Isolation of proanthocyanidins from red wine, and their inhibitory effects on melanin synthesis in vitro

Food Chem. 2018 May 15;248:61-69. doi: 10.1016/j.foodchem.2017.12.024. Epub 2017 Dec 8. Isolation of proanthocyanidins from red wine, and their inhibitory effects on melanin synthesis in vitro. Fujimaki T1, Mori S2, Horikawa M3, Fukui Y4. Author information 1 Suntory Global Innovation Center Ltd. Research Institute, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan. Electronic address: tf206510@nodai.ac.jp. 2 Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan. Electronic address: mori@sunbor.or.jp. 3 Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan. Electronic address: horikawa@sunbor.or.jp. 4 Suntory Global Innovation Center Ltd. Research Institute, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan. Electronic address: Yuko_Fukui@suntory.co.jp. Abstract The red wines made from Vitis vinifera were identified as skin-whitening effectors by using in vitro assays. OPCs in the wine were evaluated for tyrosinase activity and melanogenesis. Strong tyrosinase inhibitory activity was observed in fractions with high oligomeric proanthocyanidin (OPC) content. Among OPC dimers, a strong inhibitory effect on tyrosinase was observed with OPCs which contain (+)-catechin as an upper unit. Melanogenesis inhibitory effect was observed with OPCs which have (-)-epicatechin as upper units. Also, OPC trimers, upper and middle units joined with 4 → 8 bonds, showed stronger effects compared to trimers with 4 → 6 linkages. Interestingly, (-)-epicatechin-(4β → 8)-(-)-epicatechin 3-O-gallate, which is a unique component of grapes has potent inhibitory effects on both tyrosinase and melanogenesis. Our data provide structural information about such active compounds. These results suggest that red wines containing OPC, have high melanogenesis inhibitory effect and are supposed to have skin-whitening effect. KEYWORDS: Melanin synthesis; Oligomeric proanthocyanidin (OPC); Red wine; Skin-whitening effect; Vitis vinifera PMID: 29329871 DOI: 10.1016/j.foodchem.2017.12.024