Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae)
| Ano de defesa: | 2004 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | |
| Tipo de documento: | Dissertação |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Universidade do Estado do Amazonas
Brasil UEA Programa de Pós-Graduação em Biotecnologia e Recursos Naturais da Amazônia |
| Programa de Pós-Graduação: |
Não Informado pela instituição
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Não Informado pela instituição
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| País: |
Não Informado pela instituição
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| Palavras-chave em Português: | |
| Link de acesso: | https://ri.uea.edu.br/handle/riuea/2159 |
Resumo: | This work describes the phytochemical study of Virola michelii Heckel that occur in the Amazon Region popularly known as ucuúba-preta and its leaves are used in the popular medicine as hot poultice on the skin, to treat infections caused by fungus. The fresh smashed leaves of Virola michelii submitted to the hydrodistilation afforded a volatile oil, which analyzed through coupled system gas chromatograph to mass spectrometer evidenced the occurrence of one monoterpene and of seventeen sesquiterpenes. The ethyl alcohol extract of V. michelii leaves was fractionated by ethyl acetate and aqueous methanol partition, followed by solvent evaporation of the fractions, yielded the respective residues. The ethyl acetate residue submitted to chromatographic techniques, allowed the isolation of three compounds, two furofuran lignan, “eudesmin” (rel- (1S,2R,5R,6S)-2,6-di-(3,4-dimethoxyphenyl]-3,7-dioxabicyclo[3.3.0]octane) and “phillygenol” rel-(1S,2S,5R,6R)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-dimethoxyphenyl)-3,7- dioxabicyclo[3.3.0]octane and one phytosterol, the β-sitosterol. The structural determination was based on the interpretation of the 1 H and 13C nuclear magnetic resonance spectra and mass spectra. The isolated furofuran lignans were submitted to test for antioxidant activity with DPPH radical followed by photometric detection. It was observed that the phillygenol was more active than eudesmin, in the assay which quercetin was used as standard. |
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Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae)Volatile oil and antioxidants from michelii heckel (myristicaceae) ferrule leavesVirola micheli heckelUcuúba-pretaMedicina popularÓleo volátilFitotecniaThis work describes the phytochemical study of Virola michelii Heckel that occur in the Amazon Region popularly known as ucuúba-preta and its leaves are used in the popular medicine as hot poultice on the skin, to treat infections caused by fungus. The fresh smashed leaves of Virola michelii submitted to the hydrodistilation afforded a volatile oil, which analyzed through coupled system gas chromatograph to mass spectrometer evidenced the occurrence of one monoterpene and of seventeen sesquiterpenes. The ethyl alcohol extract of V. michelii leaves was fractionated by ethyl acetate and aqueous methanol partition, followed by solvent evaporation of the fractions, yielded the respective residues. The ethyl acetate residue submitted to chromatographic techniques, allowed the isolation of three compounds, two furofuran lignan, “eudesmin” (rel- (1S,2R,5R,6S)-2,6-di-(3,4-dimethoxyphenyl]-3,7-dioxabicyclo[3.3.0]octane) and “phillygenol” rel-(1S,2S,5R,6R)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-dimethoxyphenyl)-3,7- dioxabicyclo[3.3.0]octane and one phytosterol, the β-sitosterol. The