Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae)
Ano de defesa: | 2019 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal Rural do Rio de Janeiro
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Programa de Pós-Graduação: |
Programa de P?s-Gradua??o em Qu?mica
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Departamento: |
Instituto de Qu?mica
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País: |
Brasil
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Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | https://tede.ufrrj.br/jspui/handle/jspui/5501 |
Resumo: | The study species Simira grazielae Peixoto is popularly known as red macaw and is found in Brazil by the states of BA and ES. The aim of the present study was to contribute to the knowledge of the chemical composition of the species S. grazielae, family Rubiaceae, through the phytochemical and pharmacological study (against Rhipicephalus microplus larvae, the tyrosinase and antiinflammatory and antinociceptive enzyme) extracts and fractions. The wood material and bark was collected in the Forest Reserve of Vale do Rio Doce Company - ES, then dried at room temperature, crushed and subjected to exhaustive maceration process with methanol, without heating. The methanolic extract of the wood was subjected to liquid/liquid partition with n-hexane, dichloromethane, ethyl acetate and n-butanol, and a small amount of these partitions along with the extract were subjected to chemical prospecting. The fractions were chromatographed on standard exclusion silica gel columns (Sephadex LH-20) and analyzed by 1H and 13C NMR, GC-MS and LC-MS-IES. In addition to fractionation, extracts and partitioned fractions were subjected to dereplication analysis in the CLUE-IES-QTOF-EM/MS system in positive mode, a fast and accurate analysis for characterization of chemical profiles. The chemical prospecting tests showed positive results for the metabolites: saponins, steroids, triterpenoids, purines, coumarin derivatives, alkaloids, reducing sugars, saccharides and non-protein amino acids. Eighteen (18) substances were isolated and identified from S. grazielae wood: N-acetyl serotonin, Maxonin, Harmana, cis-N-p-coumaroyl serotonin, trans-N-p-coumaroyl serotonin, N-isoferuloil serotonin, N-feruloil serotonin (Moschamine), cis-moschamine, N-cafeloyl serotonin, Higarine, Ofiorina B, Ofiorina A, Strictosidinic Acid, Strictosidine, Mixed of Triacylglycerides, 5-Hydroxyendole-3-aldehyde, 6'-O-Vanilloylbarbutine and Desmethylisopauridiantidoyl acid unpublished in the literature. The technique of dereplication and the proposed fragmentation allowed to postulate the presence of 57 metabolites, almost all of them being indole alkaloids, of which 20 are being proposed as unpublished in the literature. The tests carried out of the species S. grazielae against the acaricidal activity on the R. microplus larvae in the fractions SGD, SGAc, SGB, SGR and on the action on the tyrosinase enzyme [Ofiorina B and the partitions (SGAc and SGB)] did not show significant results. The antiinflammatory and antinociceptive test performed on the fractions of S. grazielae wood showed to have action in these systems and this effect can be linked to the presence of serotonin-derived alkaloids. Thus, in this work we identify 18 substances isolated from S. grazielae wood and propose the additional presence of 57 metabolites through the dereplication technique involving mostly alkaloids, besides revealing the presence of fractions of the species with antiinflammatory and antinociceptive. |
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Braz Filho, RaimundoCPF: 070.100.018-04Oliveira, M?rcia Cristina Campos deLima, Helena Regina PintoMartins, Roberto Carlos CamposOliveira, Marise Maleck deMarinho, Bruno Guimar?esCPF: 124.157.347-64http://lattes.cnpq.br/9237258375836358Sanches, Mirza Nalesso Gomes2022-03-30T20:38:46Z2019-07-25SANCHES, Mirza Nalesso Gomes. Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae). 2019. 236 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2019.https://tede.ufrrj.br/jspui/handle/jspui/5501The study species Simira grazielae Peixoto is popularly known as red macaw and is found in Brazil by the states of BA and ES. The aim of the present study was to contribute to the knowledge of the chemical composition of the species S. grazielae, family Rubiaceae, through the phytochemical and pharmacological study (against Rhipicephalus microplus larvae, the tyrosinase and antiinflammatory and antinociceptive enzyme) extracts and fractions. The wood material and bark was collected in the Forest Reserve of Vale do Rio Doce Company - ES, then dried at room temperature, crushed and subjected to exhaustive maceration process with methanol, without heating. The