Piper aduncum L.: Planta Pluripotente e Fonte de Substâncias Fitoquímicas Importantes

A. M. Pohlit; A. C. S. Pinto; R. Mause

doi:10.32712/2446-4775.2006.37

Piper aduncum L.: Pluripotente Plant and Important Phytochemical Substance Source

Vol. 2 No. 01 (2006)
7-18
15/10/2013
01/06/2006
https://doi.org/10.32712/2446-4775.2006.37

A. M. Pohlit
A. C. S. Pinto
R. Mause

Keywords

Piper aduncum

dillapiol

essential oil

biological activities

synergism

Abstract

This review deals with the primary biological activities and previously isolated active principles from pimenta-longa (long pepper) or apertaruão, the Piper aduncum L. (Piperaceae). Among the most important biological activities found in extracts and for isolated substances are: antibacterial, antifungal, antioxidant, cytotoxic/anticancer, larvicidal/insecticidal, antiplatelet/antiaggregation, molusidal, leishmanicidal end antiviral. This endemic plant is found naturally in Brazil and is a source of a relatively abundant essential oil obtained from the leaves and tender branches. This oil presents many of the above biological activities and medicinal properties. Here in we present our data on pilot-scale production of this oil as well as the purification of the principal component dillapiol using chromatography and fractional vacuum distillation from this oil. This work demonstrates the technical viability of cultivated P. aduncum as a renewable source of this bioactive substance. Among the proven biological activities of this compound are: antibacterial, insecticida and larvicidal, as well as inhibition of the enzymes cytochrome P450 and epoxidase.