structural determination was based on the interpretation of the 1 H and 13C nuclear magnetic resonance spectra and mass spectra. The isolated furofuran lignans were submitted to test for antioxidant activity with DPPH radical followed by photometric detection. It was observed that the phillygenol was more active than eudesmin, in the assay which quercetin was used as standard.O presente trabalho descreve o estudo fitoquímico de Virola michelii Heckel conhecida como ucuúba-preta, que ocorre na Amazônia, cujas folhas têm sido usadas na medicina popular como emplastos à quente sobre a pele, para reduzir infecções causadas por fungos. As folhas frescas fragmentadas de Virola michelii, submetidas a uma hidrodestilação, forneceram um óleo volátil, que analisado pelo sistema cromatógrafo gasoso acoplado ao espectrômetro de massas permitiu a identificação de um monoterpeno e dezessete sesquiterpenos. O extrato etanólico das folhas de V. michelii submetido ao fracionamento por partição de solventes em acetato de etila e metanol/água rendeu frações, que por evaporação do solvente, deram origem aos respectivos resíduos. Estes, submetidos a técnicas cromatográficas, permitiram o isolamento de três substâncias, sendo duas lignanas furofurânicas, “eudesmina” {rel-(1S,2R,5R,6S)-2,6-di-(3,4–dimetoxifenil)-3,7- dioxabiciclo[3.3.0]octano} e “filigenol” {rel-(1S,2S,5R,6R)-6-(4-hidróxi-3-metoxifenil)-2-(3,4- dimetoxifenil)-3,7-dioxabiciclo[3.3.0]octano} e um fitosterol, o β-sitosterol. A elucidação estrutural foi baseada na interpretação dos espectros de ressonância magnética nuclear de 1 H e de 13C e espectro de massas. As lignanas furofurânicas isoladas foram submetidas a testes para atividades antioxidantes com o radical DPPH em ensaio fotométrico. A substância filigenol se mostrou mais ativa que a substância eudesmina, em ensaio que empregou como padrão a quercetina.Universidade do Estado do AmazonasBrasilUEAPrograma de Pós-Graduação em Biotecnologia e Recursos Naturais da AmazôniaYoshida, MassayoshiYoshida , MassayoshiPinheiro , Maria Lúcia BelémNunez , Cecilia VeronicaTorres, Zelina Estevam dos Santos2020-03-13T14:28:25Z2024-09-05T17:30:09Z2020-03-132020-03-13T14:28:25Z2004-12-15info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttps://ri.uea.edu.br/handle/riuea/2159porADAMS, R. P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publ Corp., Carol Stream, II, pp. 469. 1995. AGRAWAL, P. K.; TAKUR, R. S. 13C NMR spectroscopy of lignan and neolignan derivates, Magnetic Resonance in Chemistry, v. 23, p. 389, 1985. AGURELL, S., HOLMSTEDT, B., LINDGREN, J-E.,; SCHULTES, R. E. Alkaloids in Certain Species of Virola and other South American Plants of Ethnopharmacologic Interest. Acta Chemica Scandinavia. v. 23, p. 903, 1969. AYRES, D. C.; LOIKE, J. D. Lignans - Chemical, Biological and Clinical Properties. p. 402. Cambridge: University Press, 1990. BAILAC, P. N.; DELLACASA, A. D.; BERNASCONI, H.; FIRPO, N. H.; PONZI, M. I. Composicion del aceite esencial y actividad antimicrobiana de Eupatorium patens. Boletin de la Sociedad Chilena de Química, v. 45, p. 207-211, 2000 BANERJI, A.; PAL, S. Constituents of Piper sylvaticum: Structure of Sylvatesmin. Journal of Natural Products. V. 45, p. 672-675, 1982. BARATA, L. E. S., SANTOS, L. S., FERRI, P. H., PHILLIPSON, J. D. PAINE, A.; CROFT, S. L. Anti-leishmanial activity of neolignans from Virola species and synthetic analogues. Phytochemistry. v. 55, p. 589-595, 2000. BARROS, S. B. M.; ISHII, I.; SILVA, D. H. S.; YOSHIDA, M. Antioxidant Properties of tocotrienols isolated from Iryanthera grandis. 