Siparuna Aublet genus (Siparunaceae): from folk medicine to chemical composition and biological activity
Subject Areas : Phytochemistry: Isolation, Purification, Characterization
Ingrede
Silva
1
(Departamento de Ciências Exatas e Tecnológicas, Universidade Estadual de Santa Cruz, Ilhéus, Bahia, Brazil, 45662-900)
Fernando
Oliveira
2
(Departamento de Ciências Exatas e Tecnológicas, Universidade Estadual de Santa Cruz, Ilhéus, Bahia, Brazil, 45662-900)
Rosilene
Oliveira
3
(Departamento de Ciências Exatas e Tecnológicas, Universidade Estadual de Santa Cruz, Ilhéus, Bahia, Brazil, 45662-900)
Keywords: Antioxidant, Essential oils, Secondary metabolites, Antibacterial, Phytochemistry, Pharmacological activities,
Abstract :
Species of the genus Siparuna Aublet are found in Neotropical regions, mainly in the Andes. In the Brazilian folk medicine, some Siparuna species are used to combat fever, inflammation, pain, and infections. This paper presents a review of phytochemical studies and biological activities of species of this genus. Phytochemical studies of 18 species led to the isolation of mainly flavonoids (quercetin and kaempferol derivatives) as well as alkaloids (aporphinic derivatives). Essential oils were reported for 8 species among which S. guianensis is the most studied species. Numerous reports provide evidence of antimicrobial, antiplasmodic, larvicidal, cytotoxic, and antioxidant activities for some species of Siparuna genus. The reports of phytochemical studies and biological activities motivate the continued research of other species of the genus, remembering that a large part of the identified species are unknown from the natural products chemistry point of view.
Aguiar, R.W.S., dos Santos, S.F., Morgado, F.S., Ascencio, S.D., Lopes, M.M., Viana, K.F., Didonet, J., Ribeiro, B.M., 2015. Inseticidal and repelente activity of Siparuna guianensis Aubl. (Negramina) against Aedes aegypti and Culex quinquefasciatus. Plos One 10(1), 1-14.
Alves, J.E., de Souza. T.A., Lacerda, G.A., de Prince, P.M.A., 2016. Atividade antibacteriana do extrato hidroalcoólico de jatobá-do-cerrado (Hymenae astigonocarpa Mart. ex Hayne) e barbatimão (Stryphnodendron adstringens (Mart.) Coville). Bionorte 5(1), 1-10.
Andrade, M.A., Cardoso, M.G., de Andrade, J., Silva, L.F., Teixeira, M.L., Resende, J.M.V., Figueiredo, A.C., Barroso, J.G., 2013. Chemical Composition and antioxidant activity of essential oils from Cinnamodendron dinisii Schwacke and Siparuna guianensis Aublet. Antioxidants 2, 384-397.
Andrade, M.A., Cardoso, M.G., Gomes, M.S., de Azeredo, C.M.O., Batista, R.L., Soares., M.J., Rodrigues, L.M.A., Figueiredo, A.C.S., 2015. Biological activity of the essential oils from Cinnamodendron dinisii and Siparuna guianensis. Braz. J. Microbiol. 46(1), 189-194.
Andrade, M.A., Azevedo, C.S., Motta, F.N., dos Santos, M.L., Silva, C.L., de Santana, J.M., Bastos, I.M.D., 2016. Essential oils: in vitro activity against Leishmania amazonensis, cytotoxicity and chemical composition, BMC Complement. Altern. Med.16(444), 1-8.
Antonio, T.M., Waller, G.R., Mussinan, C.J., 1984. Composition of essential oil from the leaves of Siparuna guianensis (Monimiaceae). Chem. Ind. 14, 514-515.
Arruda, E.L., Lopes, M.B.S., Júnior, A.F.C., Fidelis, E., Santos, M., 2019. Atividade antifúngica de negramina, eucalipto e pinhão manso sobre os fitopatógenos. J. Agric. Sci. Technol. 12(2), 47-58.
Attokaran, M., 2017. Natural Food Flavors and Colorants. 2th Ed. John Wiley & Sons, New Jersey, EUA.
Bakkali, F., Averbeck, S., Averbeck, D., Idaomar, M., 2008. Biological effects of essential oils - A review. Chem. Toxicol. 46, 446-475.
