Isolation of Phytotoxic Phenols and Characterization of a New 5-Hydroxymethyl-2-isopropoxyphenol from Dothiorella vidmadera, a Causal Agent of Grapevine Trunk Disease

J Agric Food Chem. 2018 Feb 28;66(8):1760-1764. doi: 10.1021/acs.jafc.7b05248. Epub 2018 Feb 16.

Abstract

Polyphenols were characterized from Dothiorella vidmadera (DAR78993), which was isolated from a grapevine in Australia. In total, six polyphenols were isolated including a new polyphenol characterized by a spectroscopic method (essentially NMR and HR ESIMS) as 5-hydroxymethyl-2-isopropoxyphenol. Tyrosol, benzene-1,2,4-triol, resorcinol, 3-(hydroxymethyl)phenol, and protocatechuic alcohol, the latter being the main metabolite, were also isolated. Although these are already known as naturally occurring compounds in microorganisms and plants, this is the first time they have been isolated from fungal organisms involved in grapevine trunk disease. When assayed on tomato seedlings, all the compounds show similar phytotoxic effects. However, when assayed on grapevine leaves (Vitis vinifera cv Shiraz), resorcinol was the most toxic compound, followed by protocatechuic alcohol and 5-hydroxymethyl-2-isopropoxyphenol.

Keywords: Botryosphaeria dieback; Dothiorella vidmadera; grapevine; phytotoxins; protocatechuic alcohol isopropyl ether.

MeSH terms

  • Ascomycota / chemistry*
  • Ascomycota / metabolism
  • Molecular Structure
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / isolation & purification
  • Phenyl Ethers / metabolism
  • Phenyl Ethers / toxicity
  • Plant Diseases / microbiology*
  • Polyphenols / chemistry
  • Polyphenols / isolation & purification
  • Polyphenols / metabolism
  • Polyphenols / toxicity*
  • Solanum lycopersicum / drug effects
  • Vitis / microbiology*

Substances

  • Phenyl Ethers
  • Polyphenols
  • 2-isopropoxyphenol