methanolic extract of the wood was subjected to liquid/liquid partition with n-hexane, dichloromethane, ethyl acetate and n-butanol, and a small amount of these partitions along with the extract were subjected to chemical prospecting. The fractions were chromatographed on standard exclusion silica gel columns (Sephadex LH-20) and analyzed by 1H and 13C NMR, GC-MS and LC-MS-IES. In addition to fractionation, extracts and partitioned fractions were subjected to dereplication analysis in the CLUE-IES-QTOF-EM/MS system in positive mode, a fast and accurate analysis for characterization of chemical profiles. The chemical prospecting tests showed positive results for the metabolites: saponins, steroids, triterpenoids, purines, coumarin derivatives, alkaloids, reducing sugars, saccharides and non-protein amino acids. Eighteen (18) substances were isolated and identified from S. grazielae wood: N-acetyl serotonin, Maxonin, Harmana, cis-N-p-coumaroyl serotonin, trans-N-p-coumaroyl serotonin, N-isoferuloil serotonin, N-feruloil serotonin (Moschamine), cis-moschamine, N-cafeloyl serotonin, Higarine, Ofiorina B, Ofiorina A, Strictosidinic Acid, Strictosidine, Mixed of Triacylglycerides, 5-Hydroxyendole-3-aldehyde, 6'-O-Vanilloylbarbutine and Desmethylisopauridiantidoyl acid unpublished in the literature. The technique of dereplication and the proposed fragmentation allowed to postulate the presence of 57 metabolites, almost all of them being indole alkaloids, of which 20 are being proposed as unpublished in the literature. The tests carried out of the species S. grazielae against the acaricidal activity on the R. microplus larvae in the fractions SGD, SGAc, SGB, SGR and on the action on the tyrosinase enzyme [Ofiorina B and the partitions (SGAc and SGB)] did not show significant results. The antiinflammatory and antinociceptive test performed on the fractions of S. grazielae wood showed to have action in these systems and this effect can be linked to the presence of serotonin-derived alkaloids. Thus, in this work we identify 18 substances isolated from S. grazielae wood and propose the additional presence of 57 metabolites through the dereplication technique involving mostly alkaloids, besides revealing the presence of fractions of the species with antiinflammatory and antinociceptive.A esp?cie de estudo Simira grazielae Peixoto, ? conhecida popularmente como arariba-vermelha e encontra distribu?da no Brasil pelos estados da BA e do ES. O objetivo do presente estudo foi contribuir para o conhecimento da composi??o qu?mica da esp?cie S. grazielae, fam?lia Rubiaceae, atrav?s do estudo fitoqu?mico e bem como farmacol?gico (frente a Larvas de Rhipicephalus microplus, a enzima Tirosinase e anti-inflamat?ria e antinociceptiva) dos extratos e fra??es. O material vegetal da madeira e casca foi coletado na Reserva Florestal da Companhia Vale do Rio Doce - ES, posteriormente seco em temperatura ambiente, triturado e submetido ao processo de macera??o exaustiva com metanol, sem aquecimento. O extrato metan?lico da madeira foi submetido ? parti??o l?quido/l?quido com n-hexano, Diclorometano, Acetato de etila e n-butanol, e uma quantidade pequena dessas parti??es, juntamente com o extrato foi submetida ? prospec??o qu?mica. As fra??es foram cromatografadas em colunas cl?ssicas de s?lica gel por exclus?o (Sephadex LH-20) e analisadas atrav?s de RMN 1H e 13C, CG-EM e CL-EM-IES. Al?m do fracionamento, os extratos e as fra??es particionadas foram submetidos ? an?lise por desreplica??o no sistema CLUE-IES-QTOF-EM/EM no modo positivo, uma an?lise r?pida e precisa para caracteriza??o dos perfis qu?micos. Os testes de prospec??o qu?mica apresentaram resultados positivos para os metab?litos: saponinas, esteroides, triterpen?ides, purinas, derivados da cumarina, alcaloides, a??cares redutores, sacar?deos e amino?cidos n?o proteicos. Foram isoladas e identificadas da madeira de S. grazielae dezoito (18) subst?ncias: N-acetil-serotonina, Maxonina, Harmana, cis- N-p-coumaroil Serotonina, trans-N-p-coumaroil serotonina, N-isoferuloil serotonina, N-feruloil serotonina (Moschamine), cis-moschamine, N-cafeloil serotonina, Higarine, Ofiorina B, Ofiorina A, ?cido Estrictosid?nico, Estrictosidina, misturada de Triacilglicer?deos, 5-hidroxiendole-3-alde?do, 6?