Anti-leukemia activity of semi-synthetic phenolic derivatives from Polygonum limbatum Meisn
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Antoine Honore Lonfouo Nkuete
- Victor Kuete
- Davide Gozzini
- Ludovico Migliolo
- Aline Lima Oliveira
- Hippolyte K Wabo
- Pierre Tane
- Giovanni Vidari
- Thomas Efferth
- Octavio Luiz Franco
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000357444600001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1186/s13065-015-0115-2
- Externe Identifier
- Clarivate Analytics Document Solution ID: CM1MI
- PubMed Identifier: 26155305
- ISSN
- 1752-153X
- Zeitschrift
- CHEMISTRY CENTRAL JOURNAL
- Schlüsselwörter
- Phenolic compounds
- Sargisin
- Metapchromone
- LimbachalconeA
- Tsedengchalcone
- Artikelnummer
- ARTN 40
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Titel
- Anti-leukemia activity of semi-synthetic phenolic derivatives from <i>Polygonum limbatum</i> Meisn
- Sub types
- Article
- Ausgabe der Zeitschrift
- 9
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Abstract
- <jats:title>Abstract</jats:title> <jats:sec> <jats:title>Background</jats:title> <jats:p>The present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities. These compounds were prepared by modifying two naturally occurring antitumor phenols, 5,7-dihydroxy-3-(1′-hydroxy-1′-phenyl-methyl)-6-methoxy-chroman-4-one (<jats:bold>A</jats:bold>) and 2′,4′-dihydroxy-3′,6′-dimethoxychalcone (<jats:bold>B</jats:bold>), previously isolated from <jats:italic>Polygonum limbatum</jats:italic> Meisn. (Polygonaceae). The structures were elucidated by spectroscopic means and comparison with published data. The cytotoxicity of compounds was determined by using the resazurin assay in the parental drug-sensitive CCRF-CEM cell line and its multidrug-resistant P-glycoprotein-over-expressing subline, CEM/ADR5000.</jats:p> </jats:sec> <jats:sec> <jats:title>Results</jats:title> <jats:p>We describe in the present paper four new semi-synthetic derivatives of <jats:bold>A</jats:bold> and <jats:bold>B</jats:bold>: 5-hydroxy-6-methoxy-7-<jats:italic>O</jats:italic>-(3′-methylbut-2′-enyl)chroman-4-one (<jats:bold>1</jats:bold>), trivially named metapchromone, 5-acetoxy-6-methoxy-7-<jats:italic>O</jats:italic>-[3′-methylbut-2′enyl]chroman-4-one (<jats:bold>2</jats:bold>), trivially named sargisin, 2′-hydroxy-3′,6′-dimethoxy-4′-<jats:italic>O</jats:italic>-(3″-methylbut-2″-enyl)chalcone (<jats:bold>3</jats:bold>) trivially named limbachalcone A, and 2′-acetoxy-3′,6′-dimethoxy-4′-<jats:italic>O</jats:italic>-(3″-methylbut-2″-enyl)chalcone (<jats:bold>4</jats:bold>) trivially named tsedengchalcone. Their preliminary cytotoxic activities have been determined. We also report herein the isolation of 1-methylhydantoin (<jats:bold>C</jats:bold>) and betulinic acid (<jats:bold>D</jats:bold>) from <jats:italic>Polygonum limbatum</jats:italic> for the first time.</jats:p> </jats:sec> <jats:sec> <jats:title>Conclusions</jats:title> <jats:p>The study clearly suggests that semi-synthesis involving O-prenylation and acetylation of chalcones or other chromanones should be avoided in a search for anticancer drugs. This conclusion should be helpful when selecting substituents for the synthesis of potential anticancer drugs.</jats:p> </jats:sec>
- Autoren
- Antoine Honoré Lonfouo Nkuété
- Victor Kuete
- Davide Gozzini
- Ludovico Migliolo
- Aline Lima Oliveira
- Hippolyte K Wabo
- Pierre Tane
- Giovanni Vidari
- Thomas Efferth
- Octávio Luiz Franco
- DOI
- 10.1186/s13065-015-0115-2
- eISSN
- 1752-153X
- Ausgabe der Veröffentlichung
- 1
- Zeitschrift
- Chemistry Central Journal
- Sprache
- en
- Artikelnummer
- 40
- Online publication date
- 2015
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Herausgeber
- Springer Science and Business Media LLC
- Herausgeber URL
- http://dx.doi.org/10.1186/s13065-015-0115-2
- Datum der Datenerfassung
- 2021
- Titel
- Anti-leukemia activity of semi-synthetic phenolic derivatives from Polygonum limbatum Meisn.
