Antifungal Biphenyl Derivatives from Sorbus pohuashanensis Leaves Infected by Alternaria tenuissi and Their Effect against Crop Pathogens

Chem Biodivers. 2021 May;18(5):e2100079. doi: 10.1002/cbdv.202100079. Epub 2021 Apr 6.

Abstract

Eight natural biphenyl-type phytoalexins exhibiting antifungal effect were isolated from the leaves of Sorbus pohuashanensis, which invaded by Alternaria tenuissi, and their growth inhibition rate towards A. tenuissi were 50.3 %, 54.0 %, 66.4 %, 58.8 %, 48.5 %, 51.0 %, 33.3 %, and 37.0 %, respectively. In vivo activity assay verified the protective effect of these natural biphenyls on tobacco leaves. The observation of mycelial morphology revealed that these compounds possessed adverse effects on mycelial growth of A. tenuissi. Subsequently, the most potent active compounds, 3',4',5'-trimethoxy[1,1'-biphenyl]-4-ol (3) and 3,4,4',5-tetramethoxy-1,1'-biphenyl (4), were conducted to the further antifungal evaluation and showed significant activity against the other four crop pathogens, Fusarium graminearum, Helminthosporium maydis, Sclerotinia sclerotiorum, and Exserohilum turcicum. Further, the structure-activity relationships and biosynthesis of these compounds were speculated in this work.

Keywords: antifungal activity; chemical defense; crop pathogens; leaves; phytoalexins.

MeSH terms

  • Alternaria / drug effects*
  • Alternaria / growth & development
  • Alternaria / pathogenicity
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Ascomycota / drug effects
  • Ascomycota / pathogenicity
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / isolation & purification
  • Biphenyl Compounds / pharmacology*
  • Bipolaris / drug effects
  • Bipolaris / pathogenicity
  • Fusarium / drug effects
  • Fusarium / pathogenicity
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Plant Extracts
  • Plant Leaves / chemistry
  • Sorbus / chemistry*

Substances

  • Antifungal Agents
  • Biphenyl Compounds
  • Plant Extracts
  • diphenyl

Supplementary concepts

  • Bipolaris maydis
  • Exserohilum turcicum
  • Fusarium graminearum
  • Sclerotinia sclerotiorum