-O-vanilloilbarbutina e ?cido desmetilisopauridiantosideo, sendo esse ultimo in?dito na literatura. A t?cnica de desreplica??o e as propostas de fragmenta??es permitiram postular a presen?a de 57 metab?litos, sendo quase na totalidade alcaloides ind?licos, dos quais 20 est?o sendo propostos como in?ditos na literatura. Os testes realizados da esp?cie S. grazielae frente ? atividade acaricida sobre as larvas do R. microplus nas fra??es SGD, SGAc SGB, SGR, e sobre a a??o na enzima tirosinase [Ofiorina B e as parti??es (SGAc e SGB)], n?o apresentaram resultados significativos. J? o teste anti-inflamat?rio e antinociceptivo realizado nas fra??es da madeira de S. grazielae mostraram ter a??o nesses sistemas e esse efeito pode ser atrelado ? presen?a dos alcaloides derivados da serotonin. Assim, neste trabalho registra-se a identifica??o de 18 subst?ncias isoladas da madeira de S. grazielae e prop?e-se a presen?a adicional de 57 metab?litos atrav?s da t?cnica de desreplica??o envolvendo majoritariamente alcaloides, al?m de revelar a presen?a de fra??es da esp?cie com atividade anti-inflamat?ria e antinociceptiva.Submitted by Jorge Silva (jorgelmsilva@ufrrj.br) on 2022-03-30T20:38:46Z No. of bitstreams: 1 2019 - Mirza Nalesso Gomes Sanchez.pdf: 6951851 bytes, checksum: f346ebcd88603c1eca92482b457fce44 (MD5)Made available in DSpace on 2022-03-30T20:38:46Z (GMT). No. of bitstreams: 1 2019 - Mirza Nalesso Gomes Sanchez.pdf: 6951851 bytes, checksum: f346ebcd88603c1eca92482b457fce44 (MD5) Previous issue date: 2019-07-25CAPES - Coordena??o de Aperfei?oamento de Pessoal de N?vel Superiorapplication/pdfhttps://tede.ufrrj.br/retrieve/68666/2019%20-%20Mirza%20Nalesso%20Gomes%20Sanchez.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Qu?micaAMARAL, M. A. Z.; ROCHA, C. M. B. M.; FACCINI, J. L. H.; FURLONG, J.; MONTEIRO, C. M. O.; PRATA, M. C. A. Perceptions and attitudes among milk producers in Minas Gerais regarding catle tick biology and control. Rev. Bras. Parasitol. Vet., v. 20, p. 194-201, 2011a. AMARAL, M. A. Z.; ROCHA, C. M. B. M.; FACCINI, J. L. H.; FURLONG, J.; MONTEIRO, C. M. O.; PRATA, M. C. A. Strategic control of cattle ticks: milk producers perceptions. Rev. Bras. Parasitol. Vet., v. 20, p. 148-154, 2011b. AYRES, M.; AYRES JR., M.; AYRES, D. L.; SANTOS, A. S. dos BioEstat 5.0 - Aplica??es estat?sticas nas ?reas das ci?ncias biol?gicas e m?dicas. Manaus: Sociedade Civil Mamirau?/MCT-CNPq, 2007. BARRETT, C. B.; LYBBERT, T. J. Is bioprospecting a viable strategy for conserving tropical ecosystems? Ecol. Econ., v. 34, p. 293-300, 2000. BOLZANI, V. S.; JOVEM, M. C.; FURLAN, M.; CAVALHEIRO, A. J.; ARAUJO, R. A.; SILVA, D. H. Metab?litos secund?rios de esp?cies de plantas brasileiras de Rubiaceae: signific?ncia quimiotaxon?mica e biol?gica. Res. Recente Dev. Phytochem., v. 5, p. 19-31, 2001. BORGES, L. M. F.; SOUSA, L. A. D. de; BARBOSA, C. da S. Perspectives for the use of plant extracts to control the cattle tick Rhipicephalus (Boophilus) microplus. Rev. Bras. Parasitol. Vet., v. 20, n. 2, p. 89-96, 2011. BOTTCHER, T.; PITSCHEIDER, M.; SIEBER, S. A. Natural products and their biological targets: proteomic and metabolomic labeling strategies. Angew Chem. Int. Ed. Engl., v. 49, n. 15, p. 2680-2698, 2010. BUKHARI, I. A.; PIVAC, N.; ALHUMAYYD, M. S.; MAHESAR, A. L.; GILANI, A. H. O efeito analg?sico e anticonvulsivante da piperina em camundongos. J. Physiol. Pharmacol., v. 64, p. 789-794, 2013. CAMPOS, R. N. S.; BACCI, L.; ARA?JO, A. P. A.; BLANK, A. F.; ARRIGONI-BLANK, M. F.; SANTOS, G. R. A.; RONER, M. N. B. ?leos essenciais de plantas medicinais e arom?ticas no controle do carrapato Rhipicephalus microplus. Arch. Zootec., v. 61, p. 67-78, 2012. CASTRO, K. N. C.; LIMA, D. F.; VASCONCELOS, L. C.; LEITE, J. R. S. A.; SANTOS, R. C.; PAZ NETO, A. A.; COSTA-J?NIOR, L. M. Acaricide activity in vitro of Acmella oleracea against Rhipicephalus microplus. Parasitol. Res., v. 113, p. 3697-3701, 2014. CHANG, TE-SHENG. An Updated Review of Tyrosinase Inhibitors. Int. J. Mol. Sci., v. 10, p. 2440-2475, 2009. CHUNGSAMARNYART, N.; JANSAWAN, W. Acaricidal effect of practical crude-extracts of plants against tropical cattle tick (Boophilus microplus). Kasetsart J., v. 27, p. 57-64, 1993. CHUNGSAMARNYART, N.; JIWAJINDA, S.; JANSAWAN, W. Acaricidal effect of plant crude-extracts on the tropical cattle tick (Boophilus microplus). Kasetsart J., v. 25, p. 90- 100, 1991. COLLIER, H. O. J.; DINNEEN, L. C.; JOHNSON, C. A.; SCHNEIDER, C. The abdominal constriction response and its suppression by analgesic drugs in the mouse. Brit. J. Pharmacol. v. 32, n. 2, p. 295-310, 1968. DUBUISSON, D.; DENNIS, S. G. The formalin test: a quantitative study of the analgesic efects of morfine, merepidine, and brain stem stimulation in rats and cats. Pain. v. 4, p.161- 174, 1977. DUKE, S. O.; PAUL, R. N.; LEE, S. M. Biologically active natural products ? Potencial use in agriculture. In: PRATES, H. T.; LEITE, R. C.; CRAVEIRO, A. A.; OLIVEIRA, A. B. Identification of some chemical components of the essential oil from molasses grass (Melinis minutiflora Beauv.) and their activity against catle-tick (Boophilus microplus). J. Brazil. Chem. Soc., v. 9, n. 2, p. 193-197, 1998. FERRERO-MILIANI, L.; NIELSEN, O. H.; ANDERSEN, P. S.; GIRARDIN, S. E. A