References

BALDOQUI, D.C.; KATO, M.J.; CAVALHEIRO, A.J.; BOLZANI, V.S.; YOUNG, M.C.M.; FURLAN, M. A chromene and prenylated benzoic acid from Piper aduncum. Phytochemistry, v.51, n.7, p.899-902, 1999.
BASTOS, C.N.; ALBUQUERQUE, P.S.B. Efeito do Óleo de Piper aduncum no Controle em Pós-colheita de Colletotricum musae em Banana. Fitopatologia Brasileira, v.29, n.5, p.555-557, 2004.
BELZILE, A.-S.; MAJERUS, S.L.; PODESZFINSKI, C.; GUILLET, G.; DURST, T.; ARNASON, J.T. Dillapiol Derivatives as Synergists: Structure-Activity Relationship Analysis. Pesticide Biochemistry and Physiology, v.66, n.1, p.33-40, 2000.
BENCHIMOL, R.L.; SUTTON, J.C.; BASTOS, C.N.; DIASFILHO, M.. Survival of black pepper plants in soil infected with Fusarium solani f. sp. Piperis and amended with extracts or residues of Piper aduncum. Canadian Journal of Plant Pathology, v.23, p.194-210, 2001.
BERNARD, C.B.; ARNASON, J.T.; PHILOGÃˆNE, B.J.R.; LAM, J.; WADDELL, T. Effect of lignans and other secondary metabolites of the Asteraceae on the mono-oxygenase activity of the European corn borer. Phytochemistry, v.28, n.5, p.1373-1377, 1989.
BERNARD, C.B.; KRISHNAMURTY, H.G.; CHAURET, D.; DURST, T.; PHILOGÃˆNE, B.J.R.; SÁNCHEZ-VINDAS, P.; HASBUN, C.; POVEDA, L., SAN ROMÁN, L.; ARNASON, J.T.
Insecticidal defenses of Piperaceae from the Neotropics. Journal of Chemical Ecology, v.21, n.6, p.801-14, 1995.
BOTSARIS, A.S. As fórmulas mágicas das plantas: como utilizar a fitoterapia no tratamento de doenças simples. 2.ed., Rio de Janeiro: Record: Nova Era, 619 p., 1997.
BOURDY, G.; DEWALT, S.J.; CHÁVEZ DE MICHEL, L.R.; ROCA, A.; DEHARO, E.; MUÑOZ, V.; BALDERRAMA, L.; QUENEVO, C.; GIMENEZ, A. Medicinal plants uses of the Tacana, an Amazonian Bolivian ethnic group. Journal of Ethnopharmacology, v.70, n.2, p.87-109, 2000.
BUDZINSKI, J.W.; FOSTER, B.C.; VANDENHOEK, S.; ARNASON, J.T. An in vitro evaluation of human cytochrome P450 3A4 inhibition by selected commercial herbal extracts and tinctures. Phytomedicine, v.7, n.4, p.273-282, 2000.
CÁCERES, A.; MENÉNDEZ, H.; MÉNDEZ, E.; COHOBÓN, E.; SAMAYOA, B.E.; JAUREGUI, E.; PERALTA, E.; CARRILLO, G. Antigonorrhoeal activity of plants used in Guatemala for the treatment of sexually transmitted diseases. Journal of Ethnopharmacology, v.48, p.85-8, 1995.
CICCIÓ, J.F.; BALLESTERO, C.M. Constituyentes volátiles de las hojas y espigas de Piper aduncum (Piperaceae) de Costa Rica. Revista de Biología Tropical, v.45, n.2, p.783-90, 1997.
DUKE, J.A.; VASQUEZ, R. Amazonian ethnobotanical dicitionary. Boca Raton (Florida, EUA): CRC Press, 215p. il., 1994.
FAZOLIN, M.; ESTRELA, J.L.V.; CATANI, V.; LIMA, M.S.; ALÉCIO, M.R. Toxicidade do Óleo de Piper aduncum L. a Adultos de Cerotona tingomarianus Bechyné (Coleóptera: Chrysomelidae). Neotropical Entomology, v.34, n.3, p.485-489, 2005.
GAERTNER, L.S.; MURRAY, C.L.; MORRIS, C.E. Transepithelial transport of Nicotine and Vinblastine in isolated Malpighian tubules of the tobacco hornworm (Manduca sexta) suggests a P-glycoprotein-like mechanism. The Journal of Experimental Biology, v.201, p.2637-2645, 1998.
GOODMAN, L.S.; GILMAN, A. The pharmacological basis of therapeutics. In: J.G. HARDMAN, A.G. GILMAN, L.E. 9.ed. Limbird. New York: McGraw-Hill, 1905p., 1996
HERMOSO, A.; JIMÉNEZ, I.A.; MAMANI, Z.A.; BAZZOCCHI, I.L.; PIÑERO, J.E.; RAVELO, A.G.; VALLADARES, B. Antileishmanial and Activities of Dihydrochalcones from Piper elongatum and Synthetic Related Compounds. Structural Requirements for Activity. Bioorganic & Medicinal Chemistry, v.11, n.18, p.3975-3980, 2003.
JANTAN, I.; RAFI, I.A.A.; JALIL, J. Platelet-activating factor (PAF) receptor-binding antagonist activity of Malaysian medicinal plants. Phytomedicine, v.12, n.1-2, p.88-92, 2005.
KLOUCEK, P.; POLESNY, Z.; SVOBODOVA, B.; VLKOVA, E.; KOKOSKA, L. Antibacterial screening of some Peruvian medicinal plants used in Callería District. Journal of Ethnopharmacology, v.99, n.2, p.309-312, 2005.
LAROCQUE, N.; VINCENT, C.; BÉLANGER, A.; BOURASSA, J.P. Effects of tansy essential oil from Tanacetum vulgare on biology of oblique-banded leafroller, Choristoneura rosaceana. Journal of Chemical Ecology, v.25, n.6, p.1319-1330, 1999.
LENTZ, D.L.; CLARK, A.M.; HUFFORD, C.D.; MEURERGRIMES, B.; PASSREITER, C.M.; CORDERO, J.; IBRAHIMI, O.; OKUNADE, A.L. Antimicrobial properties of Honduran medicinal plants. Journal of Ethnopharmacology, v.63, p.253-63, 1998.
