Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8′- and 7,1′-linked metabolites from the Chinese liana Ancistrocladus tectorius
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Gerhard Bringmann
- Raina Seupel
- Doris Feineis
- Guoliang Zhang
- Minjuan Xu
- Jun Wu
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000389113300001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.fitote.2016.09.009
- eISSN
- 1873-6971
- Externe Identifier
- Clarivate Analytics Document Solution ID: ED8HT
- PubMed Identifier: 27646602
- ISSN
- 0367-326X
- Zeitschrift
- FITOTERAPIA
- Schlüsselwörter
- Ancistrocladus tectorius
- Ancistrocladaceae
- Naphthylisoquinoline alkaloids
- Ancistectorine D
- Antiprotozoal agents
- Antileukemic agents
- Paginierung
- 1 - 8
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Titel
- Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8′- and 7,1′-linked metabolites from the Chinese liana <i>Ancistrocladus</i> <i>tectorius</i>
- Sub types
- Article
- Ausgabe der Zeitschrift
- 115
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Gerhard Bringmann
- Raina Seupel
- Doris Feineis
- Guoliang Zhang
- Minjuan Xu
- Jun Wu
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- DOI
- 10.1016/j.fitote.2016.09.009
- ISSN
- 0367-326X
- Zeitschrift
- Fitoterapia
- Sprache
- en
- Paginierung
- 1 - 8
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.fitote.2016.09.009
- Datum der Datenerfassung
- 2018
- Titel
- Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from the Chinese liana Ancistrocladus tectorius
- Ausgabe der Zeitschrift
- 115
Datenquelle: Crossref
- Abstract
- From the twigs and stems of the Chinese liana Ancistrocladus tectorius (Ancistrocladaceae), two new 5,8'-coupled naphthylisoquinolines, ancistectorine D (5) and its 6-O-demethyl derivative 6, were isolated, along with two new 7,1'-linked alkaloids, 6-O-methylancistectorine B<sub>1</sub> (7) and ancistectorine B<sub>2</sub> (8). Two further compounds, ancistroealaine A (4) and 6-O-demethyl-8-O-methyl-7-epi-ancistrobrevine D (10), already known from related Asian and African Ancistrocladus species, were discovered for the first time in A. tectorius. The structure elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (circular dichroism) methods. Chemotaxonomically remarkable, 5,8'-coupled naphthylisoquinolines have as yet been found quite rarely in Asian Ancistrocladus species, where only two examples have so far been detected, while alkaloids with this coupling type represent the by far the largest group of constituents in African taxa. Ancistectorine D (5) shows promising activities against the protozoan parasites Trypanosoma cruzi and Leishmania donovani, and it was likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000).
- Addresses
- Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. Electronic address: bringman@chemie.uni-wuerzburg.de.
- Autoren
- Gerhard Bringmann
- Raina Seupel
- Doris Feineis
- Guoliang Zhang
- Minjuan Xu
- Jun Wu
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Thomas Efferth
- DOI
- 10.1016/j.fitote.2016.09.009
- eISSN
- 1873-6971
- Externe Identifier
- PubMed Identifier: 27646602
- Funding acknowledgements
- Alexander-von-Humboldt Foundation:
- German Excellence Initiative to the Graduate School of Life Sciences, University of Würzburg:
- Deutsche Forschungsgemeinschaft: Br699/14-2
- Open access
- false
- ISSN
- 0367-326X
- Zeitschrift
- Fitoterapia
- Schlüsselwörter
- Cell Line, Tumor
- Humans
- Leishmania donovani
- Trypanosoma cruzi
- Plant Stems
- Alkaloids
- Isoquinolines
- Naphthols
- Antineoplastic Agents, Phytogenic
- Antiprotozoal Agents
- Drug Resistance, Multiple
- Molecular Structure
- Drug Resistance, Neoplasm
- Magnoliopsida
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2016
- Paginierung
- 1 - 8
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum der Datenerfassung
- 2016
- Titel
- Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from the Chinese liana Ancistrocladus tectorius.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 115
Datenquelle: Europe PubMed Central
- Abstract
- From the twigs and stems of the Chinese liana Ancistrocladus tectorius (Ancistrocladaceae), two new 5,8'-coupled naphthylisoquinolines, ancistectorine D (5) and its 6-O-demethyl derivative 6, were isolated, along with two new 7,1'-linked alkaloids, 6-O-methylancistectorine B1 (7) and ancistectorine B2 (8). Two further compounds, ancistroealaine A (4) and 6-O-demethyl-8-O-methyl-7-epi-ancistrobrevine D (10), already known from related Asian and African Ancistrocladus species, were discovered for the first time in A. tectorius. The structure elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (circular dichroism) methods. Chemotaxonomically remarkable, 5,8'-coupled naphthylisoquinolines have as yet been found quite rarely in Asian Ancistrocladus species, where only two examples have so far been detected, while alkaloids with this coupling type represent the by far the largest group of constituents in African taxa. Ancistectorine D (5) shows promising activities against the protozoan parasites Trypanosoma cruzi and Leishmania donovani, and it was likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000).
- Date of acceptance
- 2016
- Autoren
- Gerhard Bringmann
- Raina Seupel
- Doris Feineis
- Guoliang Zhang
- Minjuan Xu
- Jun Wu
- Marcel Kaiser
- Reto Brun
- Ean-Jeong Seo
- Thomas Efferth
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/27646602
- DOI
- 10.1016/j.fitote.2016.09.009
- eISSN
- 1873-6971
- Zeitschrift
- Fitoterapia
- Schlüsselwörter
- Ancistectorine D
- Ancistrocladaceae
- Ancistrocladus tectorius
- Antileukemic agents
- Antiprotozoal agents
- Naphthylisoquinoline alkaloids
- Alkaloids
- Antineoplastic Agents, Phytogenic
- Antiprotozoal Agents
- Cell Line, Tumor
- Drug Resistance, Multiple
- Drug Resistance, Neoplasm
- Humans
- Isoquinolines
- Leishmania donovani
- Magnoliopsida
- Molecular Structure
- Naphthols
- Plant Stems
- Trypanosoma cruzi
- Sprache
- eng
- Country
- Netherlands
- Paginierung
- 1 - 8
- PII
- S0367-326X(16)30383-5
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2017
- Titel
- Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8'- and 7,1'-linked metabolites from the Chinese liana Ancistrocladus tectorius.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 115
Datenquelle: PubMed
- Beziehungen:
- Eigentum von