Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines

Mimosa caesalpiniifolia is a native plant of the Brazilian northeast, and few studies have investigated its chemical composition and biological significance. This work describes the identification of the first chemical constituents in the ethanolic extract and fractions of M. caesalpiniifolia stem b...

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Main Authors: Nayana Bruna Nery Monção, Bruno Quirino Araújo, Jurandy do Nascimento Silva, Daisy Jereissati Barbosa Lima, Paulo Michel Pinheiro Ferreira, Flavia Pereira da Silva Airoldi, Cláudia Pessoa, Antonia Maria das Graças Lopes Citó
Format: Article
Language:English
Published: MDPI AG 2015-03-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/20/3/4204
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spelling doaj-27052034f0e140338126d8e136003e262020-11-24T23:55:14ZengMDPI AGMolecules1420-30492015-03-012034204422410.3390/molecules20034204molecules20034204Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell LinesNayana Bruna Nery Monção0Bruno Quirino Araújo1Jurandy do Nascimento Silva2Daisy Jereissati Barbosa Lima3Paulo Michel Pinheiro Ferreira4Flavia Pereira da Silva Airoldi5Cláudia Pessoa6Antonia Maria das Graças Lopes Citó7Department of Chemistry, Federal University of Piauí, Teresina 64049-550, PI, BrazilDepartment of Chemistry, Federal University of Piauí, Teresina 64049-550, PI, BrazilPostgraduate Program in Pharmaceutical Sciences, Federal University of Piauí, Teresina 64049-550, PI, BrazilDepartment of Physiology and Pharmacology, Federal University of Ceará, Fortaleza 60430-270, CE, BrazilPostgraduate Program in Pharmaceutical Sciences, Federal University of Piauí, Teresina 64049-550, PI, BrazilLaboratory of Organic Geochemistry, University of Campinas, São Paulo 13083-970, SP, BrazilDepartment of Physiology and Pharmacology, Federal University of Ceará, Fortaleza 60430-270, CE, BrazilDepartment of Chemistry, Federal University of Piauí, Teresina 64049-550, PI, BrazilMimosa caesalpiniifolia is a native plant of the Brazilian northeast, and few studies have investigated its chemical composition and biological significance. This work describes the identification of the first chemical constituents in the ethanolic extract and fractions of M. caesalpiniifolia stem bark based on NMR, GC-qMS and HRMS analyses, as well as an assessment of their cytotoxic activity. GC-qMS analysis showed fatty acid derivatives, triterpenes and steroid substances and confirmed the identity of the chemical compounds isolated from the hexane fraction. Metabolite biodiversity in M. caesalpiniifolia stem bark revealed the differentiated accumulation of pentacyclic triterpenic acids, with a high content of betulinic acid and minor amounts of 3-oxo and 3β-acetoxy derivatives. Bioactive analysis based on total phenolic and flavonoid content showed a high amount of these compounds in the ethanolic extract, and ESI-(−)-LTQ-Orbitrap-MS identified caffeoyl hexose at high intensity, as well as the presence of phenolic acids and flavonoids. Furthermore, the evaluation of the ethanolic extract and fractions, including betulinic acid, against colon (HCT-116), ovarian (OVCAR-8) and glioblastoma (SF-295) tumour cell lines showed that the crude extract, hexane and dichloromethane fractions possessed moderate to high inhibitory activity, which may be related to the abundance of betulinic acid. The phytochemical and biological study of M. caesalpiniifolia stem bark thus revealed a new alternative source of antitumour compounds, possibly made effective by the presence of betulinic acid and by chemical co-synergism with other compounds.http://www.mdpi.com/1420-3049/20/3/4204Mimosa caesalpiniifoliaphenolic compoundscytotoxicitybetulinic acid
collection DOAJ
language English
format Article
sources DOAJ
author Nayana Bruna Nery Monção
Bruno Quirino Araújo
Jurandy do Nascimento Silva
Daisy Jereissati Barbosa Lima
Paulo Michel Pinheiro Ferreira
Flavia Pereira da Silva Airoldi
Cláudia Pessoa
Antonia Maria das Graças Lopes Citó
spellingShingle Nayana Bruna Nery Monção
Bruno Quirino Araújo
Jurandy do Nascimento Silva
Daisy Jereissati Barbosa Lima
Paulo Michel Pinheiro Ferreira
Flavia Pereira da Silva Airoldi
Cláudia Pessoa
Antonia Maria das Graças Lopes Citó
Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
Molecules
Mimosa caesalpiniifolia
phenolic compounds
cytotoxicity
betulinic acid
author_facet Nayana Bruna Nery Monção
Bruno Quirino Araújo
Jurandy do Nascimento Silva
Daisy Jereissati Barbosa Lima
Paulo Michel Pinheiro Ferreira
Flavia Pereira da Silva Airoldi
Cláudia Pessoa
Antonia Maria das Graças Lopes Citó
author_sort Nayana Bruna Nery Monção
title Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
title_short Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
title_full Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
title_fullStr Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
title_full_unstemmed Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
title_sort assessing chemical constituents of mimosa caesalpiniifolia stem bark: possible bioactive components accountable for the cytotoxic effect of m. caesalpiniifolia on human tumour cell lines
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2015-03-01
description Mimosa caesalpiniifolia is a native plant of the Brazilian northeast, and few studies have investigated its chemical composition and biological significance. This work describes the identification of the first chemical constituents in the ethanolic extract and fractions of M. caesalpiniifolia stem bark based on NMR, GC-qMS and HRMS analyses, as well as an assessment of their cytotoxic activity. GC-qMS analysis showed fatty acid derivatives, triterpenes and steroid substances and confirmed the identity of the chemical compounds isolated from the hexane fraction. Metabolite biodiversity in M. caesalpiniifolia stem bark revealed the differentiated accumulation of pentacyclic triterpenic acids, with a high content of betulinic acid and minor amounts of 3-oxo and 3β-acetoxy derivatives. Bioactive analysis based on total phenolic and flavonoid content showed a high amount of these compounds in the ethanolic extract, and ESI-(−)-LTQ-Orbitrap-MS identified caffeoyl hexose at high intensity, as well as the presence of phenolic acids and flavonoids. Furthermore, the evaluation of the ethanolic extract and fractions, including betulinic acid, against colon (HCT-116), ovarian (OVCAR-8) and glioblastoma (SF-295) tumour cell lines showed that the crude extract, hexane and dichloromethane fractions possessed moderate to high inhibitory activity, which may be related to the abundance of betulinic acid. The phytochemical and biological study of M. caesalpiniifolia stem bark thus revealed a new alternative source of antitumour compounds, possibly made effective by the presence of betulinic acid and by chemical co-synergism with other compounds.
topic Mimosa caesalpiniifolia
phenolic compounds
cytotoxicity
betulinic acid
url http://www.mdpi.com/1420-3049/20/3/4204
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