Composição química e atividade biológica das própolis brasileiras: verde e vermelha

Joselena Mendonça Ferreira; Giuseppina Negri

doi:10.18378/aab.v6i1.4962

Authors

Joselena Mendonça Ferreira Universidade Federal Rural do Semi-Árido.
Giuseppina Negri Universidade de São Paulo

DOI:

https://doi.org/10.18378/aab.v6i1.4962

Keywords:

Red propolis, Green propolis, Chemical compounds, Botanical origin, Biological activity

Abstract

Propolis is a complex mixture of substances collected by bees at vegetative apices and resinous exudates of plants. The bee glue is used to seal, maintain the temperature and asepsia of the hive. It has proven biological properties that varies according to the localities in which it is produced. In Brazil, the two main types of propolis traded internationally are green and red. Together, they move an international market, with an estimate of the order of millions of dollars per year. The objective of this study was to compare the chemical composition and biological activity of Brazilian propolis, green and red. Data were obtained through intensive research in the scientific literature, using the database, Scopus, Web of Science, Capes Periodic and Medline. Brazilian green propolis is produced in the southeast region, mainly in the state of Minas Gerais and has the vegetative apices of Baccharis dracunculifolia as resin source. Its main constituents are prenylated cinnamic acids and caffeoylquinic acids. The red propolis produced in the northeast region has Dalbergia ecastophyllum as resin source. Its main constituents are isoflavones, pterocarpans, chalcones and polyprenylated benzophenones. The antibacterial, antiviral, antioxidant, cytotoxic, antitumor and anti-inflammatory activities of the two propolis were attributed to phenolic compounds. The knowledge acquired about these types of Brazilian propolis is important to be used as a source of income, especially for beekeepers; and provide an important contribution to biomedical research in the discovery of new drugs.

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Author Biographies

Joselena Mendonça Ferreira, Universidade Federal Rural do Semi-Árido.

Departamento de Ciências Animais, Produção e Sanidade Animal.

Giuseppina Negri, Universidade de São Paulo

Giuseppina Negri concluiu o curso de graduação em Química (Bacharelado e Tecnologia) na Universidade Estadual de Campinas. Mestrado em Química Orgânica na Universidade Estadual de Campinas e Doutorado em Ciências na área de Química Orgânica na Universidade Estadual de Campinas sob a orientação da Profa. Dra. Concetta Kascheres. Pós-Doutorado em Química de produtos Naturais na USP, sob a supervisão do Prof. Dr. Antonio Salatino. Atualmente atua como pesquisadora do CEBRID da Universidade Federal de São Paulo, na área de Química de Produtos Naturais, concentrando as atividades principalmente nos seguintes temas: cromatografia gasosa e cromatografia líquida de alta eficiência ambas acopladas a espectrometria de massas, identificação de substâncias usando as técnicas de espectrometria de massas e ressonância magnética nuclear de 1H e 13C, sintese orgânica, relação estrutura química versus atividade biológia e análise estatísticas de processos químicos (quimiometria). Além de trabalhar com atividades biológicas, tais como antioxidante, anticolinesterásica, antiviral entre outras. Possui 70 trabalhos publicados em periódicos indexados, tais como Food Chemistry, Journal Agricultural Food Chemistry, Phytomedicine, Planta Medica, Phytochemistry, Phytotherapy Research, entre outras.

References

AGA, H.; SHIBUYA, T.; SUGIMOTO, T.; KURIMOTO, M.; NAKAJIMA, S. Isolation and identification of antimicrobial compounds in Brazilian propolis. Bioscience, Biotechnology, and Biochemistry, v. 58, n. 5, p. 945-946, 1994.

ALENCAR, S. M. OLDONI, T. L. C.; CASTRO, M. L. CABRAL, I.S.R.; COSTA-NETO, C.M.; CURY, J. A.; ROSALEN, P.L. IKEGAKI, M. Chemical composition and biological activity of a new type of Brazilian propolis: red propolis. Journal of Ethnopharmacology, v. 113, n. 2, p. 278-283, 2007.