Bessa, N.G.F., Pereira, M.A.B., Ferraz, V., Poletto, K.Q., Chagas Júnior, A.F., Alves, A., 2015. Antimicrobial activity and medicinal biomass of Siparuna guianensis in Brazilian Cerrado forest, a global hotspot. J. Med. Plants Res. 9(37), 968-980.
Bourdy, G., DeWalt, S.J., Chávez de Michel, L.R., Roca, A., Deharo, E., Muñoz, V., Balderrama, L., Quenevo, C., Gimenez, A., 2000. Medicinal plants uses of the Tacana, an Amazonian Bolivian ethnic group. J. Ethnopharmacol. 70, 87-109.
Burneo, J.I., Benítez, A., Calva, J., Velastegui, P., Morocho, V., 2021. Soil and leaf nutrients drivers on the chemical composition of the essential oil of Siparuna muricata (Ruiz & Pav.) A. DC. from Ecuador. Molecules 26(2949), 1-16.
Braz Filho, R., 2010. Contribuição da fitoquímica para o desenvolvimento de um país emergente. Quím. Nova. 33(1), 229-239.
Braz Filho, R., Gabriel, S.J., Gomes, C.M.R., Gottlieb, O.R., Bichara, M.G., Maia, J.G.S., 1976. Oxoaporphine Alkaloids from Fusea Longifolia and Siparuna guianensis. Phytochemistry 15, 1187-1188.
Caballero-Gallardo, K., Pinto-Benitez, N., Pajaro-Castro, N., Stashenko, E., Oliveira-Verbel, J., 2014. Plants cultivated in Choco, Colombia, as source of repellents against Tribolium castaneum (Herbst). J. Asia Pac. Entomol. 17, 753-759.
Camilo, C.J., Alves Nonato, C.D.F., Galvão-Rodrigues, F.F., Costa, W.D., Clemente, G.G., Sobreira Macedo, M.A.C., Galvão Rodrigues, F.F., da Costa, J.G.M., 2017. Acaricidal activity of essential oils: a review. Trends Phytochem. Res. 1, 183-198.
Carvalho, A.F., Silva, D.M., Silva., T.R.C., Scarcelli, E., Manhani, M.R., 2014. Avaliação da atividade antibacteriana de extratos etanólico e de ciclohexano a partir das flores de camomila (Matricaria chamomilla L.). Rev. Bras. Pl. Med. 16(3), 521-526.
Carvalho, V.F., Ramos, L., da Silva, C.A., Nebo, L., Moraes, D., da Silva, F.F.A., da Costa, N.C.A., Rodrigues Junior, R., de Souza, L.F., Rodrigues, R.M., 2019. In vitro anthelmintic activity of Siparuna guianensis extract and essential oil against Strongyloides venezuelensis. J. Helminthol. 1-5.
Castañeda, G.T., Dulcey, A.J.C., Martínez, J.H.I., 2016. Flavonoid glycosides from Siparuna gigantotepala leaves and their antioxidant activity. Chem. Pharm. Bull. 64(5), 502-506.
Chinchilla, M., Valerio, I., Sánchez, R., Mora, V., Bagnarello, V., Martínez, L., Gonzalez, A., Venegas, J. C., Apestegui, A., 2012. In vitro antimalarial activity of extracts of some plants from a biological reserve in Costa Rica. Rev. Biol. Trop. 60(2), 881-891.
Chiu, S.Y.C., Dobberstein, R.H., Fong, H.H.S., Farnsworth, N.R., 1982. Oxoaporphine alkaloids from Siparuna gilgiana. J. Nat. Prod. 45(2), 229-230.
Cocció, J.F., Gómez-Laurito, J., 2002. Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica, Rev. Biol. Trop. 50(3), 3-4.
Conegundes, J., da Silva, J., Mendes, R., Fernandes, M., Pinto, N., de Almeida, M., Dib, P., Andrade, R., Rodrigues, M., Castañon, M., Macedo, G., Scio, E., 2021. Anti-inflammatory and antinociceptive activity of Siparuna guianensis Aublet, an Amazonian plant traditionally used by indigenous communities. J. Ethnopharmacol. 265, 1-12.
Corrêa, M.P., 1978. Dicionário de Plantas Úteis do Brasil e das Exóticas Cultivadas, 2ª Ed. Instituto Brasileiro de Desenvolvimento Florestal. Rio de Janeiro.
