Dereplication-guided isolation of depsides thielavins S-T and lecanorins D-F from the endophytic fungus Setophoma sp.

Livia S. de Medeiros, Lucas M. Abreu, Anita Nielsen, Hanne Ingmer, Thomas Ostenfeld Larsen, Kristian Fog Nielsen, Edson Rodrigues-Filho

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    Abstract

    Dereplication methodology using UHPLC-DAD-QTOFMS was applied during the metabolic profiling investigation of the endophyte Setophoma sp., a fungus isolated from symptomless guava fruits. The approach performed allowed a fast analysis of the microbial secondary metabolites. From this fungus, seven highly C-alkylated depsides were isolated and identified as polyketides thielavins S, T, U and V and lecanorins D, E and F. Their structures were elucidated through spectroscopic methods including NMR, HRMS and especially with assistance of HRMS/MS experiments. The compounds were tested for quorum sensing regulation activity in the virulence gene expression of Staphylococcus aureus, but no inhibitory effect was detected. Nevertheless, moderate antibacterial activity was encountered in three of tested depsides, particularly with thielavin T, whose MIC was 6.25 mu g/mL against S. aureus. (C) 2014 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    JournalPhytochemistry
    Volume111
    Pages (from-to)154-162
    Number of pages9
    ISSN0031-9422
    DOIs
    Publication statusPublished - 2015

    Keywords

    • Setophoma sp.
    • Psidium guajava
    • Dereplication
    • Depsides
    • Antibacterial activity

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