Dioncophyllines C2, D2, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ileboensis with Potent Activities against Plasmodium falciparum and against Multiple Myeloma and Leukemia Cell Lines

Publication type:
Journal article
Metadata:
Autoren
  • Jun Li
  • Raina Seupel
  • Doris Feineis
  • Virima Mudogo
  • Marcel Kaiser
  • Reto Brun
  • Daniela Bruennert
  • Manik Chatterjee
  • 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:000395046900026&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1021/acs.jnatprod.6b00967
eISSN
1520-6025
Externe Identifier
  • Clarivate Analytics Document Solution ID: EM0ZL
  • PubMed Identifier: 28121440
ISSN
0163-3864
Ausgabe der Veröffentlichung
2
Zeitschrift
JOURNAL OF NATURAL PRODUCTS
Paginierung
443 - 458
Datum der Veröffentlichung
2017
Status
Published
Titel
Dioncophyllines C<sub>2</sub>, D<sub>2</sub>, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana A<i>ncistrocladus ileboensis</i> with Potent Activities against <i>Plasmodium falciparum</i> and against Multiple Myeloma and Leukemia Cell Lines
Sub types
  • Article
Ausgabe der Zeitschrift
80

Data source: Web of Science (Lite)

Other metadata sources:
Autoren
  • Jun Li
  • Raina Seupel
  • Doris Feineis
  • Virima Mudogo
  • Marcel Kaiser
  • Reto Brun
  • Daniela Brünnert
  • Manik Chatterjee
  • Ean-Jeong Seo
  • Thomas Efferth
  • Gerhard Bringmann
DOI
10.1021/acs.jnatprod.6b00967
eISSN
1520-6025
ISSN
0163-3864
Ausgabe der Veröffentlichung
2
Zeitschrift
Journal of Natural Products
Sprache
en
Online publication date
2017
Paginierung
443 - 458
Datum der Veröffentlichung
2017
Status
Published
Herausgeber
American Chemical Society (ACS)
Herausgeber URL
http://dx.doi.org/10.1021/acs.jnatprod.6b00967
Datum der Datenerfassung
2023
Titel
Dioncophyllines C<sub>2</sub>, D<sub>2</sub>, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana <i>Ancistrocladus ileboensis</i> with Potent Activities against <i>Plasmodium falciparum</i> and against Multiple Myeloma and Leukemia Cell Lines
Ausgabe der Zeitschrift
80

Data source: Crossref

Abstract
Dioncophylline F (1), the first 5,8'-coupled dioncophyllaceous alkaloid (i.e., lacking an oxygen function at C-6 and possessing an R-configuration at C-3), was isolated from the recently described Congolese liana Ancistrocladus ileboensis. Two further, likewise Dioncophyllaceae-type, alkaloids, the dioncophyllines C<sub>2</sub> (2) and D<sub>2</sub> (3), were identified, along with the Ancistrocladaceae-type compound ancistrocladisine B (4), which is oxygenated at C-6 and S-configured at C-3. The structures of the new compounds were determined by spectroscopic, chemical, and chiroptical methods. The stereostructure of 1 was further confirmed by total synthesis. As a consequence of the lack of a methyl group ortho to their biaryl axes, both dioncophylline F (1) and the 7,8'-coupled dioncophylline D<sub>2</sub> (3) occur as pairs of configurationally semistable and, thus, slowly interconverting atropo-diastereomers, whereas dioncophylline C<sub>2</sub> (2), with its 5,1'-linkage, is configurationally stable at the axis. Eight further known naphthylisoquinolines were isolated from A. ileboensis, among them dioncophylline A (P-10), its 4'-O-demethyl analogue P-11, and 5'-O-methyldioncophylline D (7), which were found to display strong cytotoxic activities against multiple myeloma INA-6 cells (P-10 even stronger than the standard drug melphalan) and against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000. Moreover, the dioncophyllines 1, 3, and 7 showed high-and specific-activities against the malaria parasite Plasmodium falciparum.
Addresses
  • Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
Autoren
  • Jun Li
  • Raina Seupel
  • Doris Feineis
  • Virima Mudogo
  • Marcel Kaiser
  • Reto Brun
  • Daniela Brünnert
  • Manik Chatterjee
  • Ean-Jeong Seo
  • Thomas Efferth
  • Thomas Efferth
  • Gerhard Bringmann
DOI
10.1021/acs.jnatprod.6b00967
eISSN
1520-6025
Externe Identifier
  • PubMed Identifier: 28121440
Funding acknowledgements
  • Deutsche Forschungsgemeinschaft: SFB 630/A2
  • Deutsche Forschungsgemeinschaft: Br 699/16-2
  • Deutsche Forschungsgemeinschaft: Br 699/14-2
Open access
false
ISSN
0163-3864
Ausgabe der Veröffentlichung
2
Zeitschrift
Journal of natural products
Schlüsselwörter
  • Humans
  • Plasmodium falciparum
  • Multiple Myeloma
  • Alkaloids
  • Isoquinolines
  • Antineoplastic Agents
  • Antimalarials
  • Nuclear Magnetic Resonance, Biomolecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Magnoliopsida
Sprache
eng
Medium
Print-Electronic
Online publication date
2017
Paginierung
443 - 458
Datum der Veröffentlichung
2017
Status
Published
Datum der Datenerfassung
2017
Titel
Dioncophyllines C<sub>2</sub>, D<sub>2</sub>, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ileboensis with Potent Activities against Plasmodium falciparum and against Multiple Myeloma and Leukemia Cell Lines.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
80

