Bioactive phenylpropanoid derivatives from the fruits of Lycium ruthenicum Murr

Bioorg Chem. 2021 Nov:116:105307. doi: 10.1016/j.bioorg.2021.105307. Epub 2021 Aug 30.

Abstract

Eight new (1-7 and 15) and 18 known (8-14 and 16-26) phenylpropanoid derivatives were isolated from the fruits of Lycium ruthenicum Murr. (black wolfberry). Their structures were determined by comprehensive spectroscopic analyses, chemical methods, and comparisons of spectroscopic data. Four known compounds (16, 17, 24, and 26) were firstly isolated from the genus Lycium. Interestingly, compounds 1/2 and 4/5 were isolated as two pairs of inseparable anomers owing to the tautomerism of the free hemiacetal at C-1'' in solution. The antioxidant, α-glucosidase inhibitory, and acetylcholinesterase (AChE) inhibitory activities of compounds 1-26 were evaluated. Some compounds possessed DPPH radical scavenging activity, and all compounds (1-26) exhibited different levels of oxygen radical absorbance capacity (ORAC). One compound displayed α-glucosidase inhibitory activity with potency close to that of the positive control (acarbose).

Keywords: Antioxidant activity; Black wolfberry; Inseparable anomers; Lycium ruthenicum Murr.; Phenylpropanoid derivatives; α-Glucosidase inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / antagonists & inhibitors
  • Cholinesterase Inhibitors / chemical synthesis
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Fruit / chemistry*
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Lycium / chemistry*
  • Molecular Structure
  • Picrates / antagonists & inhibitors
  • Propionates / chemical synthesis
  • Propionates / chemistry
  • Propionates / pharmacology*
  • Structure-Activity Relationship
  • alpha-Glucosidases / metabolism

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Cholinesterase Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Picrates
  • Propionates
  • 1,1-diphenyl-2-picrylhydrazyl
  • Acetylcholinesterase
  • alpha-Glucosidases