Ancistrobreveines A- D and related dehydrogenated naphthylisoquinoline alkaloids with antiproliferative activities against leukemia cells, from the West African liana Ancistrocladus abbreviatus
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Laurent Ake Assi
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000472461300007&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1039/c9ra03105g
- Externe Identifier
- Clarivate Analytics Document Solution ID: IE6BM
- PubMed Identifier: 35521375
- ISSN
- 2046-2069
- Ausgabe der Veröffentlichung
- 28
- Zeitschrift
- RSC ADVANCES
- Paginierung
- 15738 - 15748
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Titel
- Ancistrobreveines A- D and related dehydrogenated naphthylisoquinoline alkaloids with antiproliferative activities against leukemia cells, from the West African liana Ancistrocladus abbreviatus
- Sub types
- Article
- Ausgabe der Zeitschrift
- 9
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Abstract
- <p>Ancistrobreveines A–D belong to the rare group of naphthylisoquinoline alkaloids with a non-hydrogenated isoquinoline portion, some of them, like ancistrobreveine C, occurring in the plants only in a scalemic, yet nearly enantiopure form.</p>
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Laurent Aké Assi
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1039/c9ra03105g
- eISSN
- 2046-2069
- Ausgabe der Veröffentlichung
- 28
- Zeitschrift
- RSC Advances
- Sprache
- en
- Online publication date
- 2019
- Paginierung
- 15738 - 15748
- Status
- Published online
- Herausgeber
- Royal Society of Chemistry (RSC)
- Herausgeber URL
- http://dx.doi.org/10.1039/c9ra03105g
- Datum der Datenerfassung
- 2024
- Titel
- Ancistrobreveines A–D and related dehydrogenated naphthylisoquinoline alkaloids with antiproliferative activities against leukemia cells, from the West African liana<i>Ancistrocladus abbreviatus</i>
- Ausgabe der Zeitschrift
- 9
Data source: Crossref
- Abstract
- A unique series of six biaryl natural products displaying four different coupling types (5,1', 7,1', 7,8', and 5,8') were isolated from the roots of the West African liana <i>Ancistrocladus abbreviatus</i> (Ancistrocladaceae). Although at first sight structurally diverse, these secondary metabolites all have in common that they belong to the rare group of naphthylisoquinoline alkaloids with a fully dehydrogenated isoquinoline portion. Among the African <i>Ancistrocladus</i> species, <i>A. abbreviatus</i> is so far only the second one that was found to produce compounds with such a molecular entity. Here, we report on four new representatives, named ancistrobreveines A-D (12-14, and 6). They were identified along with the two known alkaloids 6-<i>O</i>-methylhamateine (4) and <i>ent</i>-dioncophylleine A (10). The two latter naphthylisoquinolines had so far only been detected in <i>Ancistrocladus</i> species from Southeast Asia. All of these fully dehydrogenated alkaloids have in common being optically active despite the absence of stereogenic centers, due to the presence of the rotationally hindered biaryl axis as the only element of chirality. Except for <i>ent</i>-dioncophylleine A (10), which lacks an oxygen function at C-6, the ancistrobreveines A-D (12-14, and 6) and 6-<i>O</i>-methylhamateine (4) are 6-oxygenated alkaloids, and are, thus, typical 'Ancistrocladaceae-type' compounds. Ancistrobreveine C (14), is the first - and so far only - example of a 7,8'-linked fully dehydrogenated naphthylisoquinoline discovered in nature that is configurationally stable at the biaryl axis. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR) and chiroptical (electronic circular dichroism) methods. Ancistrobreveine C (14) and 6-<i>O</i>-methylhamateine (4) exhibited strong antiproliferative activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000.
- Addresses
- Institute of Organic Chemistry, University of Würzburg Am Hubland D-97074 Würzburg Germany bringman@chemie.uni-wuerzburg.de.
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Laurent Aké Assi
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1039/c9ra03105g
- eISSN
- 2046-2069
- Externe Identifier
- PubMed Identifier: 35521375
- PubMed Central ID: PMC9064271
- Funding acknowledgements
- Deutscher Akademischer Austauschdienst, DAAD: to Shaimaa Fayez
- Deutsche Forschungsgemeinschaft: Br699/14-2
- Deutsche Forschungsgemeinschaft: SFB 630
- Open access
- true
- ISSN
- 2046-2069
- Ausgabe der Veröffentlichung
- 28
- Zeitschrift
- RSC advances
- Sprache
- eng
- Medium
- Electronic-eCollection
- Online publication date
- 2019
- Open access status
- Open Access
- Paginierung
- 15738 - 15748
- Datum der Veröffentlichung
- 2019
- Status
- Published
- Publisher licence
- CC BY-NC
- Datum der Datenerfassung
- 2022
- Titel
- Ancistrobreveines A-D and related dehydrogenated naphthylisoquinoline alkaloids with antiproliferative activities against leukemia cells, from the West African liana <i>Ancistrocladus abbreviatus</i>.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 9
Files
https://pubs.rsc.org/en/content/articlepdf/2019/ra/c9ra03105g https://europepmc.org/articles/PMC9064271?pdf=render
Data source: Europe PubMed Central
- Abstract
- A unique series of six biaryl natural products displaying four different coupling types (5,1', 7,1', 7,8', and 5,8') were isolated from the roots of the West African liana Ancistrocladus abbreviatus (Ancistrocladaceae). Although at first sight structurally diverse, these secondary metabolites all have in common that they belong to the rare group of naphthylisoquinoline alkaloids with a fully dehydrogenated isoquinoline portion. Among the African Ancistrocladus species, A. abbreviatus is so far only the second one that was found to produce compounds with such a molecular entity. Here, we report on four new representatives, named ancistrobreveines A-D (12-14, and 6). They were identified along with the two known alkaloids 6-O-methylhamateine (4) and ent-dioncophylleine A (10). The two latter naphthylisoquinolines had so far only been detected in Ancistrocladus species from Southeast Asia. All of these fully dehydrogenated alkaloids have in common being optically active despite the absence of stereogenic centers, due to the presence of the rotationally hindered biaryl axis as the only element of chirality. Except for ent-dioncophylleine A (10), which lacks an oxygen function at C-6, the ancistrobreveines A-D (12-14, and 6) and 6-O-methylhamateine (4) are 6-oxygenated alkaloids, and are, thus, typical 'Ancistrocladaceae-type' compounds. Ancistrobreveine C (14), is the first - and so far only - example of a 7,8'-linked fully dehydrogenated naphthylisoquinoline discovered in nature that is configurationally stable at the biaryl axis. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR) and chiroptical (electronic circular dichroism) methods. Ancistrobreveine C (14) and 6-O-methylhamateine (4) exhibited strong antiproliferative activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000.
- Date of acceptance
- 2019
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Laurent Aké Assi
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/35521375
- DOI
- 10.1039/c9ra03105g
- eISSN
- 2046-2069
- Externe Identifier
- PubMed Central ID: PMC9064271
- Ausgabe der Veröffentlichung
- 28
- Zeitschrift
- RSC Adv
- Sprache
- eng
- Country
- England
- Paginierung
- 15738 - 15748
- PII
- c9ra03105g
- Datum der Veröffentlichung
- 2019
- Status
- Published online
- Titel
- Ancistrobreveines A-D and related dehydrogenated naphthylisoquinoline alkaloids with antiproliferative activities against leukemia cells, from the West African liana Ancistrocladus abbreviatus.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 9
Data source: PubMed
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- Property of