Data source: Europe PubMed Central

Abstract
Dioncophylline F (1), the first 5,8'-coupled dioncophyllaceous alkaloid (i.e., lacking an oxygen function at C-6 and possessing an R-configuration at C-3), was isolated from the recently described Congolese liana Ancistrocladus ileboensis. Two further, likewise Dioncophyllaceae-type, alkaloids, the dioncophyllines C2 (2) and D2 (3), were identified, along with the Ancistrocladaceae-type compound ancistrocladisine B (4), which is oxygenated at C-6 and S-configured at C-3. The structures of the new compounds were determined by spectroscopic, chemical, and chiroptical methods. The stereostructure of 1 was further confirmed by total synthesis. As a consequence of the lack of a methyl group ortho to their biaryl axes, both dioncophylline F (1) and the 7,8'-coupled dioncophylline D2 (3) occur as pairs of configurationally semistable and, thus, slowly interconverting atropo-diastereomers, whereas dioncophylline C2 (2), with its 5,1'-linkage, is configurationally stable at the axis. Eight further known naphthylisoquinolines were isolated from A. ileboensis, among them dioncophylline A (P-10), its 4'-O-demethyl analogue P-11, and 5'-O-methyldioncophylline D (7), which were found to display strong cytotoxic activities against multiple myeloma INA-6 cells (P-10 even stronger than the standard drug melphalan) and against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000. Moreover, the dioncophyllines 1, 3, and 7 showed high-and specific-activities against the malaria parasite Plasmodium falciparum.
Autoren
  • Jun Li
  • Raina Seupel
  • Doris Feineis
  • Virima Mudogo
  • Marcel Kaiser
  • Reto Brun
  • Daniela Brünnert
  • Manik Chatterjee
  • Ean-Jeong Seo
  • Thomas Efferth
  • Gerhard Bringmann
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/28121440
DOI
10.1021/acs.jnatprod.6b00967
eISSN
1520-6025
Ausgabe der Veröffentlichung
2
Zeitschrift
J Nat Prod
Schlüsselwörter
  • Alkaloids
  • Antimalarials
  • Antineoplastic Agents
  • Humans
  • Isoquinolines
  • Magnoliopsida
  • Molecular Structure
  • Multiple Myeloma
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum
  • Structure-Activity Relationship
Sprache
eng
Country
United States
Paginierung
443 - 458
Datum der Veröffentlichung
2017
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2017
Titel
Dioncophyllines C2, D2, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ileboensis with Potent Activities against Plasmodium falciparum and against Multiple Myeloma and Leukemia Cell Lines.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
80

Data source: PubMed

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