Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium Nostoc sp. CBT1153
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Ronja Kossack
- Steffen Breinlinger
- Nguyen Trang
- Julia Moschny
- Jan Straetener
- Anne Berscheid
- Heike Broetz-Oesterhelt
- Heike Enke
- Tanja Schirmeister
- Timo HJ Niedermeyer
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000517856600024&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.jnatprod.9b00885
- eISSN
- 1520-6025
- Externe Identifier
- Clarivate Analytics Document Solution ID: KR8HM
- PubMed Identifier: 31977209
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 2
- Zeitschrift
- JOURNAL OF NATURAL PRODUCTS
- Paginierung
- 392 - 400
- Datum der Veröffentlichung
- 2020
- Status
- Published
- Titel
- Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium <i>Nostoc</i> sp. CBT1153
- Sub types
- Article
- Ausgabe der Zeitschrift
- 83
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Ronja Kossack
- Steffen Breinlinger
- Trang Nguyen
- Julia Moschny
- Jan Straetener
- Anne Berscheid
- Heike Brötz-Oesterhelt
- Heike Enke
- Tanja Schirmeister
- Timo HJ Niedermeyer
- DOI
- 10.1021/acs.jnatprod.9b00885
- eISSN
- 1520-6025
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 2
- Zeitschrift
- Journal of Natural Products
- Sprache
- en
- Online publication date
- 2020
- Paginierung
- 392 - 400
- Datum der Veröffentlichung
- 2020
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.jnatprod.9b00885
- Datum der Datenerfassung
- 2023
- Titel
- Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium <i>Nostoc</i> sp. CBT1153
- Ausgabe der Zeitschrift
- 83
Data source: Crossref
- Abstract
- Cyanobacteria are an interesting source of biologically active natural products, especially chemically diverse and potent protease inhibitors. On our search for inhibitors of the trypanosomal cysteine protease rhodesain, we identified the homodimeric cyclopentenedione (CPD) nostotrebin 6 (<b>1</b>) and new related monomeric, dimeric, and higher oligomeric compounds as the active substances in the medium extract of <i>Nostoc</i> sp. CBT1153. The oligomeric compounds are composed of two core monomeric structures, a trisubstituted CPD or a trisubstituted unsaturated δ-lactone. Nostotrebin 6 thus far has been the only known cyanobacterial CPD. It has been found to be active in a broad variety of assays, indicating that it might be a pan-assay interference compound (PAIN). Thus, we compared the antibacterial and cytotoxic activities as well as the rhodesain inhibition of selected compounds. Because a compound with a δ-lactone instead of a CPD core structure was equally active as nostotrebin 6, the bioactivities of these compounds seem to be based on the phenolic substructures rather than the CPD moiety. While the dimers were roughly equally potent, the monomer displayed slightly weaker activity, suggesting that the compounds show unspecific activity depending upon the number of free phenolic hydroxy groups per molecule.
- Addresses
- Department of Pharmaceutical Biology/Pharmacognosy, Institute of Pharmacy , University of Halle-Wittenberg , 06120 Halle (Saale) , Germany.
- Autoren
- Ronja Kossack
- Steffen Breinlinger
- Trang Nguyen
- Julia Moschny
- Jan Straetener
- Anne Berscheid
- Heike Brötz-Oesterhelt
- Heike Enke
- Tanja Schirmeister
- Timo HJ Niedermeyer
- DOI
- 10.1021/acs.jnatprod.9b00885
- eISSN
- 1520-6025
- Externe Identifier
- PubMed Identifier: 31977209
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft: INST 271/388-1
- Deutsches Zentrum für Infektionsforschung:
- Bundesministerium für Bildung und Forschung: 16GW0115
- Open access
- false
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 2
- Zeitschrift
- Journal of natural products
- Schlüsselwörter
- Nostoc
- Cyclopentanes
- Lactones
- Phenols
- Anti-Bacterial Agents
- Culture Media
- Molecular Structure
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2020
- Paginierung
- 392 - 400
- Datum der Veröffentlichung
- 2020
- Status
- Published
- Datum der Datenerfassung
- 2020
- Titel
- Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium <i>Nostoc</i> sp. CBT1153.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 83
Data source: Europe PubMed Central
- Abstract
- Cyanobacteria are an interesting source of biologically active natural products, especially chemically diverse and potent protease inhibitors. On our search for inhibitors of the trypanosomal cysteine protease rhodesain, we identified the homodimeric cyclopentenedione (CPD) nostotrebin 6 (1) and new related monomeric, dimeric, and higher oligomeric compounds as the active substances in the medium extract of Nostoc sp. CBT1153. The oligomeric compounds are composed of two core monomeric structures, a trisubstituted CPD or a trisubstituted unsaturated δ-lactone. Nostotrebin 6 thus far has been the only known cyanobacterial CPD. It has been found to be active in a broad variety of assays, indicating that it might be a pan-assay interference compound (PAIN). Thus, we compared the antibacterial and cytotoxic activities as well as the rhodesain inhibition of selected compounds. Because a compound with a δ-lactone instead of a CPD core structure was equally active as nostotrebin 6, the bioactivities of these compounds seem to be based on the phenolic substructures rather than the CPD moiety. While the dimers were roughly equally potent, the monomer displayed slightly weaker activity, suggesting that the compounds show unspecific activity depending upon the number of free phenolic hydroxy groups per molecule.
- Autoren
- Ronja Kossack
- Steffen Breinlinger
- Trang Nguyen
- Julia Moschny
- Jan Straetener
- Anne Berscheid
- Heike Brötz-Oesterhelt
- Heike Enke
- Tanja Schirmeister
- Timo HJ Niedermeyer
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/31977209
- DOI
- 10.1021/acs.jnatprod.9b00885
- eISSN
- 1520-6025
- Ausgabe der Veröffentlichung
- 2
- Zeitschrift
- J Nat Prod
- Schlüsselwörter
- Anti-Bacterial Agents
- Culture Media
- Cyclopentanes
- Lactones
- Molecular Structure
- Nostoc
- Phenols
- Sprache
- eng
- Country
- United States
- Paginierung
- 392 - 400
- Datum der Veröffentlichung
- 2020
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2021
- Titel
- Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium Nostoc sp. CBT1153.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 83
Data source: PubMed
- Autoren
- Ronja Kossack
- Steffen Breinlinger
- Trang Nguyen
- Julia Moschny
- Jan Straetener
- Anne Berscheid
- Heike Brötz-Oesterhelt
- Heike Enke
- Tanja Schirmeister
- Timo HJ Niedermeyer
- Zeitschrift
- Journal of Natural Products
- Artikelnummer
- 2
- Paginierung
- 392 - 400
- Datum der Veröffentlichung
- 2020
- Herausgeber
- American Chemical Society and American Society of Pharmacognosy
- Datum der Datenerfassung
- 2021
- Titel
- Nostotrebin 6 Related Cyclopentenediones and δ-Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium Nostoc sp. CBT1153
- Sub types
- article
- Ausgabe der Zeitschrift
- 83
Data source: Manual
- Beziehungen:
- Property of