Structure activity relationship of antioxidative property of flavonoids and inhibitory effect on matrix metalloproteinase activity in UVA-irradiated human dermal fibroblast.
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.
Sim
Gwan-Sub
GS
R & D Center, Hanbul Cosmetics Co., Chungbuk 369-830, Korea.
Lee
Bum-Chun
BC
Cho
Ho Seung
HS
Lee
Jae Woong
JW
Kim
Jin-Hwa
JH
Lee
Dong-Hwan
DH
Kim
Jin-Hui
JH
Pyo
Hyeong-Bae
HB
Moon
Dong Cheul
DC
Oh
Ki-Wan
KW
Yun
Yeo Pyo
YP
Hong
Jin Tae
JT
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
D000975:Antioxidants; D005419:Flavonoids; D016166:Free Radical Scavengers; D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors; D013481:Superoxides; D020781:Matrix Metalloproteinase 1