Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

J Chem Ecol. 2015 Jul;41(7):602-12. doi: 10.1007/s10886-015-0602-x. Epub 2015 Jul 2.

Abstract

Zinnia elegans Jacq. plants are infected by a fungus that causes dark red spots with necrosis on leaves, particularly in late spring to the middle of summer in the Mid-South of the United States. This fungal disease causes the leaves to wilt and eventually kills the plant. The fungus was isolated, cultured in potato dextrose broth, and identified as Nigrospora sphaerica by molecular techniques. Two major lactone metabolites (phomalactone and catenioblin A) were isolated from liquid culture of N. sphaerica isolated from Z. elegans. When injected into leaves of Z. elegans, phomalactone caused lesions similar to those of the fungus. The lesion sizes were proportional to the concentration of the phomalactone. Phomalactone, but not catenioblin A, was phytotoxic to Z. elegans and other plant species by inhibition of seedling growth and by causing electrolyte leakage from photosynthetic tissues of both Z. elegans leaves and cucumber cotyledons. This latter effect may be related to the wilting caused by the fungus in mature Z. elegans plants. Phomalactone was moderately fungicidal to Coletotrichum fragariae and two Phomopsis species, indicating that the compound may keep certain other fungi from encroaching into plant tissue that N. sphaerica has infected. Production of large amounts of phomalactone by N. sphaerica contributes to the pathogenic behavior of this fungus, and may have other ecological functions in the interaction of N. sphaerica with other fungi. This is the first report of isolation of catenioblin A from a plant pathogenic fungus. The function of catenioblin A is unclear, as it was neither significantly phyto- nor fungitoxic.

MeSH terms

  • Ascomycota / chemistry
  • Ascomycota / isolation & purification
  • Ascomycota / metabolism*
  • Asteraceae / growth & development
  • Asteraceae / microbiology*
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / metabolism
  • Plant Diseases / microbiology*
  • Plant Leaves / growth & development
  • Plant Leaves / microbiology*
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Pyrones / metabolism*

Substances

  • 5,6-dihydro-5-hydroxy-6-prop-2-enyl-2H-pyran-2-one
  • Lactones
  • Pyrones