Costa, F,N., da Silva, A.J.R., Leitão, G.G., 2013. Changes in the mobile phase composition on a stepwise counter-current chromatography elution for the isolation of flavonoids from Siparuna glycycarpa. J. Sep. Sci. 36, 2253-2259.
Da Silva, R.O., Evangelista, F.C.G., Sabino, A.P., da Silva, L.A.M., de Oliveira, F.F., de Oliveira, R.A., 2020. Cytotoxicity assessment of Siparuna cymosa essential oil in the presence of myeloid leukemia cells. Rev. Virtual Quim. 12(6), 1-8.
Dias, C., Alves, L., Rodrigues, K., Brito, M., Rosa, C., do Amaral, F., Monteiro, O., Andrade, E., Maia, J., Moraes, D., 2015. Chemical composition and larvicidal activity of essential oils extracted from Brazilian legal Amazon plants against Aedes aegypti L. (Diptera: Culicidae). Evid. Based Complementary Altern. Med. 2015, 1-9.
De Almeida, M.A., Conegundes, J. L., Evangelista, M., de Freitas, P.H., Scio, E., 2021. Avaliação do perfil fitoquímico e do potencial antioxidante do extrato aquoso das folhas de Siparuna guianensis Aublet. J. Biol. Pharm. Agric. Manag. 17(2), 251-270.
De Melo, D.C., Miranda, L.D., Ferreira Junior, W.G., de Andrade, P.M., Alcoba, A. E., Siva, T.S., Cazal, C.M., Martins, C.H., 2017. Anticariogenic and antimycobacterial activities of the essential oil of Siparuna guianensis Aublet (Siparunaceae). Orbital: Electron. J. Chem. 9(1), 55-60.
De Oliveira, M., da Cruz, J., da Costa, W., Silva, S., Brito, M., de Menezes, S., Chaves Netom A., Andrade, E., Carvalho Junior, R., 2020. Chemical composition, antimicrobial properties of Siparuna guianensis essential oil and a molecular docking and dynamics molecular study of its major chemical constituent. Molecules 25, 1-15.
Dos Santos, G.A., Bartolomeu, I.F., Féboli, A., 2017. Propriedades biológicas dos alcaloides. Rev. Conexão Eletrônica. 16(1), 460-467.
El-Seedi, H., Ghia, F., Torssel, K.B.G., 1994. Cadinane sesquiterpenes from Siparuna macrotepala. Phytochemistry 35(6), 1495-1497.
Facundo, V., Azevedo, M.S., Rodrigues, R.V., Nascimento, L.F., Militão, J.S.L.T., da Silva, G.V.J., Braz Filho, R., 2012. Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana. Rev. Bras. Farmacogn. 22(5), 1134-1139.
Ferreira, R.M.A., D'Haveloose, N., Cruz, R., Araújo, R., Carvalho, J., Rocha, L., Fernandes, L., da Costa, T., Fernandes, C., Souto, R., 2020. Nano-emulsification enhances the larvicidal potential of the essential oil of Siparuna guianensis (Laurales: Siparunaceae) against Aedes (Stegomyia) aegypti (Diptera: Culicidae). J. Med. Entomol. 57(3), 788-796.
Ferreira, T., Oliveira, E., Tschoeke, P., Pinheiro, R., Maia, A.M., Aguiar, R., 2017. Potential use of Negramina (Siparuna guianensis Aubl.) essential oil to control wax moths and its selectivity in relation to honey bees. Ind. Crops Prod. 109, 151-157.
Ferreira, T., Haddi, K., Corrêa, R., Zapata, V., Piau, T., Souza, L., Santos, S., Oliveira, E., Jumbo, L., Ribeiro, B., Grisolia, C., Fidelis, R., Maia, A., Aguiar, R., 2019. Prolonged mosquitocidal activity of Siparuna guianensis essential oil encapsulated in chitosan nanoparticles. Plos Negl. Trop. Dis. 13(8), 1-23.
Fischer, D.C.H., Gonçalves, M.I., Oliveira, F., Alvarenga, M.A., 1999. Constituents from Siparuna apiosyce. Fitoterapia 70, 322-323.
Fischer, D.C.H., Limberger, R.P., Henriques, A.T., Moreno, P. R. H., 2005. Essential oils from fruits and Leaves of Siparuna guianensis (Aubl.) Tulasne from Southeastern Brazil. J. Essent. Oil Res. 17, 101-102.