- Ausgabe der Zeitschrift
- 9
Data source: Crossref
- Abstract
- <h4>Background</h4>The present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities. These compounds were prepared by modifying two naturally occurring antitumor phenols, 5,7-dihydroxy-3-(1'-hydroxy-1'-phenyl-methyl)-6-methoxy-chroman-4-one (A) and 2',4'-dihydroxy-3',6'-dimethoxychalcone (B), previously isolated from Polygonum limbatum Meisn. (Polygonaceae). The structures were elucidated by spectroscopic means and comparison with published data. The cytotoxicity of compounds was determined by using the resazurin assay in the parental drug-sensitive CCRF-CEM cell line and its multidrug-resistant P-glycoprotein-over-expressing subline, CEM/ADR5000.<h4>Results</h4>We describe in the present paper four new semi-synthetic derivatives of A and B: 5-hydroxy-6-methoxy-7-O-(3'-methylbut-2'-enyl)chroman-4-one (1), trivially named metapchromone, 5-acetoxy-6-methoxy-7-O-[3'-methylbut-2'enyl]chroman-4-one (2), trivially named sargisin, 2'-hydroxy-3',6'-dimethoxy-4'-O-(3″-methylbut-2″-enyl)chalcone (3) trivially named limbachalcone A, and 2'-acetoxy-3',6'-dimethoxy-4'-O-(3″-methylbut-2″-enyl)chalcone (4) trivially named tsedengchalcone. Their preliminary cytotoxic activities have been determined. We also report herein the isolation of 1-methylhydantoin (C) and betulinic acid (D) from Polygonum limbatum for the first time.<h4>Conclusions</h4>The study clearly suggests that semi-synthesis involving O-prenylation and acetylation of chalcones or other chromanones should be avoided in a search for anticancer drugs. This conclusion should be helpful when selecting substituents for the synthesis of potential anticancer drugs.
- Addresses
- Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon ; Centro de Analises Proteômicas e Bioquimicas, Pós-Graduação em Ciencias Genomicas e Biotecnologia, Universidade Catolica de Brasilia, Brasilia, DF Brazil ; Dipartimento di Chimica, Laboratorio di Chimica delle Sostanze Organiche Naturali e Centro di Etnobiofarmacia (CISTRE), Università degli Studi di Pavia, Via Taramelli, 12-27100 Pavia, Italy.
- Autoren
- Antoine Honoré Lonfouo Nkuété
- Victor Kuete
- Davide Gozzini
- Ludovico Migliolo
- Aline Lima Oliveira
- Hippolyte K Wabo
- Pierre Tane
- Giovanni Vidari
- Thomas Efferth
- Thomas Efferth
- Octávio Luiz Franco
- DOI
- 10.1186/s13065-015-0115-2
- eISSN
- 1752-153X
- Externe Identifier
- PubMed Identifier: 26155305
- PubMed Central ID: PMC4493792
- Open access
- true
- ISSN
- 1752-153X
- Zeitschrift
- Chemistry Central journal
- Sprache
- eng
- Medium
- Electronic-eCollection
- Online publication date
- 2015
- Open access status
- Open Access
- Paginierung
- 40
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Publisher licence
- CC BY
- Datum der Datenerfassung
- 2015
- Titel
- Anti-leukemia activity of semi-synthetic phenolic derivatives from Polygonum limbatum Meisn.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 9
Files
https://ccj.biomedcentral.com/track/pdf/10.1186/s13065-015-0115-2 https://europepmc.org/articles/PMC4493792?pdf=render
Data source: Europe PubMed Central
- Abstract
- BACKGROUND: The present report describes the semi-synthesis of a few O-prenylated phenolic derivatives and their in vitro antitumor activities. These compounds were prepared by modifying two naturally occurring antitumor phenols, 5,7-dihydroxy-3-(1'-hydroxy-1'-phenyl-methyl)-6-methoxy-chroman-4-one (A) and 2',4'-dihydroxy-3',6'-dimethoxychalcone (B), previously isolated from Polygonum limbatum Meisn. (Polygonaceae). The structures were elucidated by spectroscopic means and comparison with published data. The cytotoxicity of compounds was determined by using the resazurin assay in the parental drug-sensitive CCRF-CEM cell line and its multidrug-resistant P-glycoprotein-over-expressing subline, CEM/ADR5000. RESULTS: We describe in the present paper four new semi-synthetic derivatives of A and B: 5-hydroxy-6-methoxy-7-O-(3'-methylbut-2'-enyl)chroman-4-one (1), trivially named metapchromone, 5-acetoxy-6-methoxy-7-O-[3'-methylbut-2'enyl]chroman-4-one (2), trivially named sargisin, 2'-hydroxy-3',6'-dimethoxy-4'-O-(3″-methylbut-2″-enyl)chalcone (3) trivially named limbachalcone A, and 2'-acetoxy-3',6'-dimethoxy-4'-O-(3″-methylbut-2″-enyl)chalcone (4) trivially named tsedengchalcone. Their preliminary cytotoxic activities have been determined. We also report herein the isolation of 1-methylhydantoin (C) and betulinic acid (D) from Polygonum limbatum for the first time. CONCLUSIONS: The study clearly suggests that semi-synthesis involving O-prenylation and acetylation of chalcones or other chromanones should be avoided in a search for anticancer drugs. This conclusion should be helpful when selecting substituents for the synthesis of potential anticancer drugs.
- Date of acceptance
- 2015
- Autoren
- Antoine Honoré Lonfouo Nkuété
- Victor Kuete
- Davide Gozzini
- Ludovico Migliolo
- Aline Lima Oliveira
- Hippolyte K Wabo
- Pierre Tane
- Giovanni Vidari
- Thomas Efferth
- Octávio Luiz Franco
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26155305
- DOI
- 10.1186/s13065-015-0115-2
- Externe Identifier
- PubMed Central ID: PMC4493792
- ISSN
- 1752-153X
- Zeitschrift
- Chem Cent J
- Schlüsselwörter
- LimbachalconeA
- Metapchromone
- Phenolic compounds
- Sargisin
- Tsedengchalcone
- Sprache
- eng
- Country
- England
- Paginierung
- 40
- PII
- 115
- Datum der Veröffentlichung
- 2015
- Status
- Published online
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2015
- Titel
- Anti-leukemia activity of semi-synthetic phenolic derivatives from Polygonum limbatum Meisn.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 9
Data source: PubMed
- Beziehungen:
- Property of