inflama??o cr?nica: Import?ncia da NOD2 e NALP3 na gera??o de interleucina-1?. Clin. Exp. Immunol. v. 147, p. 227-235, 2007. FURLONG, J.; MARTINS, J. R.; PRATA, M. C. A. O carrapato dos bovinos e a resist?ncia: temos o que comemorar? HV, v. 27, p. 1-7, 2007. FURLONG, J.; MARTINS, J. R. S.; PRATA, M. C. A. Controle estrat?gico do carrapato dos bovinos. HV, v. 23, p. 53-56, 2004. GOMES, G. A.; MONTEIRO, C. M. O.; SENRA, T. O. S.; ZERINGOTA, V.; CALMON, F.; MATOS, R. S., GOIS; R. W., DA S.; DAEMON, E.; SANTIAGO, G. M. P.; CARVALHO, M. G. Chemical composition and acaricidal activity of essential oil from on larvae of Rhipicephalus microplus (Acari: Ixodidae) and larvae and engorged females of Dermacentor nitens (Acari: Ixodidae). Parasitol. Res., v. 111, n. 6, p. 2423-2430, 2012. GRISI, L.; LEITE, R. C.; MARTINS, J. R.; BARROS, A. T.; CANCADO, P. H. D. Reassessment of economic impact by cattle parasites in Brazil. Rev. Brasil. Parasitol. Vet., v. 23, p. 150-156, 2014. HUNSKAAR, S.; HOLE, K. The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain, v. 30, p.103-114, 1987. IKEDA, Y.; UENO, A.; NARABA, H.; OH-ISHI. Involvement of vaniloid receptor VR1 and prostanoids in the acid-induced writhing responses of mice. Life Sci., v. 69, p. 2911- 2919, 2001. KARIOTI, A.; PROTOPAPPA, A.; MEGOULAS, N.; SKALTSA, H. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorgan. Med. Chem., v. 15, p. 2708-2714, 2007. KEMP, E. H.; GAWKRODGER, D. J.; WATSON, P. F.; WEETMAN, A. P. Immunoprecipitation of melanogenic enzyme autoantigens with vitiligo sera: evidence for cross-reactive autoantibodies to tyrosinase and tyrosinase-related protein- 2 (TRP-2). Clin. Exp. Immunol., v. 109, p. 495-500, 1997 KHAN, K. M.; MUGHAL, U. R.; KHAN, M. T. H.; ULLAH, Z.; PERVEENB, S.; CHOUDHARY, M. I. Oxazolones: New tyrosinase inhibitors; synthesis and their structure? activity relationships. Bioorgan. Med. Chem., v. 14, p. 6027-6033, 2006. KISS, T.; CADAR, D.; SP?NU, M. Tick prevention at a crossroad: new and renewed solutions. Vet. Parasitol., v. 187, p. 357-366, 2012. KLAFKE, G. M. Resist?ncia de R. (B.) microplus contra os carrapaticidas. In: PEREIRA, M. C.; LABRUNA, M. B.; SZABO, M. P. J.; KLAFKE, G. M. (Eds.). Rhipicephalus (Boophilus) microplus: Biologia, Controle e Resist?ncia. S?o Paulo: MEDVET. 2008. p. 81- 105. KOSTER, R.; ANDERSON, M.; DE BEER, E. J. Acetic acid for analgesic screening. Fed. Proc., v. 18, p. 412, 1959. LAPA, A. J.; SOUCCAR, C.; LIMA-LANDMAN, M. T. R.; CASTRO, M. S. A.; LIMA, T. C. M. M?todos de avalia??o da atividade farmacol?gica de plantas medicinais. S?o Paulo. UNIFESP/EPM, 2007. 144p. LE BARS, D.; GOZARIU, M.; CADDEN, S. W. Animals models of nociception. Pharmacol. Rev., v. 53, p. 597-652, 2001. LOBO, P. L. D.; FONTELES, C. S. R.; CARVALHO, C. B. M.; NASCIMENTO, D. F.; FONSECA, S. G. C.; JAMACARU, F. V. F.; MORAES, M. E. A. Dose-response evaluation of a novel essential oil against Mutans streptococci in vivo. Phytomedicine, v. 18, n. 1, p. 551-556, 2011. MACRINI, D. J.; SUFFREDINI I. B.; VARELLA A. D., YOUNES, R. N.; OHARA, M. T. Extracts from Amazonian plants have inhibitory activity against tyrosinase: an in vitro evaluation. Braz. J. Pharm. Sci., v. 45, n. 2, 2009. MANI, I.; SHARMA, V.; TAMBOLI, I.; RAMAN, G. Interaction of melanin with proteins - The impor tance of an acidic intramelanosomal pH. Pigm. Cell. Res., v. 14, p. 170-179, 2001. MATIAS, J.; KOLLER, W. W.; GARCIA, M. V. Classifica??o, distribui??o geogr?fica, ciclo biol?gico e import?ncia econ?mica das principais esp?cies de carapatos no Brasil. In: ANDREOTTI, R.; KOLLER, W. W. Carrapatos no Brasil: Biologia, Controle e Doen?as transmitidas. Campo Grande: Embrapa. 2013. p. 1-13. MIOT, L. D. B.; MIOT, H. A.; SILVA, M. G. da; MARQUES, M. E. A. Fisiopatologia do melasma. Na. Bras. Dermatol., v. 84, p. 623-635, 2009. MONTEIRO, C. M. O.; MATURANO, R.; DAEMON, E.; CATUNDA-JR, F. E. A.; CALMON, F.; SENRA, T. O. S.; FAZZA, A. P.; CARVALHO, M. G. Acaricidal activity of eugenol on Rhipicephalus microplus (Acari: Ixodidae) and Dermacentor nitens (Acari: Ixodidae) larvae. Parasitol. Res., v. 111, p. 1295-1300, 2012. NEWMAN, D. J.; CRAGG, G. M. Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010. J. Nat. Prod., v. 75, n. 3, p. 311-335, 2012. OKOMBI S.; RIVAL D.; BONNET S.; MARIOTTE A. M.; PERRIERB E.; BOUMENDJEL A. Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocytetyrosinase. Bioorg. Med. Chem. Lett., v. 16, n. 8, p. 2252-2255, 2006. PASQUET, V.; MORISSET, P.; IHAMMOUINE, S.; CHEPIED, A.; AUMAILLEY, L.; BERARD, J. B., SERIVE, B.; KAAS, R.; LANNELUC, I.; THIERY, V. et al. Antiproliferative activity of violaxanthin isolated from bioguided fractionation of Dunaliella tertiolecta extracts. Mar. Drugs, v. 9, p. 819-831, 2011. PATIL, S. S.; ZUCKER, M. Potato phenolases. J. Biol. Chem., v. 240, p. 3938-3943, 1965. PEREIRA, M. C. Introdu??o. In: PEREIRA, M. C.; LABRUNA, M. B.; SZAB?, M. P. J.; KLAFKE, G. M. (eds) Rhipicephalus (Boophilus) microplus: Biologia, Controle e Resist?ncia. S?o Paulo: MEDVET. 