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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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 |
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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 |
work_keys_str_mv |
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