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Physiology of secondary product formation in plants. In: Charlwood, B.V.; Rhodes, M.J.C. (ed.). Secondary products from plant tissue culture. Oxford: Clarendon, 1990. YOSHIDA, M.; KATO, M. J.; LOPES, N. P.; ALBUQUERQUE, S. Processo de obtenção das lignanas tetraidrofurânicas veraguensina e grandisina, atividade antichagásica e seu uso como antichagásico. INPI, Br n. PI 99033472-7, 18 ago.1999. YUNES, R.A; CALIXTO, J.B. Plantas Medicinais Sob a Ótica da Moderna Química Medicinal. S.l.: Ed. Argos, 2001.Atribuição-NãoComercial-SemDerivados 3.0 Brasilinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da Universidade do Estado do Amazonas (UEA)instname:Universidade do Estado do Amazonas (UEA)instacron:UEA2024-09-05T17:52:37Zoai:ri.uea.edu.br:riuea/2159Repositório InstitucionalPUBhttps://ri.uea.edu.br/server/oai/requestbibliotecacentral@uea.edu.bropendoar:2024-09-05T17:52:37Repositório Institucional da Universidade do Estado do Amazonas (UEA) - Universidade do Estado do Amazonas (UEA)false |
| dc.title.none.fl_str_mv |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) Volatile oil and antioxidants from michelii heckel (myristicaceae) ferrule leaves |
| title |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| spellingShingle |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) Torres, Zelina Estevam dos Santos Virola micheli heckel Ucuúba-preta Medicina popular Óleo volátil Fitotecnia |
| title_short |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| title_full |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| title_fullStr |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| title_full_unstemmed |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| title_sort |
Óleo volátil e antioxidantes de folhas de virola michelii heckel (myristicaceae) |
| author |
Torres, Zelina Estevam dos Santos |
| author_facet |
Torres, Zelina Estevam dos Santos |
| author_role |
author |
| dc.contributor.none.fl_str_mv |
Yoshida, Massayoshi Yoshida , Massayoshi Pinheiro , Maria Lúcia Belém Nunez , Cecilia Veronica |
| dc.contributor.author.fl_str_mv |
Torres, Zelina Estevam dos Santos |
| dc.subject.por.fl_str_mv |
Virola micheli heckel Ucuúba-preta Medicina popular Óleo volátil Fitotecnia |
| topic |
Virola micheli heckel Ucuúba-preta Medicina popular Óleo volátil Fitotecnia |
| description |
This work describes the phytochemical study of Virola michelii Heckel that occur in the Amazon Region popularly known as ucuúba-preta and its leaves are used in the popular medicine as hot poultice on the skin, to treat infections caused by fungus. The fresh smashed leaves of Virola michelii submitted to the hydrodistilation afforded a volatile oil, which analyzed through coupled system gas chromatograph to mass spectrometer evidenced the occurrence of one monoterpene and of seventeen sesquiterpenes. The ethyl alcohol extract of V. michelii leaves was fractionated by ethyl acetate and aqueous methanol partition, followed by solvent evaporation of the fractions, yielded the respective residues. The ethyl acetate residue submitted to chromatographic techniques, allowed the isolation of three compounds, two furofuran lignan, “eudesmin” (rel- (1S,2R,5R,6S)-2,6-di-(3,4-dimethoxyphenyl]-3,7-dioxabicyclo[3.3.0]octane) and “phillygenol” rel-(1S,2S,5R,6R)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-dimethoxyphenyl)-3,7- dioxabicyclo[3.3.0]octane and one phytosterol, the β-sitosterol. The structural determination was based on the interpretation of the 1 H and 13C nuclear magnetic resonance spectra and mass spectra. The isolated furofuran lignans were submitted to test for antioxidant activity with DPPH radical followed by photometric detection. It was observed that the phillygenol was more active than eudesmin, in the assay which quercetin was used as standard. |
