Anti-inflammatory dihydroxanthones from a Diaporthe species
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Markus Rohr
- Anna Maria Kiefer
- Ulrich Kauhl
- Jonathan Gross
- Till Opatz
- Gerhard Erkel
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000725679700006&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1515/hsz-2021-0192
- eISSN
- 1437-4315
- Externe Identifier
- Clarivate Analytics Document Solution ID: XH8LP
- PubMed Identifier: 34333887
- ISSN
- 1431-6730
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- BIOLOGICAL CHEMISTRY
- Schlüsselwörter
- CXCL10
- dihydroxanthones
- inflammation
- inhibitor
- Paginierung
- 89 - 101
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Titel
- Anti-inflammatory dihydroxanthones from a <i>Diaporthe </i>species
- Sub types
- Article
- Ausgabe der Zeitschrift
- 403
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Abstract
- <jats:title>Abstract</jats:title> <jats:p>In a search for anti-inflammatory compounds from fungi inhibiting the promoter activity of the small chemokine CXCL10 (Interferon-inducible protein 10, IP-10) as a pro-inflammatory marker gene, the new dihydroxanthone methyl (1<jats:italic>R</jats:italic>, 2<jats:italic>R</jats:italic>)-1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,9-dihydro-1<jats:italic>H</jats:italic>-xanthene-1-carboxylate (<jats:bold>2</jats:bold>) and the previously described dihydroxanthone AGI-B4 (<jats:bold>1</jats:bold>) were isolated from fermentations of a <jats:italic>Diaporthe</jats:italic> species. The structures of the compounds were elucidated by a combination of one- and two-dimensional NMR spectroscopy, mass spectrometry, and calculations using density functional theory (DFT). Compounds <jats:bold>1</jats:bold> and <jats:bold>2</jats:bold> inhibited the LPS/IFNγ induced CXCL10 promoter activity in transiently transfected human MonoMac6 cells in a dose-dependent manner with IC<jats:sub>50</jats:sub> values of 4.1 µM (±0.2 µM) and 1.0 µM (±0.06 µM) respectively. Moreover, compounds <jats:bold>1</jats:bold> and <jats:bold>2</jats:bold> reduced mRNA levels and synthesis of pro-inflammatory mediators such as cytokines and chemokines in LPS/IFNγ stimulated MonoMac6 cells by interfering with the Stat1 and NFκB pathway.</jats:p>
- Autoren
- Markus Rohr
- Anna Maria Kiefer
- Ulrich Kauhl
- Jonathan Groß
- Till Opatz
- Gerhard Erkel
- DOI
- 10.1515/hsz-2021-0192
- eISSN
- 1437-4315
- ISSN
- 1431-6730
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- Biological Chemistry
- Sprache
- en
- Online publication date
- 2021
- Paginierung
- 89 - 101
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Herausgeber
- Walter de Gruyter GmbH
- Herausgeber URL
- http://dx.doi.org/10.1515/hsz-2021-0192
- Datum der Datenerfassung
- 2023
- Titel
- Anti-inflammatory dihydroxanthones from a <i>Diaporthe</i> species
- Ausgabe der Zeitschrift
- 403
Data source: Crossref
- Abstract
- In a search for anti-inflammatory compounds from fungi inhibiting the promoter activity of the small chemokine CXCL10 (Interferon-inducible protein 10, IP-10) as a pro-inflammatory marker gene, the new dihydroxanthone methyl (1<i>R</i>, 2<i>R</i>)-1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,9-dihydro-1<i>H</i>-xanthene-1-carboxylate (<b>2</b>) and the previously described dihydroxanthone AGI-B4 (<b>1</b>) were isolated from fermentations of a <i>Diaporthe</i> species. The structures of the compounds were elucidated by a combination of one- and two-dimensional NMR spectroscopy, mass spectrometry, and calculations using density functional theory (DFT). Compounds <b>1</b> and <b>2</b> inhibited the LPS/IFNγ induced CXCL10 promoter activity in transiently transfected human MonoMac6 cells in a dose-dependent manner with IC<sub>50</sub> values of 4.1 µM (±0.2 µM) and 1.0 µM (±0.06 µM) respectively. Moreover, compounds <b>1</b> and <b>2</b> reduced mRNA levels and synthesis of pro-inflammatory mediators such as cytokines and chemokines in LPS/IFNγ stimulated MonoMac6 cells by interfering with the Stat1 and NFκB pathway.
- Addresses
- Department of Molecular Biotechnology and Systems Biology, University of Kaiserslautern, Paul-Ehrlich-Strasse 23, D-67663 Kaiserslautern, Germany.
- Autoren
- Markus Rohr
- Anna Maria Kiefer
- Ulrich Kauhl
- Jonathan Groß
- Till Opatz
- Gerhard Erkel
- DOI
- 10.1515/hsz-2021-0192
- eISSN
- 1437-4315
- Externe Identifier
- PubMed Identifier: 34333887
- Funding acknowledgements
- Rhineland Palatinate Natural Products Research Center:
- Stiftung Rheinland-Pfalz für Innovation:
- Open access
- false
- ISSN
- 1431-6730
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- Biological chemistry
- Schlüsselwörter
- Humans
- Ascomycota
- NF-kappa B
- Anti-Inflammatory Agents
- Cytokines
- Chemokine CXCL10
- Interferon-gamma
- Sprache
- eng
- Medium
- Electronic-Print
- Online publication date
- 2021
- Paginierung
- 89 - 101
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum der Datenerfassung
- 2021
- Titel
- Anti-inflammatory dihydroxanthones from a <i>Diaporthe</i> species.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 403
Data source: Europe PubMed Central
- Abstract
- In a search for anti-inflammatory compounds from fungi inhibiting the promoter activity of the small chemokine CXCL10 (Interferon-inducible protein 10, IP-10) as a pro-inflammatory marker gene, the new dihydroxanthone methyl (1R, 2R)-1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate (2) and the previously described dihydroxanthone AGI-B4 (1) were isolated from fermentations of a Diaporthe species. The structures of the compounds were elucidated by a combination of one- and two-dimensional NMR spectroscopy, mass spectrometry, and calculations using density functional theory (DFT). Compounds 1 and 2 inhibited the LPS/IFNγ induced CXCL10 promoter activity in transiently transfected human MonoMac6 cells in a dose-dependent manner with IC50 values of 4.1 µM (±0.2 µM) and 1.0 µM (±0.06 µM) respectively. Moreover, compounds 1 and 2 reduced mRNA levels and synthesis of pro-inflammatory mediators such as cytokines and chemokines in LPS/IFNγ stimulated MonoMac6 cells by interfering with the Stat1 and NFκB pathway.
- Date of acceptance
- 2021
- Autoren
- Markus Rohr
- Anna Maria Kiefer
- Ulrich Kauhl
- Jonathan Groß
- Till Opatz
- Gerhard Erkel
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/34333887
- DOI
- 10.1515/hsz-2021-0192
- eISSN
- 1437-4315
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- Biol Chem
- Schlüsselwörter
- CXCL10
- dihydroxanthones
- inflammation
- inhibitor
- Anti-Inflammatory Agents
- Ascomycota
- Chemokine CXCL10
- Cytokines
- Humans
- Interferon-gamma
- NF-kappa B
- Sprache
- eng
- Country
- Germany
- Paginierung
- 89 - 101
- PII
- hsz-2021-0192
- Datum der Veröffentlichung
- 2022
- Status
- Published online
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Titel
- Anti-inflammatory dihydroxanthones from a Diaporthe species.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 403
Data source: PubMed
- Beziehungen:
- Property of