Bialternacins A-F, Aromatic Polyketide Dimers from an Endophytic Alternaria sp

J Nat Prod. 2019 Apr 26;82(4):792-797. doi: 10.1021/acs.jnatprod.8b00705. Epub 2019 Feb 22.

Abstract

Six novel aromatic polyketide dimers, bialternacins A-F (1-6), were isolated from a plant endophytic Alternaria sp. The structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism analysis. Compounds 1, 2, 5, and 6 were characterized as four pairs of racemic mixtures. Compound (+)-5 was demonstrated to show acetylcholinesterase inhibitory activity with an IC50 value of 15.5 μM. A putative biosynthetic pathway for these compounds was proposed.

MeSH terms

  • Acetylcholinesterase / drug effects
  • Alternaria / chemistry*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology
  • Crystallography, X-Ray
  • Dimerization
  • Molecular Structure
  • Plant Leaves / chemistry
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / pharmacology
  • Spectrum Analysis / methods

Substances

  • Cholinesterase Inhibitors
  • Polyketides
  • Acetylcholinesterase