Ascorbyl coumarates as multifunctional cosmeceutical agents that inhibit melanogenesis and enhance collagen synthesis

Arch Dermatol Res. 2015 Sep;307(7):635-43. doi: 10.1007/s00403-015-1583-x. Epub 2015 Jun 16.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ascorbic Acid / analogs & derivatives*
  • Ascorbic Acid / chemistry
  • Ascorbic Acid / pharmacology
  • Cells, Cultured
  • Collagen / genetics
  • Collagen / metabolism*
  • Cosmeceuticals / chemistry
  • Cosmeceuticals / pharmacology*
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology*
  • Fibroblasts / metabolism
  • Gene Expression Regulation / drug effects
  • Humans
  • Melanins / genetics
  • Melanins / metabolism*
  • Mice
  • Molecular Structure

Substances

  • Cosmeceuticals
  • Coumaric Acids
  • Melanins
  • ascorbyl 2-p-coumarate
  • ascorbyl 3-p-coumarate
  • Collagen
  • Ascorbic Acid