Five new secondary metabolites from the fungus Phomopsis asparagi

Fitoterapia. 2021 Apr:150:104840. doi: 10.1016/j.fitote.2021.104840. Epub 2021 Jan 31.

Abstract

Five new compounds, including a pair of diphenylcyclopentenone enantiomers (±)-phomopsisin A (1), a sesquiterpenoid 15-hydroxylithocarin A (2), a new diketopiperazine alkaloid prenylcyclotryprostatin A (3) and 7-hydroxy-cis-L(-)-3,6-dibenzyl-2,5-dioxopiperazine (6), along with five known compounds were isolated from the fungus Phomopsis asparagi. Their structures were elucidated on the basis of spectroscopic analyses (1D and 2D NMR), theoretical electronic circular dichroism (ECD) calculation, modified Mosher's method, and X-ray crystallography. The racemates of (±)-phomopsisin A showed inhibition on α-glucosidase with IC50 of 30.07 ± 0.75 μM (positive control acarbose, 121 ± 2.7 μM).

Keywords: A-glucosidase inhibition; Diketopiperazine; Diphenylcyclopentenone; Phomopsis asparagi.

MeSH terms

  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Molecular Docking Simulation
  • Molecular Structure
  • Phomopsis / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*

Substances

  • Alkaloids
  • Glycoside Hydrolase Inhibitors
  • Sesquiterpenes