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New Phenylpropanoids from Sasa quelpaertensis Nakai with Tyrosinase Inhibition Activities

  • Sultana, Nasim (Analytical Research Division, Bangladesh Council of Scientific & ndustrial Research (BCSIR) Laboratories Dhaka) ;
  • Lee, Nam-Ho (Department of Chemistry, Cheju National University)
  • Published : 2009.08.20

Abstract

Bioactivity-guided fractionation led to the isolation of two new phenylpropanoids, 3-O-p-coumaroyl-1-(4-hydroxy- 3,5-dimethoxyphenyl)-1-propanone (1) and 3-O-p-coumaroyl-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-O-$\beta$-gulcopyranosylpropanol (2), together with three known compounds, N-p-coumaroylserotonin (3), N-feruloylserotonin (4) and p-coumaric acid (5) from the leaves of Sasa quelpaertensis Nakai. Their structures were elucidated by spectroscopic methods including 1D and 2D-NMR. Compared to arbutin (I$C_{50}$ 0.048 mM) as a control, compounds 3 and 4 exhibited stronger tyrosinase inhibition activities with an I$C_{50}$ values of 0.027 mM and 0.026 mM, respectively. Compounds 1 (I$C_{50}$ 0.055 mM) and 2 (I$C_{50}$ 0.053 mM) also showed strong activities.

Keywords

References

  1. Lee, Y. N.; Lee, K. S.; Shin, Y. H. Wild Plants of Jeju Island; Yeomiji Botanical Garden: Jeju, Korea, 2001; p 1-669
  2. Kim, J. M.; Ko, R. K.; Hyun, J. W.; Lee, N. H. Bull. Korean Chem. Soc. 2009, 30, 261 https://doi.org/10.5012/bkcs.2009.30.1.261
  3. Ko, R. K.; Lee, N. H. Bull. Korean Chem. Soc. 2008, 29, 2531 https://doi.org/10.5012/bkcs.2008.29.12.2531
  4. Sultana, N.; Lee, N. H. Phytotherapy Res. 2007, 21, 1171 https://doi.org/10.1002/ptr.2230
  5. An, S. M.; Lee, S. I.; Choi, S.-W.; Moon, S.-W.; Boo. Y. C. British J. Dematology 2008, 159, 292 https://doi.org/10.1111/j.1365-2133.2008.08653.x
  6. Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Biochimica et Biophysica Acta 1995, 247, 1
  7. Kim, Y.-J.; Uyama, H. CMLS, Cell. Mol. Life Sci. 2005, 62, 1707 https://doi.org/10.1007/s00018-005-5054-y
  8. Parvez, S.; Kang, M.; Chung, H.; Cho, C.; Hong, M.-C.; Shin, M.-K.; Bae, H. Phytotherapy Res. 2006, 20, 921 https://doi.org/10.1002/ptr.1954
  9. Watanabe, M. J. Agric. Food Chem. 1999, 47, 4500 https://doi.org/10.1021/jf990498s
  10. Sarker, S. D.; Savchenko, T.; Whiting, P.; Sik, V.; Dinan, L. N. Nat. Prod. Lett. 1997, 9, 189 https://doi.org/10.1080/10575639708048314
  11. Nakasone, Y.; Takara, K.; Wada, K.; Tanaka, J.; Yogi, S.; Nakatani, N. Biosci. Biotech. Biochem. 1996, 60, 1714 https://doi.org/10.1271/bbb.60.1714
  12. Pretch, B.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds. Tables of Spectral Data; Springer: New York, U. S. A., 2000; p 152
  13. Rho, J. S.; Han, J. Y.; Kim, J. H.; Hwang, J. K. Biol. Pharm. Bull. 2004, 27, 1976 https://doi.org/10.1248/bpb.27.1976
  14. Vanni, A.; Gastaldi, D.; Giunata. G. Annali di Chimica 1990, 80, 35

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