title: Ascorbyl coumarates as multifunctional cosmeceutical agents that inhibit melanogenesis and enhance collagen synthesis.
abstract: L-Ascorbic acid (AA) and p-coumaric acid (p-CA) are naturally occurring antioxidants that are known to enhance collagen synthesis and inhibit melanin synthesis, respectively. The purpose of this study was to examine hybrid compounds between AA and p-CA as multifunctional cosmeceutical agents. Ascorbyl 3-p-coumarate (A-3-p-C), ascorbyl 2-p-coumarate (A-2-p-C), and their parent compounds were tested for their effects on cellular melanin synthesis and collagen synthesis. At 100 μM, A-3-p-C and A-2-p-C decreased melanin content of human dermal melanocytes stimulated by L-tyrosine, by 65 and 59%, respectively, compared to 11% inhibition of AA and 70% inhibition of p-CA. A-3-p-C and A-2-p-C were less effective than p-CA but more effective than AA at inhibiting tyrosinase activity. A-3-p-C and A-2-p-C were more effective than p-CA at inhibiting the autoxidation of L-3,4-dihydroxyphenylalanine. At 100-300 μM, A-3-p-C and A-2-p-C augmented collagen release from human dermal fibroblasts by 120-144% and 125-191%, respectively, compared to 126-133% increase of AA and 120-146% increase of p-CA. They increased procollagen type I C-peptide release (A-3-p-C, and A-2-p-C) like AA, and decreased matrix metalloproteinase 1 level (A-2-p-C) like p-CA, implicating that they might regulate collagen metabolism by multiple mechanisms. This study suggests that A-3-p-C and A-2-p-C could be used as multifunctional cosmeceutical agents for the attenuation of certain aspects of skin aging.
authors.affiliation: BK21 Plus KNU Biomedical Convergence Program, Department of Molecular Medicine, Cell and Matrix Research Institute, School of Medicine, Kyungpook National University, 101 Dongin-dong 2-ga, Jung-gu, Daegu, 700-422, Republic of Korea.
authors.forename: Jun Yup
authors.initials: JY
authors.lastname: Kwak
authors.forename: Soojin
authors.initials: S
authors.lastname: Park
authors.forename: Jin Kyung
authors.initials: JK
authors.lastname: Seok
authors.forename: Kwang-Hyeon
authors.initials: KH
authors.lastname: Liu
authors.forename: Yong Chool
authors.initials: YC
authors.lastname: Boo
mesh_terms: D000818:Animals; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002478:Cells, Cultured; D003094:Collagen / Q000235:genetics / Q000378:metabolism*; D000068937:Cosmeceuticals / Q000737:chemistry / Q000494:pharmacology*; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology*; D005347:Fibroblasts / Q000378:metabolism; D005786:Gene Expression Regulation / Q000187:drug effects; D006801:Humans; D008543:Melanins / Q000235:genetics / Q000378:metabolism*; D051379:Mice; D015394:Molecular Structure
chemical_list: D000068937:Cosmeceuticals; D003373:Coumaric Acids; D008543:Melanins; C000607983:ascorbyl 2-p-coumarate; C000607982:ascorbyl 3-p-coumarate; D003094:Collagen; D001205:Ascorbic Acid