CHEMICAL CONSTITUENTS AND BIOACTIVITIES OF ESSENTIAL OILS FROM THE GENUS PIPER (PIPERACEAE): A REVIEW
Resumen
The essential oils are object of studies that aim the identification of its compounds and its possible biological activities. The present investigation is a literature review of essential oils extracted from species of the Piper genus that presented biological activities. The references selected reports the extraction of oils from different plant parts and its bioactivities. The most reported actions were: antibacterial, antifungal, antioxidant and larvicidal/insecticidal. This review is of great relevance to promote further investigations about the biological effects of volatile compounds present in the essential oils of species belonging to the family Piperaceae, hence contributing for the research on new biotechnological products, such as medicines and pesticides.
Citas
BRITO, A.M.G; RODRIGUES, S.A.; BRITO, R.G.; XAVIER-FILHO, L. Aromaterapia: da gênese a atualidade. Rev. Bras. plantas med. [online], vol.15, n.4, supl.1, pp.789-793. ISSN 1516-0572. 2013
HENRIQUES, A.T.; DANIELLI, L.J.; APEL, M.A. Óleos essenciais: importância e perspectivas terapêuticas. Capítulo IX. IN YUNES, A. R.; CHECHINEL FILHO, V. Química de produtos Naturais, novos fármacos e a moderna farmacognosia. 5 ed., rev e ampl. – Itajaí, SC: Univali, 528p. 2016
SVOBODA, K.P.; SVOBODA, T.G.; SYRED, A.A. A Closer Look: Secretory Structures of Aromatic and Medicinal Plants. HerbalGram. 53:34-43. American Botanical Council. 2001
ALBIERO, A.L.M.; PAOLI, A.A.S.; SOUZA, L.A.; MOURÃO, K.S. Morfoanatomia dos órgãos vegetativos de Piper hispidum Sw. (Piperaceae). Brazilian Journal of Pharmacognosy, v.16, p.379-391. 2006
ALBIERO, A.L.M.; PAOLI, A.A.S.; SOUZA, L.A.; MOURÃO, K.S. Morphology and anatomy of vegetative organs of Piper crassinervium H.B. K. (Piperaceae). Acta Botânica Brasílica, v.19, p.305-312. 2005a
ALBIERO, A.L.M.; SOUZA, L.A.; MOURÃO, K.S.; ALMEIDA, O.J.G.; LOPES, A.L. Morfoanatomia do caule e da folha de Piper gaudichaudianum Kuntze (Piperaceae). Acta Farmacêutica Bonaerense, v.24, p.550-554. 2005b
YUSOFF, Z.M.; NORDIN, M.N.N.; RAHIMAN, M.H.F.; ADNAN, R.; TAIB, M.N. Characterization of Down-Flowing Steam Distillation System using Step Test Analysis. IEEE CSGRC, p. 197-201. 2011
CHECHINEL, V.F.; YUNES, R.A. Novas perspectivas dos produtos naturais na Química Medicinal Moderna. Química de Produtos Naturais, novos fármacos e a moderna farmacognosia / Valdir Cechinel Filho, Rosendo Augusto Yunes (Org) – 5 ed., rev. e ampl. – Itajaí, SC: Univali. pp 269-321. 2016.
DEWICK, P.M. Medicinal Natural Products: a biosynthetic approach. New York: John Wiley & Sons. 546p. 2008.
LOBO, A.M.; LOURENÇO, A.M. Biossíntese de produtos naturais. Editora IST Press. Lisboa Portugal, 272p. 2007
SATO, T.; KIGAWA, A.; TAKAGI, R.; ADACHI, T.; HOSHINO, T. Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species. Organic & biomolecular chemistry, 6(20), 3788–3794. 2008.
SOUTO, A.L. Análise Metabolômica de Peperomia obtusifolia (L.) A. Tese de Doutorado apresentada ao Programa de Pós Graduação em Produtos Naturais e Sintéticos - UFPB. João Pessoa – PB. Disponivel em: http://tede.biblioteca.ufpb.br/handle/tede/8052. Acesso realizado em: 27 de setembro de 2017, às 18h 21min. 2015
FREITAS, G.C.; BATISTA, J.M.; FRANCHI, G.C.; NOWILL, A.E.; YAMAGUCHI, L.F.; VILCACHAGUA, J.D.; KATO, M.J. Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC. Phytochemistry. 97, 81–87. 2014.
