2. Academic Validation
  3. Omnipolyphilins A and B: Chlorinated Cyclotetrapeptides and Naphtho-α-pyranones from the Plant Nematode-Derived Fungus Polyphilus sieberi

Omnipolyphilins A and B: Chlorinated Cyclotetrapeptides and Naphtho-α-pyranones from the Plant Nematode-Derived Fungus Polyphilus sieberi

  • J Agric Food Chem. 2024 Apr 3;72(13):6998-7009. doi: 10.1021/acs.jafc.4c00572.
Jan-Peer Wennrich 1 2,  Sherif S Ebada 1 3,  Ellen Sepanian 1,  Caren Holzenkamp 1 2,  Syeda J Khalid 1 2,  Hedda Schrey 1 2,  Wolfgang Maier 4,  Attila Mándi 5,  Tibor Kurtán 5,  Samad Ashrafi 4 6,  Marc Stadler 1 2
Affiliations

Affiliations

  • 1 Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI) and German Centre for Infection Research (DZIF), Inhoffenstraße 7, 38124 Braunschweig, Germany.
  • 2 Institute of Microbiology, Technische Universität Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany.
  • 3 Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, 11566 Cairo, Egypt.
  • 4 Institute for Epidemiology and Pathogen Diagonstics, Julius Kühn Institut (JKI) - Federal Research Center for Cultivated Plants, Messeweg 11-12, 38104 Braunschweig, Germany.
  • 5 Department of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, Hungary.
  • 6 Institute for Crop and Soil Science, Julius Kühn Institute (JKI) - Federal Research Centre for Cultivated Plants, Bundesallee 58, 38116 Braunschweig, Germany.
PMID: 38507729 DOI: 10.1021/acs.jafc.4c00572
Abstract

Chemical exploration for two isolates of the recently described ascomycete species Polyphilus sieberi, derived from the eggs of the plant parasitic nematode Heterodera filipjevi, afforded the identification of many compounds that belong to various metabolite families: two previously undescribed chlorinated cyclotetrapeptides, omnipolyphilins A (1) and B (2), one new pyranonaphthoquinone, ventiloquinone P (3), a 6,6'-binaphto-α-pyranone dimer, talaroderxine D (4) in addition to nine known metabolites (5-13) were isolated from this biocontrol candidate. All isolated compounds were characterized by comprehensive 1D, 2D NMR, and HR-ESI-MS analyses. The absolute configurations of the cyclotetrapeptides were determined by a combination of advanced Marfey's method, ROE correlation aided by conformational analysis, and TDDFT-ECD calculations, while ECD calculations, Mosher's method, and experimental ECD spectra were used for ventiloquinone P (3) and talaroderxine D (4). Among the isolated compounds, talaroderxine D (4) showed potent antimicrobial activities against Bacillus subtilis and Staphylococcus aureus with MIC values of 2.1 and 8.3 μg mL-1, respectively. Additionally, promising inhibitory effects on talaroderxine D (4) against the formation of S. aureus biofilms were observed up to a concentration of 0.25 μg mL-1. Moreover, ophiocordylongiiside A (10) showed activity against the free-living nematode Caenorhabditis elegans.

Keywords

antimicrobial; cyclotetrapeptides; helotiales; naphthopyranones; nematicidal.

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