Undescribed morroniside-like secoiridoid diglycosides with α-glucosidase inhibitory activity from Corni Fructus

Phytochemistry. 2020 Mar:171:112232. doi: 10.1016/j.phytochem.2019.112232. Epub 2020 Jan 3.

Abstract

Corni Fructus, also known as the fruit of Cornus officinalis Sieb. et Zucc., has long been used as a traditional Chinese medicine and is widely consumed as a nutritional food in the form of function drink and wine. Recently, Corni Fructus has attracted considerable interest because of its anti-diabetic effects. A systematic phytochemical investigation of Corni Fructus was performed to find anti-diabetic components, which led to the isolation of 10 unreported iridoid glycosides, cornusdiglycosides A-J (1-8, 9a/9b and 10a/10b). Their chemical structures were determined through spectroscopic analysis (ultraviolet [UV], infrared [IR], high-resolution electrospray ionisation mass spectroscopy [HRESIMS], one-dimensional [1D] and two-dimensional [2D] nuclear magnetic resonance [NMR]). Such morroniside-type diglycosides were first reported from natural sources, and all isolates were evaluated for α-glucosidase inhibitory activity. The results showed that all compounds (1-10) exhibited α-glucosidase (from Saccharomyces cerevisiae) inhibitory activities with IC50 values ranging from 78.9 ± 4.09 to 162.2 ± 9.17 μM, whereas acarbose, the positive control, displayed α-glucosidase inhibitory activity with IC50 value of 118.9 ± 7.89 μM.

Keywords: Corni Fructus; Diabetes mellitus; Iridoid glycosides; Morroniside-type; α-glucosidase inhibitor.

MeSH terms

  • Cornus / chemistry*
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Humans
  • Iridoid Glucosides / chemistry
  • Iridoid Glucosides / isolation & purification
  • Iridoid Glucosides / pharmacology*
  • Molecular Conformation
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology*
  • alpha-Glucosidases / metabolism*

Substances

  • Glycoside Hydrolase Inhibitors
  • Glycosides
  • Iridoid Glucosides
  • Phytochemicals
  • morroniside
  • alpha-Glucosidases