LOPEZ, S.N.; BATISTA, M.; BATISTA, A.N.L.; MOTA, J.S.; CASS, Q.B.; KATO, M.J. Structure Elucidation and Absolute Stereochemistry of Isomeric Monoterpene Chromane Esters. J. Org. Chem. (June 2016), 2603–2612. 2011
MONTEIRO, D.; GUIMARÃES, E.F. Flora do Parque Nacional do Iatiaia – Brasil: Manekia e Piper (Piperaceae) do Parque Nacional do Itatiaia. Rodriguésia. 60 (4): 999-1024. 2009
PARMAR, V.S.; JAIN, S.C.; BISHT, K.S.; JAIN, R.; TANEJA, P.; JHA, A.; BOLL, P.M. Phytochemistry of the genus Piper. Phytochemistry, 46(4), 597–673. 1997
SINGH, Y.N. Kava: an overview. J Ethnopharmacol. Aug; 37(1):13-45. Review.PubMed PMID: 1453702. 1992
WANKE S, SAMAIN MS, VANDERSCHAEVE L, MATHIEU G, GOETGHEBEUR P, NEINHUIS C. (2006) Phylogeny of the genus Peperomia (Piperaceae) inferred from the trnK/matK region (cpDNA). Plant Biology. 8(1), 93–102.
YUNES, A.R.; CHECHINEL-FILHO, V. Novas Perspectivas dos produtos naturais da Química Medicinal Moderna. Capítulo I. In. YUNES, A. R.; CHECHINEL FILHO, V. Química de produtos Naturais, novos fármacos e a moderna farmacognosia. 5 ed., rev e ampl. – Itajaí, SC: Univali. 528p. 2016
FACUNDO, V.A.; DA SILVEIRA, A.S.P.; MORAIS, S.M. Constituents of Piper alatabaccum Trel & Yuncker (Piperaceae). Biochemical Systematics and Ecology. 33(7), 753–756. 2005
JOHRI, R.K.; THUSU, N.; KHAJURIA, A.; ZUTSHI, U. Piperine-mediated changes in the permeability of rat intestinal epithelial cells. The status of γ-glutamyl transpeptidase activity, uptake of amino acids and lipid peroxidation. Biochemical Pharmacology. 43(7), 1401–1407. 1992
ANDRADE, E.; HELIO, M.; SILVA, L.; PARAENSE, M.; GOELDI, E.; MAIA, A.G.S.; SANTOS, A.S. Constituents of the essential oil of Piper aduncum L . growing wild in the Amazon region. Flavour and Fragance Journal. 1026(JULY 1998), 269–272. 2016
BIZZO, H.R.; LOPES, D.; ABDALA, R.V.; PIMENTEL, F.A.; DE SOUZA, J.A.; PEREIRA, M.V.G.; GUIMARÃES, E.F. Sarisan from leaves of Piper affinis hispidinervum C. DC (long pepper). Flavour and Fragrance Journal. 16(2), 113–115. 2001
CABALLERO-GALLARDO, K.; OLIVERO-VERBEL, J.; PINO-BENÍTEZ, N.; STASHENKO, E.E. Chemical composition and bioactivity of Piper auritum and P . multiplinervium essential oils against the red flour beetle , Tribolium castaneum ( Herbst ). Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas. 13(1), 10–19. 2014
FACUNDO, V.A.; DE MORAIS, S.M. Essential oil of Piper tuberculatum var. Tuberculatum (Micq.) CDC leaves. Journal of Essential Oil Research. 17(3), 304–305. 2005
FACUNDO, V.A.; POLLI, A.R.; RODRIGUES, R.V.; MILITÃO, J.S.L.T.; STABELLI, R.G.; CARDOSO, C.T. Constituintes químicos fixos e voláteis dos talos e frutos de Piper tuberculatum Jacq. e das raízes de P. hispidum H. B. K. Acta Amazonica. 38(4), 743–748. 2008
OYEDEJI, A.O.; ADENIYI, B.A.; AJAYI, O.; KÖNIG, W.A. Essential oil composition of Piper guineense and its antimicrobial activity. Another chemotype from Nigeria. Phytotherapy Research. 19(4), 362–364. 2005
