Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana

Detalhes bibliográficos
Autor(a) principal: Carvalho Junior, Almir Ribeiro de
Data de Publicação: 2013
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações da UFRRJ
Texto Completo: https://tede.ufrrj.br/jspui/handle/jspui/3459
Resumo: The genus Eugenia (Myrtaceae) comprises about 550 species of trees and shrubs, mainly found in Central and South America. Several species are used in folk medicine to treat diseases such as diabetes, chronic diarrhea, body aches, skin rash, etc. This has motivated diverse studies related to both the chemical composition and the biological properties of the genus. The objective of this work was to study the chemical profile of the species Eugenia copacabanensis, besides evaluating its antioxidant and atimicrobiano potential. The compounds described in this work were isolated from chromatographic techniques and identified by 1H and 13C NMR, GC-MS experiments besides comparison with literature data. From leaves of E. copacabanenis were isolated and -amyrin, ursolic acid, 30-hydroxy-ursolic acid (rubif?lico), betulin, -sitosterol, -sitosterol glycoside, clovanodiol, globulol, viridiflorol and the flavonoids kaempferol-3-O-ramnosideo, quercetin-3-O-arabinoside, and quercetin. While from branches were isolated, friedelin, friedelan-3,4-lactone, taraxerol, octacosanyl coumarate, heptacosanyl coumarate, hexacosanyl coumarate and teracosanyl coumarate. From acetylation and methylation reactions of acid 30-hydroxy-ursolic it were obtained: diacetyl rubifolic acid methyl diacetyl rubifolato respectively. The antioxidant activity of the extracts and fractions was evaluated by DPPH and -carotene-linoleic acid methods. In both cases, we obtained excellent results with EC50 values ranging between 0.92 ?0.04 and 40.7 ? 1.0 g/ml and % inhibition between 28.7 ?7.9 to 90.0 ? 0.1%. Antimicrobial activity was evaluated against the microorganisms, Staphylococcus aureus, Candida albicans, Cryptococcus neoformans and Rhizopus oryzae and extracts and fractions of E. copacabanensis were not active until the concentration of 2.5 mg / mL.
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spelling Carvalho, Mario Geraldo de257.152.327-91http://lattes.cnpq.br/9794451665032168Figueiredo, Maria RaquelOliveira, Rodrigo Rodrigues deOliveira, Marcia Cristina Campos de125.085.417-29http://lattes.cnpq.br/7191491222073956Carvalho Junior, Almir Ribeiro de2020-04-27T14:46:09Z2013-04-16CARVALHO JUNIOR, Almir Ribeiro de. Metab?litos Especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana. 2013. 126 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013.https://tede.ufrrj.br/jspui/handle/jspui/3459The genus Eugenia (Myrtaceae) comprises about 550 species of trees and shrubs, mainly found in Central and South America. Several species are used in folk medicine to treat diseases such as diabetes, chronic diarrhea, body aches, skin rash, etc. This has motivated diverse studies related to both the chemical composition and the biological properties of the genus. The objective of this work was to study the chemical profile of the species Eugenia copacabanensis, besides evaluating its antioxidant and atimicrobiano potential. The compounds described in this work were isolated from chromatographic techniques and identified by 1H and 13C NMR, GC-MS experiments besides comparison with literature data. From leaves of E. copacabanenis were isolated and -amyrin, ursolic acid, 30-hydroxy-ursolic acid (rubif?lico), betulin, -sitosterol, -sitosterol glycoside, clovanodiol, globulol, viridiflorol and the flavonoids kaempferol-3-O-ramnosideo, quercetin-3-O-arabinoside, and quercetin. While from branches were isolated, friedelin, friedelan-3,4-lactone, taraxerol, octacosanyl coumarate, heptacosanyl coumarate, hexacosanyl coumarate and teracosanyl coumarate. From acetylation and methylation reactions of acid 30-hydroxy-ursolic it were obtained: diacetyl rubifolic acid methyl diacetyl rubifolato respectively. The antioxidant activity of the extracts and fractions was evaluated by DPPH and -carotene-linoleic acid methods. In both cases, we obtained excellent results with EC50 values ranging between 0.92 ?0.04 and 40.7 ? 1.0 g/ml and % inhibition between 28.7 ?7.9 to 90.0 ? 0.1%. Antimicrobial activity was evaluated against the microorganisms, Staphylococcus aureus, Candida albicans, Cryptococcus neoformans and Rhizopus oryzae and extracts and fractions of E. copacabanensis were not active until the concentration of 2.5 mg / mL.O g?nero Eugenia (Myrtaceae) compreende cerca 550 esp?cies de ?rvores e arbustos, principalmente, encontrados nas Am?ricas do Sul e Central. V?rias esp?cies do g?nero s?o usadas na medicina popular no tratamento de enfermidades, tais como: diabetes, diarreia cr?nica, dores no corpo, irrita??o na pele, etc. Isto tem motivado diversos estudos relacionados tanto a composi??o qu?mica, quanto ?s propriedades biol?gicas do g?nero. O objetivo deste trabalho foi estudar o perfil qu?mico da esp?cie Eugenia copacabanensis Kiaersk, al?m de avaliar o potencial antioxidante e atimicrobiano da mesma. As subst?ncias descritas nesse trabalho foram isoladas a partir de t?cnicas cromatogr?ficas e identificadas atrav?s de experimentos de RMN de 1H e 13C e compara??o com dados da literatura. Das folhas de E. copacabanenis foram isolados os triterpenos e -amirina, ?cido urs?lico, ?cido 30-hidroxi-urs?lico (?cido rubif?lico) e betulina, os sesquiterpenos clovanodiol, globulol, viridiflorol, esteroides -sitosterol, -sitosterol glicosilado e flavonoides canferol-3-O-ramnosideo, quercetina-3-O-arabinosideo, quercetina. Enquanto que dos galhos foram isolados, friedelina, friedelan-3,4-lactona, taraxerol e os cumaratos de octacosanila, heptacosanila, hexacosanila e teracosanila. A partir de rea??es de acetila??o e metila??o do ?cido 30-hidroxi-urs?lico foram obtidos dos derivados: o ?cido diacetil rubif?lico e diacetil metil rubifolato, respectivamente. A atividade antioxidante dos extratos e fra??es foi avaliada pelos m?todos DPPH e -caroteno-?cido linoleico. Em ambos os casos, obteve-se ?timos resultados, com valores de CE50 variando entre 0,92?0,04 e 40,7?1,0 g/mL e % de inibi??o de degrada??o entre 28,7?7,9 a 90,0?0,1%. A atividade antimicrobiana foi avaliada frente aos microorganismos , Candida albicans, Cryptococcus neoformans e Rhizopus oryzae e os extratos e fra??es de E. copacabanensis n?o foram ativos at? a concentra??o de 2,5 mg/mL.Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2020-04-27T14:46:08Z No. of bitstreams: 1 2013 - Almir Ribeiro de Carvalho Junior.pdf: 4989381 bytes, checksum: a1fb407e438d1562ab935c38fb3637f6 (MD5)Made available in DSpace on 2020-04-27T14:46:09Z (GMT). No. of bitstreams: 1 2013 - Almir Ribeiro de Carvalho Junior.pdf: 4989381 bytes, checksum: a1fb407e438d1562ab935c38fb3637f6 (MD5) Previous issue date: 2013-04-16Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico, CNPq, Brasilapplication/pdfhttps://tede.ufrrj.br/retrieve/14376/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/17428/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/23770/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/30138/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/36576/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/42960/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/49260/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpghttps://tede.ufrrj.br/retrieve/55700/2013%20-%20Almir%20Ribeiro%20de%20Carvalho%20Junior.