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Registro Completo |
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Biblioteca(s): |
Embrapa Amazônia Ocidental. |
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Data corrente: |
04/04/2013 |
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Data da última atualização: |
29/01/2018 |
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Tipo da produção científica: |
Artigo em Periódico Indexado |
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Autoria: |
LIMA, E. S.; PINTO, A. C. S.; NOGUEIRA, K. L.; SILVA, L. F. R. e; ALMEIDA, P. D. O. de; VASCONCELLOS, M. C. de; CHAVES, F. C. M.; TADEI, W. P.; POHLIT, A. M. |
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Afiliação: |
Emerson Silva Lima, UFAM; Ana Cristina Silva Pinto, INPA; Karla Lagos Nogueira, INPA; Luiz Francisco Rocha e Silva, INPA; Patricia Danielle Oliveira de Almeida, UFAM; Marne Carvalho de Vasconcellos, UFAM; FRANCISCO CELIO MAIA CHAVES, CPAA; Wanderli Pedro Tadei, INPA; Adrian Martin Pohlit, INPA. |
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Título: |
Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol. |
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Ano de publicação: |
2013 |
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Fonte/Imprenta: |
Molecules, v. 18, n. 1, p. 178-189, jan. 2013. |
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ISSN: |
1420-3049 |
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DOI: |
10.3390/molecules18010178 |
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Idioma: |
Inglês |
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Conteúdo: |
4-nerolidylcatechol (4-NC) is an unstable natural product that exhibits important antioxidant, anti-inflammatory and other properties. It is readily obtainable on a multi-gram scale through straightforward solvent extraction of the roots of cultivated Piper peltatum or P. umbellatum, followed by column chromatography on the resulting extract. Semi-synthetic derivatives of 4-NC with one or two substituent groups (methyl, acetyl, benzyl, benzoyl) on the O atoms have been introduced that have increased stability compared to 4-NC and significant in vitro inhibitory activity against the human malaria parasite Plasmodium falciparum. Antioxidant and anti-inflammatory properties may be important for the antiplasmodial mode of action of 4-NC derivatives. Thus, we decided to investigate the antioxidant properties, cytotoxicity and stability of 4-NC derivatives as a means to explore the potential utility of these compounds. 4-NC showed high antioxidant activity in the DPPH and ABTS assays and in 3T3-L1 cells (mouse embryonic fibroblast), however 4-NC was more cytotoxic (IC50 = 31.4 µM) and more unstable than its derivatives and lost more than 80% of its antioxidant activity upon storage in solution at −20 °C for 30 days. DMSO solutions of mono-O-substituted derivatives of 4-NC exhibited antioxidant activity and radical scavenging activity in the DPPH and ABTS assays that was comparable to that of BHA and BHT. In the cell-based antioxidant model, most DMSO solutions of derivatives of 4-NC were less active on day 1 than 4-NC, quercetin and BHA and more active antioxidants than BHT. After storage for 30 days at −20 °C, DMSO solutions of most of the derivatives of 4-NC were more stable and exhibited more antioxidant activity than 4-NC, quercetin and BHA and exhibited comparable antioxidant activity to BHT. These findings point to the potential of derivatives of 4-NC as antioxidant compounds. Menos4-nerolidylcatechol (4-NC) is an unstable natural product that exhibits important antioxidant, anti-inflammatory and other properties. It is readily obtainable on a multi-gram scale through straightforward solvent extraction of the roots of cultivated Piper peltatum or P. umbellatum, followed by column chromatography on the resulting extract. Semi-synthetic derivatives of 4-NC with one or two substituent groups (methyl, acetyl, benzyl, benzoyl) on the O atoms have been introduced that have increased stability compared to 4-NC and significant in vitro inhibitory activity against the human malaria parasite Plasmodium falciparum. Antioxidant and anti-inflammatory properties may be important for the antiplasmodial mode of action of 4-NC derivatives. Thus, we decided to investigate the antioxidant properties, cytotoxicity and stability of 4-NC derivatives as a means to explore the potential utility of these compounds. 4-NC showed high antioxidant activity in the DPPH and ABTS assays and in 3T3-L1 cells (mouse embryonic fibroblast), however 4-NC was more cytotoxic (IC50 = 31.4 µM) and more unstable than its derivatives and lost more than 80% of its antioxidant activity upon storage in solution at −20 °C for 30 days. DMSO solutions of mono-O-substituted derivatives of 4-NC exhibited antioxidant activity and radical scavenging activity in the DPPH and ABTS assays that was comparable to that of BHA and BHT. In the cell-based antioxidant model, most DMSO solutions of derivatives... Mostrar Tudo |
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Palavras-Chave: |
Antioxidantes; Piper peltatum. |
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Categoria do assunto: |
-- |
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URL: |
https://ainfo.cnptia.embrapa.br/digital/bitstream/item/80487/1/molecules-18-00178-v2.pdf
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Marc: |
LEADER 02680naa a2200265 a 4500
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008 2013 bl uuuu u00u1 u #d
022 $a1420-3049
024 7 $a10.3390/molecules18010178$2DOI
100 1 $aLIMA, E. S.
245 $aStability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol.
260 $c2013
520 $a4-nerolidylcatechol (4-NC) is an unstable natural product that exhibits important antioxidant, anti-inflammatory and other properties. It is readily obtainable on a multi-gram scale through straightforward solvent extraction of the roots of cultivated Piper peltatum or P. umbellatum, followed by column chromatography on the resulting extract. Semi-synthetic derivatives of 4-NC with one or two substituent groups (methyl, acetyl, benzyl, benzoyl) on the O atoms have been introduced that have increased stability compared to 4-NC and significant in vitro inhibitory activity against the human malaria parasite Plasmodium falciparum. Antioxidant and anti-inflammatory properties may be important for the antiplasmodial mode of action of 4-NC derivatives. Thus, we decided to investigate the antioxidant properties, cytotoxicity and stability of 4-NC derivatives as a means to explore the potential utility of these compounds. 4-NC showed high antioxidant activity in the DPPH and ABTS assays and in 3T3-L1 cells (mouse embryonic fibroblast), however 4-NC was more cytotoxic (IC50 = 31.4 µM) and more unstable than its derivatives and lost more than 80% of its antioxidant activity upon storage in solution at −20 °C for 30 days. DMSO solutions of mono-O-substituted derivatives of 4-NC exhibited antioxidant activity and radical scavenging activity in the DPPH and ABTS assays that was comparable to that of BHA and BHT. In the cell-based antioxidant model, most DMSO solutions of derivatives of 4-NC were less active on day 1 than 4-NC, quercetin and BHA and more active antioxidants than BHT. After storage for 30 days at −20 °C, DMSO solutions of most of the derivatives of 4-NC were more stable and exhibited more antioxidant activity than 4-NC, quercetin and BHA and exhibited comparable antioxidant activity to BHT. These findings point to the potential of derivatives of 4-NC as antioxidant compounds.
653 $aAntioxidantes
653 $aPiper peltatum
700 1 $aPINTO, A. C. S.
700 1 $aNOGUEIRA, K. L.
700 1 $aSILVA, L. F. R. e
700 1 $aALMEIDA, P. D. O. de
700 1 $aVASCONCELLOS, M. C. de
700 1 $aCHAVES, F. C. M.
700 1 $aTADEI, W. P.
700 1 $aPOHLIT, A. M.
773 $tMolecules$gv. 18, n. 1, p. 178-189, jan. 2013.
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Registro original: |
Embrapa Amazônia Ocidental (CPAA) |
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