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

Lívia S. de Medeiros; Lucas M. Abreu; Anita Nielsen; Hanne Ingmer; Thomas O. Larsen; Kristian F. Nielsen; Edson Rodrigues-Filho

doi:10.1016/j.phytochem.2014.12.020

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

Lívia S. de Medeiros, Lucas M. Abreu, Anita Nielsen, Hanne Ingmer, Thomas O. Larsen, Kristian F. Nielsen, Edson Rodrigues-Filho

Food Safety and Zoonoses

8 Citations (Scopus)

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 6.25μg/mL against S. aureus.

Original language	English
Journal	Phytochemistry
Volume	111
Pages (from-to)	154-162
Number of pages	9
ISSN	0031-9422
DOIs	https://doi.org/10.1016/j.phytochem.2014.12.020
Publication status	Published - Mar 2015

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10.1016/j.phytochem.2014.12.020

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@article{cab6dc8549f641f5a9b4974b5b3530a5,

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 6.25μg/mL against S. aureus.",

author = "{de Medeiros}, {L{\'i}via S.} and Abreu, {Lucas M.} and Anita Nielsen and Hanne Ingmer and Larsen, {Thomas O.} and Nielsen, {Kristian F.} and Edson Rodrigues-Filho",

year = "2015",

month = mar,

doi = "10.1016/j.phytochem.2014.12.020",

language = "English",

volume = "111",

pages = "154--162",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Pergamon Press",

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TY - JOUR

T1 - Dereplication-guided isolation of depsides thielavins S-T and lecanorins D-F from the endophytic fungus Setophoma sp.

AU - de Medeiros, Lívia S.

AU - Abreu, Lucas M.

AU - Nielsen, Anita

AU - Ingmer, Hanne

AU - Larsen, Thomas O.

AU - Nielsen, Kristian F.

AU - Rodrigues-Filho, Edson

PY - 2015/3

Y1 - 2015/3

N2 - 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 6.25μg/mL against S. aureus.

AB - 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 6.25μg/mL against S. aureus.

U2 - 10.1016/j.phytochem.2014.12.020

DO - 10.1016/j.phytochem.2014.12.020

M3 - Journal article

C2 - 25586883

SN - 0031-9422

VL - 111

SP - 154

EP - 162

JO - Phytochemistry

JF - Phytochemistry

ER -

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

Abstract

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