Secondary Metabolites with Agricultural Antagonistic Potentials from Beauveria felina, a Marine-Derived Entomopathogenic Fungus

J Agric Food Chem. 2020 Dec 16;68(50):14824-14831. doi: 10.1021/acs.jafc.0c05696. Epub 2020 Dec 2.

Abstract

Soil-borne pathogens and weeds could synergistically affect vegetable growth and result in serious losses. The investigation of antagonistic metabolites from a marine-derived entomopathogenic fungus, Beauveria felina, obtained polyhydroxy steroid (1), tricyclic diterpenoid (2), isaridin (3), and destruxin cyclodepsipeptides (4-6). The structures and absolute configurations of new 1-3 were elucidated by extensive spectroscopic and X-ray crystallographic analyses, as well as electronic circular dichroism (ECD) calculations. Compounds 1 and 2 showed antifungal activities against carbendazim-resistant strains of Botrytis cinerea, with the minimum inhibitory concentration (MIC) values ranging from 16 to 32 μg/mL, which were significantly better than those of carbendazim (MIC = 256 μg/mL). Compound 5 exhibited significant antagonistic activity against the radicle growth of Amaranthus retroflexus seedlings, which was almost identical to that of the positive control (2,4-dichlorophenoxyacetic acid). The structure-activity differences of 4-6 suggested that the Cl atom in HMPA1 and β-Me in Pro2 should be the key factors to their herbicidal activities. Besides, compounds 3-6 showed moderate nematicidal activities against Meloidogyne incognita. These antagonistic effects of 1-6 were first reported and further revealed the synergistically antagonistic potential of B. felina to be developed into the biopesticide.

Keywords: Beauveria felina; agricultural antagonistic potential; antifungal activity; herbicidal activity; secondary metabolites.

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology*
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / metabolism
  • Antinematodal Agents / pharmacology*
  • Beauveria / chemistry*
  • Beauveria / isolation & purification
  • Beauveria / metabolism*
  • Botrytis / drug effects
  • Botrytis / growth & development
  • Crystallography, X-Ray
  • Depsipeptides / chemistry
  • Depsipeptides / metabolism
  • Depsipeptides / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Seawater / microbiology
  • Secondary Metabolism
  • Tylenchoidea / drug effects
  • Tylenchoidea / growth & development

Substances

  • Antifungal Agents
  • Antinematodal Agents
  • Depsipeptides

Supplementary concepts

  • Beauveria felina
  • Botrytis cinerea