Antioxidant and Chemosensitizing Effects of Flavonoids with Hydroxy and/or Methoxy Groups and Structure-Activity Relationship

Authors

  • Ju-Mi Jeong Research Center for Resistant Cells and Department of Pharmacology, Chosun University Medical School, Gwangju 501-759
  • Cheol-Hee Choi Dept of Pharmaoclogy, Chosun Univ Med Sch
  • Su-Kyeong Kang Department of Beauty Science, Gwangju Women’s University, Gwangju 506-713, South Korea
  • In-Hwa Lee Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production,Chosun University, Gwangju 501-759, South Korea
  • Ji-Yoon Lee Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production,Chosun University, Gwangju 501-759, South Korea
  • Hyuk Jung Chosun University Medical School

DOI:

https://doi.org/10.18433/J3KW2Z

Abstract

Purpose. Flavonoids have been used as antioxidant, chemopreventive and chemosensitizing agents. In this study, eleven flavonoids containing a variety of hydroxy (OH) and/or methoxy (OMe) groups were evaluated for their antioxidant, cytotoxic and chemosensitizing effects to create a structure-activity relationship (SAR). Methods. 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radical solution-based chemical assay and and 2',7'-dichlorofluorescin diacetate (DCFH-DA) cellular-based assay were used to compare the free radical scavenging activity on the same molar concentration basis using the AML-2/DX100 cells which are characterized by the down-regulated expression of catalase and resulting supersensitiviy to hydrogen peroxide. The chemosensitization and cytotoxicity were determined by the MTT assay in the presence or absence of an anticancer drug using the P-glycoprotein-overexpressing AML-2 subline AML-2/D100 cells. Results. The antioxidant activity of the flavonoid (3,5,7,3’,4’-OH) was higher than that of the flavonoid (5,7,3’,4’-OH). Flavonoids substituted with the various number of OMe decreased antioxidant activity. Flavonoids with 7-OH or 5,7-OH groups have the highest cytotoxicity, and flavonoids with 5,7-OMe group intermediate cytotoxicity. The IC50 values of flavonoid (5,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe, 4’-OMe), 0.4 M and 1.4 M. The IC50 values of flavonoid (5,6,7-OMe, 3’,4’-OMe) and flavonoid (5,6,7-OMe, 3’,4’,5’-OMe), 3.2 uM and 0.9 M, respectively, and those of flavonoid (5,6,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe,3’,4’,5’-OMe) were 0.9 M and 0.4 M, respectively. Conclusions. These results suggest that flavonoids with 3-OH group play a positive role in antioxidant activities, flavonoids with 5-OH and/or 7-OH groups show the higher cytotoxicity, and flavonoids with 3’-OMe and/or 5’-OMe groups plays positive but 6-OMe groups negative roles in the P-glycoprotein (Pgp) inhibition. It is believed that these SAR results can be taken into account for the development of flavonoids with high therapeutic index.

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Author Biographies

Ju-Mi Jeong, Research Center for Resistant Cells and Department of Pharmacology, Chosun University Medical School, Gwangju 501-759

Department of Pharmacology (graduate student)

Cheol-Hee Choi, Dept of Pharmaoclogy, Chosun Univ Med Sch

Deptment of pharmcology (professor)

Su-Kyeong Kang, Department of Beauty Science, Gwangju Women’s University, Gwangju 506-713, South Korea

Department of Beauty Science (Professor)

In-Hwa Lee, Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production,Chosun University, Gwangju 501-759, South Korea

Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production (Professor)

Ji-Yoon Lee, Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production,Chosun University, Gwangju 501-759, South Korea

Department of Environmental Engineering and BK21 Team for Bio Hydrogen Production (graduate student)

Published

2007-10-26

How to Cite

Jeong, J.-M., Choi, C.-H., Kang, S.-K., Lee, I.-H., Lee, J.-Y., & Jung, H. (2007). Antioxidant and Chemosensitizing Effects of Flavonoids with Hydroxy and/or Methoxy Groups and Structure-Activity Relationship. Journal of Pharmacy & Pharmaceutical Sciences, 10(4), 537–546. https://doi.org/10.18433/J3KW2Z

Issue

Section

Pharmaceutical Sciences; Review Articles