. Commun. 2009, 39, 1425. https://doi.org/10.1080/00397910802528944
  13. Guiso, M.; Marra, C.; Farina, A. Tetrahedron Lett. 2002, 43,597. https://doi.org/10.1016/S0040-4039(01)02227-4
  14. Choi, S. Z.; Jang, K. U.; Chung, S. H.; Park, S. H.; Kang,H. C.; Yang, E. Y.; Cho, H. J.; Lee, K. R. Arch Pharm. Res. 2005,28, 1027. https://doi.org/10.1007/BF02977396
  15. Ko, S. K.; Lee, S. M.; Whang, W. K. Arch Pharm. Res. 1999, 22, 401. https://doi.org/10.1007/BF02979065
  16. Nerya, O.; Musa, R.; Khatib, S.; Tamir, S.; Vaya, J. Phytochemistry 2004, 65, 1389. https://doi.org/10.1016/j.phytochem.2004.04.016
  17. Likhitwitayawuid, K.; Sritularak, B. J. Nat. Prod. 2001, 64, 1457. https://doi.org/10.1021/np0101806
  18. Shimizu, K.; Kondo, R.; Sakai, K. Planta Med. 2000,66, 11. https://doi.org/10.1055/s-2000-11113
  19. Lee, B. W.; Lee, J. H.; Gal, S. W.; Moon, Y. H.; Park, K. H. Biosci. Biotechnol. Biochem. 2006, 70, 427. https://doi.org/10.1271/bbb.70.427

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