LOHÉZIC-LE DÉVÉHAT, F.; BAKHTIAR, A.; BÉZIVIN, C.; AMOROS, M.; BOUSTIE, J. Antiviral and cytotoxic activities of some Indonesian plants. Fitoterapia, v.73, n.5, p.400-405, 2002.
MAIA, J.G.S.; ZOHGBI, M.G.B.; ANDRADE, E.H.A.; SANTOS, A.S.; SILVA, M.H.L.; LUZ, A.I.R.; BASTOS, C.N. Constituents of the essential oil of Piper aduncum L. growing wild in the Amazon region. Flavour and Fragrance Journal, v.13, p.269-72, 1998. 23. MAIA, J.G.S.; ZOGHBI, M.G.B.; ANDRADE, E.H.A. Plantas aromáticas na Amazônia e seus óleos essenciais. Belém: Museu Paraense Emílio Goeldi, p.123-127, 2001.
MILLIKEN, W. Plants for Malaria Plants for Fever: Medicinal species in Latin America - a bibliographic survey. Inglaterra: Whitestable Litho Ltda. 116 p., 1997.
MORANDIM, A.A.; BERGAMO, D.C.B.; CAVALHEIRO, A.J.; LOPES, M.N.; YOUNG, M.C.M.; KATO, M.J.; BOLZANI. V.S.; FURLAN, M. Potencial antifúngico e antitumoral de metabólitos de Piper aduncum. 25ª. Reunião Anual da Sociedade Brasileira de Química, 2002.
NAIR, M.G.; BURKE, B.A. Antimicrobial Piper metabolite and related compounds. Journal of Agricultural and Food Chemistry, v.38, p.1093-1096, 1990.
OKUNADE, A.L.; HUFFORD, C.D.; CLARK, A.M.; LENTZ, D. Antimicrobial properties of the constituents of Piper aduncum. Phytotherapy Research, v.11, p.142-144, 1997.
OMAR, S.; GODARD, K.; INGHAM, A.; HUSSAIN, H.; WONGPANICH, V.; PEZZUTO, J.; DURST, T.; EKLU, C.; GBEASSOR, M.; SANCHEZ-VINDAS, P.; POVEDA, L.; PHILOGENE, B.J.R.; ARNASON, J.T. Antimalarial activities of gedunin and 7-methoxygedunin and synergistic activity with dillapiol. Annals of Applied Biology, v.143, n.2, p.135-141, 2003.
ORJALA, J.; ERDELMEIER, C.A.J.; WRIGHT, A.D.; RALI, T.; STICHER, O. Chromenes and a prenylated benzoic acid derivative from Piper aduncum. Phytochemistry, v.34, n.3, p.813-818, 1993a.
ORJALA, J.; ERDELMEIER, C.A.J.; WRIGHT, A.D.; RALI, T.; STICHER, O. Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. Planta Medica, v.59, p.547-551, 1993b.
ORJALA, J.; WRIGHT, A.D.; ERDELMEIER, C.A.J.; STICHER, O. New monoterpene-substituted dihydrochalcones from Piper aduncum. Helvetica Chimica Acta, v.76, p.1481-1488, 1993c.
ORJALA, J.; WRIGHT, A.D.; BEHRENDS, H.; FOLKERS, G.; STICHER, O. Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. Journal of Natural Products, v.57, n.1, p.18-26, 1994.
Pharmacopéia dos Estados Unidos do Brasil. Redigida: DA SILVA, R.A.D. São Paulo: Companhia Editora Nacional, 1926.
Pharmacopéia Brasileira. 4.ed. Parte II. São Paulo: Atheneu Editora, 2000.
PIO CORRÊA, M. Dicionário das plantas úteis do Brasil e das exóticas cultivadas. v.I. Rio de Janeiro: Imprensa Nacional, 1926.
RAMOS, A.; VISOZO, A.; PILOTO, J.; GARCIA, A.; RODRIGUEZ, C.A.; RIVERO, R. Screening of antimutagenicity via antioxidant activity in Cuban medicinal plants. Journal of Ethnopharmacology, v.87, n.2-3, p.241-246, 2003.
REVILLA, J. Plantas da Amazônia: Oportunidades econômicas e sustentáveis. Manaus: SEBRAE / INPA. 405p. il., 2000.
RIBEIRO, J.E.L.S.; HOPKINS, M.J.G.; VICENTINI, A.; SOTHERS, C.A.; COSTA, M.A.S.; BRITO, J.M.; SOUZA, M.A.D.; MARTINS, L.H.P.; LOHMANN, L.G.; ASSUNÇÃO, P.A.C.L.; PEREIRA, E.C.; SILVA, C.F.; MESQUITA, M.R.; PROCÓPIO, L.C. Flora da Reserva Ducke: Guia de identificação das plantas vasculares de uma floresta de terrafirme na Amazônia Central. Manaus: INPA. 816p. il., 1999.
RODRIGUES, R.M. A Flora da Amazônia. Belém: CEJUP, 462p., 1989.
SCHULTES, R.E.; RAFFAUF, R.F. The healing forest: Medicinal and toxic plants of the Northwest Amazonia. Historical, ethno- and economic botany series: v. 2. Portland (Oregon, EUA): Dioscorides Press, 484p. il., 1992.
TOMAR, S.S.; MAHESHWARI, M.L.; MUKERJEE, S.K. Syntheses and Synergistic Activity of Some Pyrethrum Synergists from Dillapiole. Agricultural and Biological Chemistry, v.43, n.7, p.1479-1483, 1979a.
TOMAR, S.S.; MAHESHWARI, M.L.; MUKERJEE, S.K. Synthesis and Synergistic Activity of Dillapiole Based Pyrethrum Synergists. Journal of Agricultural and Food Chemistry, v.27, n.3, p.547-550, 1979b.
TORRES-SANTOS, E.C.; MOREIRA, D.L.; KAPLAN, M.A.C.; MEIRELLES, M.N.; ROSSI-BERGMANN, B. Selective effect of 2’,6’-dihydroxy-4’-methoxychalcone isolated from Piper aduncum on Leishmania amazonensis. Antimicrobial Agents and Chemotherapy, v.43, n.5, p.1234-1241, 1999.