2008. p.1?5. S?NCHEZ-MATEO, C. C.; BONKANKA, C. X.; HERN?NDEZ-P?REZ, M.; RABANAL, R. M. Avalia??o dos efeitos anti-inflamat?rios analg?sicos e t?picos do Hypericum reflexum L. fil. J. Ethnopharmacol., v. 107, p. 1-6, 2006. SANTOS, C. M,; SANCHES, M. N. G.; S. A. C. D.; CARVALHO, M. G.; BRAZ-FILHO, R.; MARINHO, B. G. Participation of cytokines, opioid, and serotoninergic systems on antinociceptive and anti-inflammatory activities of Simira grazielae peixoto (Rubiaceae). Pharmacogn. Res. v. 11, p. 51-59, 2019. SANTOS, G.C; FERNANDES, R.D; BARROS, T.R; ABREU HDOS S.; SUZART, L.R.; CARVALHO, M.G.; BRAZ-FILHO, R.; MARINHO, B.G. Antinociceptive and anti-inflammatory activities of the methanolic extract from the stem bark of Lophanthera lactescens. Planta Med. v.81, p.1688-96, 2015. SCHMITT EK, MOORE CM, KRASTEL P, PETERSEN F. Natural products as catalysts for innovation: a pharmaceutical industry perspective. Curr. Opin. Chem. Biol., v. 15, n. 4, p. 497-504, 2011. SEO, S. Y.; SHARMA, V. K.; SHARMA, N. Mushroom tytosinase: recent prospects. J. Agr. Food Chem., v. 51, p. 2837-2853, 2003. STONE, B. F.; HAYDOCK, K. P. A method for measuring the acaricide susceptibility of the cattle B. microplus (Can.). B. Entomol. Res., v. 53, p. 563-578, 1962. TJOLSEN, A.; O. G. BERGE; S. HUNSKAAR; J. H. ROSLAND; K. HOLE. The formalin test: an evaluation of the method. Pain. v. 51, p. 5-17, 1992. TSALA, D. E.; AMADOU, D.; HABTEMARIAN, S. Natural wound healing and bioactive natural products. Phytopharmacology, v. 4, n. 3, p. 532-560, 2013. UJANG, Z. B.; SUBRAMANIAM, T.; DIAH, M. M.; WAHID, H. B.; ABDULLAH, B. B.; RASHID, A. H. B. A.; APPLETON, D. Bioguided Fractionation and Purification of Natural Bioactives Obtained from Alpinia conchigera Water Extract with Melanin Inhibition Activity. J. Biomaterials and Nanobiotechnology, v. 4, p. 265-272, 2013. WADLEIGH, D. J.; REDDY, S. T.; KOPP, E.; GHOSH, S.; HERSCHMAN, H. R. Transcriptional activation of the cyclooxygenase-2 gene in endotoxin-treated RAW 264.7 macrophages. J. Biol. Chem., v. 275, p. 6259-6266, 2000. WORLD HEALTH ORGANIZATION (WHO). The world medicines situation 2011: traditional medicines: global situation, issues and challenges. 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dc.title.por.fl_str_mv |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
dc.title.alternative.eng.fl_str_mv |
Phytochemical and biological study of Simira grazielae (Rubiaceae) |
title |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
spellingShingle |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) Sanches, Mirza Nalesso Gomes Determina??o estrutural Alcaloides ind?licos Desreplica??o Structural determination Indolic alkaloids Dereplication Qu?mica |
title_short |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
title_full |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
title_fullStr |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
title_full_unstemmed |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
title_sort |
Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae) |
author |
Sanches, Mirza Nalesso Gomes |
author_facet |
Sanches, Mirza Nalesso Gomes |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Braz Filho, Raimundo |
dc.contributor.advisor1ID.fl_str_mv |
CPF: 070.100.018-04 |
dc.contributor.referee1.fl_str_mv |
Oliveira, M?rcia Cristina Campos de |
dc.contributor.referee2.fl_str_mv |
Lima, Helena Regina Pinto |
dc.contributor.referee3.fl_str_mv |
Martins, Roberto Carlos Campos |
dc.contributor.referee4.fl_str_mv |
Oliveira, Marise Maleck de |
dc.contributor.referee5.fl_str_mv |
Marinho, Bruno Guimar?es |
dc.contributor.authorID.fl_str_mv |
CPF: 124.157.347-64 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9237258375836358 |
dc.contributor.author.fl_str_mv |
Sanches, Mirza Nalesso Gomes |
contributor_str_mv |
Braz Filho, Raimundo Oliveira, M?rcia Cristina Campos de Lima, Helena Regina Pinto Martins, Roberto Carlos Campos Oliveira, Marise Maleck de Marinho, Bruno Guimar?es |
dc.subject.por.fl_str_mv |
Determina??o estrutural Alcaloides ind?licos Desreplica??o |
topic |
Determina??o estrutural Alcaloides ind?licos Desreplica??o Structural determination Indolic alkaloids Dereplication Qu?mica |
dc.subject.eng.fl_str_mv |
Structural determination Indolic alkaloids Dereplication |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
