Journal of the Korean Wood Science and Technology

The Korean Society of Wood Science & Technology (한국목재공학회)
권호 표지

Study on the Relationship between the Structure and Antioxidant Activities of Chalcones

  • Park, Youngki (Div. Biotechnology, Korea Forest Research Institute) ;
  • Lee, Hak-Ju (Div. Wood Chemistry & Microbiology, KFRI) ;
  • Lee, Wi Young (Div. Biotechnology, Korea Forest Research Institute) ;
  • Ahn, Jin-Kwon (Div. Biotechnology, Korea Forest Research Institute) ;
  • Hwang, Byung-Ho (Dept. of Wood Science & Engineering, Kangwon National University)
  • Received : 2005.06.25
  • Accepted : 2005.10.17
  • Published : 2006.03.25
Download PDF
⟨ Previous Next ⟩

Abstract

The purpose of this study is to examine the relationship between antioxidant activities and chemical structures of various chalcones. Twenty-two chalcones were assessed for their radical scavenging activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Of 22 compounds tested, the most active on DPPH radical was 2',4-dihydroxy-3,3'5-trimethoxy-5'-propylchacone (4) (72.6% at 100 ppm). It was followed by 3',4'-dihydroxy-3,4,5-trimethoxy-6'-methylchalcone (6), 2',4,4'-trihydroxy-3-methoxy-5-propenylchalcone (7) and 2',4,4'-trihydroxy-3,5-dimethoxychalcone (13). Based on the results, we concluded that the scavenging activity is controlled by the number and the position of the substitution in the compound.

Keywords

References

  1. Cotelle, N., J. L. Bernier, J. P. Cattean, J. C. Wallet, and E. M. Graydon. 1996. Antioxidant properties of hydroxyl-flavones. Free Radical Biology and Medicine. 20: 35 -43 https://doi.org/10.1016/0891-5849(95)02014-4
  2. Guo, Q., B. Zhao, S. Shen, J. Hou, J. Hu, and W. Xin. 1999. ESR study on the structure-antioxidant activity relationship of tea catechins and epimers. Biochimica et Biophysica Acta 1427: 13 -23 https://doi.org/10.1016/S0304-4165(98)00168-8
  3. Haraguchi, H., H. Isshikawa, K. Mizutani, Y. Tamura, and T. Kinoshita. 1998. Antioxidatie and superoxide scavenging activities of Retrochalcones in Glycyrrhiza injlata. Bioorganic & medicinal chemistry 6: 339 - 347 https://doi.org/10.1016/S0968-0896(97)10034-7
  4. Javanmardi, J. C, S. E. Locke, and J. M. Vivanco. 2003. Antioxidant activity and total phenolic content of Iranian Ocimum accessions. Food Chem. 83: 547 - 550 https://doi.org/10.1016/S0308-8146(03)00151-1
  5. Khatib, S., O. Nerya, R. Musa, M. Shmuel, S. Tamir, and J. Vaya. 2005. Chalcones as potent tyrosinase inhibitors: the importance of a 2,4substituted resorcinol moiety. Bioorganic & Medicinal Chemistry. 13: 433-441 https://doi.org/10.1016/j.bmc.2004.10.010
  6. Maxwell, S. J. 1995. Prospects for the use of antioxidant therapies. Drug. 49: 345 - 361 https://doi.org/10.2165/00003495-199549030-00003
  7. Modak, B., M. L. Contreras, F. Gonzalez-Nile, and R. Torres. 2005. Structure-antioxi-dant activity relationships of flavonoids isolated from the resinous exudate of Heliotropium sinuatum. Bioorganic & Medicinal Chemistry Letters 15: 309-312 https://doi.org/10.1016/j.bmcl.2004.10.081
  8. Nanjo, F., K. Goto, R. Seto, M. Suzuki, M. Sakai, and Y. Hara. 1996. Scavenging effects of tea catechins and their derivatives on 1,1,-diphenyl- 2-picrylhydrazyl radicals. Free radicalBiology & Medicine. 21: 895 - 902 https://doi.org/10.1016/0891-5849(96)00237-7
  9. Park, Y. K., D. H. Choi, H. J. Lee, S. S. Lee, W. Y. Lee, and J. K. Ahn. 2004. Structureantioxidant activity relationships of isoflavonoids. Journal of the Korean Wood Science and Technology. 32: 66 -70
  10. Pietta, P. G. 2000. Flavonoids as antioxidants. J. Nat. Prod. 63. 1035-1042 https://doi.org/10.1021/np9904509
  11. Rice-Evance, C. A., N. J. Miller, and G. Paganga. 1996. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology & Medicine. 20: 933 - 956 https://doi.org/10.1016/0891-5849(95)02227-9
  12. Satyanarayana, K. and M. N. A. Rao. 1993. Anti-inflammotory, analgesic and anti-pyretic activities of 3-(4-(3-(4-dimethylaminophenyl)-1-oxo- 2-propenyl)phenyl) sydnone. Indian Drugs. 30. 313-318
  13. Star, A. E. and T. J. Mabry. 1971. Flavonoid frond exudates from two Jamaican ferns, Pityrogramma tartare a and P. calomelanos. Phytochemistry. 10: 2812-2817
  14. Yayli, N., O. Ucuncu, E. Aydin, Y. Gok, A. Yasar, C. Baltaci, N. Yildirim, and M. Kucuk. 2005. Stereoselective photochemistry of heteroaryl chalcones in solution and the antioxidant activities. J. Photochem. Photobiol. 169: 229-234 https://doi.org/10.1016/j.jphotochem.2004.06.015
  15. Yu, J., L. Wang, R. L. Walzem, E. G. Miller, L M. Pike, and B. S. Patil. 2005. Antioxidant activity of Citrus limonoids, flavonoids and coumarins. J. Agric. Food Chem. 53: 2009-2014 https://doi.org/10.1021/jf0484632