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Author(s)

A. M. Pohlit
Instituto Nacional de Pesquisas da Amazônia, Coordenação de Pesquisas em Produtos Naturais Laboratório de Princípios Ativos da Amazônia Avenida André Araújo, 2936, Petrópolis, CEP 69083-000 Manaus, Amazonas, Brasil
A. C. S. Pinto
Programa de Pós-Graduação em Biotecnologia, Universidade Federal do Amazonas Av. Gen. Rodrigo Octávio Jordão Ramos, 3000, Campus Universitário, Coroado I, 69077-000, Manaus, AM
R. Mause
SIEMA Eco Essências da Amazônia Ltda Conjunto Colina do Aleixo, 69083-600 Manaus, AM

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Piper aduncum L.: Pluripotente Plant and Important Phytochemical Substance Source. Rev Fitos [Internet]. 2006 Jun. 1 [cited 2024 Nov. 22];2(01):7-18. Available from: https://revistafitos.far.fiocruz.br/index.php/revista-fitos/article/view/37

This work is licensed under a Creative Commons Attribution 4.0 International License.

[1] BALDOQUI, D.C.; KATO, M.J.; CAVALHEIRO, A.J.; BOLZANI, V.S.; YOUNG, M.C.M.; FURLAN, M. A chromene and prenylated benzoic acid from Piper aduncum. Phytochemistry, v.51, n.7, p.899-902, 1999.

[2] BASTOS, C.N.; ALBUQUERQUE, P.S.B. Efeito do Óleo de Piper aduncum no Controle em Pós-colheita de Colletotricum musae em Banana. Fitopatologia Brasileira, v.29, n.5, p.555-557, 2004.

[3] BELZILE, A.-S.; MAJERUS, S.L.; PODESZFINSKI, C.; GUILLET, G.; DURST, T.; ARNASON, J.T. Dillapiol Derivatives as Synergists: Structure-Activity Relationship Analysis. Pesticide Biochemistry and Physiology, v.66, n.1, p.33-40, 2000.

