Ancistrocyclinones A and B, unprecedented pentacyclic N,C-coupled naphthylisoquinoline alkaloids, from the Chinese liana Ancistrocladus tectorius

Publication type:
Journal article
Metadata:
Autoren
  • Raina Seupel
  • Yasmin Hemberger
  • Doris Feineis
  • Minjuan Xu
  • 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:000429266600020&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1039/c7ob03092d
eISSN
1477-0539
Externe Identifier
  • Clarivate Analytics Document Solution ID: GB7PM
  • PubMed Identifier: 29443340
ISSN
1477-0520
Ausgabe der Veröffentlichung
9
Zeitschrift
ORGANIC & BIOMOLECULAR CHEMISTRY
Paginierung
1581 - 1590
Datum der Veröffentlichung
2018
Status
Published
Titel
Ancistrocyclinones A and B, unprecedented pentacyclic <i>N</i>,<i>C</i>-coupled naphthylisoquinoline alkaloids, from the Chinese liana <i>Ancistrocladus tectorius</i>
Sub types
  • Article
Ausgabe der Zeitschrift
16

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<p>The pentacyclic berberine-like ancistrocyclinones A and B represent a new subtype of naphthylisoquinoline alkaloids, with an intriguing helical 3D structure.</p>
Autoren
  • Raina Seupel
  • Yasmin Hemberger
  • Doris Feineis
  • Minjuan Xu
  • Ean-Jeong Seo
  • Thomas Efferth
  • Gerhard Bringmann
DOI
10.1039/c7ob03092d
eISSN
1477-0539
ISSN
1477-0520
Ausgabe der Veröffentlichung
9
Zeitschrift
Organic &amp; Biomolecular Chemistry
Sprache
en
Online publication date
2018
Paginierung
1581 - 1590
Status
Published online
Herausgeber
Royal Society of Chemistry (RSC)
Herausgeber URL
http://dx.doi.org/10.1039/c7ob03092d
Datum der Datenerfassung
2024
Titel
Ancistrocyclinones A and B, unprecedented pentacyclic <i>N</i>,<i>C</i>-coupled naphthylisoquinoline alkaloids, from the Chinese liana <i>Ancistrocladus tectorius</i>
Ausgabe der Zeitschrift
16

Data source: Crossref

Abstract
Two unique pentacyclic N,C-coupled naphthylisoquinolines, the ancistrocyclinones A (5) and B (6), were discovered in the Chinese liana Ancistrocladus tectorius. Furthermore, six known, likewise N,C-coupled alkaloids, viz., ancistrocladinium A (7a) and its mono- and bisphenolic analogs 8a and 9a were isolated, along with their atropo-diastereomers 7b, 8b, and 9b. The stereostructures of 5 and 6 were determined by HRESIMS, 1D and 2D NMR, oxidative degradation, and ECD calculations. The pentacyclic ancistrocyclinones A (5) and B (6) are structurally similar to berberine alkaloids - yet arising from a most different biosynthetic pathway: they are apparently formed by N,C-coupling of their polyketide-derived molecular halves, followed by oxidative cyclo-condensation. Biomimetic conversion of the co-occurring 4'-O-demethylancistrocladinium A (8a) to ancistrocyclinone A (5) via a quinoid intermediate supported the postulated pathway. Ancistrocyclinone A (5) was found to significantly inhibit the viability of drug-sensitive human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000) with comparable efficacies.
Addresses
  • Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de.
Autoren
  • Raina Seupel
  • Yasmin Hemberger
  • Doris Feineis
  • Minjuan Xu
  • Ean-Jeong Seo
  • Thomas Efferth
  • Thomas Efferth
  • Gerhard Bringmann
DOI
10.1039/c7ob03092d
eISSN
1477-0539
Externe Identifier
  • PubMed Identifier: 29443340
Funding acknowledgements
  • Deutsche Forschungsgemeinschaft: Br 699/14-2
  • Alexander von Humboldt-Stiftung:
Open access
false
ISSN
1477-0520
Ausgabe der Veröffentlichung
9
Zeitschrift
Organic & biomolecular chemistry
Schlüsselwörter
  • Cell Line, Tumor
  • Humans
  • Alkaloids
  • Isoquinolines
  • Antineoplastic Agents, Phytogenic
  • Drug Resistance, Multiple
  • Cell Proliferation
  • Caryophyllales
Sprache
eng
Medium
Print
Paginierung
1581 - 1590
Datum der Veröffentlichung
2018
Status
Published
Datum der Datenerfassung
2018
Titel
Ancistrocyclinones A and B, unprecedented pentacyclic N,C-coupled naphthylisoquinoline alkaloids, from the Chinese liana Ancistrocladus tectorius.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
16

Data source: Europe PubMed Central

Abstract
Two unique pentacyclic N,C-coupled naphthylisoquinolines, the ancistrocyclinones A (5) and B (6), were discovered in the Chinese liana Ancistrocladus tectorius. Furthermore, six known, likewise N,C-coupled alkaloids, viz., ancistrocladinium A (7a) and its mono- and bisphenolic analogs 8a and 9a were isolated, along with their atropo-diastereomers 7b, 8b, and 9b. The stereostructures of 5 and 6 were determined by HRESIMS, 1D and 2D NMR, oxidative degradation, and ECD calculations. The pentacyclic ancistrocyclinones A (5) and B (6) are structurally similar to berberine alkaloids - yet arising from a most different biosynthetic pathway: they are apparently formed by N,C-coupling of their polyketide-derived molecular halves, followed by oxidative cyclo-condensation. Biomimetic conversion of the co-occurring 4'-O-demethylancistrocladinium A (8a) to ancistrocyclinone A (5) via a quinoid intermediate supported the postulated pathway. Ancistrocyclinone A (5) was found to significantly inhibit the viability of drug-sensitive human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000) with comparable efficacies.
Autoren
  • Raina Seupel
  • Yasmin Hemberger
  • Doris Feineis
  • Minjuan Xu
  • Ean-Jeong Seo
  • Thomas Efferth
  • Gerhard Bringmann
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/29443340
DOI
10.1039/c7ob03092d
eISSN
1477-0539
Ausgabe der Veröffentlichung
9
Zeitschrift
Org Biomol Chem
Schlüsselwörter
  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Caryophyllales
  • Cell Line, Tumor
  • Cell Proliferation
  • Drug Resistance, Multiple
  • Humans
  • Isoquinolines
Sprache
eng
Country
England
Paginierung
1581 - 1590
Datum der Veröffentlichung
2018
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2019
Titel
Ancistrocyclinones A and B, unprecedented pentacyclic N,C-coupled naphthylisoquinoline alkaloids, from the Chinese liana Ancistrocladus tectorius.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
16

Data source: PubMed

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