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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
001 1954997
005 2018-01-29
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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| Registros recuperados : 26 | |
| 4. |  | RODRIGUES, J. B.; TADEI, W. P.; DIAS, J. M. C. S. A study of the larvicidal activity of Bacillus sphaericus on vectors of malaria in Amazonia. In: ANNUAL MEETING SOCIETY FOR INVERTEBRATE PATHOLOGY, 29., INTERNATIONAL COLLOQUIUM ON BACILLUS THURINGIENSIS, 3., 1996, Cordoba, Espanha. Program and abstracts. Cordoba: Universidad de Cordoba, 1996. p.68. Resumo| Biblioteca(s): Embrapa Recursos Genéticos e Biotecnologia. |
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| 12. | | PINTO, A. C. S.; NOGUEIRA, K. L.; CHAVES, F. C. M.; SILVA, L. V. S. da; TADEI, W. P.; POHLIT, A. M. Adulticidal activity of dillapiol and semi-synthetic derivatives of dillapiol against adults of Aedes aegypti (L.) (Culicidae). Journal of Mosquito Research, v. 2, n. 1, p. 1-7, jun. 2012.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: C - 0 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 13. | | MELO, I. da C.; RAMOS, G. Q.; AMARAL, A. C. F.; TADEI, W. P.; CHAVES, F. C. M.; SANCHES, E. A.; FONSECA FILHO, H. D. da. Chemical composition, cytotoxicity, larvicidal, antimicrobial, adulticidal activities against Aedes aegypti of essential oils from leaves of Piper cytorphodon and Piper krukoffii Yunck. European Academic Research, v. 8, n. 11, p. 7032-7046, Febr. 2021.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: C - 0 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
|  |
| 15. | | PINTO, A. C. da S.; CHAVES, F. C. M.; SANTOS, P. A. dos; NUNEZ, C. V.; TADEI, W. P.; POHLIT, A. M. Piper peltatum: biomass and 4-nerolidylcatechol production. Planta Medica, New York, v. 76, n. 13, p. 1473-1475, 2010.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 2 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 16. | | OLIVEIRA, L. A.; SAID, M. M.; VIEIRA, G.; PRUDENTE, A. L. C.; RODRIGUES, M. R. L.; FORSBERG, B. R.; TADEI, W. P.; TEIXEIRA, W. G. Rede CTPetro Amazônia: estruturação e funcionamento de uma rede de pesquisas para a recuperação de áreas degradadas pela exploração de petróleo e gás natural na Amazônia. In: SIMPÓSIO NACIONAL [SOBRE] RECUPERAÇÃO DE ÁREAS DEGRADADAS, 7., 2008, Curitiba. Anais... Curitiba: FUPEF, 2008. p. 567-574.| Tipo: Artigo em Anais de Congresso / Nota Técnica |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 17. | | OLIVEIRA, M. R. de; KATAK, R. de M.; SILVA, G. F. da; MARINOTTI, O.; TERENIUS, O.; TADEI, W. P.; SOUZA, A. D. L. de; SOUZA, A. Q. L. de. Extracts of Amazonian fungi with larvicidal activities against Aedes aegypti. Frontiers in Microbiology, v. 12, art. 743246, Dec. 2021.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 18. | | 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. Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol. Molecules, v. 18, n. 1, p. 178-189, jan. 2013.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 19. | | SILVA, J. M. S. da; RABELO, M. da S.; LIMA, S. X.; ROCHA, A. L. F.; FONSECA FILHO, H. D. da; OLIVEIRA, A. C. de; TADEI, W. P.; CHAVES, F. C. M.; BEZERRA, J. de A.; BIONDO, M. M.; CAMPELO, P. H.; SANCHES, E. A. Biodegradable nanoparticles loaded with Lippia alba essential oil: a sustainable alternative for Aedes aegypti larvae control. European Academic Research, v. 7, n. 12, p. 6237-6258, Mar. 2020.| Tipo: Artigo em Periódico Indexado | Circulação/Nível: C - 0 |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| 20. | | POHLIT, A. M.; PINTO, A. C. da S.; CAVALCANTI, B. C.; PESSOA, C. do O.; SILVA, E. C. C. e; CHAVES, F. C. M.; NOGUEIRA, K. L.; LOTUFO, L.; SILVA, L. F. R. e; MELO, M. R. S.; VIEIRA, P. P. R.; MAUSE, R.; AMORIM, R. C. da N.; TADEI, W. P.; ANDRADE-NETO, V. de. Biopharmaceuticals synthesis. In: CARIOCA, J. O. B. (Ed.). Brazilian network on green chemistry - awareness, responsability and action. Benfica: UFC, 2008. p. 347-372.| Tipo: Capítulo em Livro Técnico-Científico |
| Biblioteca(s): Embrapa Amazônia Ocidental. |
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| Registros recuperados : 26 | |
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