Fonseca, T.L., Von Groll, A., Leitão, G.G., Scaini, C.J., Ramos, D.F., da Silva, P.E.A., 2008. Atividade antimicobacteriana de extratos vegetais frente a Mycobacterium fortuitum e Mycobacterium malmoense. Vitalle. 20(1), 65-71.
Frei, B., Baltisberger, M., Sticher, O., Heinrich, M., 1998. Medical ethnobotany of the Zapotecs of the Isthmus-Sierra (Oaxaca, Mexico): Documentation and assessment of indigenous uses. J. Ethnopharmacol. 62, 149-165.
García, J., Gilardoni, G., Cumbicus, N., Morocho, V., 2020. Chemical analysis of the essential oil from Siparuna echinata (Kunth) A. DC. (Siparunaceae) of Ecuador and isolation of the rare terpenoid sipaucin A. Plants. 9, 187-195.
Gerard, R.V., MacLean, D.B., Antonio, T.M., 1986. Examination of three Siparuna species for alkaloid content. Phytochemistry 25(9), 2155-2156.
Global Biodiversity Information Facility (GBIF). 1999. https://www.gbif.org/species/407 (Accessed on: 03/08/2021).
Gomez, M., Rocha, E.A., Gomberg, E., 2016. Análise das publicações etnobotânicas sobre plantas medicinais da Mata Atlântica na Região Sul do Estado da Bahia, Brasil. Fitos, 10(5), 115-140.
Guevara, A.J., Pardo, A.I., Díaz, J., Arias-Palacios, J., Celis, C., Loaiza, A., 2016. Identification and in vitro evaluation of antifungal activity of alkaloids from Siparuna sessiliflora kunth A. DC. leaves. Pharmacologyonline 2, 38-41.
Hall, C.F; Meirelles, J., 2017. Flora das cangas da serra dos carajás, Pará, Brasil: Siparunaceae. Rodriguésia 68(3), 1151-1153.
Hitziger, M., Heinrich, M., Edwards, P., Poll, E., Lopez, M., Krutli, P., 2016. Maya phytomedicine in Guatemala - Can cooperative research change ethnopharmacological paradigms?. J. Ethnopharmacol. 186, 61-72.
Jenett-Siems, K., Siems, K., Jakupovic, J., Gupta, M.P., Mockenhaupt, F.P., Bienzle, U., Eich, E., 2000. Sipandinolide: a butenolide including a novel type of carbon skeleton from Siparuna andina. Planta Med. 66, 384-385.
Jenett-Siems, K., Kraft, C., Siems, K., Jakupovic, J., Solis, P.N., Gupta, M.P., Bienzle, U., 2003. Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora. Phytochemistry 63, 377-381.
Leal, C. M., Leitão, S.G., Sausset, R., Mendonça, S., Nascimento, P.H., Cheohen, C.F., Esteves, M.E., Da Silva, M.L., Gondim, T., Monteiro, M.E., Tucci, A., Fintelman-Rodrigues, N., Siqueira, M., Miranda, M., Costa, F., Simas, R., Leitão, G.G., 2021. Flavonoids from Siparuna cristata as potential inhibitors of SARS‑CoV‑2 Replication. Rev. Bras. Farmacogn. 1-9.
Leitão, G.G., Simas, N.K., Soares, S.S.V., de Brito, A.P.P., Claros, B.M.G., Brito, T.B.M., Monache, F.D., 1999. Chemistry and pharmacology of Monimiaceae: a special focus on Siparuna and Mollinedia. J. Ethnopharmacol. 65, 87-102.
Leitão, G.G., Soares, S.S.V., Brito, T.B.M., Monache, F.D., 2000. Kaempferol glycosides from Siparuna apiosyce. Phytochemistry. 55, 679-682.
Leitão, G.G., El-Adji, S.S., de Melo, Q.A.L., 2005. Separation of Free and Glycosylated Flavonoids from Siparuna guianensis by Gradient and Isocratic CCC. J. Liq. Chrom. Relat. Tech. 28, 2041-2051.
Lentz, D., Clark, A.M., Hufford, C.D., Meurer-Grimes, B., Passreiter, C.M., Cordero, J., Ibrahimi, O., Okunade, A.L., 1998. Antimicrobial properties of Honduran medicinal plants. J. Ethnopharmacol. 63, 253-263.
