Cytotoxic bufadienolides from the leaves of a medicinal plant Melianthus comosus collected in South Africa

Publication type:
Journal article
Metadata:
Autoren
  • Kibrom Gebreheiwot Bedane
  • Lukas Brieger
  • Carsten Strohmann
  • Ean-Jeong Seo
  • Thomas Efferth
  • Michael Spiteller
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000565190700004&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1016/j.bioorg.2020.104102
eISSN
1090-2120
Externe Identifier
  • Clarivate Analytics Document Solution ID: NI2MX
  • PubMed Identifier: 32721779
ISSN
0045-2068
Zeitschrift
BIOORGANIC CHEMISTRY
Schlüsselwörter
  • Melianthus comosus
  • Melianthaceae
  • Occurrence
  • Bufadienolides
  • Cytotoxicity
Artikelnummer
ARTN 104102
Datum der Veröffentlichung
2020
Status
Published
Titel
Cytotoxic bufadienolides from the leaves of a medicinal plant <i>Melianthus comosus</i> collected in South Africa
Sub types
  • Article
Ausgabe der Zeitschrift
102

Data source: Web of Science (Lite)

Other metadata sources:
Autoren
  • Kibrom Gebreheiwot Bedane
  • Lukas Brieger
  • Carsten Strohmann
  • Ean-Jeong Seo
  • Thomas Efferth
  • Michael Spiteller
DOI
10.1016/j.bioorg.2020.104102
ISSN
0045-2068
Zeitschrift
Bioorganic Chemistry
Sprache
en
Artikelnummer
104102
Paginierung
104102 - 104102
Datum der Veröffentlichung
2020
Status
Published
Herausgeber
Elsevier BV
Herausgeber URL
http://dx.doi.org/10.1016/j.bioorg.2020.104102
Datum der Datenerfassung
2022
Titel
Cytotoxic bufadienolides from the leaves of a medicinal plant Melianthus comosus collected in South Africa
Ausgabe der Zeitschrift
102

Data source: Crossref

Abstract
From the leaves of South African medicinal plant Melianthus comosus, four previously undescribed bufadienolides, 16β-formyloxymelianthugenin (1), 2β-acetoxymelianthusigenin (2), 2β-hydroxy-3β,5β-di-O-acetylhellebrigenin (3), and 2β-acetoxy-5β-O-acetylhellebrigenin (4) were isolated together with two known bufadienolides. The structural elucidation of the compounds was based on 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and other spectroscopic methods. The relative configurations were determined by single-crystal X-ray crystallography analysis and NOESY correlations. The isolated compounds displayed strong cytotoxicity against MCF-7 breast cancer cells, sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. Compound 1 showed the most potent activity, with IC<sub>50</sub> values of 0.07 μM towards CCRF-CEM, 0.06 μM towards CEM/ADR5000 and 0.36 μM towards MCF-7 followed by compound 4 with IC<sub>50</sub> values of 0.13 μM towards CCRF-CEM, 0.08 μM towards CEM/ADR5000 and 0.53 μM towards MCF-7.
Addresses
  • Department of Chemistry, Addis Ababa University, P.O. Box 33658, Addis Ababa, Ethiopia; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany. Electronic address: kibrom.gebrehiwot@aau.edu.et.
Autoren
  • Kibrom Gebreheiwot Bedane
  • Lukas Brieger
  • Carsten Strohmann
  • Ean-Jeong Seo
  • Thomas Efferth
  • Michael Spiteller
DOI
10.1016/j.bioorg.2020.104102
eISSN
1090-2120
Externe Identifier
  • PubMed Identifier: 32721779
Funding acknowledgements
  • Bundesministerium für Bildung und Forschung:
Open access
false
ISSN
0045-2068
Zeitschrift
Bioorganic chemistry
Schlüsselwörter
  • Cell Line, Tumor
  • Humans
  • Plant Leaves
  • Plants, Medicinal
  • Bufanolides
  • Antineoplastic Agents, Phytogenic
  • Drug Screening Assays, Antitumor
  • Cell Proliferation
  • Molecular Conformation
  • Structure-Activity Relationship
  • Dose-Response Relationship, Drug
  • Stereoisomerism
  • South Africa
Sprache
eng
Medium
Print-Electronic
Online publication date
2020
Paginierung
104102
Datum der Veröffentlichung
2020
Status
Published
Datum der Datenerfassung
2020
Titel
Cytotoxic bufadienolides from the leaves of a medicinal plant Melianthus comosus collected in South Africa.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
102

Data source: Europe PubMed Central

Abstract
From the leaves of South African medicinal plant Melianthus comosus, four previously undescribed bufadienolides, 16β-formyloxymelianthugenin (1), 2β-acetoxymelianthusigenin (2), 2β-hydroxy-3β,5β-di-O-acetylhellebrigenin (3), and 2β-acetoxy-5β-O-acetylhellebrigenin (4) were isolated together with two known bufadienolides. The structural elucidation of the compounds was based on 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and other spectroscopic methods. The relative configurations were determined by single-crystal X-ray crystallography analysis and NOESY correlations. The isolated compounds displayed strong cytotoxicity against MCF-7 breast cancer cells, sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. Compound 1 showed the most potent activity, with IC50 values of 0.07 μM towards CCRF-CEM, 0.06 μM towards CEM/ADR5000 and 0.36 μM towards MCF-7 followed by compound 4 with IC50 values of 0.13 μM towards CCRF-CEM, 0.08 μM towards CEM/ADR5000 and 0.53 μM towards MCF-7.
Date of acceptance
2020
Autoren
  • Kibrom Gebreheiwot Bedane
  • Lukas Brieger
  • Carsten Strohmann
  • Ean-Jeong Seo
  • Thomas Efferth
  • Michael Spiteller
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/32721779
DOI
10.1016/j.bioorg.2020.104102
eISSN
1090-2120
Zeitschrift
Bioorg Chem
Schlüsselwörter
  • Bufadienolides
  • Cytotoxicity
  • Melianthaceae
  • Melianthus comosus
  • Occurrence
  • Antineoplastic Agents, Phytogenic
  • Bufanolides
  • Cell Line, Tumor
  • Cell Proliferation
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Conformation
  • Plant Leaves
  • Plants, Medicinal
  • South Africa
  • Stereoisomerism
  • Structure-Activity Relationship
Sprache
eng
Country
United States
Paginierung
104102
PII
S0045-2068(20)31399-7
Datum der Veröffentlichung
2020
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2021
Titel
Cytotoxic bufadienolides from the leaves of a medicinal plant Melianthus comosus collected in South Africa.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
102

Data source: PubMed

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