Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production

Chem Pharm Bull (Tokyo). 2011;59(4):502-7. doi: 10.1248/cpb.59.502.


Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β(1-42)-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / metabolism*
  • Amyloid beta-Peptides / antagonists & inhibitors
  • Amyloid beta-Peptides / metabolism
  • Cell Line, Tumor
  • Humans
  • Peptide Fragments / antagonists & inhibitors
  • Peptide Fragments / metabolism
  • Quinic Acid / analogs & derivatives*
  • Quinic Acid / chemical synthesis
  • Quinic Acid / chemistry
  • Quinic Acid / pharmacology
  • Structure-Activity Relationship


  • Amyloid beta-Peptides
  • Peptide Fragments
  • amyloid beta-protein (1-42)
  • caffeoylquinic acid
  • Quinic Acid
  • Adenosine Triphosphate