Antileukemic ancistrobenomine B and related 5,1'-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius

Autoren

Gerhard Bringmann
Raina Seupel
Doris Feineis
Minjuan Xu
Guoliang Zhang
Marcel Kaiser
Reto Brun
Ean-Jeong Seo
Thomas Efferth

DOI

10.1016/j.fitote.2017.07.001

ISSN

0367-326X

Zeitschrift

Fitoterapia

Sprache

en

Paginierung

76 - 85

Datum der Veröffentlichung

2017

Status

Published

Herausgeber

Elsevier BV

Herausgeber URL

http://dx.doi.org/10.1016/j.fitote.2017.07.001

Datum der Datenerfassung

2022

Titel

Antileukemic ancistrobenomine B and related 5,1′-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius

Ausgabe der Zeitschrift

121

Data source: Crossref

Abstract

A striking feature of the metabolite pattern of the Southeast Asian liana Ancistrocladus tectorius (Ancistrocladaceae) is the predominance of 5,1'-coupled naphthylisoquinoline alkaloids. About 20 alkaloids of this coupling type have so far been discovered in this plant species. Here, we report on the isolation of four new 5,1'-linked naphthylisoquinolines from the twigs and stems of A. tectorius. Two of them, the ancistrobenomines B (5) and C (6), belong to the very rare group of alkaloids with a fully dehydrogenated isoquinoline portion. Likewise unusual for naphthylisoquinoline alkaloids is the presence of a hydroxymethylene group at C-3. Within the large class of meanwhile ca. 180 such natural products, this structural peculiarity had so far been known only from two other representatives isolated from the Malaysian species A. benomensis, and from one single naphthalene-devoid 3-hydroxymethyleneisoquinoline from A. tectorius. Seven further 5,1'-linked alkaloids, previously isolated from related Asian and African Ancistrocladus species, have now been identified for the first time in A. tectorius. Their structural elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (electronic circular dichroism) methods. Ancistrobenomine B (5) exhibited moderate effects against Plasmodium falciparum and Trypanosoma brucei rhodesiense in vitro, and it was found to display strong cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, 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
Minjuan Xu
Guoliang Zhang
Marcel Kaiser
Reto Brun
Ean-Jeong Seo
Thomas Efferth
Thomas Efferth

DOI

10.1016/j.fitote.2017.07.001

eISSN

1873-6971

Externe Identifier

PubMed Identifier: 28688886

Funding acknowledgements

Deutsche Forschungsgemeinschaft: Br699/14-2
Alexander-von-Humboldt Foundation:
University of Würzburg:

Open access

false

ISSN

0367-326X

Zeitschrift

Fitoterapia

Schlüsselwörter

Cell Line, Tumor
Humans
Plasmodium falciparum
Trypanosoma brucei rhodesiense
Plant Stems
Alkaloids
Isoquinolines
Naphthalenes
Antineoplastic Agents, Phytogenic
Antimalarials
Molecular Structure
Magnoliopsida

Sprache

eng

Medium

Print-Electronic

Online publication date

2017

Paginierung

76 - 85

Datum der Veröffentlichung

2017

Status

Published

Datum der Datenerfassung

2017

Titel

Antileukemic ancistrobenomine B and related 5,1'-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius.

Sub types

Journal Article

Ausgabe der Zeitschrift

121

Data source: Europe PubMed Central

Abstract

A striking feature of the metabolite pattern of the Southeast Asian liana Ancistrocladus tectorius (Ancistrocladaceae) is the predominance of 5,1'-coupled naphthylisoquinoline alkaloids. About 20 alkaloids of this coupling type have so far been discovered in this plant species. Here, we report on the isolation of four new 5,1'-linked naphthylisoquinolines from the twigs and stems of A. tectorius. Two of them, the ancistrobenomines B (5) and C (6), belong to the very rare group of alkaloids with a fully dehydrogenated isoquinoline portion. Likewise unusual for naphthylisoquinoline alkaloids is the presence of a hydroxymethylene group at C-3. Within the large class of meanwhile ca. 180 such natural products, this structural peculiarity had so far been known only from two other representatives isolated from the Malaysian species A. benomensis, and from one single naphthalene-devoid 3-hydroxymethyleneisoquinoline from A. tectorius. Seven further 5,1'-linked alkaloids, previously isolated from related Asian and African Ancistrocladus species, have now been identified for the first time in A. tectorius. Their structural elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (electronic circular dichroism) methods. Ancistrobenomine B (5) exhibited moderate effects against Plasmodium falciparum and Trypanosoma brucei rhodesiense in vitro, and it was found to display strong cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000.

Date of acceptance

2017

Autoren

Gerhard Bringmann
Raina Seupel
Doris Feineis
Minjuan Xu
Guoliang Zhang
Marcel Kaiser
Reto Brun
Ean-Jeong Seo
Thomas Efferth

Autoren-URL

https://www.ncbi.nlm.nih.gov/pubmed/28688886

DOI

10.1016/j.fitote.2017.07.001

eISSN

1873-6971

Zeitschrift

Fitoterapia

Schlüsselwörter

Ancistrobenomines
Ancistrocladaceae
Ancistrocladus tectorius
Antileukemic agents
Antiplasmodial agents
Naphthylisoquinoline alkaloids
Alkaloids
Antimalarials
Antineoplastic Agents, Phytogenic
Cell Line, Tumor
Humans
Isoquinolines
Magnoliopsida
Molecular Structure
Naphthalenes
Plant Stems
Plasmodium falciparum
Trypanosoma brucei rhodesiense

Sprache

eng

Country

Netherlands

Paginierung

76 - 85

PII

S0367-326X(17)30746-3

Datum der Veröffentlichung

2017

Status

Published

Datum, an dem der Datensatz öffentlich gemacht wurde

2017

Titel

Antileukemic ancistrobenomine B and related 5,1'-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius.

Sub types

Journal Article

Ausgabe der Zeitschrift

121

Data source: PubMed

Antileukemic ancistrobenomine B and related 5,1'-coupled naphthylisoquinoline alkaloids from the Chinese liana Ancistrocladus tectorius

Tools