Butenolide Derivatives with α-Glucosidase Inhibitions from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10

Mar Drugs. 2019 Jun 3;17(6):332. doi: 10.3390/md17060332.

Abstract

Three new butenolide derivatives, namely aspernolides N-P (1-3), together with six known analogues (4-9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1-3 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6-9 exhibited remarkable inhibitory effects against α-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 μM, respectively, being much more active than the positive control acarbose (190.2 μM).

Keywords: Aspergillus terreus YPGA10; butenolide derivatives; deep-sea-derived fungus; α-glucosidase.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Acetates / chemistry
  • Aquatic Organisms / chemistry*
  • Aspergillus / chemistry*
  • Circular Dichroism
  • Enzyme Activation / drug effects
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry

Substances

  • Acetates
  • Glycoside Hydrolase Inhibitors
  • ethyl acetate
  • butenolide
  • 4-Butyrolactone