Quinic acid esters from Erycibe obtusifolia with antioxidant and tyrosinase inhibitory activities

Nat Prod Res. 2021 Sep;35(18):3026-3032. doi: 10.1080/14786419.2019.1684285. Epub 2019 Nov 4.

Abstract

AbstractA new quinic acid derivative, 3-O-syringoylquinic acid methyl ester (1), along with eight known quinic acid derivatives (2-9), three coumarins (10-12), one phenylpropanoid (13), three feruloyltyramine derivatives (14-16), one lignan (17) and two isoflavones (18-19) were isolated from an ethyl acetate-soluble fraction of the roots and stems of Erycibe obtusifolia. The structure was elucidated on the basis of spectroscopic methods such as 1D and 2D-NMR, including HR-ESI-MS spectrometry. All of these compounds were investigated for their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and inhibitory effects on mushroom tyrosinase. Compounds 2-9, quinic acid derivatives with caffeoyl moiety, showed significant DPPH radical scavenging activity. Moreover, compounds 2 and 5-10 showed weak mushroom tyrosinase inhibitory effects.

Keywords: 1,1-diphenyl-2-picrylhydrazyl (DPPH); Erycibe obtusifolia; convolvulaceae; quinic acid derivatives; tyrosinase.

MeSH terms

  • Antioxidants* / isolation & purification
  • Antioxidants* / pharmacology
  • Convolvulaceae / chemistry*
  • Esters / isolation & purification
  • Esters / pharmacology*
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Roots / chemistry
  • Plant Stems / chemistry
  • Quinic Acid / isolation & purification
  • Quinic Acid / pharmacology*

Substances

  • Antioxidants
  • Esters
  • Phytochemicals
  • Quinic Acid
  • Monophenol Monooxygenase