Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Jun Li
- Nasir Tajuddeen
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- 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:000994635800001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.bmcl.2023.129258
- eISSN
- 1464-3405
- Externe Identifier
- Clarivate Analytics Document Solution ID: H2XA3
- PubMed Identifier: 36972793
- ISSN
- 0960-894X
- Zeitschrift
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Schlüsselwörter
- Axial chirality
- Jozibrevine D
- Naphthylisoquinolines
- Dimers
- Alkaloids
- Antiplasmodial
- Antileukemic
- Artikelnummer
- ARTN 129258
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Titel
- Jozibrevine D from<i> Ancistrocladus</i><i> ileboensis,</i> the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities
- Sub types
- Article
- Ausgabe der Zeitschrift
- 86
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Jun Li
- Nasir Tajuddeen
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1016/j.bmcl.2023.129258
- ISSN
- 0960-894X
- Zeitschrift
- Bioorganic & Medicinal Chemistry Letters
- Sprache
- en
- Artikelnummer
- 129258
- Paginierung
- 129258 - 129258
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.bmcl.2023.129258
- Datum der Datenerfassung
- 2023
- Titel
- Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities
- Ausgabe der Zeitschrift
- 86
Data source: Crossref
- Abstract
- A new dimeric naphthylisoquinoline alkaloid, jozibrevine D (4e), was isolated from the Central-African liana Ancistrocladus ileboensis. It is a Dioncophyllaceae-type metabolite, being R-configured at C-3 and lacking an oxygen function at C-6 in both isoquinoline moieties. The two identical monomers of jozibrevine D are symmetrically linked via the sterically constrained 3',3''-positions of the naphthalene units so that the central biaryl linkage is rotationally hindered and the alkaloid is, thus, C<sub>2</sub>-symmetric. With the two outer biaryl bonds being chiral, too, 4e possesses three consecutive stereogenic axes. The absolute stereostructure of the new compound was assigned by 1D and 2D NMR, ruthenium-mediated oxidative degradation, and electronic circular dichroism (ECD) spectroscopy. Jozibrevine D (4e) is the fifth discovered isomer in a series of six possible natural atropo-diastereomeric dimers. It shows potent, and selective, antiprotozoal activity against P. falciparum (IC<sub>50</sub> = 0.14 μM), and it also exhibits good cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells (IC<sub>50</sub> = 11.47 μM) and their multidrug-resistant CEM/ADR5000 subline (IC<sub>50</sub> = 16.61 μM).
- Addresses
- Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany; Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011 Urumqui, People's Republic of China.
- Autoren
- Jun Li
- Nasir Tajuddeen
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- DOI
- 10.1016/j.bmcl.2023.129258
- eISSN
- 1464-3405
- Externe Identifier
- PubMed Identifier: 36972793
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft:
- Open access
- false
- ISSN
- 0960-894X
- Zeitschrift
- Bioorganic & medicinal chemistry letters
- Schlüsselwörter
- Alkaloids
- Antineoplastic Agents
- Antiparasitic Agents
- Antiprotozoal Agents
- Antimalarials
- Molecular Structure
- Caryophyllales
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2023
- Paginierung
- 129258
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum der Datenerfassung
- 2023
- Titel
- Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 86
Data source: Europe PubMed Central
- Abstract
- A new dimeric naphthylisoquinoline alkaloid, jozibrevine D (4e), was isolated from the Central-African liana Ancistrocladus ileboensis. It is a Dioncophyllaceae-type metabolite, being R-configured at C-3 and lacking an oxygen function at C-6 in both isoquinoline moieties. The two identical monomers of jozibrevine D are symmetrically linked via the sterically constrained 3',3''-positions of the naphthalene units so that the central biaryl linkage is rotationally hindered and the alkaloid is, thus, C2-symmetric. With the two outer biaryl bonds being chiral, too, 4e possesses three consecutive stereogenic axes. The absolute stereostructure of the new compound was assigned by 1D and 2D NMR, ruthenium-mediated oxidative degradation, and electronic circular dichroism (ECD) spectroscopy. Jozibrevine D (4e) is the fifth discovered isomer in a series of six possible natural atropo-diastereomeric dimers. It shows potent, and selective, antiprotozoal activity against P. falciparum (IC50 = 0.14 μM), and it also exhibits good cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells (IC50 = 11.47 μM) and their multidrug-resistant CEM/ADR5000 subline (IC50 = 16.61 μM).
- Date of acceptance
- 2023
- Autoren
- Jun Li
- Nasir Tajuddeen
- Doris Feineis
- Virima Mudogo
- Marcel Kaiser
- Ean-Jeong Seo
- Thomas Efferth
- Gerhard Bringmann
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/36972793
- DOI
- 10.1016/j.bmcl.2023.129258
- eISSN
- 1464-3405
- Zeitschrift
- Bioorg Med Chem Lett
- Schlüsselwörter
- Alkaloids
- Antileukemic
- Antiplasmodial
- Axial chirality
- Dimers
- Jozibrevine D
- Naphthylisoquinolines
- Antiparasitic Agents
- Antimalarials
- Molecular Structure
- Alkaloids
- Antiprotozoal Agents
- Antineoplastic Agents
- Caryophyllales
- Sprache
- eng
- Country
- England
- Paginierung
- 129258
- PII
- S0960-894X(23)00136-1
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2023
- Titel
- Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 86
Data source: PubMed
- Beziehungen:
- Property of