title: Structure activity relationship of antioxidative property of flavonoids and inhibitory effect on matrix metalloproteinase activity in UVA-irradiated human dermal fibroblast.
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 examined in 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.
authors.affiliation: R & D Center, Hanbul Cosmetics Co., Chungbuk 369-830, Korea.
authors.forename: Gwan-Sub
authors.initials: GS
authors.lastname: Sim
authors.forename: Bum-Chun
authors.initials: BC
authors.lastname: Lee
authors.forename: Ho Seung
authors.initials: HS
authors.lastname: Cho
authors.forename: Jae Woong
authors.initials: JW
authors.lastname: Lee
authors.forename: Jin-Hwa
authors.initials: JH
authors.lastname: Kim
authors.forename: Dong-Hwan
authors.initials: DH
authors.lastname: Lee
authors.forename: Jin-Hui
authors.initials: JH
authors.lastname: Kim
authors.forename: Hyeong-Bae
authors.initials: HB
authors.lastname: Pyo
authors.forename: Dong Cheul
authors.initials: DC
authors.lastname: Moon
authors.forename: Ki-Wan
authors.initials: KW
authors.lastname: Oh
authors.forename: Yeo Pyo
authors.initials: YP
authors.lastname: Yun
authors.forename: Jin Tae
authors.initials: JT
authors.lastname: Hong
mesh_terms: D000975:Antioxidants / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D005347:Fibroblasts / Q000201:enzymology / Q000528:radiation effects; D005419:Flavonoids / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000494:pharmacology; D006801:Humans; D020781:Matrix Metalloproteinase 1 / Q000235:genetics; D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors / Q000494:pharmacology*; D012867:Skin / Q000166:cytology / Q000201:enzymology / Q000528:radiation effects; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism; D014466:Ultraviolet Rays
chemical_list: D000975:Antioxidants; D005419:Flavonoids; D016166:Free Radical Scavengers; D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors; D013481:Superoxides; D020781:Matrix Metalloproteinase 1