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias ExatasAHN, M. R.; KUMAZAWA, S.; USUI, Y.; NAKAMURA, J.; MATSUKA, M.; ZHU, F.; NAKAYAMA, T. Antioxidant activity and constituents of pr?polis collected in variou ?reas of china. Food Chem, 101, 1383-1392, 2007. ALVES, C. Q.; DAVID, J. M.; DAVID, P. J.; BAHIA, M. V.; AGUIAR, R. M. M?todos para determina??o de atividade antioxidante in vitro em substratos org?nicos. Quim. Nova 33 (10), 2202-2210, 2010. AMORIM, A. C. L.; LIMA, C. K. F.; HOVELL, A. M.; MIRANDA, A. L. P.; REZENDE, C. M. Antinociceptive and hipothermic avaluation of the leaf essential oil and isolated terpenoids from Eugenia uniflora (Brazilian Pitanga). Phytomedicine 16, 923-928, 2009. ATOUI, A. K.; MANSOURI, A.; BOSKOU, G.; KEFALAS, P. Tea and herbal infusions: their antioxidant activity and phenolic profile. Food Chem. 89 (1), 27-36, 2005. BAHIA, M. V. Ocorr?ncia de biflavonoides e derivado de ?cido benzoico do cerne e folhas de Caesalpinia pyramidalis e Peltophorum dubium (Leguminosae). Tese de doutorado. Programa de P?s-gradua??o em Qu?mica, Instituto de Qu?mica, Universidade Federal da Bahia, 2007. BANDEIRA, P. N.; LEMOS, T. L. G.; COSTA, S. M. O.; DOS SANTOS, H. S. Obten??o de derivados da mistura triterpenoidica a e b-amirina. Rev. Bras. Farmacogn. 17 (2), 204-208, 2007. BANNON, C. D.; RONALD, A.; SIMES, J. J. H. Extractives of Australian timbers. XVI The constituents of the wood of Eugenia crebrinervis (syn Syzygium crebrinerve) and Eugenia gustavinoides (syn Syzygium gustavinoides). Aust. J. Chem. 29, 1135-1141, 1976. BARREIROS, A. L. B. S.; DAVID, J.. M.; DAVID, J. P. Estresse oxidativo: rela??o entre gera??o de esp?cies reativas e defesa do organismo. Quim. Nova 29 (1), 113-123, 2006. 116 BENAVENT-GARCIA, O.; CASTILLO, J.; LORENTE, J.; ORTUNO, A.; DELRIO, J. A. Antioxidant activity of phenolic extracted from Olea europaea L. leaves. Food Chem-Review 72, 145-171, 2001. BERT?, T. E. Estudo da atividade anticolinester?sica dos compostos taraxerol e ?cido urs?lico: implica??es sobre processo da mem?ria. Disserta??o de Mestrado, Programa de P?s-gradua??o em Ci?ncias Farmac?uticas, Universidade do Vale do Itaja?, 2009. BHARGAVA, K. K.; DAYAL, R.; SESHADRI, T. R. Chemical components of Eugenia jambolana stem bark. Current Science 43 (20), 645-646, 1974. BRASILEIRO, B. G.; PIZZIOLO, V. R.; MATOS, D. S.; GERMANO, A. M.; JAMAL, C.M Plantas medicinais utilizadas pela popula??o atendida no ?Programa de Sa?de da Fam?lia?, Governador Valadares, MG, Brasil. Rev. Bras. Cienc. Farma. 44 (4), 629-636, 2008. BRIGGS, L. H.; CAMBIE, R. C.; LOWRY, J. B.; SEELVE, R. N. Constituents of Eugenia maire A. Cunn. Part I. A trimethyl ether acid and mairin, a new triterpene. J. Chem. Soc. 642-645, 1961. CALA, A. R. S.; MACHADO, D. G.; BRITTO, L. E. B.; COLLA, G.; MAGINA, M. D. A.; BRIGHENTE, I. M .C.; RODRIGUES, A. L. S. Involvement of monoaminergic systems in the antidepressant-like effects of Eugenia brasiliensi Lam. (Myrtaceae) in the tail suspension test in mice. J. Ethnopharmacol. 143, 720-731, 2012. CAMPOS, M. G.; WEBBY, R. F.; MARKHAM, K. R.; MITCHELL, K. A.; DA CUBHA, A. P. Age-induced diminution of free radical scavenging capacity in bee pollens and the contribution of constituent flavonoids. Journal of Agricultural and Food Chem 51 (3), 742-745, 2003. CANDY, H. A.; MACGARRY, E. J.; PEGEL, K. H. Constituents of Syzygium cordatum. Phytochemistry 7 (5), 889-890, 1968. CARDOSO, C. M. V.; SAJO, M. G. Nerva??o em esp?cies brasileira de Myrtaceae Adans. Acta bot. Br?s. 20 (3), 657-669, 2006. CARVALHO JR, A. R.; GOMES, G. A.; CORDEIRO, G. M.; CARVALHO, M. G. Triterpenes and Flavonoid from Eugenia copacabanensis and DPPH Scavenging Activity. III International Symposium Medicinal and Nutraceutical Plants, Aracaju-SE, 2012. CARVALHO JR, A. R.; GOMES, G. A.; GOMES, T. R. C.; CARVALHO, M. G. Metabolitos especiais isolados de Eugenia copacabanensis (Myrtaceae). 35? Reuni?o Anual da Sociedade Brasileira de Qu?mica, ?guas de Lind?ia-SP, 2011. 117 CARVALHO, M.G. DE, ROCHA JUNIOR, G. G.; CAVATTI, L.C.; SUZART, L.R.; CORNELIUS, M.T.F.; SILVA, V.C. DA; CARDOSO, M.A.R.; Determina??o Estrutural de Flavon?ides com An?lie de Espectros de RMN de 1H e Incorpora??o de Diazometano. Rev. Univ. Rural, S?r. Ci. Exatas e da Terra. Serop?dica, RJ, EDUR, v. 25, n. 1-2., 46-60, 2006. CASSANITI, C.; LEONARD, C.; FLOWERS, T. The effect of sodium chloride on ornamental shrubs. Sci Hortic-Amsterdan 122, 586-593, 2009. CHANDRASEKARAN, M.; VENKATESALU, V. Antibacterial and antifungal activity of Syzygium jambolanum seeds. J. Ethnopharmacol. 91, 105-108, 2004. CHANDRASEKARAN, M.; VENKATESALU, V. Antibacterial and antifungal activity of Syzygium jambolanum seeds. J. Ethnopharcol. 91, 105-108, 2004. CHUN, D.; JIAN, L.; BAIS, B.-R.; PENG, S.-L.; DING, L.-S. A new glucosidade gallate from the flower buds of Eugenia caryophyllate. Chinese Journal of Natural Medicine 8 (3), 180-182, 2010. CLINICAL AND LABORATORY STANDARDS INSTITUTS (CLSI). Methods for dilution antimicrobial susceptibility tests. 4th ed. Wayne (PA),. Approved Standard, Normas M27-A3, M38-A2, M11-A6 e M7-A4 2008. COLE, R. A.; BANSAL, A.; MORIARITY, D. M.; HABER, W. A.; SETZER, W. N. Chemical composition and cytotoxic activity of the leaf essential oil of Eugenia zuchowskiae from Monteverde, Costa Rica. J. Nat. Med. 61, 414-417, 2007. COSTA, D. P.; FILHO, E. G. A.; SILVA, L. M. A.; SANTOS, S. C.; PASSOS, X. S.; SILVA, M. R. R.; SERAPHIN, J. C.; FERRI, P. H. Influence of fruit biotypes on the chemical composition and antifungal activity of the essential oils of Eugenia uniflora leaves. J. Braz. Chem. Soc. 21 (5), 851-858, 2010 CRUZ, A. V. M.; KAPLAN, M. A. C. Uso medicinal de esp?cies das fam?lias Myrtaceae e Melastomataceae no Brasil. Floresta e Ambiente 11, 47-52, 2004. DE OLIVEIRA, A. M.; HUMBERTO, M. M. S.; DA SILVA, J. M.; DE ALMEIDA ROCHA, R. F.; SANT?ANA, A. E. G. Estudo fitoqu?mico e avalia??o das atividades moluscicida e larvicida dos extratos de casca do caule e folha de Eugenia malacsensis L. (Myrtaceae). Rev. Bras. Farmacogn. 16 (supl), 618-624, 2006. DE OLIVEIRA, A., M.; HUMBERTO, M. M. s.; DA SILVA, J. M.; DE ALMEIDA ROCHA, R. F.; SANT?ANA, A. E. G. Estudo fitoqu?mico e avalia??o das atividades 118 moluscida e larvicida dos extratos da casca do caule e folha de Eugenia malaccensis L. (Myrtaceae). Rev. Bras. Farmacogn. 16 (supl), 618-624, 2006. DE OLIVEIRA, R. N.; DIAS, I. J. M.; C?MARA, C. A. G. Estudo comparativo do ?leo essencial de Eugenia punicifolia (HBK) DC. De diferentes localidades de Pernambuco. Rev. Bras. Farmacogn. 15 (1), 39-43, 2005. DEFAVERI, A. C. A.; SATO, A.; BON?, L. B.; AGUIAR, D. L. M.; SAN GIL, R. A. S.; ARRUDA, R. C. O.; RIEHL, C. A. A. Eugenia neotida and Eugenia rotundifolia Casar. (Myrtaceae) essential oils: composition, seasonality influence, antioxidant activiy and leaf histochemistry. J. Braz. Chem. Soc. 22, 1531-1538, 2011. DELGADO, G.; C?RDENAS, H.; PEL?EZ, G.; VIVAR, A. R. Terpenoids from Vigueira oaxacana. J. Nat. Prod., 47, 6, 1042-1045, 1984. DEWIR, Y. H.; SINGH, N.; MNGOMEZULU, S.; OMAR, A. M. K. Micropropagation and detection of important triterpenes in vitro and Field growon plants of Syzygium cordatum. J. Med. Pants Res. 5 (14), 3078-3083, 2011. DHAMARATNE, H. R. W.; SOTHEESWARAN, S.; BALASUBRAMANIAM, S. Triterpenes and Neoflavonoids of Calophyllum lankaensis and Calophyllum thwaitesii. Phytochemistry, 23, 2601-2603, 1984. DIAS, M. O.; HAMERSKI, L.; PINTO, A. C. Separa??o semipreparativa de e -amirina por cromatografia l?quida de alta efici?ncia. Quim. Nova 34 (4), S1-S6, 2011. DJOUKENG, J. D.; ABOU-MANSOUR, E.; TABACCHI, R.; TAPONDJOU, A. L.; BOUDA, H.; LMAONTSI, D. Antibacterial triterpenes from Syzygium guineense (Myrtaceae). J. Ethnopharmacol. 