AWALE, S.; LI, F.; ONOZUKA, H.; ESUMI, H.; TEZUKA, Y.; KADOTA, S. Constituents of Brazilian red propolis and their preferential cytotoxic activity aagagainst human pancreatic PANC-1 cancer cell line in nutrient-deprived condition. Bioorganic & Medicinal Chemistry, v. 16, n. 1, p. 181-189, 2008.

BANKOVA V. MARCUCCI, M.C.; SIMOVA, S.; NIKOLOVA, N.; KUJUMGIEV, A.; POPOV, S. Antibacterial diterpenic acids from Brazilian própolis. Zeitschrift für Naturforschung, v.51, n. 5-6, p. 277-280, 1996.

BANKOVA, V.; POPOVA, M.; TRUSHEVA, B. Propolis volatile compounds: chemical diversity and biological activity: a review. Chem. Cent. J., v. 8, p. 28, 2014.

BANSKOTA, A. H.; NAGAOKA, T.; SUMIOKA, L. Y.; TEZUKA, Y.; AWALE, S.; MIDORIKAWA, K.; MATSUSHIGE, K.; KADOTA, S. Antioproliferative activity of the Netherlands propolis and its active principles in cancer cell lines. Journal of Ethnopharmacology, v. 80, n.1, p. 67-73, 2002.

BASTOS, E. M. A. F.; SIMONE, M.; MACEDOJORGE, D.; ESPENCER, A.; SOARES, E.; SPIVAK, M. In vitro study of the antimicrobial activity of Brazilian propolis against Paenibacillus larvae. Journal of Invertebrate Pathology, v. 97, n.3, p. 273-281, 2008.

BERRETTA, A.A.; ARRUDA, C.; MIGUEL, F.G.; BAPTISTA, N.; NASCIMENTO, A. P.; MARQUELE-OLIVEIRA, F.; HORI, J.I.; HERNANE DA SILVA BARUD, H.; DAMASO, B.; RAMOS, C.; FERREIRA, R.; BASTOS J. K. Functional Properties of Brazilian Propolis: From Chemical Composition Until the Market. Agricultural and Biological Sciences "Superfood and Functional Food - An Overview of Their Processing and Utilization", book edited by Viduranga Waisundara and Naofumi Shiomi, ISBN 978-953-51-2920-2. 2017.

BRASIL. Ministério da Agricultura, Pecuária e Abastecimento. Portaria nº 3, de 19/01/2001, Instrução Normativa Nº 3, de 19 de Janeiro de 2001.

BUENO-SILVA, B.; ALENCAR, S. M.; KOO, H.; IKEGAKI, M.; SILVA, G. V. J.; NAPIMOGA, M. H.; ROSALEN, P. L. Anti-Inflammatory and Antimicrobial Evaluation of Neovestitol and Vestitol Isolated from Brazilian Red Propolis. Journal of Agricultural and Food Chemistry, v.61, n. 19, p. 4546–4550, 2013.

BURDOCK, G.A. Review of the biological properties and toxicity of bee propolis (propolis). Food and Chemical Toxicology, v. 36, n. 4, p. 347-363, 1998.

BUSCH, V. M.; PEREYRA-GONZALEZ, A.; ŠEGATIN, N.; SANTAGAPITA, P. R.; POKLAR ULRIH, N.; BUERA, M. P. Propolis encapsulation by spray drying: Characterization and stability. LWT - Food Science and Technology, v. 75, p. 227-235, 2017.

CASTRO, M. L. Bioassay guided purification of the antimicrobial fraction of a Brazilian propolis from Bahia state. BMC Complementary and Alternative Medicine, v. 9, n. 25, p. 1-6, 2009.