López, J.A., Laurito, J.G., Lin, F., Duah, F.K., Sharaf, M., Aly, Y., Wong, L.K., Schiff, P.L., 1989. Alkaloids of Siparuna tonduziana. Planta Med.. 56, 492.
López, J.A., Laurito, J.G., Lin, F., Sharaf, M., Wong, L.K., Schiff, P.L., 1993. Alkaloids of Siparuna griseo-flavescens. Planta Med. 59, 100-101.
Lourenço, A.M., Haddi, K., Ribeiro, B., Corrêia, R., Tomé, H.V., Santos-Amaya, O., Pereira, E., Guedes, R., Santos, G.R., Oliveira, E., Aguiar, R.W., 2018. Essential oil of Siparuna guianensis as an alternative tool for improved lepidopteran control and resistance management practices. Sci. Rep. 15, 1-13.
Marti, G., Eparvier, V., Morleo, B., Le Ven, J., Apel, C., Bodo, B., Amand, S., Dumontet, V., Lozach, O., Meijer, L., Guéritte, F., Litaudon, M., 2013. Natural aristolactams and aporphine alkaloids as inhibitors of CDK1/Cyclin B and DYRK1A. Molecules 18, 3018-3027.
Martins, R., Xavier-Júnior, F., Barros, M., Menezes, T., Assis, C., Melo, A.C., Veras, B., Ferraz, V., Filho, A.A.M., Yogui, G., Bezerra, R., Seabra, G., Neves, J., Tadei, W., 2021. Impact on cholinesterase-inhibition and in silico investigations of sesquiterpenoids from Amazonian Siparuna guianensis Aubl. Spectrochim. Acta A Mol. Biomol. Spectrosc. 252, 1-11.
Milani, L.I.G., Terra, N.N., Fries, L.L.M., Cichoski, A.J., Rezer, A.P.S., Rackes, A.M., Parodia, C.G., 2012. Atividade antioxidante e antimicrobiana in vitro de extratos de caqui (Diospyroskaki L.) cultivar Rama Forte. Braz. J. Food Technol. 15(2), 118-124.
Mohammadhosseini, M., Frezza, C., Venditti, A., Mahdavi, B., 2021a. An overview of the genus Aloysia Palau (Verbenaceae): Essential oil composition, ethnobotany and biological activities. Nat. Prod. Res. DOI: org/10.1080/14786419.2021.1907576
Mohammadhosseini, M., Venditti, A., Frezza, C., Serafini, M., Bianco, A., Mahdavi, B., 2021b. The genus Haplophyllum Juss.: Phytochemistry and bioactivities—A review. Molecules 26, 4664.
Moura, W.S., Souza, S.R., Campos, F.S., Cangussu, A.S.R., Santos, E.M.S., Andrade, B.S., Gomes, C.H.B., Viana, K.F., Haddi, K., Oliveira, E.E., Nascimento, V.L., Aguiar, W.S., 2020. Antibacterial activity of Siparuna guianensis essential oil mediated by impairment of membrane permeability and replication of pathogenic bacteria. Ind. Crops Prod. 146, 1-10.
Nahar, L., El-Seedi, H.R., Khalifa, S.A.M., Mohammadhosseini, M., Sarker, S.D., 2021. Ruta essential oils: Composition and bioactivities. Molecules 26(16), 4766, 1-37.
Nascimento, J.C., Lage, L.F.O., Camargos, C.R.D., Amaral, J.C., Costa, L.M., Sousa, A.N., Oliveira, F.Q., 2011. Determinação da atividade antioxidante pelo método DPPH e doseamento de flavonoides totais em extratos de folhas da Bauhinia variegata. Rev. Bras. Farm. 92(4), 327-332.
Negri, G., Santi, D., Tabach, R., 2012. Chemical composition of hydroethanolic extracts from Siparuna guianensis, medicinal plant used as anxiolytics in Amazon region. Rev. Bras. Farmacogn. 22(5), 1024-1034.
Noriega, P., Guerrini, A., Sacchetti, G., Grandini, A., Ankuash, E., Manfredini, S., 2019. Chemical composition and biological activity of five essential oils from the Ecuadorian Amazon. Molecules 24, 1-12.