101, 283-286, 2005. DONATINI, R. S.; ISHIKAWA, T.; BARROS, S. B. M.; BAECHI, E. M. Atividade anti?lcera e antioxidante do extrato de folhas de Syzygium jambos (L.) Alston (Myrtaceae). Rev. Bras. Farmacogn. 19 (1A), 89-94, 2009. FLORES, G.; DASTMALCHI, K.; PAULINO, S.; WHALEN, K.; DABO, A. J.; REYNERTSON, K. A.; FORONJY, R. F.; AMIENTO, J. M. D.; KENNELY, E. J. Anthocyanins from Eugenia brasiliensis edible fruits as potential therapeutics for COPD treatment. Food Chem. 134, 1256-1262, 2012. 119 FRIGHETTO, N.; WELENDORF, R. M.; DA SILVA, A. M. P.; NAKAMURA, M. J.; SIANI, A. C. Purification of betulinic acid from Eugenia florida (Myrtaceae) by high-speed counter current chromatography. Phytochem. Anal. 16, 411-414, 2005. GOMES DA SILVA, A. L.; PINHEIRO, M. C. B. Biologia floral e da poliniza??o de quatro esp?cies de Eugenia L. (Myrtaceae). Acta bot. br?s. 21 (1), 235-247, 2007. GOMES, M. S. R. Constituintes qu?micos isolados da raiz de Piptadenia rigida (Leguminosae-Mimosoideae). Disserta??o de mestrado. Programa de P?s-gradua??o em Qu?mica Org?nica, Instintuto de Ci?ncias Exatas, Departamento de Qu?mica, Universidade Federal Rural do Rio de Janeiro, 2002. GOPAN, R.; VARUGHESE, G.; NEDIYAPARAMBIL, P.; MATHUR, S. Volatile constituents and antibacterial activity of Eugenia rottleriana Wight et Arn. Leaf oil. J. Essent. Oil Res. 19 (6), 588-590, 2007. GOTTLIEB, O. R.; DA SILVA, L.; MARIA, J. G. S. Eucalyptin from Eugenia and Myrcia species. Phytochemistry 11, 1185-1186, 1972. GRANGEIRO, M. S.; CALHEIROS-LIMA, A. P.; MARTINS, M. K.; ARRUDA, L. F.; GARCEZ-DO-CARMO, ?.; SANTOS, W. C. Pharmacological effects of Eugenia punicifolia (Myrtaceae) in cholinergic neurotransmission. J. Ethnopharmacol. 108 (1) 26-30, 2006. GU, J.-Q.; PARK, E. J.; LUYENGI, L.; HAWTHORNE, M.; KINGHORN, A. D. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochemistry 58, 121-127, 2001. GUIMAR?ES, A. G.; MELO, M. S.; BONFIM, R. R.; PASSOS, L. O.; MACHADO, S. M. F.; RIBEIRO, A. DE S.; SOBRAL, M.; THOMAZZI, S. M.; QINTANS-J?NIOR, L. J. Antinoceptive and anti-inflammatory effects of the essential oil of Eugenia candolleana DC., Myrtaceae, on mice. Rev. Bras. Farmacog. 19 (4), 883-887, 2009. GUPTA, G. S.; SHARMA, D. P. Triterpenoids and other constituents of Eugenia jambolana leaves. Phytochemistry 13 (9), 2013-2014, 1974. HANSON, J. T.; HITCHCOCK, P. B.; MANICKAVASAGAR, R. The Hidroxilation of Globulol and 7-Epiglobulol by Cephalosporium Aphidicola. Phytochemistry 37, 1023-1025, 1994. HARON, N. W.; MOORE, D. M.; HARBORNE, J. B. Distribution and taxonomic significance of flavonoids in the genus Eugenia (Myrtaceae). Biochem. Syst. Ecol. 20 (3), 265-268, 1992. 120 HARRIS, S.M.; MCFEETERS, H.; OGUNGBE, I.; CRUZ, V. L.; SELTZER, W. N.; WILLIAN, N.; JAKES, B. R.; MCFEETERS, R. L. Peptidyl-tRNA hydrolase screening with molecular docking reveals the antibiotic potential of Syzygium johnsonii bark extract. Nat. Prod. Commun. 6 (10), 1421-1424, 2011. HENRIQUES, A. T.; SOBRAL, M.; CAUDURO, A. D.; SCHAPOVAL, E. E. S.; BASSANI, V. L.; LOMATY, G.; MENUT, C.; BESSIERE, J. M. Aromatic plants from Brazil. II. The chemical composition of some Eugenia essential oils. J. Essent. Oil. Res. 5, 501-505, 1993. HUSSEIN, S. A. M.; HASHEM, A. N. M.; SALIEM, M. A.; LINDEQUIST, U.; NAWWAR, M. A. M. Polyoxynated flavonoids from Eugenia edulis. Phytochemistry 64, 883-889, 2003. HUSSEIN, S. A. M.; HASHEN, A. N. M.; SALIEM, M. A.; LINDEQUIST, U.; NAWWAR, M. A. M. Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry 64, 883-889, 2003. JAYASINGHE, U. L. B.; RATNAYAKE, R. M. S.; MEDAWALA, M. M. W. S.; FUJIMOTO, Y. Nat. Prod. Res. 21 (6), 551-554, 2007. JORGE, T. C. M. Estudo qu?mico e farmacol?gico de duas esp?cies da fam?lia Rubiaceae: Cephalanthus glabratus e Palicourea crocea. Tese de doutorado, Programa de P?s-gradua??o em Qu?mica, CCE, Departamento de Qu?mica, Universidade Estadual de Maring?, 2005. JOTHI, G. J.; BENNIAMIN, A.; MARIDASS, M.; RAJU, G. Identification of essential oils composition and antifungal activity of Eugenia singampattiana fruits. Pharmacologyonline (2, News Letters), 727-733, 2009. JUNGES, M. J.; FERNANDES, J. B.; VIEIRA, P. C.; DA SILVA, M. F. G. F.; FILHO, E. R. The use of 13C and 1H-NMR in the structural elucidation of a new nor-lupane triterpene. J. Braz. Chem. Soc. 10 (4), 317-320, 1999. KALA, S. M. J.; BALASUBRAMANIAN, T.; SORIS, P. T.; MOHAN, V. R. GC-MS determination of bioactive components of Eugenia singampattiana Bedd. Int. J. Chem Tec Res. 3 (3), 1534-1537, 2011. KIM, H. J.; LEE, J. S.; WOO, E.-R.; KIM, M. K.; YANG, B. S.; YU, Y. G.; PARK, H.; LEE, Y. S. Isolation of virus-cell fusion inhibitory components from Eugenia caryophyllate. Planta Med. 67, 277-279, 2001. 121 KIM, Y.-J.; KIM, H.-C.; KO, H.; AMOR, E.-C.; LEE, J. W. Inhibitory effects of aurentiacin from Syzygium samarangense on lipolysaccharide-induced inflammatory response in mouse macrophages. Food Chem. Toxicol. 50, 1027-1035, 2012. KOUIDHI, B.; ZMANTAR, T.; BAKHROUT, A. Anticariogenic and cytotoxic activity of clove essential oil (Eugenia caryophyllata) against a large number of oral pathogens. Ann. Microbiol. 60, 599-604, 2010. KUIATE, J.-R.; MOUOKEU, S.; WABO, H. K.; TANE, P. Antidermatophytic triterpenoids from Syzygium jambos (L) Aston (Myrtaceae). Phytother. Res. 21, 149-152, 2007. KUO, Y.-C.; YANG, L.-M.; LIN, L.-C. Isolation and imunomodulatory effect of flavonoids from Syzygium samarangense. Planta Med. 70, 1237-1239, 2004. KUSKOSKI, E. M.; VEJA, J. M.; RIOS, J. J.; FETT, R.; TRONCOSO, A. M.; AURERO, A. G. Characterization of anthocyanins from the fruits of bagua?u (Eugenia umbelliflora Berg). J. Agric. Food Chem. 51, 5450-5454, 2003 LAPHOOKIEO, S.; KARALAI, C.; PONGLIMANONT, C. New sesquiterpenoid and triterpenoids from the fruit of Rhizophora mucronata. Chem Pharm Bull. 52, 883-885, 2004. LEE, J. H.; LEE, K. T.; YANG, J. H.; BAEK, N. I.; KIM, D. K. Acetylcholinesterase inhibitors from tthe Twings of Vaccinium Oldhami Miquel. Arch. Pharm. Res, v. 27, n. 1, p. 53-56, 2004. LIMA, T. B.; SILVA, O. N.; OLIVEIRA, J. T. A.; VASCONCELOS, I. M.; SCALOBRIN, F. B.; ROCHA, T. L.; GROSSI-DE-S?, M. F.; SILVA, L. P.; GUADONIN, R. V.; QUIRINO, B. F.; CASTRO, C. F. S.; LEONARDECZ, E.; FRANCO, O. L. Identification on Eugenia dysenterica laxative peptide: A novel strategy in the treatment of chronic constipation and irritable bowel syndrome. Peptides 31, 1426-1433, 2010. LIU, J.-X.; DI, D.-L.; SHI, Y.-P. Diversity of chemical constituents from Saxifraga Montana H. J. Chin. Chem. Soc. 55 (4), 863-870, 2008. LOCHER, C. P.; BURCH, M. T.; MOWER, H. R.; BERESTECKY, J.; DAVIS, H.; POIL, B.; LASURE, A.; VANDEN BERGHE, D. A.; VLIETINCK, A. S. Anti-microbial activity and anti-complement activity of extracts obtained from selected Hawaiian medicinal plants. J. Ethnopharmacol. 49, 23-32, 1995. LUNARD, I.; PEIXOTO, J. L. B.; DA SILVA, C. C.; SHUQUEL, I. T. A.; BASSO, E. A.; VIDOTTI, G. J. J. Braz. Chem. Soc. 12 (2), 180-183, 2001. 122 MACEDO, A. F.; OSHIIWA, M.; GUARIDO, C. F. Ocorr?ncia do uso de plantas medicinais por moradores de bairro do munic?pio de Mar?lia-SP. Rev. Cienc. Farm. Apl. 28 (1), 123-128, 2007. MACHADO, K. E.; FILHO, V. C.; CRUZ, R. C. B.; MEYRE-SILVA, C.; CRUZ, A. B. Antifungal activity of Eugenia umbelliflora against dermatophytes. Nat. Prod. Commun. 4 (9), 1181-1184, 2009. MAGINA, M. A.; GILIOLI, A.; MORESCO, H. H.; COLLA, G.; PIZZOLATTI, M. G.; BRIGHENTE, I. M. C. Atividade antioxidante de tr?s esp?cies de Eugenia (Myrtaceae). Lat. J. Am. J. Pharm. 