Isolation of Secondary Metabolites from the Soil-Derived Fungus Clonostachys rosea YRS-06, a Biological Control Agent, and Evaluation of Antibacterial Activity

J Agric Food Chem. 2016 Mar 23;64(11):2298-306. doi: 10.1021/acs.jafc.6b00556. Epub 2016 Mar 14.

Abstract

The fungus Clonostachys rosea is widely distributed all over the world. The destructive force of this fungus, as a biological control agent, is very strong to lots of plant pathogenic fungi. As part of the ongoing search for antibiotics from fungi obtained from soil samples, the secondary metabolites of C. rosea YRS-06 were investigated. Through efficient bioassay-guided isolation, three new bisorbicillinoids possessing open-ended cage structures, tetrahydrotrichodimer ether (1) and dihydrotrichodimer ether A and B (2 and 3), and 12 known compounds were obtained. Their structures were determined via extensive NMR, HR-ESI-MS, and CD spectroscopic analyses and X-ray diffraction data. Compounds 1-3 are rare bisorbicillinoids with a γ-pyrone moiety. The biological properties of 1-15 were evaluated against six different Gram-positive and Gram-negative bacteria. Bisorbicillinoids, 2-5, and TMC-151 C and E, 14 and 15, showed potent antibacterial activity.

Keywords: Clonostachys rosea YRS-06; TMC-151; antibacterial activity; antifungal activity; dihydrotrichodimer ether; tetrahydrotrichodimer ether.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects
  • Biological Control Agents* / chemistry
  • Biological Control Agents* / isolation & purification
  • Bridged-Ring Compounds
  • Circular Dichroism
  • Hypocreales / chemistry
  • Hypocreales / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Soil
  • Soil Microbiology*
  • Spectrometry, Mass, Electrospray Ionization
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Biological Control Agents
  • Bridged-Ring Compounds
  • Soil