Structure activity relationship of antioxidative property of flavonoids and inhibitory effect on matrix metalloproteinase activity in UVA-irradiated human dermal fibroblast

  • Gwan-Sub Sim
  • Bum-Chun Lee
  • Ho Seung Cho
  • Jae Woong Lee
  • Jin-Hwa Kim
  • Dong-Hwan Lee
  • Jin-Hui Kim
  • Hyeong-Bae Pyo
  • Dong Cheul Moon
  • Ki-Wan Oh
  • Yeo Pyo Yun
  • Jin Tae Hong
Drug Design

DOI: 10.1007/BF02977608

Cite this article as:
Sim, GS., Lee, BC., Cho, H.S. et al. Arch Pharm Res (2007) 30: 290. doi:10.1007/BF02977608
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Abstract

Collagenase, a matrix metalloproteinases (MMPs), is a key regulator in the photoaging process of skin due to the reactive oxygen species generated after exposure to ultraviolet A (UVA). Flavonoid compounds have been demonstrated to possess antioxidant properties, and could be useful in the prevention of photoaging. In this study, to investigate the structure-activity relationship of flavonoid compounds on their antioxidant property and inhibitory effects against the MMP activity, the effects of several flavonoids; myricetin, quercetin, kaempferol, luteolin, apigenin and chrysin, on the reactive oxygen species scavengering activity and inhibitory effect against the MMP activity were examinedin vitro and in human dermal fibroblasts induced by UVA. The relative order of antioxidative efficacy, as determined using the 1, 1 -diphenyl-2-picrylhydrazyl (DPPH) method and the xanthine/xanthine oxidase system, was as follows; flavones: luteolin > apigenin > chrysin, flavonols: myricetin > quercetin > kaempferol, and correlated with the respective number of OH group on their B-ring. In good correlation with the antioxidant properties, the flavonoids inhibited the collagenase activities, in a dose-dependent manner, and the MMP expression. These results suggested the UVA induced antioxidative activity and inhibitory effects of flavonoids on the collagenase in human dermal fibroblasts depends on the number of OH group in the flavonoid structure, and those with a higher number of OH group may be more useful in the prevention of UV stressed skin aging.

Key words

Flavonoids Antioxidant MMP Structure activity relationship Human skin fibro-blast 

Copyright information

© The Pharmaceutical Society of Korea 2007

Authors and Affiliations

  • Gwan-Sub Sim
    • 2
  • Bum-Chun Lee
    • 2
  • Ho Seung Cho
    • 1
  • Jae Woong Lee
    • 1
  • Jin-Hwa Kim
    • 2
  • Dong-Hwan Lee
    • 2
  • Jin-Hui Kim
    • 2
  • Hyeong-Bae Pyo
    • 2
  • Dong Cheul Moon
    • 1
  • Ki-Wan Oh
    • 1
  • Yeo Pyo Yun
    • 1
  • Jin Tae Hong
    • 1
  1. 1.College of PharmacyChungbuk National UniversityCheungjuKorea
  2. 2.R & D CenterHanbul Cosmetics Co.ChungbukKorea

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