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Matrix metalloproteinases (MMPs) and free radicals such as reactive oxygen species (ROS) caused by ultraviolet (UV) exposure are known to play an important role in photoaging by mediating the degradation of extracellular matrix proteins. In this study, to develop a new anti-photoaging agent, we have synthesized 3,9-diferuloyl-6-oxopterocarpen (DFO), an antioxidant activity and inhibitory effect on type I matrix metalloproteinase (MMP-1) expression. In this study, we investigated the effects of DFO on antioxidantive effects, and inhibitory effects on activity and expression of UVA-induced MMPs in human dermal fibroblasts (HDF). DFO was found to show scavenging activities of radicals and ROS with the IC?? values of 0.2 mM against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and 0.05 mM against superoxide radicals in the xanthine/xanthineoxidase system, respectively. Fluorometric assays of the proteolytic activities of MMP-1 were performed using fluorescent collagen substrates. DFO inhibited the activities of MMP-1 in a dose-dependent manner, and the IC?? value calculated from semi-log plot was 0.025 mM. In addition, UVA induced MMP-1 expression was reduced by 85% following treatment with DFO at 0.8 iM in a dose-dependent manner. The results of clinical study showed that a cream containing 4.8 mM DFO reduced significantly wrinkle formation compared with placebo control. All these results suggest that DFO exert an anti-wrinkle activity acting as an antioxidant and reducing UVA-induced MMP-1 activity, without any significant toxicity and thus DFO could be a promising candidate for anti-aging cosmetic ingredient.

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