3,9-Dihydro-6-oxopterocarpen과 ferulic acid의 에스테르 반응을 통해 페룰산 유도체인 3,9-diferuloyl-6-oxopterocarpen (Tensolin-$F_{(R)}$ )를 합성하여 이를 함유한 주름개선 화장품을 개발하였다. Tensolin-$F_{(R)}$ 는 농도 의존적으로 DPPH와 superoxide radical에 대한 소거효과를 나타냈으며, 각각 0.8 mM에서 78%, 0.053 mM에서 92.9%로 DPPH와 superoxide radical을 소거하여 우수한 항산화 효과를 나타내었다. MMP-1 효소 활성 저해 효과도 0.16 mM에서 74%를 저해하였다. HDF에서 UVA에 의해 발현이 증가되는 MMP-1의 발현 저해 효과는 Tensolin-$F_{(R)}$ 0.8 uM에서 85.5%로 단백질 수준에서 모두 농도 의존적으로 발현 저해효과가 나타났다. Tensolin-$F_{(R)}$ 를 함유한 제품의 피부 주름개선 효과 평가 결과, Tensolin-$F_{(R)}$ 를 함유한 화장품을 약 8주 간 도포한 경우 유의한 주름개선 효과가 있음을 확인 할 수 있었다. 본 연구를 통하여 Tensolin-$F_{(R)}$ 는 항산화 효과와 MMP-1활성 저해 효과 및 UVA에 의한 MMP-1의 발현을 저해하는 효과가 나타났으며 새로운 주름개선 기능성 화장품으로 이용될 수 있을 것이다.
As a novel anti-wrinkle agent, 3,9-diferuloyl-6-oxopterocarpen (Tensolin-F$^{(R)}$) has been synthesized and its anti-aging effects have been investigated. In the present study, to investigate the relationship between aging and Tensolin-F$^{(R)}$, we examined its effect on scavenging activities of radicals and reactive oxygen species (ROS), in vitro inhibition activity of matrix-metalloproteinase (MMP) and expression of UVA-induced MMPs in human dermal fibroblasts (HDF). Tensolin-F$^{(R)}$ was found to show activities of scavenging radicals and ROS with the $IC_{50}$/ values of 0.2 mM and 0.95 mM against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and superoxide radicals, respectively, in the xanthine/xanthine oxidase system. Fluorometric assays for the proteolytic activities of MMP-l (collagenase) were performed using fluorescent collagen substrates. Tensolin-F$^{(R)}$ inhibited the activities of MMP-l in a dose-dependent manner and the $IC_{50}$/ values calculated from semi-log plots were 0.025 mM. Also, UVA induced MMP-1 expression was reduced 85％ by treatment with Tensolin-F$^{(R)}$ at 0.8 uM, which was reduced dose-dependent manner. The results of clinical study showed that 4.8 mM Tensolin-F$^{(R)}$ treated group reduced wrinkle significantly compared with placebo treated group (P 〈 0.05). Taken together, these result suggest that Tensolin-F$^{(R)}$ act as an anti-wrinkle agent by taking effects to antioxidation and reducing UVA-induced MMP-l production.-l production.