| publishDate |
2004 |
| dc.date.none.fl_str_mv |
2004-12-15 2020-03-13T14:28:25Z 2020-03-13 2020-03-13T14:28:25Z 2024-09-05T17:30:09Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
| format |
masterThesis |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
https://ri.uea.edu.br/handle/riuea/2159 |
| url |
https://ri.uea.edu.br/handle/riuea/2159 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.none.fl_str_mv |
ADAMS, R. P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publ Corp., Carol Stream, II, pp. 469. 1995. AGRAWAL, P. K.; TAKUR, R. S. 13C NMR spectroscopy of lignan and neolignan derivates, Magnetic Resonance in Chemistry, v. 23, p. 389, 1985. AGURELL, S., HOLMSTEDT, B., LINDGREN, J-E.,; SCHULTES, R. E. Alkaloids in Certain Species of Virola and other South American Plants of Ethnopharmacologic Interest. Acta Chemica Scandinavia. v. 23, p. 903, 1969. AYRES, D. C.; LOIKE, J. D. Lignans - Chemical, Biological and Clinical Properties. p. 402. Cambridge: University Press, 1990. BAILAC, P. N.; DELLACASA, A. D.; BERNASCONI, H.; FIRPO, N. H.; PONZI, M. I. Composicion del aceite esencial y actividad antimicrobiana de Eupatorium patens. Boletin de la Sociedad Chilena de Química, v. 45, p. 207-211, 2000 BANERJI, A.; PAL, S. Constituents of Piper sylvaticum: Structure of Sylvatesmin. Journal of Natural Products. V. 45, p. 672-675, 1982. BARATA, L. E. 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M.; SARKANEN, S.; LEWIS, N. G. Stereoselective Bimolecular Phenoxy Radical Coupling by an Auxiliary (Dirigent) Protein Without an Active Center. Science. v. 275, p. 306-366, 1997. DAVINO, S. C.; BARROS, S.; BARROS, S. B. M.; SILVA D. H. S.; YOSHIDA, M.Antioxidant Activity of iryanthera sagotiana Leaves. Fitoterapia. v. 69, p. 185-6, 1998. De-EKNAMKUL, W.; POTDUANG, B. Byosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry. v. 62, p. 389-398, 2003. DÍAZ, L.H; RODRÍGUES JORGE, M.; GARCÍA, D.; ALEA, J.P. Actividad antidermatofítica in vitro de aceites esenciales. Revista Cubana de Plantas Medicinales, 2003, vol. 8, no. 02. Disponível em < http://bvs.sld.cu/revistas/pla/vol8_2_03/pla04203.htm >. Acesso em: 13 jan. 2005. GOTTLIEB, O. R., Loureiro, A. A., Carneiro, M. S. & Rocha, A. I. Distribution of diarylpropanoids in amazonian Virola species. Phytochemistry. v. 12, p. 1830, 1973. 85 GOTTLIEB, O.R. Chemical studies on Medicinal Myristicaceae from Amazonia. Journal of Ethnopharmacology, v. 1, p. 309-323, 1979. GOTTLIEB, O.R. Micromolecular evolution, systematics and ecology, an essay into a novel botanical discipline. p.170. Heidelberg: Springer, 1982. GOTTLIEB, O. R.; YOSHIDA, M. Lignóides com atenção especial à química das lignanas. Química Nova. v. 7, p. 250-273, 1984. GOTTLIEB, O. R. Lignóides de Plantas Amazônicas: investigações biológicas e químicas. Acta Amazônica. v.18, p. 333-344, Suplemento, 1988. HALLIWELL, B.; GUTTERRIDGE, J. M. C., eds. Free Radicals in Biology and Medicine, Oxford: Clarendon Press, 1999. IIDA, T.; NAKANO, M.; ITO, K. Hydroperoxysesquiterpene na lignan constituents of Magnolia kobus. Phytochemistry. v. 21, p. 673-675, 1982. KATO, M.J., YOSHIDA, M.; GOTTLIEB, O.R. Lignoids and arylalkanones from fruits of Virola elongata Phytochemistry. v. 29, p. 1799-1810, 1990. KATO, M.J., YOSHIDA, M.; GOTTLIEB, O.R. Flavones and lignans in flowers, fruits and