The study species Simira grazielae Peixoto is popularly known as red macaw and is found in Brazil by the states of BA and ES. The aim of the present study was to contribute to the knowledge of the chemical composition of the species S. grazielae, family Rubiaceae, through the phytochemical and pharmacological study (against Rhipicephalus microplus larvae, the tyrosinase and antiinflammatory and antinociceptive enzyme) extracts and fractions. The wood material and bark was collected in the Forest Reserve of Vale do Rio Doce Company - ES, then dried at room temperature, crushed and subjected to exhaustive maceration process with methanol, without heating. The methanolic extract of the wood was subjected to liquid/liquid partition with n-hexane, dichloromethane, ethyl acetate and n-butanol, and a small amount of these partitions along with the extract were subjected to chemical prospecting. The fractions were chromatographed on standard exclusion silica gel columns (Sephadex LH-20) and analyzed by 1H and 13C NMR, GC-MS and LC-MS-IES. In addition to fractionation, extracts and partitioned fractions were subjected to dereplication analysis in the CLUE-IES-QTOF-EM/MS system in positive mode, a fast and accurate analysis for characterization of chemical profiles. The chemical prospecting tests showed positive results for the metabolites: saponins, steroids, triterpenoids, purines, coumarin derivatives, alkaloids, reducing sugars, saccharides and non-protein amino acids. Eighteen (18) substances were isolated and identified from S. grazielae wood: N-acetyl serotonin, Maxonin, Harmana, cis-N-p-coumaroyl serotonin, trans-N-p-coumaroyl serotonin, N-isoferuloil serotonin, N-feruloil serotonin (Moschamine), cis-moschamine, N-cafeloyl serotonin, Higarine, Ofiorina B, Ofiorina A, Strictosidinic Acid, Strictosidine, Mixed of Triacylglycerides, 5-Hydroxyendole-3-aldehyde, 6'-O-Vanilloylbarbutine and Desmethylisopauridiantidoyl acid unpublished in the literature. The technique of dereplication and the proposed fragmentation allowed to postulate the presence of 57 metabolites, almost all of them being indole alkaloids, of which 20 are being proposed as unpublished in the literature. The tests carried out of the species S. grazielae against the acaricidal activity on the R. microplus larvae in the fractions SGD, SGAc, SGB, SGR and on the action on the tyrosinase enzyme [Ofiorina B and the partitions (SGAc and SGB)] did not show significant results. The antiinflammatory and antinociceptive test performed on the fractions of S. grazielae wood showed to have action in these systems and this effect can be linked to the presence of serotonin-derived alkaloids. Thus, in this work we identify 18 substances isolated from S. grazielae wood and propose the additional presence of 57 metabolites through the dereplication technique involving mostly alkaloids, besides revealing the presence of fractions of the species with antiinflammatory and antinociceptive. |
publishDate |
2019 |
dc.date.issued.fl_str_mv |
2019-07-25 |
dc.date.accessioned.fl_str_mv |
2022-03-30T20:38:46Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SANCHES, Mirza Nalesso Gomes. Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae). 2019. 236 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2019. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/5501 |
identifier_str_mv |
SANCHES, Mirza Nalesso Gomes. Estudo fitoqu?mico e biol?gico de Simira grazielae (Rubiaceae). 2019. 236 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2019. |
url |
https://tede.ufrrj.br/jspui/handle/jspui/5501 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.references.por.fl_str_mv |
AMARAL, M. A. Z.; ROCHA, C. M. B. M.; FACCINI, J. L. H.; FURLONG, J.; MONTEIRO, C. M. O.; PRATA, M. C. A. Perceptions and attitudes among milk producers in Minas Gerais regarding catle tick biology and control. Rev. Bras. Parasitol. Vet., v. 20, p. 194-201, 2011a. AMARAL, M. A. Z.; ROCHA, C. M. B. M.; FACCINI, J. L. H.; FURLONG, J.; MONTEIRO, C. M. O.; PRATA, M. C. A. Strategic control of cattle ticks: milk producers perceptions. Rev. Bras. Parasitol. Vet., v. 20, p. 148-154, 2011b. AYRES, M.; AYRES JR., M.; AYRES, D. L.; SANTOS, A. S. dos BioEstat 5.0 - Aplica??es estat?sticas nas ?reas das ci?ncias biol?gicas e m?dicas. Manaus: Sociedade Civil Mamirau?