CAVENDISH, R. L.; SANTOS, J. S.; BELO NETO, R.; PAIXÃO, A. O.; OLIVEIRA, J. V.; ARAÚJO, E. D.; SILVA, A. A. B.; THOMAZZI, A. M.; CARDOZO, J. C.; GOMES, M. Z. Antinociceptive and anti-inflammatory effects of Brazilian red propolis extract and formononetin in rodents. Journal of Ethnopharmacology, v. 173, n. 15 p. 127-133, 2015.

CHAN, G. C. F.; CHEUNG, K. W.; SZE, D. M. The Immunomodulatory and Anticancer Properties of Propolis. Clinical Reviews in Allergy & Immunology, v. 44, n. 3, p. 262-273, 2013.

CHANG, R.; PILÓ-VELOSO, D.; MORAIS, S. A. L.; NASCIMENTO, E. A. Analysis of a Brazilian green propolis from Baccharis dracunculifolia by HPLC-APCI-MS and GC-MS. Revista Brasileira de Farmacognosia, v. 18, n. 4, p. 549-556, 2008.

CHEN, Y. W.; WU, S. W.; HO, K. K.; LIN, S. B.; HUANG, C.Y.; CHEN, C. N. Characterisation of Taiwanese propolis collected from different locations and seasons. Journal of the Science of Food and Agriculture, v. 88, n. 3, p. 412-419, 2007.

COELHO, G. R. MENDONÇA, R. Z.; VILAR, K. S.; FIGUEIREDO, C. A.; BADARI, J. C.; TANIWAKI, N.; NAMIYAMA, G. OLIVEIRA, M. I.; CURTI, S. P.; SILVA, P. E.; NEGRI, G. Antiviral action of hydroethanolic extract of geopropolis from Scaptotrigona postica against anti-herpes simplex virus (HSV-1). Evidence based Complementary and Alternative medicine, Article Number: 296086, p. 1-10, 2015.

CRANE, E. The World History of Beekeeping and Honey Hunting. Great Britain: New York, 1999.

ČIŽMÁRIK, J.; MATEL, I. Examination of the chemical composition of propolis I. Isolation and identification of the 3,4-dihydroxycinnamic acid (caffeic acid) from propolis. Experientia, v. 26, n. 7, p. 713 -713, 1970.

DAUGSCH, A.; MORAES, C. S.; FORT, P. PARK, Y. K. Brazilian Red Propolis Chemical Composition and Botanical Origin. Evidence-Based Complementary and Alternative Medicine, v. 5, n. 4, p. 435-441, 2008.

DE LUCA, M. P.; FRANCA, J. R.; MACEDO, F. A. F. F.; GRENHO, L.; CORTES, M. E.; FARACO, A. A. G.; MOREIRA, A. N.; SANTOS, V. R. Propolis varnish: antimicrobial properties against cariogenic bacteria, cytotoxicity, and sustained‐release profile. Biomed Research International. 2014. Article ID 348647. DOI: 10.1155/2014/348647.

DE MENDONÇA, I.C. G.; PORTO, I.C.C.M.; DO NASCIMENTO, T.G.; DE SOUZA, N. S.; OLIVEIRA, J. M. S.; ARRUDA, R.E.S.; MOUSINHO, K. C.; DOS SANTOS, A. F.; BASÍLIO‐JÚNIOR, I.D.; PAROLIA, A.; BARRETO, F.S. Brazilian red propolis: phytochemical screening, antioxidant activity and effect against cancer cells. BMC Complementary and Alternative Medicine. V. 15:357, 2015.

FERNANDES-SILVA, C. C.; SALATINO, A.; SALATINO, M. L. F.; BREYER, E. D. H.; NEGRI, G. Chemical profiling of six samples of Brazilian própolis. Química Nova, v. 36, n. 2, p. 237-240, 2013.

FERNANDES-SILVA, C. C.; LIMA, C. A.; NEGRI, G.; SALATINO, M. L. F.; SALATINO, A.; MAYWORM, M. A. S. Composition of the volatile fraction of a sample of Brazilian green propolic and its phytotoxic activity. Journal of the Science of Food and Agriculture, v. 95, n. 15, p. 3091-3095, 2015.

