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Mitochondria-Targeted Vitamin E Protects Skin from UVB-Irradiation
김원석,김익연,김왕균,최주연,김두영,문성국,민형근,송민규,성종혁 한국응용약물학회 2016 Biomolecules & Therapeutics(구 응용약물학회지) Vol.24 No.3
Mitochondria-targeted vitamin E (MVE) is designed to accumulate within mitochondria and is applied to decrease mitochondrial oxidative damage. However, the protective effects of MVE in skin cells have not been identified. We investigated the protective effect of MVE against UVB in dermal fibroblasts and immortalized human keratinocyte cell line (HaCaT). In addition, we studied the wound-healing effect of MVE in animal models. We found that MVE increased the proliferation and survival of fibroblasts at low concentration (i.e., nM ranges). In addition, MVE increased collagen production and downregulated matrix metalloproteinase1. MVE also increased the proliferation and survival of HaCaT cells. UVB increased reactive oxygen species (ROS) production in fibroblasts and HaCaT cells, while MVE decreased ROS production at low concentration. In an animal experiment, MVE accelerated wound healing from laser-induced skin damage. These results collectively suggest that low dose MVE protects skin from UVB irradiation. Therefore, MVE can be developed as a cosmetic raw material.
Dileep Kumar Singh,김진우,성종혁,김익연 대한화학회 2018 Bulletin of the Korean Chemical Society Vol.39 No.2
Biological screening of the natural products from Dalbergia oliveri identified that (6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan and (3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone significantly increased the proliferation of dermal papilla cells and subcutaneous injection of these compounds induced the anagen of hair cycle in animal models. These interesting biological activities led us to design a practical synthetic route to these natural products for further pharmacological evaluation. Here we report the first total syntheses of naturally occurring pterocarpan ((6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan), isoflavan ((3R)-5′-methoxyvestitol), and isoflavanone ((3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone) in a racemic form. A mild ZnCl2-mediated [3 + 2] annulation method was utilized with chromenes and 2-methoxy-1,4-benzoquinone to construct a pterocarpan framework in a one-pot manner. O-methylation and reductive cleavage of the benzylic C─O bond afforded 5′-methoxyvestitol, which was transformed to isoflavanone, 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone, via a three-step sequence including DDQ-mediated benzylic oxidation.
김원석,김왕균,최나현,서원희,이진우,김대덕,김익연,성종혁 한국응용약물학회 2018 Biomolecules & Therapeutics(구 응용약물학회지) Vol.26 No.3
In a previous study, we have demonstrated that S-methylmethionine sulfonium (SMMS) confers wound-healing and photoprotective effects on the skin, suggesting that SMMS can be used as a cosmetic raw material. However, it has an unpleasant odor. Therefore, in the present study, we synthesized odor-free SMMS derivatives by eliminating dimethyl sulfide, which is the cause of the unpleasant odor and identified two derivatives that exhibited skin-protective effects: one derivative comprised (2S,4S)- and (2R,4S)-2-phenylthiazolidine-4-carboxylic acid and the other comprised (2S,4R)-, (2S,4S)-, (2R,4R)-, and (2R,4S)-2-phenyl-1,3- thiazinane-4-carboxylic acid. We performed in vitro proliferation assays using human dermal fibroblasts (hDFs) and an immortalized human keratinocyte cell line (HaCaT). The two SMMS derivatives were shown to increase hDF and HaCaT cell proliferation as well as improve their survival by protecting against ultraviolet exposure. Moreover, the derivatives regulated the expression of collagen type I and MMP mRNAs against ultraviolet exposure in hDFs, suggesting that these derivatives can be developed as cosmetic raw materials.