Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Virima Mudogo
- 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:000443663800017&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.fitote.2018.06.009
- eISSN
- 1873-6971
- Externe Identifier
- Clarivate Analytics Document Solution ID: GS4YM
- PubMed Identifier: 29936193
- ISSN
- 0367-326X
- Zeitschrift
- FITOTERAPIA
- Schlüsselwörter
- Ancistrocladus likoko
- Ancistrocladaceae
- Naphthylisoquinoline alkaloids
- Ancistrolikokines
- Antileukemic agents
- Paginierung
- 114 - 125
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Titel
- Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana <i>Ancistrocladus</i> <i>likoko</i> and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells
- Sub types
- Article
- Ausgabe der Zeitschrift
- 129
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Virima Mudogo
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1016/j.fitote.2018.06.009
- ISSN
- 0367-326X
- Zeitschrift
- Fitoterapia
- Sprache
- en
- Paginierung
- 114 - 125
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.fitote.2018.06.009
- Datum der Datenerfassung
- 2020
- Titel
- Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells
- Ausgabe der Zeitschrift
- 129
Data source: Crossref
- Abstract
- The Congolese liana Ancistrocladus likoko (Ancistrocladaceae) produces naphthylisoquinoline alkaloids that are, chemotaxonomically remarkable, all based on the same coupling type, with the biaryl axis located between C-5 and C-8'. About 20 alkaloids, belonging to the subclass of 5,8'-linked naphthylisoquinolines, have so far been discovered in this plant species. Here, we report on the isolation and structure elucidation of six further such 5,8'-coupled monomeric alkaloids, named ancistrolikokines I (9), C<sub>3</sub> (10), F<sub>2</sub> (11), J (12), J<sub>2</sub> (13), and J<sub>3</sub> (14). They were identified in the twigs of A. likoko, along with the two new atropo-diastereomeric dimers michellamines A<sub>8</sub> (15a) and B<sub>8</sub> (15b) and the naphthalene-devoid dihydroisoquinoline ent-ealaine D (19). The latter had previously only been known from total synthesis and has now been identified for the first time as an authentic natural product. Three of the new alkaloids, 12-14, are the only fully dehydrogenated naphthylisoquinolines with a 5,8'-biaryl linkage, apart from one single known other example previously likewise found in A. likoko. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR), chemical (oxidative degradation), and chiroptical (electronic circular dichroism) methods. The new ancistrolikokines exhibited moderate to strong cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and against cells of their multidrug-resistant subline, CEM/ADR5000. A first structure-activity relationship (SAR) study on a small library of 5,8'-coupled naphthylisoquinolines from the twigs of A. likoko suggests that the oxygenation patterns in the isoquinoline portion at C-6 and C-8 play a crucial role for the antileukemic activities within this group of alkaloids.
- Addresses
- Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Virima Mudogo
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1016/j.fitote.2018.06.009
- eISSN
- 1873-6971
- Externe Identifier
- PubMed Identifier: 29936193
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft:
- German Academic Exchange Service:
- Deutscher Akademischer Austauschdienst:
- Open access
- false
- ISSN
- 0367-326X
- Zeitschrift
- Fitoterapia
- Schlüsselwörter
- Cell Line, Tumor
- Humans
- Alkaloids
- Antineoplastic Agents, Phytogenic
- Drug Resistance, Multiple
- Molecular Structure
- Drug Resistance, Neoplasm
- Caryophyllales
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2018
- Paginierung
- 114 - 125
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum der Datenerfassung
- 2018
- Titel
- Ancistrolikokine I and further 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 129
Data source: Europe PubMed Central
- Abstract
- The Congolese liana Ancistrocladus likoko (Ancistrocladaceae) produces naphthylisoquinoline alkaloids that are, chemotaxonomically remarkable, all based on the same coupling type, with the biaryl axis located between C-5 and C-8'. About 20 alkaloids, belonging to the subclass of 5,8'-linked naphthylisoquinolines, have so far been discovered in this plant species. Here, we report on the isolation and structure elucidation of six further such 5,8'-coupled monomeric alkaloids, named ancistrolikokines I (9), C3 (10), F2 (11), J (12), J2 (13), and J3 (14). They were identified in the twigs of A. likoko, along with the two new atropo-diastereomeric dimers michellamines A8 (15a) and B8 (15b) and the naphthalene-devoid dihydroisoquinoline ent-ealaine D (19). The latter had previously only been known from total synthesis and has now been identified for the first time as an authentic natural product. Three of the new alkaloids, 12-14, are the only fully dehydrogenated naphthylisoquinolines with a 5,8'-biaryl linkage, apart from one single known other example previously likewise found in A. likoko. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR), chemical (oxidative degradation), and chiroptical (electronic circular dichroism) methods. The new ancistrolikokines exhibited moderate to strong cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and against cells of their multidrug-resistant subline, CEM/ADR5000. A first structure-activity relationship (SAR) study on a small library of 5,8'-coupled naphthylisoquinolines from the twigs of A. likoko suggests that the oxygenation patterns in the isoquinoline portion at C-6 and C-8 play a crucial role for the antileukemic activities within this group of alkaloids.
- Date of acceptance
- 2018
- Autoren
- Shaimaa Fayez
- Doris Feineis
- Virima Mudogo
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/29936193
- DOI
- 10.1016/j.fitote.2018.06.009
- eISSN
- 1873-6971
- Zeitschrift
- Fitoterapia
- Schlüsselwörter
- Ancistrocladaceae
- Ancistrocladus likoko
- Ancistrolikokines
- Antileukemic agents
- Naphthylisoquinoline alkaloids
- Alkaloids
- Antineoplastic Agents, Phytogenic
- Caryophyllales
- Cell Line, Tumor
- Drug Resistance, Multiple
- Drug Resistance, Neoplasm
- Humans
- Molecular Structure
- Sprache
- eng
- Country
- Netherlands
- Paginierung
- 114 - 125
- PII
- S0367-326X(18)30776-7
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2018
- Titel
- Ancistrolikokine I and further 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 129
Data source: PubMed
- Beziehungen:
- Property of