29 (3), 376-382, 2010. MAGINA, M. D. A.; DALMARCO, E. M.; DALMARCO, J. B. Bioactive triterpenes and phenolics of leave of Eugenia brasiliensis. Quim. Nova 35 (6), 1184-1188, 2012. MAGINA, M. D. A.; DALMARCO, J. B.; PIZZOLATTI, M. G.; BRIGHENTE, I. M. C. Chemical composition and antibacterial activity of essential oils of Eugenia species. J. Nat. Med. 63, 345-350, 2009. MAGINA, M. D. A.; PIETROVSKI, E. F.; GOMIG, F.; FALKENBERG, D. B.; CABRINI, D. A.; OTUKI, M. F.; PIZZOLATI, M. G.; BRIGHENTE, I. M. C. Topical antiinflamatory activity and chemical composition of the epicuticular wax from the leaves of Eugenia meaurepaireana (Myrtaceae). Braz. J.Pharm. Sci. 45, 171-, 2009. MAHMOUD, I. I.; MARZOUK, M. S. A.; MOHARRAM, F. A.; EL-GIND, M. R.; HASSAN, A. M. K. Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry 58, 1239-1244, 2001. MAJUMDAR, S. G.; THAKUR, S. Chemical investigation of the leaves of Eugenia formosa. J. Indian Chem. Soc. 47 (2), 181-182, 1970. MANOHARAN, K. P.; SONG, F. J.; BENNY, T. K. H.; YANG, D. Triterpenoids from Eugenia grandis: structure elucidation by NMR espectroscopy. Magn. Reson. Chem 45, 279-281, 2007. MARIDASS, M. Composition and anti-inflamatory activity of the essential oil of Eugenia dysenterica (Myrtaceae). Journal of Essential Oil Therapeutics 2 (4), 163-166, 2008. MEDA, A.; LAMIEM, C. E.; ROMITO, M.; MILLOGO, J.; NACOULMA, O. G. Determination of the total phenolic, flvonoide and proline contents in Burkina Fasan honey, as well as their radica scavenging activity. Food Chem, 91, 571-577, 2005. 123 MELEND?Z, P.A., CAPRILES, V.A. Antibacterial properties of tropical plants from Puerto Rico. Phytomedicine. v.13 p. 272-276, 2006. MORA, F. D.; AVILA, J. L.; ROJAS, L. B.; RAMIREZ, R.; USUBILLAGA, A.; SEGNINNI, S.; CARMONA, J.; SILVA, B. Chemical composition and larvicidal activity of Eugenia triquetra essential oil from venezuelan Andes. Nat. Prod. Commun. 5 (6), 965-968, 2010. NAIR, A. G. R.; KRISHNAN, S.; RAVIKRISHNA, L.; MADHUSUDANAN, K. P. New and rare flavonol glycosides from leaves of Syzygium samarangense. Fitoterapia 70, 148-151, 1999. NEWMAN , D. J.; CRAGG, G. M.; SNADER, K. M. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66, 1022-1037, 2003. NONAKA, G.-I.; HARADA, M.; NISHIOKA, I. Eugeniin, a new ellagitannin from cloves. Chem. Pharm. Bull. 28 (2), 685-687, 1980. NONAKA, G.-I.; ISHIMARU, K.; WATANABE, M.; NISHIOKA, I.; YAMAUCHI, T.; WAN, A. S. C. Tannins and related compounds. LI. Elucidation of the stereochemistry of the triphenoyl moiety in castalagin and vescalagin, and isolation of 1-O-galloyl castalagin from Eugenia grnadis. Chem. Pharm. Bull. 35 (1), 217-220, 1987. OLIVEIRA, M. E. S.; PANTOJA, L.; DUARTE, W. F.; COLLELA, C. F.; VALARELLI, L. T.; SCHWAN, R. F.; DIAS, D. R. Fruit wine produced from caigata (Eugenia dysenterica DC) by both free and imonobilised yeast cell fermentation. Food Res. Int. 44, 2391-2400, 2011. OMAR, R.; LI, L.; YUAN, T.; SERAM, N. a-glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds. J. Nat. Prod. 75, 1505-1509, 2012. PAINULY, P.; TANDON, J. S. Two 3-C-methylflavone glycosides from Eugenia Kurzii. Phytochemistry 22 (1), 243-245, 1983. PATRA, A.; CHAUDHURI, S. K.; ACHRYYA, A. K. Applications of two-dimensional NMR in spectral assignments of some friedelanes and secofriedelanes. Magn. Reson. Chem. 28, 85-89, 1990. P?REZ, R. A. Amino acid composition na antioxidant capacity of Spanish honeys. J. Agric. Food Chem. 55, 360-365, 2007. PIETA, P. G. Flavonoids as antioxidants. J. Nat. Prod. 63, 1035-1042, 2000. 124 RAJASEKARA, M.; BAPNA, J. S.; LAKSHMANAN, S.; NAIR, A. G. R.; VELRATH, A. J.; PANCHANADAN, M. Antifertility efect in male rats of oleanolic acid, a triterpene from Eugenia jambolana flowers. J. Ethnopharmacol. 24, 115-121, 1988. RAMFUL, D.; AUMJAUD, B.; NEERGUEEN, V. S.; SOOBRATTEE, M. A.; GOOGOOLYE, K.; ARUOMA, O. I.; BAHORUN, T. Polyphenolic content and antioxidant activity of Eugenia pollicina leaf extract in vitro and in model emulsion system. Food Res. Int. 44, 1190-1196, 2011. REVILLA, J. Plantas ?teis da bacia amaz?nica. Impa, Rio de Janeiro, 2002. REYNERTSON, K. A.; YANG, H.; JIANG, B.; BASILE, M. J.; KENNELLY, E. J. Quantitative analisys of antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chem. 109, 883-890, 2008 ROMAGNOLO, M. B.; SOUZA, M. C. O g?nero Eugenia L. (Myrtaceae) na plan?cie de alag?vel do Alto Rio Paran?, Estados de Mato Grosso do Sul e Parana, Brasil. Acta bot. br?s. 20 (3), 529-548, 2006. SANTOS, K. K. A.; MATIAS, E. F. F.; TINTINO, S. R.; SOUZA, C. E. S.; BRAGA, M. F. B. M; GUEDES, G. M. M.; ROL?N, M.; VEJA, C.; ARIAS, A. R.; COSTA, J. G. M.; MENEZES, I. R. A.; COUTINHO, H. D. M. Anti-Trypanosoma cruzi and cytotoxic activities of Eugenia uniflora L. Exp. Parasitol. 131, 130-132, 2012. SETZER, W. N.; SCHMIDT, J. M.; NOLETTO, J. A.; VOGLER, B. Leaf oil composition and bioactivities of abaco bush medicines. Pharmacology on line 3, 794-802, 2006. SIMIRGIOTIS, M. J.; ADACHI, S. A.; TO, S.; YANG, H.; REYNERTSON, K. A.; BASILE, M. J.; GIL, R. R.; WEINTEIN, I. B.; KENNELLY, E. J. Cytotoxi, chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Food Chem. 107, 813-819, 2008. SLOWING, K.; S?LLHUBER, M.; CARRETERO, E.; VILLAR, A. Flavonoid glycosides from Eugenia jambos. Phytochemistry 37, 255-258, 1994. SOOD, R.; SWARUP, D.; BHATIA, S.; KULKARNI, D. D.; DEY, S.; SAINI, M.; DUBEY, S. C. Antiviral activity of crude extracts of Eugenia jambolana Lam. Against highly pathogenic avian influenza (H5N1) virus. Indian J. Exp. Biol. 50, 179-186, 2012. SRIVASTAVA, R.; SHAW, A. K.; KULSHRESHTHA, D. K. Triterpenoids and chalcone from Syzygium samarangense. Phytochemistry 38 (3), 687-689, 1995. 125 STEFANELLO, M. E .A.; CURVI, A. C.; ITO, I. Y.; SALVADOR, H. J.; WISNIEWSKI JR, A.; SIMIONATTO, E. L. Chemical composition and antimicrobial activity of essential oils from Eugenia chlorophylla (Myrtaceae) J. Essent. Oil. Res. 20, 75-78, 2008. SUBRAMANIAN, S.; NAIR, A. G. R. Flavonoids of the flowers of Eugenia jambolana. Curr Sci India 41 (19), 703-704, 1972. SULTAMA, B.; ANWAR, F.; PRIZYBYLSKI, R. Antioxidant activity of phenolic components present in barks of Azadirachta indica, Termina arjuna, Acacia nilotica, and Eugenia jambolana Lam. Trees. Food Chem. 104, 1106-1114, 2007. TALAPATRA, S. K.; SARKAR, A. C.; TALAPATRA, B. Two pentacyclic triterpenes from Rubia Cordifolia. Phytochemistry 20 (8), 1923-1927, 1981. TANAKA, T.; ORII, Y.; NONAKA, G.-I.; NISHIOKA, I. Tannins and related compounds. CXXIII. Chromone, acetophenone and phenylpropanoid glycosides and their galloyl and/or hexahydroxydiphenoyl esters from the leaves of Syzygium aromaticum Meer. et Perry. Chem. Pharm. Bull. 41 (7), 1232-1237, 1993. TANAKA, T.; ORII, Y.; NONAKA, G.-I.; NISHIOKA, I.; KOUNO, I. Syzyginins A and B, two ellagitannins from Syzygium aromaticum. Phytochemistry 43 (6), 1345-1348, 1996. THORNHILL, A. H.; POPPLE, L. W.; CARTER, R. J.; HO, S. Y. W.; CRISP, M. D. Are pollen fossils usefull for calibrating relaxed molecular clock dating of phylogenies? A comparative study using Myrtaceae. Mol. Phylogenet. Evol. 63, 15-27, 2012. TIMBOLA, A. K.; SZPONICZ, B.; BRANCO, A.; MONACHE, F. D.; PIZZOLATTI, M. G. A new flavonol from leaves of Eugenia jambolana. Fitgoterapia 73, 174-176, 2002. VAN DER MERWE, M. M.; VAN WYK, A. E.; BOTHA, A. M. Molecular phytogenetic of Eugenia L. (Myrtaceae), with enphasis on southern African taxa. Plant Syst. Evol. 251, 21-34, 2005. VELANDIA, J. R. Constituintes qu?micos de Ouratea semiserrata e transforma??es qu?micas da neolignana aureina. Tese de doutorado, Programa de P?s-gradua??o em Qu?mica, Instituto de Ciencias Exatas, Departamento de Qu?mica, Universidade Federal Rural do Rio de Janeiro, 1997. VEIGAS, J. M.; NARAYAN, M. S.; LAXMAN, P. M.; NEELWARNE, B. Chemical nature, stability and bioefficacies of anthocyanins from fruit pell of Syzygium cumini Skeels. Food. Chem. 105, 619-627, 2007. 