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article · Journal of Natural Products

Dactylfungins and Tetralones: Bioactive Metabolites from a Nematode-Associated <i>Laburnicola nematophila</i>

20244 citationsOpen accessAin Shams University

Abstract

A chemical investigation of <i>Laburnicola nematophila</i>, isolated from cysts of the plant parasitic nematode <i>Heterodera filipjevi</i>, affored three dactylfungin derivatives (<b>1</b>-<b>3</b>) and three tetralone congeners (<b>4</b>-<b>6</b>). Dactylfungin C (<b>1</b>), laburnicolin (<b>4</b>), and laburnicolenone (<b>5</b>) are previously undescribed natural products. Chemical structures of the isolated compounds were determined based on 1D and 2D NMR spectroscopic analyses together with HR-ESI-MS spectrometry and comparison with data reported in the literature. The relative configurations of compounds <b>1</b>, <b>2</b>, and <b>4</b>-<b>6</b> were determined based on their ROESY data and analysis of their coupling constants (<i>J</i> values). The absolute configurations of <b>4</b>-<b>6</b> were determined through the comparison of their measured and calculated TDDFT-ECD spectra. Compounds <b>1</b>-<b>3</b> were active against azole-resistant <i>Aspergillus fumigatus</i>.

Research topics

  • Chemical synthesis and alkaloids
  • Nematode management and characterization studies
  • Fungal Biology and Applications

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DOI: 10.1021/acs.jnatprod.4c00623

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