FERREIRA, J. M.; FERNANDES-SILVA, C. C.; SALATINO, A.; NEGRI, G.; MESSAGE, D. New propolis type from north-east Brazil: chemical composition, antioxidant activity and botanical origin. Journal of the Science of Food and Agriculture, V. 97, p. 3552-3558, 2017..

FIORDALISI, S. A.; HONORATO, L. A.; LOIKO, M. R.; AVANCINI, C. A.; VELEIRINHO, M. B.; MACHADO FILHO, L.C.; KUHNEN, S. The effects of Brazilian propolis on etiological agents of mastitis and the viability of bovine mammary gland explants. Journal of Dairy Science. V. 99, p. 2308–2318, 2016 .

FOKT, H.; PEREIRA, A.; FERREIRA, A. M.; CUNHA, A.; AGUIAR, C. How do bees prevent hive infections? The antimicrobial properties of propolis. Current Research, Technology and Education. Topics in Applied Microbiology and Microbial Biotechnology, v. 1, p. 481–493, 2010.

FRANCISCO, L.; PINTO, D.; ROSSETO, H.; TOLEDO, L.; SANTOS, R.; TOBALDINI-VALÉRIO, F.; SVIDZINSKI, T.; BRUSCHI, M.; SARMENTO, B.; OLIVEIRA, M. B. P. P.; RODRIGUES, F. Evaluation of radical scavenging activity, intestinal cell viability and antifungal activity of Brazilian propolis by-product. Food Research International, v. 105, p. 537-547, 2018.

GOMES, F.; HENRIQUES, M. Control of Bovine Mastitis: Old and Recent Therapeutic Approaches. Current microbiology, v. 72, p. 377–382, 2016.

GRANGE, J. M.; DAVEY, R. W. Antibacterial properties of propolis (bee glue). Journal of the Royal Society of Medicine, v. 83, n. 1, p. 159-160, 1990.

GROOT, A. C. Propolis: A Review of Properties, Applications, Chemical Composition, Contact Allergy, and Other Adverse Effects. Dermatitis, v. 24, n. 6, p. 263–282, 2013.

HATANO, A.; NONAKA, T.; YOSHINO, M.; AHN, M.; TAZAWA, S.; ARAKI, Y.; KUMAZAWA, S. Antioxidant Activity and Phenolic Constituents of Red Propolis from Shandong, China. Food Science and Technology Research, v. 18, n. 4, p. 577 – 584, 2012.

HATTORI, H.; OKUDA, K.; MURASE, T.; SHIGETSURA, Y.; NARISE, K.; SEMENZA, G. L.; NAGASAWA, H. Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis. Bioorganic & Medicinal Chemistry, v.19, n. 18, p. 5392-5401, 2011.

HUANG, S., ZHANG, C.-P., WANG, K., LI, G., HU, F.-L.. Recent Advances in the Chemical Composition of Propolis. Molecules v. 19, p. 19610–19632, 2014.

ISHIDA, V. F. C.; NEGRI, G.; SALATINO, A.; BANDEIRA, M. F. C. L. A new type of Brazilian propolis: Prenylated benzophenones in propolis from Amazon and effects against cariogenic bacteria. Food Chemistry. v. 125, n. 3, p. 966-972, 2011.

INUI, S.; HATANO, A.; YOSHINO, M.; HOSOYA, T.; SHIMAMURA, Y.; MASUDA, S.; AHN, M. R.; TAZAWA, S.; ARAKI, Y.; KUMAZAWA, S. Identification of the phenolic compounds contributing to antibacterial activity in ethanol extracts of Brazilian red propolis. Natural Product Research. V. 28, p. 1293–1296, 2014.

