title: Dereplication-guided isolation of depsides thielavins S-T and lecanorins D-F from the endophytic fungus Setophoma sp.
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 μg/mL against S. aureus.
authors.affiliation: Department of Chemistry, Universidade Federal de São Carlos, LaBioMMi, Rod. Washington Luís, Km 265, 13565-905 São Carlos, SP, Brazil. Electronic address: liviasoman@gmail.com.
authors.forename: Lívia S
authors.initials: LS
authors.lastname: de Medeiros
authors.affiliation: Department of Phytopathology, Universidade Federal de Lavras, 37200-000 Lavras, MG, Brazil.
authors.forename: Lucas M
authors.initials: LM
authors.lastname: Abreu
authors.affiliation: Department of Veterinary Disease Biology, Food Safety and Zoonoses Faculty of Health and Medical Sciences, University of Copenhagen, Stigbøjlen 4, DK-1870 Frederiksberg, Copenhagen, Denmark.
authors.forename: Anita
authors.initials: A
authors.lastname: Nielsen
authors.affiliation: Department of Veterinary Disease Biology, Food Safety and Zoonoses Faculty of Health and Medical Sciences, University of Copenhagen, Stigbøjlen 4, DK-1870 Frederiksberg, Copenhagen, Denmark.
authors.forename: Hanne
authors.initials: H
authors.lastname: Ingmer
authors.affiliation: Department of Systems Biology, Center for Microbial Biotechnology, Technical University of Denmark, Søltofts Plads Building 221, 2800 Kgs. Lyngby, Denmark.
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Larsen
authors.affiliation: Department of Systems Biology, Center for Microbial Biotechnology, Technical University of Denmark, Søltofts Plads Building 221, 2800 Kgs. Lyngby, Denmark.
authors.forename: Kristian F
authors.initials: KF
authors.lastname: Nielsen
authors.affiliation: Department of Chemistry, Universidade Federal de São Carlos, LaBioMMi, Rod. Washington Luís, Km 265, 13565-905 São Carlos, SP, Brazil.
authors.forename: Edson
authors.initials: E
authors.lastname: Rodrigues-Filho
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D053630:Depsides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005638:Fruit / Q000382:microbiology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D031647:Psidium / Q000382:microbiology*; D013211:Staphylococcus aureus / Q000187:drug effects*
chemical_list: D000900:Anti-Bacterial Agents; D053630:Depsides
keywords: Antibacterial activity; Depsides; Dereplication; Psidium guajava; Setophoma sp.