[4] BENCHIMOL, R.L.; SUTTON, J.C.; BASTOS, C.N.; DIASFILHO, M.. Survival of black pepper plants in soil infected with Fusarium solani f. sp. Piperis and amended with extracts or residues of Piper aduncum. Canadian Journal of Plant Pathology, v.23, p.194-210, 2001.

[5] BERNARD, C.B.; ARNASON, J.T.; PHILOGÃˆNE, B.J.R.; LAM, J.; WADDELL, T. Effect of lignans and other secondary metabolites of the Asteraceae on the mono-oxygenase activity of the European corn borer. Phytochemistry, v.28, n.5, p.1373-1377, 1989.

[6] BERNARD, C.B.; KRISHNAMURTY, H.G.; CHAURET, D.; DURST, T.; PHILOGÃˆNE, B.J.R.; SÁNCHEZ-VINDAS, P.; HASBUN, C.; POVEDA, L., SAN ROMÁN, L.; ARNASON, J.T.

[7] Insecticidal defenses of Piperaceae from the Neotropics. Journal of Chemical Ecology, v.21, n.6, p.801-14, 1995.

[8] BOTSARIS, A.S. As fórmulas mágicas das plantas: como utilizar a fitoterapia no tratamento de doenças simples. 2.ed., Rio de Janeiro: Record: Nova Era, 619 p., 1997.

[9] BOURDY, G.; DEWALT, S.J.; CHÁVEZ DE MICHEL, L.R.; ROCA, A.; DEHARO, E.; MUÑOZ, V.; BALDERRAMA, L.; QUENEVO, C.; GIMENEZ, A. Medicinal plants uses of the Tacana, an Amazonian Bolivian ethnic group. Journal of Ethnopharmacology, v.70, n.2, p.87-109, 2000.

[10] BUDZINSKI, J.W.; FOSTER, B.C.; VANDENHOEK, S.; ARNASON, J.T. An in vitro evaluation of human cytochrome P450 3A4 inhibition by selected commercial herbal extracts and tinctures. Phytomedicine, v.7, n.4, p.273-282, 2000.

[11] CÁCERES, A.; MENÉNDEZ, H.; MÉNDEZ, E.; COHOBÓN, E.; SAMAYOA, B.E.; JAUREGUI, E.; PERALTA, E.; CARRILLO, G. Antigonorrhoeal activity of plants used in Guatemala for the treatment of sexually transmitted diseases. Journal of Ethnopharmacology, v.48, p.85-8, 1995.

[12] CICCIÓ, J.F.; BALLESTERO, C.M. Constituyentes volátiles de las hojas y espigas de Piper aduncum (Piperaceae) de Costa Rica. Revista de Biología Tropical, v.45, n.2, p.783-90, 1997.

[13] DUKE, J.A.; VASQUEZ, R. Amazonian ethnobotanical dicitionary. Boca Raton (Florida, EUA): CRC Press, 215p. il., 1994.

[14] FAZOLIN, M.; ESTRELA, J.L.V.; CATANI, V.; LIMA, M.S.; ALÉCIO, M.R. Toxicidade do Óleo de Piper aduncum L. a Adultos de Cerotona tingomarianus Bechyné (Coleóptera: Chrysomelidae). Neotropical Entomology, v.34, n.3, p.485-489, 2005.

[15] GAERTNER, L.S.; MURRAY, C.L.; MORRIS, C.E. Transepithelial transport of Nicotine and Vinblastine in isolated Malpighian tubules of the tobacco hornworm (Manduca sexta) suggests a P-glycoprotein-like mechanism. The Journal of Experimental Biology, v.201, p.2637-2645, 1998.