/MCT-CNPq, 2007. BARRETT, C. B.; LYBBERT, T. J. Is bioprospecting a viable strategy for conserving tropical ecosystems? Ecol. Econ., v. 34, p. 293-300, 2000. BOLZANI, V. S.; JOVEM, M. C.; FURLAN, M.; CAVALHEIRO, A. J.; ARAUJO, R. A.; SILVA, D. H. Metab?litos secund?rios de esp?cies de plantas brasileiras de Rubiaceae: signific?ncia quimiotaxon?mica e biol?gica. Res. Recente Dev. Phytochem., v. 5, p. 19-31, 2001. BORGES, L. M. F.; SOUSA, L. A. D. de; BARBOSA, C. da S. Perspectives for the use of plant extracts to control the cattle tick Rhipicephalus (Boophilus) microplus. Rev. Bras. Parasitol. Vet., v. 20, n. 2, p. 89-96, 2011. BOTTCHER, T.; PITSCHEIDER, M.; SIEBER, S. A. Natural products and their biological targets: proteomic and metabolomic labeling strategies. Angew Chem. Int. Ed. Engl., v. 49, n. 15, p. 2680-2698, 2010. BUKHARI, I. A.; PIVAC, N.; ALHUMAYYD, M. S.; MAHESAR, A. L.; GILANI, A. H. O efeito analg?sico e anticonvulsivante da piperina em camundongos. J. Physiol. Pharmacol., v. 64, p. 789-794, 2013. CAMPOS, R. N. S.; BACCI, L.; ARA?JO, A. P. A.; BLANK, A. F.; ARRIGONI-BLANK, M. F.; SANTOS, G. R. A.; RONER, M. N. B. ?leos essenciais de plantas medicinais e arom?ticas no controle do carrapato Rhipicephalus microplus. Arch. Zootec., v. 61, p. 67-78, 2012. CASTRO, K. N. C.; LIMA, D. F.; VASCONCELOS, L. C.; LEITE, J. R. S. A.; SANTOS, R. C.; PAZ NETO, A. A.; COSTA-J?NIOR, L. M. Acaricide activity in vitro of Acmella oleracea against Rhipicephalus microplus. Parasitol. Res., v. 113, p. 3697-3701, 2014. CHANG, TE-SHENG. An Updated Review of Tyrosinase Inhibitors. Int. J. Mol. Sci., v. 10, p. 2440-2475, 2009. CHUNGSAMARNYART, N.; JANSAWAN, W. Acaricidal effect of practical crude-extracts of plants against tropical cattle tick (Boophilus microplus). Kasetsart J., v. 27, p. 57-64, 1993. CHUNGSAMARNYART, N.; JIWAJINDA, S.; JANSAWAN, W. Acaricidal effect of plant crude-extracts on the tropical cattle tick (Boophilus microplus). Kasetsart J., v. 25, p. 90- 100, 1991. COLLIER, H. O. J.; DINNEEN, L. C.; JOHNSON, C. A.; SCHNEIDER, C. The abdominal constriction response and its suppression by analgesic drugs in the mouse. Brit. J. Pharmacol. v. 32, n. 2, p. 295-310, 1968. DUBUISSON, D.; DENNIS, S. G. The formalin test: a quantitative study of the analgesic efects of morfine, merepidine, and brain stem stimulation in rats and cats. Pain. v. 4, p.161- 174, 1977. DUKE, S. O.; PAUL, R. N.; LEE, S. M. Biologically active natural products ? Potencial use in agriculture. In: PRATES, H. T.; LEITE, R. C.; CRAVEIRO, A. A.; OLIVEIRA, A. B. Identification of some chemical components of the essential oil from molasses grass (Melinis minutiflora Beauv.) and their activity against catle-tick (Boophilus microplus). J. Brazil. Chem. Soc., v. 9, n. 2, p. 193-197, 1998. FERRERO-MILIANI, L.; NIELSEN, O. H.; ANDERSEN, P. S.; GIRARDIN, S. E. A inflama??o cr?nica: Import?ncia da NOD2 e NALP3 na gera??o de interleucina-1?. Clin. Exp. Immunol. v. 147, p. 227-235, 2007. FURLONG, J.; MARTINS, J. R.; PRATA, M. C. A. O carrapato dos bovinos e a resist?ncia: temos o que comemorar? HV, v. 27, p. 1-7, 2007. FURLONG, J.; MARTINS, J. R. S.; PRATA, M. C. A. Controle estrat?gico do carrapato dos bovinos. HV, v. 23, p. 53-56, 2004. GOMES, G. A.; MONTEIRO, C. M. O.; SENRA, T. O. S.; ZERINGOTA, V.; CALMON, F.; MATOS, R. S., GOIS; R. W., DA S.; DAEMON, E.; SANTIAGO, G. M. P.; CARVALHO, M. G. Chemical composition and acaricidal activity of essential oil from on larvae of Rhipicephalus microplus (Acari: Ixodidae) and larvae and engorged females of Dermacentor nitens (Acari: Ixodidae). Parasitol. Res., v. 111, n. 6, p. 2423-2430, 2012. GRISI, L.; LEITE, R. C.; MARTINS, J. R.; BARROS, A. T.; CANCADO, P. H. D. Reassessment of economic impact by cattle parasites in Brazil. Rev. Brasil. Parasitol. Vet., v. 23, p. 150-156, 2014. HUNSKAAR, S.; HOLE, K. The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain, v. 30, p.103-114, 1987. IKEDA, Y.; UENO, A.; NARABA, H.; OH-ISHI. Involvement of vaniloid receptor VR1 and prostanoids in the acid-induced writhing responses of mice. Life Sci., v. 69, p. 2911- 2919, 2001. KARIOTI, A.; PROTOPAPPA, A.; MEGOULAS, N.; SKALTSA, H. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorgan. Med. Chem., v. 15, p. 2708-2714, 2007. KEMP, E. H.; GAWKRODGER, D. J.; WATSON, P. F.; WEETMAN, A. P. Immunoprecipitation of melanogenic enzyme autoantigens with vitiligo sera: evidence for cross-reactive autoantibodies to tyrosinase and tyrosinase-related protein- 2 (TRP-2). Clin. Exp. Immunol., v. 109, p. 495-500, 1997 KHAN, K. M.; MUGHAL, U. R.; KHAN, M. T. H.; ULLAH, Z.; PERVEENB, S.; CHOUDHARY, M. I. Oxazolones: New tyrosinase inhibitors; synthesis and their structure? activity relationships. Bioorgan. Med. Chem., v. 14, p. 6027-6033, 2006. KISS, T.; CADAR, D.; SP?NU, M. Tick prevention at a crossroad: new and renewed solutions. Vet. Parasitol., v. 187, p. 357-366, 2012. KLAFKE, G. M. Resist?ncia de R. (B.) microplus contra os carrapaticidas. In: PEREIRA, M. C.; LABRUNA, M. B.; SZABO, M. P. J.; KLAFKE, G. M. (Eds.). Rhipicephalus (Boophilus) microplus: Biologia, Controle e Resist?ncia. S?o Paulo: MEDVET. 2008. p. 81- 105. KOSTER, R.; ANDERSON, M.; DE BEER, E. J. Acetic acid for analgesic screening. Fed. Proc., v. 18, p. 412, 1959. LAPA, A. J.; SOUCCAR, C.; LIMA-LANDMAN, M. T. R.; CASTRO, M. S. A.; LIMA, T. C. M. M?todos de avalia??o da atividade farmacol?gica de plantas medicinais. S?o Paulo. UNIFESP/EPM, 2007. 