KIMOTO, T.; KOYA-MIYATA, S.; HINO, K.; MICALLEF, M. J.; HANAYA, T.; ARAI, S.; IKEDA, M.; KURIMOTO, M. Pulmonary carcinogenesis induced by ferric nitrilotriacetate in mice and protection from it by Brazilian propolis and artepillin C. Virchows Archiv, v. 438, n. 3, p. 259-70, 2001.

KUMAZAWA, S.; GOTO, H.; HAMASAKA, T.; FUKUMOTO, S.; FUJIMOTO, T.; NAKAYAMA, T. A new prenylated flavonoid from propolis collected in Okinawa, Japan. Bioscience, Biotechnology, and Biochemistry, v. 68, n. 1, p.260-262, 2004a.

KUMAZAWA, S.; HAMASAKA, T.; NAKAYAMA, T. Antioxidant activity of propolis of various geographic origins. Food Chemistry, v. 84, n. 3, 329-339, 2004b.

LAITINEN, H. A. History of analytical chemistry in the U.S.A. Talanta, v. 36 n. 1-2, p. 1-9, 1989.

LI, F.; AWALE, S.; TEZUKA, Y.; ESUMI, H.; KADOTA, S. Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells. Journal of Natural Products, v. 73, n. 4, p. 623-627, 2010.

LIMA, M. G. A produção de própolis no Brasil. São João da Boa Vista: São Sebastião Editora e Gráfica, 2006, 120p.

LOPÉZ, B. G. C.; SCHMIDT, E. M.; EBERLIN, M. N.; SAWAYA, A. C. H. F. Phytochemical markers of different types of red propolis. Food Chemistry, v. 146, n. 1, p. 174–180, 2014.

LOTII, C.; FERNANDEZ, M. C.; PICCINELLI, A. L.; CUESTA-RUBIO, O.; HERNÁNDEZ, I. M.; RASTRELLI, L. Chemical Constituents of Red Mexican Propolis. Journal of Agricultural and Food Chemistry, v. 58, n. 4, p. 2209-2213, 2010.

LUO, C.; ZOU, X.; LI, Y.; SUN, C.; JIANG, Y.; WU, Z. Determination of flavonoids in propolis-rich functional foods by reversed phase high performance liquid chromatography with diode array detection. Food Chemistry, v. 127, n. 1, p. 314-320, 2011.

LUSTOSA, S. R.; GALINDO, A. B.; NUNES, L. C. C.; RANDAU, K. P.; ROLIM NETO, P. J.. Própolis: atualizações sobre a química e a farmacologia. Revista Brasileira de Farmacognosia, v.18, n.3, p. 447-454, 2008.

MACHADO, C. S.; MOKOCHINSKI, J. B.; DE LIRA, T. O.; DE OLIVEIRA, F. C. E.; CARDOSO, M. V.; FERREIRA, R. G.; SAWAYA, A. C. H.F.; FERREIRA, A. G.; PESSOA, C.; CUESTA-RUBIO, O.; MONTEIRO, M. C.; DE CAMPOS, M. S.; TORRES, Y.R. Comparative Study of Chemical Composition and Biological Activity of Yellow, Green, Brown, and Red Brazilian Propolis. Evidence-based Complementary and Alternative medicine, article number – 6057650, 2016.

MENDONÇA-MELO, L. MOTA, E.; LOPEZ, B.; SAWAYA, A.; FREITAS, L.; JAIN, S.; BATISTA, M.; ARAÚJO, E. Chemical and genetic similarity between Dalbergia ecastaphyllum and red propolis from the Northeastern Brazil. Journal of Apicultural Research, v. 56, n.1, p.1-8, 2017.

MOREIRA, T. F. Chemical composition of propolis: vitamins and amino acids. Revista Brasileira de Farmacognosia, v. 1, n. 1, p. 12-19, 1986.

