Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Gabin Thierry M Bitchagno
- Anja Schueffler
- Jonathan Gross
- Matthias Krumb
- Pierre Tane
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000821745600001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.jnatprod.2c00055
- eISSN
- 1520-6025
- Externe Identifier
- Clarivate Analytics Document Solution ID: 2S4EC
- PubMed Identifier: 35704432
- ISSN
- 0163-3864
- Zeitschrift
- JOURNAL OF NATURAL PRODUCTS
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Titel
- Sesquiterpene Lactones from <i>Vernonia tufnelliae</i>: Structural Characterization and Biological Evaluation
- Sub types
- Article
- Early Access
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Gabin Thierry M Bitchagno
- Anja Schüffler
- Jonathan Gross
- Matthias Krumb
- Pierre Tane
- Till Opatz
- DOI
- 10.1021/acs.jnatprod.2c00055
- eISSN
- 1520-6025
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Journal of Natural Products
- Sprache
- en
- Online publication date
- 2022
- Paginierung
- 1681 - 1690
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.jnatprod.2c00055
- Datum der Datenerfassung
- 2023
- Titel
- Sesquiterpene Lactones from <i>Vernonia tufnelliae</i>: Structural Characterization and Biological Evaluation
- Ausgabe der Zeitschrift
- 85
Datenquelle: Crossref
- Abstract
- The genus <i>Vernonia</i> is an extremely rich source of biologically active sesquiterpene lactones. The present report describes the spectroscopic structure elucidation and the cytotoxic and antimicrobial properties of five hitherto unknown germacranolide-like sesquiterpenoids and several known compounds. These new derivatives include a compound (<b>1</b>) with an unprecedented 10/5/5/6 tetracyclic framework featuring a hexahydro-1<i>H</i>,3<i>H</i>,7<i>H</i>-furo[3',4':3,4]furo[3,2-<i>c</i>]pyridin-1-one core resulting from an intramolecular cyclization cascade involving a methacrylate substituent and a low molecular weight amine. Furthermore, an elemane-germacranolide hybrid (<b>2</b>) and three amino acid-derived lactones (<b>3</b>-<b>5</b>) were characterized. A plausible biosynthetic pathway to the key alkaloid is presented, while shielding tensor calculations using DFT in combination with the DP4+ method were applied to elucidate its stereostructure. The newly characterized compounds along with ten known sesquiterpene lactones and phenolic compounds have been isolated from <i>Vernonia tufnelliae</i>, a medicinal plant from the western region of Cameroon. Their structures were consistent with spectroscopic and spectrometric data recorded. The present report is the first investigation of the chemistry and biology of <i>V. tufnelliae</i>.
- Addresses
- Department of Chemistry, Johannes Gutenberg-University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
- Autoren
- Gabin Thierry M Bitchagno
- Anja Schüffler
- Jonathan Gross
- Matthias Krumb
- Pierre Tane
- Till Opatz
- DOI
- 10.1021/acs.jnatprod.2c00055
- eISSN
- 1520-6025
- Externe Identifier
- PubMed Identifier: 35704432
- Funding acknowledgements
- Deutscher Akademischer Austauschdienst: 57381410
- Rhineland Palatinate Natural Producs Research Center:
- Open access
- false
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Journal of natural products
- Schlüsselwörter
- Vernonia
- Sesquiterpenes
- Lactones
- Antineoplastic Agents
- Molecular Structure
- Phytochemicals
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2022
- Paginierung
- 1681 - 1690
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum der Datenerfassung
- 2022
- Titel
- Sesquiterpene Lactones from <i>Vernonia tufnelliae</i>: Structural Characterization and Biological Evaluation.
- Sub types
- Research Support, Non-U.S. Gov't
- Review
- Journal Article
- Ausgabe der Zeitschrift
- 85
Datenquelle: Europe PubMed Central
- Abstract
- The genus Vernonia is an extremely rich source of biologically active sesquiterpene lactones. The present report describes the spectroscopic structure elucidation and the cytotoxic and antimicrobial properties of five hitherto unknown germacranolide-like sesquiterpenoids and several known compounds. These new derivatives include a compound (1) with an unprecedented 10/5/5/6 tetracyclic framework featuring a hexahydro-1H,3H,7H-furo[3',4':3,4]furo[3,2-c]pyridin-1-one core resulting from an intramolecular cyclization cascade involving a methacrylate substituent and a low molecular weight amine. Furthermore, an elemane-germacranolide hybrid (2) and three amino acid-derived lactones (3-5) were characterized. A plausible biosynthetic pathway to the key alkaloid is presented, while shielding tensor calculations using DFT in combination with the DP4+ method were applied to elucidate its stereostructure. The newly characterized compounds along with ten known sesquiterpene lactones and phenolic compounds have been isolated from Vernonia tufnelliae, a medicinal plant from the western region of Cameroon. Their structures were consistent with spectroscopic and spectrometric data recorded. The present report is the first investigation of the chemistry and biology of V. tufnelliae.
- Autoren
- Gabin Thierry M Bitchagno
- Anja Schüffler
- Jonathan Gross
- Matthias Krumb
- Pierre Tane
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/35704432
- DOI
- 10.1021/acs.jnatprod.2c00055
- eISSN
- 1520-6025
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- J Nat Prod
- Schlüsselwörter
- Antineoplastic Agents
- Lactones
- Molecular Structure
- Phytochemicals
- Sesquiterpenes
- Vernonia
- Sprache
- eng
- Country
- United States
- Paginierung
- 1681 - 1690
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Titel
- Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation.
- Sub types
- Journal Article
- Review
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 85
Datenquelle: PubMed
- Beziehungen:
- Eigentum von