Nunes, H.S., Miguel, M.G., 2017. Rosa damascena essential oils: a brief review about chemical composition and biological properties. Trends Phytochem. Res. 1, 111-128.
Ootani, M.A., Aguiar., R.W., Ramos, A.C.C., Brito, D.R., da Silva, J.B., Cajazeira, J.P., 2013. Utilização de óleos essenciais na agricultura. J. Biotec. Biodivers. 4(2), 162-175.
Peckolt, T.; Peckolt, G., 1888. Histórias das Plantas Medicinais e Úteis do Brasil. v. 1, Lemmert & Cia, Rio de Janeiro.
Pérez-Jaramillo, C., Sánchez-Peralta, W., Murillo-Arango, W., Méndez-Arteaga, J., 2017. Acción antioxidante conjunta de extractos etanólicos de Mollinedia lanceolata, Croton leptostachyus y Siparuna sessiliflora. Rev. Acad. Colomb. Cienc. Ex. Fis. Nat. 41(158), 64-70.
Pina, N., Dolabela, M., Ferreira, M., Gontijo, D., Brandão, G., Nascimento, M., de Oliveira, A.B., 2016. Atividade antiplasmódica e fitoquímica de Siparuna poeppigii (Siparunaceae). XXIV Simpósio de Plantas Medicinais do Brasil, Belo Horizonte, Minas Gerais.
Pinto, J.M., Souza, E.A., Oliveira, D.F., 2010. Use of plant extracts in the control of common bean anthracnose. J. Crop Prot. 29(8), 838-842.
Portella, A.C., Munaro, M., Ascênio, S.D., Siqueira, C., Ferreira, T.P., Aguiar, R.W., 2014. Caracterização fisico-química do óleo essencial da Siparuna guianensis Aublet. Quim. Nova. 37(5), 844-849.
Rabêlo, S.V., Da Costa, M.M., Libório, R.C., Almeida, J.R.G.S., 2014. Atividade antioxidante e antimicrobiana de extratos de Atemoia (Annona Cherimola Mill. x A. squamosa L.). V Congresso Internacional & Encontro Brasileiro sobre Annonaceae, 36(1), 265-271.
Flora do Brasil 2020. Jardim Botânico do Rio de Janeiro. 2020. http://reflora.jbrj.gov.br/reflora/floradobrasil/FB223. Accessed on: 07/07/2020.
Renner, S.S., Hausner, G., 2000. New species of Siparuna (Siparunaceae) IV. A new subcanopy tree from whitesand areas in Brazil and Venezuela. Novon. 15(1), 202-206.
Rivera, P.F.N., Guerrini, A., Tsamaraint, E.A., 2014. Composición química del aceite esencial de hojas de Siparuna schimpffii Diels (limoncillo). Rev. Cubana Plant Med. 19(2), 128-137.
Rodrigues, O.G., Angélico, E.C., da Costa, J.G.M., Lucena, M.F.A., Queiroga Neto, V., Silva, W.W., 2016. Avaliação da atividade antioxidante dos extratos botânicos de Croton heliotrpiifolius Kunth. e Croton blanchetianus Baill: resultados preliminares. ACSA 12(3), 237-241.
Saltos, M.B.V., Puente, B.F.N., Malafronte, N., Braca, A., 2014. A new monoterpene glycoside from Siparuna thecaphora. Nat. Prod. Res. 28(1), 57-60.
Santos, D.S., Rodrigues, M.M.F., 2017. Atividades farmacológicas dos flavonoides: um estudo de revisão. Estação Científica, 7(3), 29-35.
Santos, S.C., Ferreira, F. S., Rossi-Alva, J. C., Fernandez, L.G., 2007. Atividade antimicrobiana in vitro do extrato de Abarema cochliocarpos (Gomes) Barneby & Grimes. Rev. Bras. Farmacogn. 17(2), 215-219.
Schultes, R.E., Raffauf, R.F., 1990. The Healing Forest: Medicinal and Toxic Plants of the Northwest Amazonia. Dioscorides Press: Portland.
Sousa, C., Silva, H., Vieira-Jr, G., Ayres, M., da Costa, C., Araújo, D., Cavalcante, L., Barros, E., Araújo, P., Brandão, M., Chaves, M., 2007. Fenóis totais e atividade antioxidante de cinco plantas medicinais. Quim. Nova 30(2), 351-355.