[16] GOODMAN, L.S.; GILMAN, A. The pharmacological basis of therapeutics. In: J.G. HARDMAN, A.G. GILMAN, L.E. 9.ed. Limbird. New York: McGraw-Hill, 1905p., 1996

[17] HERMOSO, A.; JIMÉNEZ, I.A.; MAMANI, Z.A.; BAZZOCCHI, I.L.; PIÑERO, J.E.; RAVELO, A.G.; VALLADARES, B. Antileishmanial and Activities of Dihydrochalcones from Piper elongatum and Synthetic Related Compounds. Structural Requirements for Activity. Bioorganic & Medicinal Chemistry, v.11, n.18, p.3975-3980, 2003.

[18] JANTAN, I.; RAFI, I.A.A.; JALIL, J. Platelet-activating factor (PAF) receptor-binding antagonist activity of Malaysian medicinal plants. Phytomedicine, v.12, n.1-2, p.88-92, 2005.

[19] KLOUCEK, P.; POLESNY, Z.; SVOBODOVA, B.; VLKOVA, E.; KOKOSKA, L. Antibacterial screening of some Peruvian medicinal plants used in Callería District. Journal of Ethnopharmacology, v.99, n.2, p.309-312, 2005.

[20] LAROCQUE, N.; VINCENT, C.; BÉLANGER, A.; BOURASSA, J.P. Effects of tansy essential oil from Tanacetum vulgare on biology of oblique-banded leafroller, Choristoneura rosaceana. Journal of Chemical Ecology, v.25, n.6, p.1319-1330, 1999.

[21] LENTZ, D.L.; CLARK, A.M.; HUFFORD, C.D.; MEURERGRIMES, B.; PASSREITER, C.M.; CORDERO, J.; IBRAHIMI, O.; OKUNADE, A.L. Antimicrobial properties of Honduran medicinal plants. Journal of Ethnopharmacology, v.63, p.253-63, 1998.

[22] LOHÉZIC-LE DÉVÉHAT, F.; BAKHTIAR, A.; BÉZIVIN, C.; AMOROS, M.; BOUSTIE, J. Antiviral and cytotoxic activities of some Indonesian plants. Fitoterapia, v.73, n.5, p.400-405, 2002.

[23] MAIA, J.G.S.; ZOHGBI, M.G.B.; ANDRADE, E.H.A.; SANTOS, A.S.; SILVA, M.H.L.; LUZ, A.I.R.; BASTOS, C.N. Constituents of the essential oil of Piper aduncum L. growing wild in the Amazon region. Flavour and Fragrance Journal, v.13, p.269-72, 1998. 23. MAIA, J.G.S.; ZOGHBI, M.G.B.; ANDRADE, E.H.A. Plantas aromáticas na Amazônia e seus óleos essenciais. Belém: Museu Paraense Emílio Goeldi, p.123-127, 2001.

[24] MILLIKEN, W. Plants for Malaria Plants for Fever: Medicinal species in Latin America - a bibliographic survey. Inglaterra: Whitestable Litho Ltda. 116 p., 1997.

[25] MORANDIM, A.A.; BERGAMO, D.C.B.; CAVALHEIRO, A.J.; LOPES, M.N.; YOUNG, M.C.M.; KATO, M.J.; BOLZANI. V.S.; FURLAN, M. Potencial antifúngico e antitumoral de metabólitos de Piper aduncum. 25ª. Reunião Anual da Sociedade Brasileira de Química, 2002.

[26] NAIR, M.G.; BURKE, B.A. Antimicrobial Piper metabolite and related compounds. Journal of Agricultural and Food Chemistry, v.38, p.1093-1096, 1990.

[27] OKUNADE, A.L.; HUFFORD, C.D.; CLARK, A.M.; LENTZ, D. Antimicrobial properties of the constituents of Piper aduncum. Phytotherapy Research, v.11, p.142-144, 1997.

[28] OMAR, S.; GODARD, K.; INGHAM, A.; HUSSAIN, H.; WONGPANICH, V.; PEZZUTO, J.; DURST, T.; EKLU, C.; GBEASSOR, M.; SANCHEZ-VINDAS, P.; POVEDA, L.; PHILOGENE, B.J.R.; ARNASON, J.T. Antimalarial activities of gedunin and 7-methoxygedunin and synergistic activity with dillapiol. Annals of Applied Biology, v.143, n.2, p.135-141, 2003.