seedlings of Virola venosa. Phytochemistry. v. 31, p. 283, 1992. KIJJOA, A.; GIESBRECHT, A.M.; GOTTLIEB, O.R.; GOTTLIEB, H.E. 1,3-diaryl-propanes and propan-2-ols from Virola species. Phytochemistry. v. 20, p. 1385, 1981. JACKSON, D.E. & DEWICK, P.M. Tumour-inhibitory aryltetralin lignans from Podophyllum pleianthum. Phytochemistry. v. 24, p. 2407, 1985. LEWIS, N.G.; KATO, M.J.; LOPES, N. & DAVIN, L.B. Lignans: Diversity, Biosynthesis and Function. Chemistry of the Amazon, American Chemical Society, cap. 13, p. 136-167, 1994. LIMA, E.O., MAIA, R.F., SANTOS, L.S., MATOS, A.L.S. Atividade antimicrobiana das cascas e folhas de Virola michelii Heckel (Myristicaceae). Anais da 16a Reunião Anual da Sociedade Brasileira de Química – Caxambu- MG, QB-10. 1993. LOPES, L. M. X.; YOSHIDA, M.; GOTTLIEB, O. R. Dibenzylbutyrolactone lignans from Virola sebifera. Phytochemistry. v. 22, p. 1516, 1983. 86 LOPES, N. P.; KATO, M. J.; ANDRADE, E. H. de A.; MAIA, J. G. S.; YOSHIDA, M. Circadian and seasonal variation in the essential oil from Virola surinamensis leaves. Phytochemistry. v. 46, p. 689, 1997. LOPES, N. P.; KATO, M. J.; ANDRADE, E. H. de A.; MAIA, J. G. S.; YOSHIDA, M.; PLANCHART A. R.; KATZIN, A. M. Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb. by Waiãpi Amazon Indians. Journal of Ethnopharmacology. v. 67, p. 313, 1999b. LOPES, N.P.; SANTOS, P.A.; KATO, M. J.; YOSHIDA M. New butenolides in plantlets of Virola surinamensis (Myristicaceae). Chemical and Pharmaceutical Bulletin. v. 52, p. 1255-1257, 2004. MACRAE, W.D.; TOWERS, G.N.N. Biological activities of lignans. Phytochemistry. v. 23, p. 1207, 1984. MC LAFFERTY, F.W.; STAUFFER, D. The Wiley/NBS Registry of Mass Spectral Data. New York: John Wiley Sons, 1989. MENSOR, L. L.; MENEZES, F. S.; LEITÃO, G. G.; REIS, A. S.; SANTOS, T.C.; COUBE, C.S.; LEITÃO, S.G. Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method. Phytotherapy Research. v. 15, p.127-130, 2001. MIAO, JINLING; et al., Studies on the reaction of sylvatesmin and lantbeside with oxidizing free radical. Radiation Physics And Chemistry. v. 69, p. 25-29, 2004. MIDDLETON JR., E.; KANDASWAMI, C.; THEOHARIDES, T. C. The effects of plant flavonoids en Mammalian cells: Inplications for inflammation, heart disease, and cancer. Pharmacological Reviews. v. 52, p. 673-751, 2000. MOBOT: Missouri Botanical Garden. W3 Tropicos. Disponível em: Acesso em: 09 de set. 2005. NIKAIDO, T.; OHMOTO, T.; KINOSHITA, T.; SANKAWA, U. Nishibe, S. & Hisada, S. Inhibition of cyclic AMP phosphodiesterase by lignans. Chemical and Pharmaceutical Bulletin. v. 29, p. 3586, 1981. NISHIBE, S.; KINOSHITA, H.; TAKEDA, H.; OKANO, G. Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats. 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Plants Drug Analysis: A thin layer chromatography Atlas. 2 ed. 384 p. New York: Springer, 1996. WARD, R.S. Lignans, neolignans and related compounds. Natural Products Reports. v. 14 (1), p. 43-47, 1997. WEIL, A.T. Nutmeg as Narcotic. Economic Botany. v. 19, p. 194. 1965. WINK, M. Physiology of secondary product formation in plants. In: Charlwood, B.V.; Rhodes, M.J.C. (ed.). Secondary products from plant tissue culture. Oxford: Clarendon, 1990. YOSHIDA, M.; KATO, M. J.; LOPES, N. P.; ALBUQUERQUE, S. Processo de obtenção das lignanas tetraidrofurânicas veraguensina e grandisina, atividade antichagásica e seu uso como antichagásico. INPI, Br n. PI 99033472-7, 18 ago.1999. YUNES, R.A; CALIXTO, J.B. Plantas Medicinais Sob a Ótica da Moderna Química Medicinal. S.l.: Ed. Argos, 2001. |
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