New Fusaric Acid Derivatives from the Endophytic Fungus Fusarium oxysporum and Their Phytotoxicity to Barley Leaves

J Agric Food Chem. 2016 Apr 27;64(16):3127-32. doi: 10.1021/acs.jafc.6b00219. Epub 2016 Apr 13.

Abstract

Chemical investigation of the endophytic fungus Fusarium oxysporum isolated from fruits of Drepanocarpus lunatus afforded eight new fusaric acid derivatives, fusaricates A-G, 1-7, and 10-hydroxy-11-chlorofusaric acid, 8, along with four known compounds. Their structures were elucidated by one- and two-dimensional NMR as well as MS data and by comparison with the literature. The absolute configurations of fusaricates C-E, 3-5, were determined using chiral GC-MS. Fusaricates A-G, 1-7, represent the first examples of fusaric acid linked to a polyalcohol moiety via an ester bond. All isolated fusaric acid derivatives 1-8 showed significant phytotoxicity to leaves of barley.

Keywords: Fusarium oxysporum; fusaricates A−G; phytotoxicity; structural elucidation.

MeSH terms

  • Fusaric Acid / toxicity*
  • Fusarium / chemistry*
  • Hordeum / microbiology*
  • Plant Diseases / microbiology*
  • Plant Leaves / drug effects*
  • Plant Leaves / microbiology
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Fusaric Acid