α-Glucosidase Inhibitors from Preussia minimoides ‡

J Nat Prod. 2017 Mar 24;80(3):582-587. doi: 10.1021/acs.jnatprod.6b00574. Epub 2016 Sep 27.

Abstract

Extensive fractionation of an extract from the grain-based culture of the endophytic fungus Preussia minimoides led to the isolation of two new polyketides with novel skeletons, minimoidiones A (1) and B (2), along with the known compounds preussochromone C (3), corymbiferone (4), and 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (5). The structures of 1 and 2 were elucidated using 1D and 2D NMR data analysis, along with DFT calculations of 1H NMR chemical shifts. The absolute configuration of 1 was established by a single-crystal X-ray diffraction analysis and TDDFT-ECD calculations. Compounds 1-4 significantly inhibited yeast α-glucosidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Ascomycota / chemistry*
  • Crystallography, X-Ray
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification*
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / isolation & purification*
  • Hypoglycemic Agents / pharmacology*
  • Mexico
  • Molecular Conformation
  • Molecular Structure
  • Naphthoquinones
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / pharmacology*
  • alpha-Glucosidases / drug effects*

Substances

  • 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Naphthoquinones
  • Polyketides
  • minimoidione A
  • minimoidione B
  • alpha-Glucosidases