126 VICTORIA, F. N.; LENARD?O, E. J.; SAVEGNAGO, L.; PERIN, G.; JACOB, R. G.; ALVES, D.; DA SILVA, W. P.; DA MOTTA, A. S.; NASCENTE, P. S. Essential oil of the leaves of Eugenia uniflora L.: Antioxidante and antimicrobial properties. Food Chem. Toxicol. 50, 2668-2674, 2012. VIEGAS JR, C.; BOLZANI, V. S. Os produtos naturais e a qu?mica medicinal moderna. Quim. Nova 29 (2), 326-337, 2006. VIEIRA, T. R.; BARBOSA, L. C. A.; MALTHA, C. R. A. Constituintes Qu?micos de Melaleuca alternif?lia (Myrtaceae). Quim. Nova 27 (4), 536-539, 2004. WOISKY, R. G.; SALATINO, A. Analisys of pr?polis: some parameters and procedures for chemical quality control. J. Apic. Res. 37, 99-105, 1998. YANG, L. L.; LEE, C. Y.; YEN, K. Y. Induction of apoptosis by hydrolysable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett. 157, 65-75, 2000. YANG, L.-L.; LEE, C.-Y.; YEN, K.-Y. Induction of apoptosis by hydrolysable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett. 157, 65-75, 2000. YE, C.-L.; LU, Y.-H.; WEI, D.-Z. Flavonoids from Cleistocalyx operculatus. Phytochemistry 65, 445-447, 2004. YOO, C.-B.; HAN, K.-T.; CHO, K.-S.; HA, J.; PARK, H.-S.; NAM, S.-H.; KIL, U.-H.; LEE, K.-T. Eugenol isolated from the essential oil of Eugenia caryophillata induces a reative oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. 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dc.title.por.fl_str_mv Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
dc.title.alternative.eng.fl_str_mv Special metabolites isolated from Eugenia copacabanensis Kiaersk (Myrtaceae) and evaluation of antioxidant and antimicrobial activities
title Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
spellingShingle Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
Carvalho Junior, Almir Ribeiro de
E. copacabanensis
triterpenos
atividade antioxidante
E. copacabanensis
triterpenes
antioxidant activity
Qu?mica
title_short Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
title_full Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
title_fullStr Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
title_full_unstemmed Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
title_sort Metab?litos especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana
author Carvalho Junior, Almir Ribeiro de
author_facet Carvalho Junior, Almir Ribeiro de
author_role author
dc.contributor.advisor1.fl_str_mv Carvalho, Mario Geraldo de
dc.contributor.advisor1ID.fl_str_mv 257.152.327-91
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/9794451665032168
dc.contributor.referee1.fl_str_mv Figueiredo, Maria Raquel
dc.contributor.referee2.fl_str_mv Oliveira, Rodrigo Rodrigues de
dc.contributor.referee3.fl_str_mv Oliveira, Marcia Cristina Campos de
dc.contributor.authorID.fl_str_mv 125.085.417-29
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/7191491222073956
dc.contributor.author.fl_str_mv Carvalho Junior, Almir Ribeiro de
contributor_str_mv Carvalho, Mario Geraldo de
Figueiredo, Maria Raquel
Oliveira, Rodrigo Rodrigues de
Oliveira, Marcia Cristina Campos de
dc.subject.por.fl_str_mv E. copacabanensis
triterpenos
atividade antioxidante
topic E. copacabanensis
triterpenos
atividade antioxidante
E. copacabanensis
triterpenes
antioxidant activity
Qu?mica
dc.subject.eng.fl_str_mv E. copacabanensis
triterpenes
antioxidant activity
dc.subject.cnpq.fl_str_mv Qu?mica
description The genus Eugenia (Myrtaceae) comprises about 550 species of trees and shrubs, mainly found in Central and South America. Several species are used in folk medicine to treat diseases such as diabetes, chronic diarrhea, body aches, skin rash, etc. This has motivated diverse studies related to both the chemical composition and the biological properties of the genus. The objective of this work was to study the chemical profile of the species Eugenia copacabanensis, besides evaluating its antioxidant and atimicrobiano potential. The compounds described in this work were isolated from chromatographic techniques and identified by 1H and 13C NMR, GC-MS experiments besides comparison with literature data. From leaves of E. copacabanenis were isolated and -amyrin, ursolic acid, 30-hydroxy-ursolic acid (rubif?lico), betulin, -sitosterol, -sitosterol glycoside, clovanodiol, globulol, viridiflorol and the flavonoids kaempferol-3-O-ramnosideo, quercetin-3-O-arabinoside, and quercetin. While from branches were isolated, friedelin, friedelan-3,4-lactone, taraxerol, octacosanyl coumarate, heptacosanyl coumarate, hexacosanyl coumarate and teracosanyl coumarate. From acetylation and methylation reactions of acid 30-hydroxy-ursolic it were obtained: diacetyl rubifolic acid methyl diacetyl rubifolato respectively. The antioxidant activity of the extracts and fractions was evaluated by DPPH and -carotene-linoleic acid methods. In both cases, we obtained excellent results with EC50 values ranging between 0.92 ?0.04 and 40.7 ? 1.0 g/ml and % inhibition between 28.7 ?7.9 to 90.0 ? 0.1%. Antimicrobial activity was evaluated against the microorganisms, Staphylococcus aureus, Candida albicans, Cryptococcus neoformans and Rhizopus oryzae and extracts and fractions of E. copacabanensis were not active until the concentration of 2.5 mg / mL.
publishDate 2013
dc.date.issued.fl_str_mv 2013-04-16
dc.date.accessioned.fl_str_mv 2020-04-27T14:46:09Z
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.citation.fl_str_mv CARVALHO JUNIOR, Almir Ribeiro de. Metab?litos Especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana. 2013. 126 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013.
dc.identifier.uri.fl_str_mv https://tede.ufrrj.br/jspui/handle/jspui/3459
identifier_str_mv CARVALHO JUNIOR, Almir Ribeiro de. Metab?litos Especiais isolados de Eugenia copacabanensis Kiaersk (Myrtaceae) e avalia??o de atividades antioxidante e antimicrobiana. 2013. 126 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2013.
url https://tede.ufrrj.br/jspui/handle/jspui/3459
dc.language.iso.fl_str_mv por
language por
dc.relation.references.por.fl_str_mv AHN, M. R.; KUMAZAWA, S.; USUI, Y.; NAKAMURA, J.; MATSUKA, M.; ZHU, F.; NAKAYAMA, T. Antioxidant activity and constituents of pr?polis collected in variou ?reas of china. Food Chem, 101, 1383-1392, 2007. ALVES, C. Q.; DAVID, J. M.; DAVID, P. J.; BAHIA, M. V.; AGUIAR, R. M. M?todos para determina??o de atividade antioxidante in vitro em substratos org?nicos. Quim. Nova 33 (10), 2202-2210, 2010. AMORIM, A. C. L.; LIMA, C. K. F.; HOVELL, A. M.; MIRANDA, A. L. P.; REZENDE, C. M. Antinociceptive and hipothermic avaluation of the leaf essential oil and isolated terpenoids from Eugenia uniflora (Brazilian Pitanga). Phytomedicine 16, 923-928, 2009. ATOUI, A. K.; MANSOURI, A.; BOSKOU, G.; KEFALAS, P. Tea and herbal infusions: their antioxidant activity and phenolic profile. Food Chem. 89 (1), 27-36, 2005. BAHIA, M. V. Ocorr?ncia de biflavonoides e derivado de ?cido benzoico do cerne e folhas de Caesalpinia pyramidalis e Peltophorum dubium (Leguminosae). Tese de doutorado. Programa de P?s-gradua??o em Qu?mica, Instituto de Qu?mica, Universidade Federal da Bahia, 2007. BANDEIRA, P. N.; LEMOS, T. L. G.; COSTA, S. M. O.; DOS SANTOS, H. S. Obten??o de derivados da mistura triterpenoidica a e b-amirina. Rev. Bras. Farmacogn. 17 (2), 204-208, 2007. BANNON, C. D.; RONALD, A.; SIMES, J. J. H. Extractives of Australian timbers. XVI The constituents of the wood of Eugenia crebrinervis (syn Syzygium crebrinerve) and Eugenia gustavinoides (syn Syzygium gustavinoides). Aust. J. Chem. 29, 1135-1141, 1976. BARREIROS, A. L. B. S.; DAVID, J.. M.; DAVID, J. P. Estresse oxidativo: rela??o entre gera??o de esp?cies reativas e defesa do organismo. Quim. Nova 29 (1), 113-123, 2006. 