[29] ORJALA, J.; ERDELMEIER, C.A.J.; WRIGHT, A.D.; RALI, T.; STICHER, O. Chromenes and a prenylated benzoic acid derivative from Piper aduncum. Phytochemistry, v.34, n.3, p.813-818, 1993a.

[30] ORJALA, J.; ERDELMEIER, C.A.J.; WRIGHT, A.D.; RALI, T.; STICHER, O. Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves. Planta Medica, v.59, p.547-551, 1993b.

[31] ORJALA, J.; WRIGHT, A.D.; ERDELMEIER, C.A.J.; STICHER, O. New monoterpene-substituted dihydrochalcones from Piper aduncum. Helvetica Chimica Acta, v.76, p.1481-1488, 1993c.

[32] ORJALA, J.; WRIGHT, A.D.; BEHRENDS, H.; FOLKERS, G.; STICHER, O. Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. Journal of Natural Products, v.57, n.1, p.18-26, 1994.

[33] Pharmacopéia dos Estados Unidos do Brasil. Redigida: DA SILVA, R.A.D. São Paulo: Companhia Editora Nacional, 1926.

[34] Pharmacopéia Brasileira. 4.ed. Parte II. São Paulo: Atheneu Editora, 2000.

[35] PIO CORRÊA, M. Dicionário das plantas úteis do Brasil e das exóticas cultivadas. v.I. Rio de Janeiro: Imprensa Nacional, 1926.

[36] RAMOS, A.; VISOZO, A.; PILOTO, J.; GARCIA, A.; RODRIGUEZ, C.A.; RIVERO, R. Screening of antimutagenicity via antioxidant activity in Cuban medicinal plants. Journal of Ethnopharmacology, v.87, n.2-3, p.241-246, 2003.

[37] REVILLA, J. Plantas da Amazônia: Oportunidades econômicas e sustentáveis. Manaus: SEBRAE / INPA. 405p. il., 2000.

[38] RIBEIRO, J.E.L.S.; HOPKINS, M.J.G.; VICENTINI, A.; SOTHERS, C.A.; COSTA, M.A.S.; BRITO, J.M.; SOUZA, M.A.D.; MARTINS, L.H.P.; LOHMANN, L.G.; ASSUNÇÃO, P.A.C.L.; PEREIRA, E.C.; SILVA, C.F.; MESQUITA, M.R.; PROCÓPIO, L.C. Flora da Reserva Ducke: Guia de identificação das plantas vasculares de uma floresta de terrafirme na Amazônia Central. Manaus: INPA. 816p. il., 1999.

[39] RODRIGUES, R.M. A Flora da Amazônia. Belém: CEJUP, 462p., 1989.

[40] SCHULTES, R.E.; RAFFAUF, R.F. The healing forest: Medicinal and toxic plants of the Northwest Amazonia. Historical, ethno- and economic botany series: v. 2. Portland (Oregon, EUA): Dioscorides Press, 484p. il., 1992.

[41] TOMAR, S.S.; MAHESHWARI, M.L.; MUKERJEE, S.K. Syntheses and Synergistic Activity of Some Pyrethrum Synergists from Dillapiole. Agricultural and Biological Chemistry, v.43, n.7, p.1479-1483, 1979a.

[42] TOMAR, S.S.; MAHESHWARI, M.L.; MUKERJEE, S.K. Synthesis and Synergistic Activity of Dillapiole Based Pyrethrum Synergists. Journal of Agricultural and Food Chemistry, v.27, n.3, p.547-550, 1979b.

[43] TORRES-SANTOS, E.C.; MOREIRA, D.L.; KAPLAN, M.A.C.; MEIRELLES, M.N.; ROSSI-BERGMANN, B. Selective effect of 2’,6’-dihydroxy-4’-methoxychalcone isolated from Piper aduncum on Leishmania amazonensis. Antimicrobial Agents and Chemotherapy, v.43, n.5, p.1234-1241, 1999.