MOURA, S. A. L.; NEGRI, G.; SALATINO, A.; LIMA, L. D. DA C.; DOURADO, L. P. A.; MENDES, J. B.; ANDRADE, S. P.; FERREIRA, M. A. N. D.; CARA, D. C. Aqueous extract of Brazilian Green Propolis: Primary components, evaluation of inflammation and wound healing by using subcutaneous implanted sponges. Evidence-based Complementary and Alternative medicine, Article Number: 748283, p. 1-8, 2011.

NASCIMENTO, A. P.; FERREIRA, N. U.; BARIZON, E. A.; ROCHA, B. A.; VAZ, M. M. O. L. L.; BERRETTA, A. A. Methodologies for the evaluation of the antibacterial activity of propolis. African Journal of Microbiology Research. V.7, p. 2344–2350, 2013.

NEGRI, G.; SALATINO, M. L. F.; SALATINO, A. ‘Green propolis’: unreported constituents and a novel compound from chloroform extracts. Journal of Apicultural Research, v. 42, n. 3, p. 39-41, 2003a.

NEGRI, G.; SALATINO, M. L. F.; SALATINO, A. Unusual chemical composition of a sample of Brazilian propolis as assessed by analysis of a chloroform extract. Journal Apicultural Research, v. 42, n. 4, p. 53-56, 2003b.

NUNES, L. C. C.; La ROCA, M. F. DE; RANDAU, K. P.; SOARES SOBRINHO, J. L.; CITO, A. M. DAS G. L.; ROLIM NETO, P. J. Avaliação das propriedades físico-químicas e aspetos legais de extratos de própolis comercializados no mercado brasileiro. Revista Brasileira de Farmacognosia, v. 89, n.1 p. 59-63, 2008.

NUNES, L. C.; GALINDO, A. B.; DE DEUS A. S. O.; RUFINO, D. A.; RANDAU, K. P.; XAVIER, H. S.; CITÓ, A. M. G. L.; ROLIM NETO, P. J. Seasonal variability of the constituents of propolis and bioactivity in saline Artermia. Brazilian Journal of Pharmacognosy. V. 19, p. 524–529, 2009.

OLIVEIRA V. D. C, BASTOS E. M. Aspectos morfo-anatômicos da folha de Baccharis dracunculifolia DC. (Asteraceae) visando a identificação da origem botânica da própolis. Acta Botanica Brasilica, v. 12, n. 3, p. 431-439, 1998.

PARK, K. Y.; ALENCAR, S. M.; AGUIAR, C. L. Botanical origin and chemical composition of Brazilian propolis. Journal of Agricultural and Food Chemistry, v. 50, n. 9, p. 2502-2506, 2002.

PEREIRA A. dos S.; RAMOS, M. F. S.; POÇAS, E. S. C.; DIAS, P. C. M.; SANTOS, E. P.; SILVA, J. F. M.; CARDOSO, J. N.; AQUINO NETO, F. R. Study of propolis by High Temperature High Resolution Gas Chromatography-Mass Spectrometry. Zeitschrift für Naturforschung, v. 54c, p. 395-400, 1999.

PEREIRA, A. S. SEIXAS, F. R. M. S.; AQUINO NETO, F. R. Própolis: 100 anos de pesquisa e suas perspectivas futuras. Química Nova, v. 25, p. 321-326, 2002.

PICCINELLI, A. L. FERNANDEZ, M. C.; CUESTA-RUBIO, O.; HERNÁNDEZ, I. M.; SIMONE, F. de; RASTRELLI, L. Isoflavonoids isolated from Cuban propolis. Journal of Agricultural and Food Chemistry, v. 53, n. 23, p. 9010-9016, 2005.

PICCINELLI, A. L.; LOTTI, C.; CAMPONE, L.; CUESTA-RUBIO, O.; FERNANDEZ, M. C.; RASTRELLI, L. Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography–Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry. Journal of Agricultural and Food Chemistry, v. 59, n. 12, p. 6484-6491, 2011.