116 BENAVENT-GARCIA, O.; CASTILLO, J.; LORENTE, J.; ORTUNO, A.; DELRIO, J. A. Antioxidant activity of phenolic extracted from Olea europaea L. leaves. Food Chem-Review 72, 145-171, 2001. BERT?, T. E. Estudo da atividade anticolinester?sica dos compostos taraxerol e ?cido urs?lico: implica??es sobre processo da mem?ria. Disserta??o de Mestrado, Programa de P?s-gradua??o em Ci?ncias Farmac?uticas, Universidade do Vale do Itaja?, 2009. BHARGAVA, K. K.; DAYAL, R.; SESHADRI, T. R. Chemical components of Eugenia jambolana stem bark. Current Science 43 (20), 645-646, 1974. BRASILEIRO, B. G.; PIZZIOLO, V. R.; MATOS, D. S.; GERMANO, A. M.; JAMAL, C.M Plantas medicinais utilizadas pela popula??o atendida no ?Programa de Sa?de da Fam?lia?, Governador Valadares, MG, Brasil. Rev. Bras. Cienc. Farma. 44 (4), 629-636, 2008. BRIGGS, L. H.; CAMBIE, R. C.; LOWRY, J. B.; SEELVE, R. N. Constituents of Eugenia maire A. Cunn. Part I. A trimethyl ether acid and mairin, a new triterpene. J. Chem. Soc. 642-645, 1961. CALA, A. R. S.; MACHADO, D. G.; BRITTO, L. E. B.; COLLA, G.; MAGINA, M. D. A.; BRIGHENTE, I. M .C.; RODRIGUES, A. L. S. Involvement of monoaminergic systems in the antidepressant-like effects of Eugenia brasiliensi Lam. (Myrtaceae) in the tail suspension test in mice. J. Ethnopharmacol. 143, 720-731, 2012. CAMPOS, M. G.; WEBBY, R. F.; MARKHAM, K. R.; MITCHELL, K. A.; DA CUBHA, A. P. Age-induced diminution of free radical scavenging capacity in bee pollens and the contribution of constituent flavonoids. Journal of Agricultural and Food Chem 51 (3), 742-745, 2003. CANDY, H. A.; MACGARRY, E. J.; PEGEL, K. H. Constituents of Syzygium cordatum. Phytochemistry 7 (5), 889-890, 1968. CARDOSO, C. M. V.; SAJO, M. G. Nerva??o em esp?cies brasileira de Myrtaceae Adans. Acta bot. Br?s. 20 (3), 657-669, 2006. CARVALHO JR, A. R.; GOMES, G. A.; CORDEIRO, G. M.; CARVALHO, M. G. Triterpenes and Flavonoid from Eugenia copacabanensis and DPPH Scavenging Activity. III International Symposium Medicinal and Nutraceutical Plants, Aracaju-SE, 2012. CARVALHO JR, A. R.; GOMES, G. A.; GOMES, T. R. C.; CARVALHO, M. G. Metabolitos especiais isolados de Eugenia copacabanensis (Myrtaceae). 35? Reuni?o Anual da Sociedade Brasileira de Qu?mica, ?guas de Lind?ia-SP, 2011. 117 CARVALHO, M.G. DE, ROCHA JUNIOR, G. G.; CAVATTI, L.C.; SUZART, L.R.; CORNELIUS, M.T.F.; SILVA, V.C. DA; CARDOSO, M.A.R.; Determina??o Estrutural de Flavon?ides com An?lie de Espectros de RMN de 1H e Incorpora??o de Diazometano. Rev. Univ. Rural, S?r. Ci. Exatas e da Terra. Serop?dica, RJ, EDUR, v. 25, n. 1-2., 46-60, 2006. CASSANITI, C.; LEONARD, C.; FLOWERS, T. The effect of sodium chloride on ornamental shrubs. Sci Hortic-Amsterdan 122, 586-593, 2009. CHANDRASEKARAN, M.; VENKATESALU, V. Antibacterial and antifungal activity of Syzygium jambolanum seeds. J. Ethnopharmacol. 91, 105-108, 2004. CHANDRASEKARAN, M.; VENKATESALU, V. Antibacterial and antifungal activity of Syzygium jambolanum seeds. J. Ethnopharcol. 91, 105-108, 2004. CHUN, D.; JIAN, L.; BAIS, B.-R.; PENG, S.-L.; DING, L.-S. A new glucosidade gallate from the flower buds of Eugenia caryophyllate. Chinese Journal of Natural Medicine 8 (3), 180-182, 2010. CLINICAL AND LABORATORY STANDARDS INSTITUTS (CLSI). Methods for dilution antimicrobial susceptibility tests. 4th ed. Wayne (PA),. Approved Standard, Normas M27-A3, M38-A2, M11-A6 e M7-A4 2008. COLE, R. A.; BANSAL, A.; MORIARITY, D. M.; HABER, W. A.; SETZER, W. N. Chemical composition and cytotoxic activity of the leaf essential oil of Eugenia zuchowskiae from Monteverde, Costa Rica. J. Nat. Med. 61, 414-417, 2007. COSTA, D. P.; FILHO, E. G. A.; SILVA, L. M. A.; SANTOS, S. C.; PASSOS, X. S.; SILVA, M. R. R.; SERAPHIN, J. C.; FERRI, P. H. Influence of fruit biotypes on the chemical composition and antifungal activity of the essential oils of Eugenia uniflora leaves. J. Braz. Chem. Soc. 21 (5), 851-858, 2010 CRUZ, A. V. M.; KAPLAN, M. A. C. Uso medicinal de esp?cies das fam?lias Myrtaceae e Melastomataceae no Brasil. Floresta e Ambiente 11, 47-52, 2004. DE OLIVEIRA, A. M.; HUMBERTO, M. M. S.; DA SILVA, J. M.; DE ALMEIDA ROCHA, R. F.; SANT?ANA, A. E. G. Estudo fitoqu?mico e avalia??o das atividades moluscicida e larvicida dos extratos de casca do caule e folha de Eugenia malacsensis L. (Myrtaceae). Rev. Bras. Farmacogn. 16 (supl), 618-624, 2006. DE OLIVEIRA, A., M.; HUMBERTO, M. M. s.; DA SILVA, J. M.; DE ALMEIDA ROCHA, R. F.; SANT?ANA, A. E. G. Estudo fitoqu?mico e avalia??o das atividades 118 moluscida e larvicida dos extratos da casca do caule e folha de Eugenia malaccensis L. (Myrtaceae). Rev. Bras. Farmacogn. 16 (supl), 618-624, 2006. DE OLIVEIRA, R. N.; DIAS, I. J. M.; C?MARA, C. A. G. Estudo comparativo do ?leo essencial de Eugenia punicifolia (HBK) DC. De diferentes localidades de Pernambuco. Rev. Bras. Farmacogn. 15 (1), 39-43, 2005. DEFAVERI, A. C. A.; SATO, A.; BON?, L. B.; AGUIAR, D. L. M.; SAN GIL, R. A. S.; ARRUDA, R. C. O.; RIEHL, C. A. A. Eugenia neotida and Eugenia rotundifolia Casar. (Myrtaceae) essential oils: composition, seasonality influence, antioxidant activiy and leaf histochemistry. J. Braz. Chem. Soc. 22, 1531-1538, 2011. DELGADO, G.; C?RDENAS, H.; PEL?EZ, G.; VIVAR, A. R. Terpenoids from Vigueira oaxacana. J. Nat. Prod., 47, 6, 1042-1045, 1984. DEWIR, Y. H.; SINGH, N.; MNGOMEZULU, S.; OMAR, A. M. K. Micropropagation and detection of important triterpenes in vitro and Field growon plants of Syzygium cordatum. J. Med. Pants Res. 5 (14), 3078-3083, 2011. DHAMARATNE, H. R. W.; SOTHEESWARAN, S.; BALASUBRAMANIAM, S. Triterpenes and Neoflavonoids of Calophyllum lankaensis and Calophyllum thwaitesii. Phytochemistry, 23, 2601-2603, 1984. DIAS, M. O.; HAMERSKI, L.; PINTO, A. C. Separa??o semipreparativa de e -amirina por cromatografia l?quida de alta efici?ncia. Quim. Nova 34 (4), S1-S6, 2011. DJOUKENG, J. D.; ABOU-MANSOUR, E.; TABACCHI, R.; TAPONDJOU, A. L.; BOUDA, H.; LMAONTSI, D. Antibacterial triterpenes from Syzygium guineense (Myrtaceae). J. Ethnopharmacol. 101, 283-286, 2005. DONATINI, R. S.; ISHIKAWA, T.; BARROS, S. B. M.; BAECHI, E. M. Atividade anti?lcera e antioxidante do extrato de folhas de Syzygium jambos (L.) Alston (Myrtaceae). Rev. Bras. Farmacogn. 19 (1A), 89-94, 2009. FLORES, G.; DASTMALCHI, K.; PAULINO, S.; WHALEN, K.; DABO, A. J.; REYNERTSON, K. A.; FORONJY, R. F.; AMIENTO, J. M. D.; KENNELY, E. J. Anthocyanins from Eugenia brasiliensis edible fruits as potential therapeutics for COPD treatment. Food Chem. 134, 1256-1262, 2012. 119 FRIGHETTO, N.; WELENDORF, R. M.; DA SILVA, A. M. P.; NAKAMURA, M. J.; SIANI, A. C. Purification of betulinic acid from Eugenia florida (Myrtaceae) by high-speed counter current chromatography. Phytochem. Anal. 16, 411-414, 2005. GOMES DA SILVA, A. L.; PINHEIRO, M. C. B. Biologia floral e da poliniza??o de quatro esp?cies de Eugenia L. (Myrtaceae). Acta bot. br?s. 21 (1), 235-247, 2007. GOMES, M. S. R. Constituintes qu?micos isolados da raiz de Piptadenia rigida (Leguminosae-Mimosoideae). Disserta??o de mestrado. Programa de P?s-gradua??o em Qu?mica Org?nica, Instintuto de Ci?ncias Exatas, Departamento de Qu?mica, Universidade Federal Rural do Rio de Janeiro, 2002. GOPAN, R.; VARUGHESE, G.; NEDIYAPARAMBIL, P.; MATHUR, S. Volatile constituents and antibacterial activity of Eugenia rottleriana Wight et Arn. Leaf oil. J. Essent. Oil Res. 19 (6), 588-590, 2007. GOTTLIEB, O. R.; DA SILVA, L.; MARIA, J. G. S. Eucalyptin from Eugenia and Myrcia species. Phytochemistry 11, 1185-1186, 1972. GRANGEIRO, M. S.; CALHEIROS-LIMA, A. P.; MARTINS, M. K.; ARRUDA, L. F.; GARCEZ-DO-CARMO, ?.; SANTOS, W. C. Pharmacological effects of Eugenia punicifolia (Myrtaceae) in cholinergic neurotransmission. J. Ethnopharmacol. 