144p. LE BARS, D.; GOZARIU, M.; CADDEN, S. W. Animals models of nociception. Pharmacol. Rev., v. 53, p. 597-652, 2001. LOBO, P. L. D.; FONTELES, C. S. R.; CARVALHO, C. B. M.; NASCIMENTO, D. F.; FONSECA, S. G. C.; JAMACARU, F. V. F.; MORAES, M. E. A. Dose-response evaluation of a novel essential oil against Mutans streptococci in vivo. Phytomedicine, v. 18, n. 1, p. 551-556, 2011. MACRINI, D. J.; SUFFREDINI I. B.; VARELLA A. D., YOUNES, R. N.; OHARA, M. T. Extracts from Amazonian plants have inhibitory activity against tyrosinase: an in vitro evaluation. Braz. J. Pharm. Sci., v. 45, n. 2, 2009. MANI, I.; SHARMA, V.; TAMBOLI, I.; RAMAN, G. Interaction of melanin with proteins - The impor tance of an acidic intramelanosomal pH. Pigm. Cell. Res., v. 14, p. 170-179, 2001. MATIAS, J.; KOLLER, W. W.; GARCIA, M. V. Classifica??o, distribui??o geogr?fica, ciclo biol?gico e import?ncia econ?mica das principais esp?cies de carapatos no Brasil. In: ANDREOTTI, R.; KOLLER, W. W. Carrapatos no Brasil: Biologia, Controle e Doen?as transmitidas. Campo Grande: Embrapa. 2013. p. 1-13. MIOT, L. D. B.; MIOT, H. A.; SILVA, M. G. da; MARQUES, M. E. A. Fisiopatologia do melasma. Na. Bras. Dermatol., v. 84, p. 623-635, 2009. MONTEIRO, C. M. O.; MATURANO, R.; DAEMON, E.; CATUNDA-JR, F. E. A.; CALMON, F.; SENRA, T. O. S.; FAZZA, A. P.; CARVALHO, M. G. Acaricidal activity of eugenol on Rhipicephalus microplus (Acari: Ixodidae) and Dermacentor nitens (Acari: Ixodidae) larvae. Parasitol. Res., v. 111, p. 1295-1300, 2012. NEWMAN, D. J.; CRAGG, G. M. Natural Products As Sources of New Drugs over the 30 Years from 1981 to 2010. J. Nat. Prod., v. 75, n. 3, p. 311-335, 2012. OKOMBI S.; RIVAL D.; BONNET S.; MARIOTTE A. M.; PERRIERB E.; BOUMENDJEL A. Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocytetyrosinase. Bioorg. Med. Chem. Lett., v. 16, n. 8, p. 2252-2255, 2006. PASQUET, V.; MORISSET, P.; IHAMMOUINE, S.; CHEPIED, A.; AUMAILLEY, L.; BERARD, J. B., SERIVE, B.; KAAS, R.; LANNELUC, I.; THIERY, V. et al. Antiproliferative activity of violaxanthin isolated from bioguided fractionation of Dunaliella tertiolecta extracts. Mar. Drugs, v. 9, p. 819-831, 2011. PATIL, S. S.; ZUCKER, M. Potato phenolases. J. Biol. Chem., v. 240, p. 3938-3943, 1965. PEREIRA, M. C. Introdu??o. In: PEREIRA, M. C.; LABRUNA, M. B.; SZAB?, M. P. J.; KLAFKE, G. M. (eds) Rhipicephalus (Boophilus) microplus: Biologia, Controle e Resist?ncia. S?o Paulo: MEDVET. 2008. p.1?5. S?NCHEZ-MATEO, C. C.; BONKANKA, C. X.; HERN?NDEZ-P?REZ, M.; RABANAL, R. M. Avalia??o dos efeitos anti-inflamat?rios analg?sicos e t?picos do Hypericum reflexum L. fil. J. Ethnopharmacol., v. 107, p. 1-6, 2006. SANTOS, C. M,; SANCHES, M. N. G.; S. A. C. D.; CARVALHO, M. G.; BRAZ-FILHO, R.; MARINHO, B. G. Participation of cytokines, opioid, and serotoninergic systems on antinociceptive and anti-inflammatory activities of Simira grazielae peixoto (Rubiaceae). Pharmacogn. Res. v. 11, p. 51-59, 2019. SANTOS, G.C; FERNANDES, R.D; BARROS, T.R; ABREU HDOS S.; SUZART, L.R.; CARVALHO, M.G.; BRAZ-FILHO, R.; MARINHO, B.G. Antinociceptive and anti-inflammatory activities of the methanolic extract from the stem bark of Lophanthera lactescens. Planta Med. v.81, p.1688-96, 2015. SCHMITT EK, MOORE CM, KRASTEL P, PETERSEN F. Natural products as catalysts for innovation: a pharmaceutical industry perspective. Curr. Opin. Chem. Biol., v. 15, n. 4, p. 497-504, 2011. SEO, S. Y.; SHARMA, V. K.; SHARMA, N. Mushroom tytosinase: recent prospects. J. Agr. Food Chem., v. 51, p. 2837-2853, 2003. STONE, B. F.; HAYDOCK, K. P. A method for measuring the acaricide susceptibility of the cattle B. microplus (Can.). B. Entomol. Res., v. 53, p. 563-578, 1962. TJOLSEN, A.; O. G. BERGE; S. HUNSKAAR; J. H. ROSLAND; K. HOLE. The formalin test: an evaluation of the method. Pain. v. 51, p. 5-17, 1992. TSALA, D. E.; AMADOU, D.; HABTEMARIAN, S. Natural wound healing and bioactive natural products. Phytopharmacology, v. 4, n. 3, p. 532-560, 2013. UJANG, Z. B.; SUBRAMANIAM, T.; DIAH, M. M.; WAHID, H. B.; ABDULLAH, B. B.; RASHID, A. H. B. A.; APPLETON, D. Bioguided Fractionation and Purification of Natural Bioactives Obtained from Alpinia conchigera Water Extract with Melanin Inhibition Activity. J. Biomaterials and Nanobiotechnology, v. 4, p. 265-272, 2013. WADLEIGH, D. J.; REDDY, S. T.; KOPP, E.; GHOSH, S.; HERSCHMAN, H. R. Transcriptional activation of the cyclooxygenase-2 gene in endotoxin-treated RAW 264.7 macrophages. J. Biol. Chem., v. 275, p. 6259-6266, 2000. WORLD HEALTH ORGANIZATION (WHO). The world medicines situation 2011: traditional medicines: global situation, issues and challenges. Geneva: WHO, 2011. 12p. |
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