Dibenzo-α-pyrones: a new class of larvicidal metabolites against Aedes aegypti from the endophytic fungus Hyalodendriella sp. Ponipodef12

Pest Manag Sci. 2017 Jul;73(7):1478-1485. doi: 10.1002/ps.4481. Epub 2017 Jan 5.

Abstract

Background: In our search for new agrochemicals from endophytic fungi, the crude extract of the endophytic Hyalodendriella sp. Ponipodef12 associated with the hybrid 'Neva' of Populus deltoides Marsh × P. nigra L. was found to possess larvicidal activity against Aedes aegypti.

Results: Fractionation of the extract has led to the isolation of 11 dibenzo-α-pyrones (1-11), including three new congeners: hyalodendriols A-C (1-3). The structures of the new compounds were elucidated by comprehensive spectroscopic analyses, including the modified Mosher's method for the assignment of the absolute configuration. Compounds 2-7 showed potent larvicidal activities against the fourth-instar larvae of A. aegypti with IC50 values ranging from 7.21 to 120.81 µg mL-1 . Among them, penicilliumolide D (6) displayed the strongest activity (IC50 = 7.21 µg mL-1 ). A structure-larvicidal activity relationship was discussed. The possible mode of action of these compounds was assessed for their acetylcholinesterase inhibitory activities. In addition, hyalodendriol C (3) displayed antibacterial activity against Bacillus subtilis and Xanthomonas vesicatoria, and exhibited strong inhibition against the spore germination of Magnaporthe oryzae.

Conclusion: Our study revealed dibenzo-α-pyrones to be a new class of larvicidal metabolites against A. aegypti. © 2016 Society of Chemical Industry.

Keywords: Aedes aegypti; Hyalodendriella; antibacterial; antifungal; dibenzo-α-pyrone; larvicidal activity; mosquito.

MeSH terms

  • Aedes / drug effects*
  • Animals
  • Anti-Bacterial Agents / pharmacology
  • Ascomycota / chemistry*
  • Ascomycota / metabolism
  • Bacillus subtilis / drug effects
  • Biological Products / chemistry*
  • Biological Products / pharmacology*
  • Fungicides, Industrial / pharmacology
  • Insecticides*
  • Larva / drug effects
  • Magnaporthe / drug effects
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Pyrones / pharmacology
  • Structure-Activity Relationship
  • Xanthomonas vesicatoria / drug effects

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Fungicides, Industrial
  • Insecticides
  • Pyrones