Dual effects of caffeoyl-amino acidyl-hydroxamic acid as an antioxidant and depigmenting agent

Bioorg Med Chem Lett. 2011 Sep 15;21(18):5155-8. doi: 10.1016/j.bmcl.2011.07.064. Epub 2011 Jul 26.

Abstract

Anti-aging and depigmentation have both been an important subject of study for skin disease and the cosmetic industry. Caffeic acid (CA) has shown synergistically enhanced antioxidant activity when conjugated with amino acids. Hydroxamic acid (NHOH) is a well-known metal chelator, potentially having both tyrosinase inhibitory activity and free radical scavenging activity. We prepared caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) and found that caffeoyl-prolyl-hydroxamic acid (CA-Pro-NHOH) contained excellent antioxidant activity and tyrosinase inhibitory activity by various bioassay systems. Also, CA-Pro-NHOH showed mild melanogenesis inhibitory activity in Mel-Ab cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology
  • Amino Acids / chemistry
  • Amino Acids / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Caffeic Acids / chemistry
  • Caffeic Acids / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology*
  • Lipid Peroxidation / drug effects
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monophenol Monooxygenase / metabolism
  • Skin Pigmentation / drug effects*
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Antioxidants
  • Caffeic Acids
  • Enzyme Inhibitors
  • Hydroxamic Acids
  • Monophenol Monooxygenase
  • caffeic acid