RIGHI, A. A.; ALVES, T. R.; NEGRI, G.; MARQUES, L. M.; BREYER, H.; SALATINO, A. Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities. Journal of Agricultural and Food Chemistry, v. 91, n. 13, p. 2363-2370, 2011.

RIGHI, A. A.; NEGRI, G.; SALATINO, A. Comparative chemistry of propolis from eight Brazilian localities. Evidence-based Complementary and Alternative medicine. Article Number: 267878, p. 1-14, 2013.

SALATINO, A.; TEIXEIRA, E. W.; NEGRI, G.; MESSAGE, D. Origin and Chemical Variation of Brazilian Propolis. Evidence-Based Complementary and Alternative Medicine, v. 2, n. 1, p. 33-38, 2005.

SALATINO, A.; FERNANDES-SILVA, C. C.; RIGHI, A. A.; SALATINO, M. L. F. Propolis research and the chemistry of plant products. Natural Product Reports, v. 28, p. 925–936, 2011.

SFORCIN, J. M.; BANKOVA, V. Propolis: Is there a potential for the development of new drugs? Journal of Ethnopharmacology, v. 133, n. 2, p. 253-260, 2011.

SILVA, R. P. D.; MACHADO, B. A. S.; COSTA, S. S.; BARRETO, G. A.; PADILHA, F. F.; UMSZA-GUEZ, M. A. Aplicação de Extrato de Própolis em Produtos Alimentícios: Uma Prospecção Baseada em Documentos de Patentes. Revista Virtual de Química, v. 8, n.5, p. 1-11, 2016.

SIMÕES-AMBROSIO, L. M. C.; GREGÓRIO, L. E.; SOUSA, J. P. B.; FIGUEIREDO-RINHEL, A. S. G.; AZZOLINI, A. E. C. S.; BASTOS, J. K.; LUCISANO-VALIM, Y. M. The role of seasonality on the inhibitory effect of Brazilian green propolis on the oxidative metabolism of neutrophils. Fitoterapia, v.81, n.8, p. 1102-1108, 2010.

SIQUEIRA, A.B.S.; GOMES, B.S.; CAMBUIM, I.; MAIA, R.; ABREU, S.; SOUZA MOTTA, C.M.; DE QUEIROZ, L.A.; PORTO, A.L.F. Trichophyton species susceptibility to green and red propolis from Brazil. Letters in Applied Microbiology. V. 48, p. 90–96, 2009.

SHIMIZU, T.; TAKESHITA, Y.; TAKAMORI, Y.; KAI, H.; SAWAMURA, R.; YOSHIDA, H.; WATANABE, W.; TSUTSUMI, A.; PARK, Y.K.; YASUKAWA, K.; MATSUNO, K.; SHIRAKI, K.; KUROKAWA, M. Efficacy of Brazilian propolis against herpes simplex virus type 1 infection in mice and their modes of antiherpetic efficacies. Evidence‐Based Complementary and Alternative Medicine, article number – 976196, 2011.

SOARES, A. K. A.; CARMO, G. C.; QUENTAL, D. P.; NASCIMENTO, D. F.; BEZERRA, F. A. F.; MORAES, M. O.; MORAES, M. E. A. Avaliação da segurança clínica de um fitoterápico contendo Mikania glomerata, Grindelia robusta, Copaifera officinalis, Myroxylon toluifera, Nasturtium officinale, própolis e mel em voluntários saudáveis. Revista Brasileira de Farmacognosia, v. 16, n. 4, p. 447-454, 2006.

TAKEMURA, T.; URUSHISAKI, T.; FUKUOKA, M.; HOSOKAWA‐MUTO, J.; HATA, T.; OKUDA, Y.; HORI, S.; SHIGEMI, T.; ARAKI, Y.; KUWATA, K. 3,4-Dicaffeoylquinic acid, a major constituent of Bra‐ zilian propolis, increases TRAIL expression and extends the lifetimes of mice infected with the influenza A virus. Evidence‐Based Complementary and Alternative Medicine, article number 946867, 2012.