108 (1) 26-30, 2006. GU, J.-Q.; PARK, E. J.; LUYENGI, L.; HAWTHORNE, M.; KINGHORN, A. D. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochemistry 58, 121-127, 2001. GUIMAR?ES, A. G.; MELO, M. S.; BONFIM, R. R.; PASSOS, L. O.; MACHADO, S. M. F.; RIBEIRO, A. DE S.; SOBRAL, M.; THOMAZZI, S. M.; QINTANS-J?NIOR, L. J. Antinoceptive and anti-inflammatory effects of the essential oil of Eugenia candolleana DC., Myrtaceae, on mice. Rev. Bras. Farmacog. 19 (4), 883-887, 2009. GUPTA, G. S.; SHARMA, D. P. Triterpenoids and other constituents of Eugenia jambolana leaves. Phytochemistry 13 (9), 2013-2014, 1974. HANSON, J. T.; HITCHCOCK, P. B.; MANICKAVASAGAR, R. The Hidroxilation of Globulol and 7-Epiglobulol by Cephalosporium Aphidicola. Phytochemistry 37, 1023-1025, 1994. HARON, N. W.; MOORE, D. M.; HARBORNE, J. B. Distribution and taxonomic significance of flavonoids in the genus Eugenia (Myrtaceae). Biochem. Syst. Ecol. 20 (3), 265-268, 1992. 120 HARRIS, S.M.; MCFEETERS, H.; OGUNGBE, I.; CRUZ, V. L.; SELTZER, W. N.; WILLIAN, N.; JAKES, B. R.; MCFEETERS, R. L. Peptidyl-tRNA hydrolase screening with molecular docking reveals the antibiotic potential of Syzygium johnsonii bark extract. Nat. Prod. Commun. 6 (10), 1421-1424, 2011. HENRIQUES, A. T.; SOBRAL, M.; CAUDURO, A. D.; SCHAPOVAL, E. E. S.; BASSANI, V. L.; LOMATY, G.; MENUT, C.; BESSIERE, J. M. Aromatic plants from Brazil. II. The chemical composition of some Eugenia essential oils. J. Essent. Oil. Res. 5, 501-505, 1993. HUSSEIN, S. A. M.; HASHEM, A. N. M.; SALIEM, M. A.; LINDEQUIST, U.; NAWWAR, M. A. M. Polyoxynated flavonoids from Eugenia edulis. Phytochemistry 64, 883-889, 2003. HUSSEIN, S. A. M.; HASHEN, A. N. M.; SALIEM, M. A.; LINDEQUIST, U.; NAWWAR, M. A. M. Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry 64, 883-889, 2003. JAYASINGHE, U. L. B.; RATNAYAKE, R. M. S.; MEDAWALA, M. M. W. S.; FUJIMOTO, Y. Nat. Prod. Res. 21 (6), 551-554, 2007. JORGE, T. C. M. Estudo qu?mico e farmacol?gico de duas esp?cies da fam?lia Rubiaceae: Cephalanthus glabratus e Palicourea crocea. Tese de doutorado, Programa de P?s-gradua??o em Qu?mica, CCE, Departamento de Qu?mica, Universidade Estadual de Maring?, 2005. JOTHI, G. J.; BENNIAMIN, A.; MARIDASS, M.; RAJU, G. Identification of essential oils composition and antifungal activity of Eugenia singampattiana fruits. Pharmacologyonline (2, News Letters), 727-733, 2009. JUNGES, M. J.; FERNANDES, J. B.; VIEIRA, P. C.; DA SILVA, M. F. G. F.; FILHO, E. R. The use of 13C and 1H-NMR in the structural elucidation of a new nor-lupane triterpene. J. Braz. Chem. Soc. 10 (4), 317-320, 1999. KALA, S. M. J.; BALASUBRAMANIAN, T.; SORIS, P. T.; MOHAN, V. R. GC-MS determination of bioactive components of Eugenia singampattiana Bedd. Int. J. Chem Tec Res. 3 (3), 1534-1537, 2011. KIM, H. J.; LEE, J. S.; WOO, E.-R.; KIM, M. K.; YANG, B. S.; YU, Y. G.; PARK, H.; LEE, Y. S. Isolation of virus-cell fusion inhibitory components from Eugenia caryophyllate. Planta Med. 67, 277-279, 2001. 121 KIM, Y.-J.; KIM, H.-C.; KO, H.; AMOR, E.-C.; LEE, J. W. Inhibitory effects of aurentiacin from Syzygium samarangense on lipolysaccharide-induced inflammatory response in mouse macrophages. Food Chem. Toxicol. 50, 1027-1035, 2012. KOUIDHI, B.; ZMANTAR, T.; BAKHROUT, A. Anticariogenic and cytotoxic activity of clove essential oil (Eugenia caryophyllata) against a large number of oral pathogens. Ann. Microbiol. 60, 599-604, 2010. KUIATE, J.-R.; MOUOKEU, S.; WABO, H. K.; TANE, P. Antidermatophytic triterpenoids from Syzygium jambos (L) Aston (Myrtaceae). Phytother. Res. 21, 149-152, 2007. KUO, Y.-C.; YANG, L.-M.; LIN, L.-C. Isolation and imunomodulatory effect of flavonoids from Syzygium samarangense. Planta Med. 70, 1237-1239, 2004. KUSKOSKI, E. M.; VEJA, J. M.; RIOS, J. J.; FETT, R.; TRONCOSO, A. M.; AURERO, A. G. Characterization of anthocyanins from the fruits of bagua?u (Eugenia umbelliflora Berg). J. Agric. Food Chem. 51, 5450-5454, 2003 LAPHOOKIEO, S.; KARALAI, C.; PONGLIMANONT, C. New sesquiterpenoid and triterpenoids from the fruit of Rhizophora mucronata. Chem Pharm Bull. 52, 883-885, 2004. LEE, J. H.; LEE, K. T.; YANG, J. H.; BAEK, N. I.; KIM, D. K. Acetylcholinesterase inhibitors from tthe Twings of Vaccinium Oldhami Miquel. Arch. Pharm. Res, v. 27, n. 1, p. 53-56, 2004. LIMA, T. B.; SILVA, O. N.; OLIVEIRA, J. T. A.; VASCONCELOS, I. M.; SCALOBRIN, F. B.; ROCHA, T. L.; GROSSI-DE-S?, M. F.; SILVA, L. P.; GUADONIN, R. V.; QUIRINO, B. F.; CASTRO, C. F. S.; LEONARDECZ, E.; FRANCO, O. L. Identification on Eugenia dysenterica laxative peptide: A novel strategy in the treatment of chronic constipation and irritable bowel syndrome. Peptides 31, 1426-1433, 2010. LIU, J.-X.; DI, D.-L.; SHI, Y.-P. Diversity of chemical constituents from Saxifraga Montana H. J. Chin. Chem. Soc. 55 (4), 863-870, 2008. LOCHER, C. P.; BURCH, M. T.; MOWER, H. R.; BERESTECKY, J.; DAVIS, H.; POIL, B.; LASURE, A.; VANDEN BERGHE, D. A.; VLIETINCK, A. S. Anti-microbial activity and anti-complement activity of extracts obtained from selected Hawaiian medicinal plants. J. Ethnopharmacol. 49, 23-32, 1995. LUNARD, I.; PEIXOTO, J. L. B.; DA SILVA, C. C.; SHUQUEL, I. T. A.; BASSO, E. A.; VIDOTTI, G. J. J. Braz. Chem. Soc. 12 (2), 180-183, 2001. 122 MACEDO, A. F.; OSHIIWA, M.; GUARIDO, C. F. Ocorr?ncia do uso de plantas medicinais por moradores de bairro do munic?pio de Mar?lia-SP. Rev. Cienc. Farm. Apl. 28 (1), 123-128, 2007. MACHADO, K. E.; FILHO, V. C.; CRUZ, R. C. B.; MEYRE-SILVA, C.; CRUZ, A. B. Antifungal activity of Eugenia umbelliflora against dermatophytes. Nat. Prod. Commun. 4 (9), 1181-1184, 2009. MAGINA, M. A.; GILIOLI, A.; MORESCO, H. H.; COLLA, G.; PIZZOLATTI, M. G.; BRIGHENTE, I. M. C. Atividade antioxidante de tr?s esp?cies de Eugenia (Myrtaceae). Lat. J. Am. J. Pharm. 29 (3), 376-382, 2010. MAGINA, M. D. A.; DALMARCO, E. M.; DALMARCO, J. B. Bioactive triterpenes and phenolics of leave of Eugenia brasiliensis. Quim. Nova 35 (6), 1184-1188, 2012. MAGINA, M. D. A.; DALMARCO, J. B.; PIZZOLATTI, M. G.; BRIGHENTE, I. M. C. Chemical composition and antibacterial activity of essential oils of Eugenia species. J. Nat. Med. 63, 345-350, 2009. MAGINA, M. D. A.; PIETROVSKI, E. F.; GOMIG, F.; FALKENBERG, D. B.; CABRINI, D. A.; OTUKI, M. F.; PIZZOLATI, M. G.; BRIGHENTE, I. M. C. Topical antiinflamatory activity and chemical composition of the epicuticular wax from the leaves of Eugenia meaurepaireana (Myrtaceae). Braz. J.Pharm. Sci. 45, 171-, 2009. MAHMOUD, I. I.; MARZOUK, M. S. A.; MOHARRAM, F. A.; EL-GIND, M. R.; HASSAN, A. M. K. Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry 58, 1239-1244, 2001. MAJUMDAR, S. G.; THAKUR, S. Chemical investigation of the leaves of Eugenia formosa. J. Indian Chem. Soc. 47 (2), 181-182, 1970. MANOHARAN, K. P.; SONG, F. J.; BENNY, T. K. H.; YANG, D. Triterpenoids from Eugenia grandis: structure elucidation by NMR espectroscopy. Magn. Reson. Chem 45, 279-281, 2007. MARIDASS, M. Composition and anti-inflamatory activity of the essential oil of Eugenia dysenterica (Myrtaceae). Journal of Essential Oil Therapeutics 2 (4), 163-166, 2008. MEDA, A.; LAMIEM, C. E.; ROMITO, M.; MILLOGO, J.; NACOULMA, O. G. Determination of the total phenolic, flvonoide and proline contents in Burkina Fasan honey, as well as their radica scavenging activity. Food Chem, 91, 571-577, 2005. 