Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Dieudonne Tshitenge Tshitenge
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Reto Brun
- 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:000431165100023&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.jnatprod.7b01041
- eISSN
- 1520-6025
- Externe Identifier
- Clarivate Analytics Document Solution ID: GE4DS
- PubMed Identifier: 29560715
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- JOURNAL OF NATURAL PRODUCTS
- Paginierung
- 918 - 933
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Titel
- Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana <i>Ancistrocladus ealaensis</i> with Antiparasitic and Antileukemic Activities
- Sub types
- Article
- Ausgabe der Zeitschrift
- 81
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Dieudonné Tshitenge Tshitenge
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1021/acs.jnatprod.7b01041
- eISSN
- 1520-6025
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Journal of Natural Products
- Sprache
- en
- Online publication date
- 2018
- Paginierung
- 918 - 933
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.jnatprod.7b01041
- Datum der Datenerfassung
- 2023
- Titel
- Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana <i>Ancistrocladus ealaensis</i> with Antiparasitic and Antileukemic Activities
- Ausgabe der Zeitschrift
- 81
Data source: Crossref
- Abstract
- Four new dimeric naphthylisoquinoline alkaloids, michellamine A<sub>5</sub> (2) and mbandakamines C-E (4-6), were isolated from the Congolese plant Ancistrocladus ealaensis, along with the known dimer mbandakamine A (3). They represent constitutionally unsymmetric dimers, each consisting of two 5,8'-coupled naphthylisoquinoline monomers. While the molecular halves of michellamine A<sub>5</sub> (2) are linked via C-6' of both of the naphthalene moieties, i.e., via the least-hindered positions, so that the central biaryl axis is configurationally unstable and not an additional element of chirality, the mbandakamines 3-6 possess three consecutive stereogenic axes. Their monomeric units are linked through an unprecedented 6',1″-coupling in the binaphthalene core, leading to a high steric load, since the central axis is located in one of the peri-positions, neighboring one of the outer axes. In addition, four new 5,8'-coupled monomeric naphthylisoquinolines, viz., ancistroealaines C-F (7-10), were identified, along with four "naphthalene-devoid" tetra- and dihydroisoquinolines, named ealaines A-D (11-14). The new mbandakamines C (4) and D (5) showed pronounced activities against the malaria parasite Plasmodium falciparum, and they were likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multi-drug-resistant tumor cells (CEM/ADR5000).
- Addresses
- Institute of Organic Chemistry , University of Würzburg , Am Hubland , D-97074 Würzburg , Germany.
- Autoren
- Dieudonné Tshitenge Tshitenge
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1021/acs.jnatprod.7b01041
- eISSN
- 1520-6025
- Externe Identifier
- PubMed Identifier: 29560715
- Funding acknowledgements
- Else Kröner-Fresenius-Stiftung:
- Deutsche Forschungsgemeinschaft: SFB 630
- Open access
- false
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Journal of natural products
- Schlüsselwörter
- Cell Line, Tumor
- Humans
- Plasmodium falciparum
- Alkaloids
- Isoquinolines
- Quinolines
- Naphthalenes
- Antineoplastic Agents, Phytogenic
- Antiparasitic Agents
- Antimalarials
- Africa, Central
- Caryophyllales
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2018
- Paginierung
- 918 - 933
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum der Datenerfassung
- 2018
- Titel
- Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 81
Data source: Europe PubMed Central
- Abstract
- Four new dimeric naphthylisoquinoline alkaloids, michellamine A5 (2) and mbandakamines C-E (4-6), were isolated from the Congolese plant Ancistrocladus ealaensis, along with the known dimer mbandakamine A (3). They represent constitutionally unsymmetric dimers, each consisting of two 5,8'-coupled naphthylisoquinoline monomers. While the molecular halves of michellamine A5 (2) are linked via C-6' of both of the naphthalene moieties, i.e., via the least-hindered positions, so that the central biaryl axis is configurationally unstable and not an additional element of chirality, the mbandakamines 3-6 possess three consecutive stereogenic axes. Their monomeric units are linked through an unprecedented 6',1″-coupling in the binaphthalene core, leading to a high steric load, since the central axis is located in one of the peri-positions, neighboring one of the outer axes. In addition, four new 5,8'-coupled monomeric naphthylisoquinolines, viz., ancistroealaines C-F (7-10), were identified, along with four "naphthalene-devoid" tetra- and dihydroisoquinolines, named ealaines A-D (11-14). The new mbandakamines C (4) and D (5) showed pronounced activities against the malaria parasite Plasmodium falciparum, and they were likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multi-drug-resistant tumor cells (CEM/ADR5000).
- Autoren
- Dieudonné Tshitenge Tshitenge
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/29560715
- DOI
- 10.1021/acs.jnatprod.7b01041
- eISSN
- 1520-6025
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- J Nat Prod
- Schlüsselwörter
- Africa, Central
- Alkaloids
- Antimalarials
- Antineoplastic Agents, Phytogenic
- Antiparasitic Agents
- Caryophyllales
- Cell Line, Tumor
- Humans
- Isoquinolines
- Naphthalenes
- Plasmodium falciparum
- Quinolines
- Sprache
- eng
- Country
- United States
- Paginierung
- 918 - 933
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2019
- Titel
- Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 81
Data source: PubMed
- Beziehungen:
- Property of