TANI, H.; HASUMI, K.; TATEFUJI, T.; HASHIMOTO, K.; KOSHINO, H.; TAKAHASHI, S. Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes. Bioorganic & Medicinal Chemistry, v. 18, n.1, p. 151-157, 2010.

TAZAWA, S.; ARAI, Y.; HOTTA, S.; MITSUI, T.; NOZAKI, T.; ICHIHANA, K. Discovery of a Novel Diterpene in Brown Propolis from the State of Parana, Brazil. Natural Product Communications, v. 11, n. 2, p. 201-205, 2016.

TEIXEIRA, E. W.; NEGRI, G.; MEIRA, R. M. S. A.; MESSAGE, D.; SALATINO, A. Plant origin of green propolis: Bee behavior, plant anatomy and Chemistry. Evidence-Based Complementary and Alternative Medicine, v. 2, n. 1, p. 85-92, 2005.

TEIXEIRA, E. W.; MESSAGE, D.; NEGRI, G.; SALATINO, A. Bauer-7-en-3b-yl acetate: a major constituent of unusual samples of Brazilian propolis. Química Nova, v. 29, n. 2, p. 245-246, 2006.

TRUSHEVA, B.; POPOVA, M.; NAYDENSKI, H.; TSVETKOVA, I.; RODRIGUEZ, J. G.; BANKOVA, V. New polyisoprenylated benzophenones from Venezuelan propolis. Fitoterapia, v. 75, n. 7-8, p. 683-689, 2004.

TRUSHEVA, B.; POPOVA, M.; BANKOVA, V.; SIMOVA, S.; MARCUCCI, M. M.; MIORIN, P. L.; PASIN, F. R.; TSVETKOVA, I. et al. Bioactive Constituents of Brazilian Red Propolis. Evidence-Based Complementary and Alternative Medicine, v. 3, n. 2, p. 249-254, 2006.

URUSHISAKI, T.; TAKEMURA, T.; TAZAWA, S.; FUKUOKA, M.; HOSOKAWA‐MUTO, J.; ARAKI, Y.; KUWATA, K (2011). Caffeoylquinic acids are major constituents with potent anti-influenza effects in Brazilian green propolis water extract. Evidence‐Based Complementary and Alternative Medicine, Article number – 254914, 2011.

VALENCIA, D.; ALDAY, E.; ROBLES-ZEPEDA, R.; GARIBAY-ESCOBAR, A.; GALVEZ-RUIZ, J. C.; SALAS-REYES, M.; JIMÉNEZ-ESTRADA, M.; VELAZQUEZ-CONTRERAS, E.; HERNANDEZ, J.; VELAZQUEZ, C. Seasonal effect on chemical composition and biological activities of Sonoran propolis. Food Chemistry, v. 131, n. 2, p. 645-651, 2012.

VEIGA, R. S.; DE MENDONÇA, S.; MENDES, P. B.; PAULINO, N.; MIMICA, M. J.; LAGAREIRO NETTO, A. A.; LIRA, I. S.; LÓPEZ, B. G.; NEGRÃO, V.; MARCUCCI, M. C. Artepillin C and phenolic compounds responsible for antimicrobial and antioxidant activity of green propolis and Baccharis dracunculifolia DC. Journal of Applied Microbiology, v. 122, n.4, p.911-920, 2017.

WAGH, V. D. Propolis: A Wonder Bees Product and Its Pharmacological Potentials. Advances in Pharmacological Sciences, v. 2013, n. 2013, p.1-11, 2013.

ZAREI, M.; JAFARIAN, A. H.; HARANDI, A.; JAVIDI, M.; GHARECHAHI, M. Evaluation of the expression of VIII factor and VEGF in the regeneration of non-vital teeth in dogs using propolis. Iranian Journal of Basic Medical Sciences, v. 20, n. 2, p.172–177, 2017.