123 MELEND?Z, P.A., CAPRILES, V.A. Antibacterial properties of tropical plants from Puerto Rico. Phytomedicine. v.13 p. 272-276, 2006. MORA, F. D.; AVILA, J. L.; ROJAS, L. B.; RAMIREZ, R.; USUBILLAGA, A.; SEGNINNI, S.; CARMONA, J.; SILVA, B. Chemical composition and larvicidal activity of Eugenia triquetra essential oil from venezuelan Andes. Nat. Prod. Commun. 5 (6), 965-968, 2010. NAIR, A. G. R.; KRISHNAN, S.; RAVIKRISHNA, L.; MADHUSUDANAN, K. P. New and rare flavonol glycosides from leaves of Syzygium samarangense. Fitoterapia 70, 148-151, 1999. NEWMAN , D. J.; CRAGG, G. M.; SNADER, K. M. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66, 1022-1037, 2003. NONAKA, G.-I.; HARADA, M.; NISHIOKA, I. Eugeniin, a new ellagitannin from cloves. Chem. Pharm. Bull. 28 (2), 685-687, 1980. NONAKA, G.-I.; ISHIMARU, K.; WATANABE, M.; NISHIOKA, I.; YAMAUCHI, T.; WAN, A. S. C. Tannins and related compounds. LI. Elucidation of the stereochemistry of the triphenoyl moiety in castalagin and vescalagin, and isolation of 1-O-galloyl castalagin from Eugenia grnadis. Chem. Pharm. Bull. 35 (1), 217-220, 1987. OLIVEIRA, M. E. S.; PANTOJA, L.; DUARTE, W. F.; COLLELA, C. F.; VALARELLI, L. T.; SCHWAN, R. F.; DIAS, D. R. Fruit wine produced from caigata (Eugenia dysenterica DC) by both free and imonobilised yeast cell fermentation. Food Res. Int. 44, 2391-2400, 2011. OMAR, R.; LI, L.; YUAN, T.; SERAM, N. a-glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds. J. Nat. Prod. 75, 1505-1509, 2012. PAINULY, P.; TANDON, J. S. Two 3-C-methylflavone glycosides from Eugenia Kurzii. Phytochemistry 22 (1), 243-245, 1983. PATRA, A.; CHAUDHURI, S. K.; ACHRYYA, A. K. Applications of two-dimensional NMR in spectral assignments of some friedelanes and secofriedelanes. Magn. Reson. Chem. 28, 85-89, 1990. P?REZ, R. A. Amino acid composition na antioxidant capacity of Spanish honeys. J. Agric. Food Chem. 55, 360-365, 2007. PIETA, P. G. Flavonoids as antioxidants. J. Nat. Prod. 63, 1035-1042, 2000. 124 RAJASEKARA, M.; BAPNA, J. S.; LAKSHMANAN, S.; NAIR, A. G. R.; VELRATH, A. J.; PANCHANADAN, M. Antifertility efect in male rats of oleanolic acid, a triterpene from Eugenia jambolana flowers. J. Ethnopharmacol. 24, 115-121, 1988. RAMFUL, D.; AUMJAUD, B.; NEERGUEEN, V. S.; SOOBRATTEE, M. A.; GOOGOOLYE, K.; ARUOMA, O. I.; BAHORUN, T. Polyphenolic content and antioxidant activity of Eugenia pollicina leaf extract in vitro and in model emulsion system. Food Res. Int. 44, 1190-1196, 2011. REVILLA, J. Plantas ?teis da bacia amaz?nica. Impa, Rio de Janeiro, 2002. REYNERTSON, K. A.; YANG, H.; JIANG, B.; BASILE, M. J.; KENNELLY, E. J. Quantitative analisys of antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chem. 109, 883-890, 2008 ROMAGNOLO, M. B.; SOUZA, M. C. O g?nero Eugenia L. (Myrtaceae) na plan?cie de alag?vel do Alto Rio Paran?, Estados de Mato Grosso do Sul e Parana, Brasil. Acta bot. br?s. 20 (3), 529-548, 2006. SANTOS, K. K. A.; MATIAS, E. F. F.; TINTINO, S. R.; SOUZA, C. E. S.; BRAGA, M. F. B. M; GUEDES, G. M. M.; ROL?N, M.; VEJA, C.; ARIAS, A. R.; COSTA, J. G. M.; MENEZES, I. R. A.; COUTINHO, H. D. M. Anti-Trypanosoma cruzi and cytotoxic activities of Eugenia uniflora L. Exp. Parasitol. 131, 130-132, 2012. SETZER, W. N.; SCHMIDT, J. M.; NOLETTO, J. A.; VOGLER, B. Leaf oil composition and bioactivities of abaco bush medicines. Pharmacology on line 3, 794-802, 2006. SIMIRGIOTIS, M. J.; ADACHI, S. A.; TO, S.; YANG, H.; REYNERTSON, K. A.; BASILE, M. J.; GIL, R. R.; WEINTEIN, I. B.; KENNELLY, E. J. Cytotoxi, chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Food Chem. 107, 813-819, 2008. SLOWING, K.; S?LLHUBER, M.; CARRETERO, E.; VILLAR, A. Flavonoid glycosides from Eugenia jambos. Phytochemistry 37, 255-258, 1994. SOOD, R.; SWARUP, D.; BHATIA, S.; KULKARNI, D. D.; DEY, S.; SAINI, M.; DUBEY, S. C. Antiviral activity of crude extracts of Eugenia jambolana Lam. Against highly pathogenic avian influenza (H5N1) virus. Indian J. Exp. Biol. 50, 179-186, 2012. SRIVASTAVA, R.; SHAW, A. K.; KULSHRESHTHA, D. K. Triterpenoids and chalcone from Syzygium samarangense. Phytochemistry 38 (3), 687-689, 1995. 125 STEFANELLO, M. E .A.; CURVI, A. C.; ITO, I. Y.; SALVADOR, H. J.; WISNIEWSKI JR, A.; SIMIONATTO, E. L. Chemical composition and antimicrobial activity of essential oils from Eugenia chlorophylla (Myrtaceae) J. Essent. Oil. Res. 20, 75-78, 2008. SUBRAMANIAN, S.; NAIR, A. G. R. Flavonoids of the flowers of Eugenia jambolana. Curr Sci India 41 (19), 703-704, 1972. SULTAMA, B.; ANWAR, F.; PRIZYBYLSKI, R. Antioxidant activity of phenolic components present in barks of Azadirachta indica, Termina arjuna, Acacia nilotica, and Eugenia jambolana Lam. Trees. Food Chem. 104, 1106-1114, 2007. TALAPATRA, S. K.; SARKAR, A. C.; TALAPATRA, B. Two pentacyclic triterpenes from Rubia Cordifolia. Phytochemistry 20 (8), 1923-1927, 1981. TANAKA, T.; ORII, Y.; NONAKA, G.-I.; NISHIOKA, I. Tannins and related compounds. CXXIII. Chromone, acetophenone and phenylpropanoid glycosides and their galloyl and/or hexahydroxydiphenoyl esters from the leaves of Syzygium aromaticum Meer. et Perry. Chem. Pharm. Bull. 41 (7), 1232-1237, 1993. TANAKA, T.; ORII, Y.; NONAKA, G.-I.; NISHIOKA, I.; KOUNO, I. Syzyginins A and B, two ellagitannins from Syzygium aromaticum. Phytochemistry 43 (6), 1345-1348, 1996. THORNHILL, A. H.; POPPLE, L. W.; CARTER, R. J.; HO, S. Y. W.; CRISP, M. D. Are pollen fossils usefull for calibrating relaxed molecular clock dating of phylogenies? A comparative study using Myrtaceae. Mol. Phylogenet. Evol. 63, 15-27, 2012. TIMBOLA, A. K.; SZPONICZ, B.; BRANCO, A.; MONACHE, F. D.; PIZZOLATTI, M. G. A new flavonol from leaves of Eugenia jambolana. Fitgoterapia 73, 174-176, 2002. VAN DER MERWE, M. M.; VAN WYK, A. E.; BOTHA, A. M. Molecular phytogenetic of Eugenia L. (Myrtaceae), with enphasis on southern African taxa. Plant Syst. Evol. 251, 21-34, 2005. VELANDIA, J. R. Constituintes qu?micos de Ouratea semiserrata e transforma??es qu?micas da neolignana aureina. Tese de doutorado, Programa de P?s-gradua??o em Qu?mica, Instituto de Ciencias Exatas, Departamento de Qu?mica, Universidade Federal Rural do Rio de Janeiro, 1997. VEIGAS, J. M.; NARAYAN, M. S.; LAXMAN, P. M.; NEELWARNE, B. Chemical nature, stability and bioefficacies of anthocyanins from fruit pell of Syzygium cumini Skeels. Food. Chem. 105, 619-627, 2007. 126 VICTORIA, F. N.; LENARD?O, E. J.; SAVEGNAGO, L.; PERIN, G.; JACOB, R. G.; ALVES, D.; DA SILVA, W. P.; DA MOTTA, A. S.; NASCENTE, P. S. Essential oil of the leaves of Eugenia uniflora L.: Antioxidante and antimicrobial properties. Food Chem. Toxicol. 50, 2668-2674, 2012. VIEGAS JR, C.; BOLZANI, V. S. Os produtos naturais e a qu?mica medicinal moderna. Quim. Nova 29 (2), 326-337, 2006. VIEIRA, T. R.; BARBOSA, L. C. A.; MALTHA, C. R. A. Constituintes Qu?micos de Melaleuca alternif?lia (Myrtaceae). Quim. Nova 27 (4), 536-539, 2004. WOISKY, R. G.; SALATINO, A. Analisys of pr?polis: some parameters and procedures for chemical quality control. J. Apic. Res. 37, 99-105, 1998. YANG, L. L.; LEE, C. Y.; YEN, K. Y. Induction of apoptosis by hydrolysable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett. 157, 65-75, 2000. YANG, L.-L.; LEE, C.-Y.; YEN, K.-Y. Induction of apoptosis by hydrolysable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett. 157, 65-75, 2000. YE, C.-L.; LU, Y.-H.; WEI, D.-Z. Flavonoids from Cleistocalyx operculatus. Phytochemistry 65, 445-447, 2004. YOO, C.-B.; HAN, K.-T.; CHO, K.-S.; HA, J.; PARK, H.-S.; NAM, S.-H.; KIL, U.-H.; LEE, K.-T. Eugenol isolated from the essential oil of Eugenia caryophillata induces a reative oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett. 225, 41-52, 2005.
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