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

Publication type:
Journal article
Metadata:
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

Data source: Web of Science (Lite)

Other metadata sources:
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

Data source: 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

Data source: 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

Data source: PubMed

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