Souza, C,O., Melo, T.R.R., Melo, C.S.B., Menezes, Ê,M., Carvalho, A.C., Monteiro, L.C.R., 2016. Escherichia coli enteropatogênica: uma categoria diarreiogênica versátil. Rev. Pan-Amaz. Saúde. 7(2), 79-91.
Stashenko, E., Martinez, J.R., 2017. Essential Oils in Food Processing: Chemistry, Safety and Applications. John Wiley & Sons, New Jersey, EUA.
Tareau, M. A., Palisse, M., Odonne, G., 2017. As vivid as a weed…Medicinal and cosmetic plant uses amongst the urban youth in French Guiana. J. Ethnopharmacol. 203, 200-213.
Taylor, P., Arsenak, M., Abad, M., Fernández, Á., Milano, B., Gonto, R., Ruiz, M., Fraile, S., Taylor, S., Estrada, O., Michelangeli, F., 2012. Screening of Venezuelan medicinal plant extracts for cytostatic and cytotoxic activity against tumor cell lines. Phytother. Res. 27, 530-539.
Tempone, A.G., Borborema, T., Andrade Jr, H.F., Gualda, N.C., Yogi, A., Carvalho, C.S., Bachiega, D., Lupo, F., Bonotto, S.V., Fischer, D.C.H., 2005. Antiprotozoal activity of Brazilian plants extracts from isoquinoline alkaloid producing families. Phytomedicine 12, 382-390.
Tene, V., Malagón, O., Finzi, P.V., Vidari, G., Armijos, C., Zaragoza, T., 2007. An ethnobotanical survey of medicinal plants used in Loja and Zamora-Chinchipe, Ecuador. J. Ethnopharmacol. 111, 63-81.
Toledo, P., Ferreira, T., Bastos, I., Rezende, S., Jumbo, L., Didonet, J., Andrade, B., Melo, T., Smagghe, G., Oliveira, E., Aguiar, R., 2019. Essential oil from Negramina (Siparuna guianensis) plants controls aphids without impairing survival and predatory abilities of nontarget ladybeetles. Environ. Pollut. 225, 1-12.
Valadeau, C., Pabon, A., Deharo, E., Albán-Castillo, J., Estevez, Y., Lores, F.A., Rojas, R., Gamboa, D., Sauvain, M., Castillo, D., Bourdy, G., 2009. Medicinal plants from the Yanesha (Peru): Evaluation of the leishmanicidal and antimalarial activity of selected extracts. J. Ethnopharmacol.123, 412-422.
Valentini, C.M.A., Rodrigues-Ortiz, C.E., Coelho, M.F.B., 2010a. Siparuna guianensis Aublet (negramina): uma revisão. Rev. Bras. Pl. Med. 12(1), 96-104.
Valentini, C.M.A., da Silva, L.E., Maciel, E., Franceschini, E., de Sousa Jr, P., Dall'Óglio, E., 2010b. Variação anual do rendimento e composição química dos componentes voláteis da Siparuna guianensis Aublet. Quím. Nova 33(7), 1506-1509.
Vásquez, J., Jiménez, S.L., Gómez, I.C., Rey, J., Henao, A., Marín, D.N., Romero, J., Alarcón, J., 2013. Snakebites and ethnobotany in the Eastern region of Antioquia, Colombia — The traditional use of plants. J. Ethnopharmacol. 146, 449-455.
Viana, F.A., Andrade-Neto, M., Pouliquen, Y.B.M., Uchoa, D., Sobral, M.M., Morais, S., 2002. Essential Oil of Siparuna guianensis Aublet from the Amazon Region of Brazil. J. Essent. Oil Res. 14, 60-62.
Viegas Junior, C., Bolzani, V.S., Barreiro, E.J., 2006. The natural products and the modern medicinal chemistry. Quím. Nova 29(2), 2326-337.
Wansi, J.D., Sewald, N., Nahar, L., Martin, C., Sarker, S.D., 2018. Bioactive essential oils from the Cameroonian rain forest: A review - Part I. Trends Phytochem. Res. 2, 187-234.
Zoghbi, M.G., Andrade, E.H.A., Santos, A.S., Silva, M.H.L., Maia, J.G., 1998. Essential oils of Siparuna guianensis Aubl. J. Essent. Oil Res. 10(5), 543-546.