PHLIT, A.; PINTO, A.; MAUSE, R. Piper aduncum L.: Planta Pluripotente e Fonte de Substâncias. Pluripotente Plant. Revista Fitos. 2, 7–18. 2006
SOUSA, P.J.C.; BARROS, C.A.L.; ROCHA, J.C.S.; LIRA, D.S.; MONTEIRO, G.M.; MAIA, J.G.S. Avaliação toxicológica do óleo essencial de Piper aduncum L. Brazilian Journal of Pharmacognosy. 18(2), 217–221. 2008
BAGHERI, H.; ABDUL-MANAP, M.Y.; BIN-SOLATI, Z. Antioxidant activity of Piper nigrum L. essential oil extracted by supercritical CO2 extraction and hydro-distillation. Talanta. 121, 220–228. 2014
CRUZ, S.M.; CÁCERES, A.; ÁLVAREZ, L.; MORALES, J.; APEL, M.A.; HENRIQUES, A.T.; GUPTA, M.P. Chemical composition of essential oils of Piper jacquemontianum and Piper variabile from Guatemala and bioactivity of the dichloromethane and methanol extracts. Brazilian Journal of Pharmacognosy. 21(4), 587–593. 2011
MESSIANO, G.B.; SANTOS, R.A.; FERREIRA, L.D.S.; SIMÕES, R.A.; JABOR, V.A.P.; KATO, M.J.; DE OLIVEIRA, A.R.M. In vitro metabolism study of the promising anticancer agent the lignan (-)-grandisin. Journal of Pharmaceutical and Biomedical Analysis. 72, 240–244. 2013
NAVICKIENE, H.M.D.; MORANDIM, A.A.; ALÉCIO, A.C.; REGASINI, L.O.; BERGAMO, D.C.B.; TELASCREA, M.; CAVALHEIRO, A.J.; LOPES, M.N.; BOLZANI, V.S.; FURLAN, M.; MARQUES, M.O.M.; YOUNG, M.C.M.; KATO, M.J. Composition and antifungal activity of essential oils from Piper aduncum, Piper arboreum and Piper tuberculatum. Química Nova. 29: 467-470. 2006
OLIVEIRA, G.L.; CARDOSO, S.K.; LARA-JÚNIOR, C.R.; VIEIRA, T.M.; GUIMARÃES, E.F.; FIGUEIREDO, L.S.; KAPLAN, M.A.C. Chemical study and larvicidal activity against Aedes aegypti of essential oil of Piper aduncum L. (Piperaceae). Anais da Academia Brasileira de Ciências. 85(4), 1227–1234. 2013
PARISE-FILHO, R.; PASTRELLO, M.; PEREIRA CAMERLINGO, C.E.; SILVA, G.J.; AGOSTINHO, L.A.; DE SOUZA, T.; POLLI, M.C. The anti-inflammatory activity of dillapiole and some semisynthetic analogues. Pharmaceutical Biology. 49(11), 1173–1179. 2011
ROCHA, D.S.; DA SILVA, J.M.; NAVARRO, D.M.A.F.; CAMARA, C.A.G.; DE LIRA, C.S.; RAMOS, C.S. Potential antimicrobial and chemical composition of essentialoils from Piper caldense tissues. Journal of the Mexican Chemical Society. July-September, Vol.60(3), pp.148-151. 2016
SACCHETTI, G.; MAIETTI, S.; MUZZOLI, M.; SCAGLIANTI, M.; MANFREDINI, S.; RADICE, M.; BRUNI, R. Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food Chemistry. 91(4), 621–632. 2005
SETZER, W.N.; PARK, G.; AGIUS, B.R.; STOKES, S.L.; WALKER, T.M.; HABER, W.A. Chemical compositions and biological activities of leaf essential oils of twelve species of Piper from Monteverde, Costa Rica. NatProdComm. 3(8), 1367–1374. 2008
SOUTO, R.N.P.; HARADA, A.Y.; ANDRAD, E.H.A.; MAIA, J.G.S. Insecticidal Activity of Piper Essential Oils from the Amazon Against the Fire Ant Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). Neotropical Entomology. 41(6), 510–517. 2012
TAUFIQ-UR-RAHMAN, M.; SHILPI, J.A.; AHMED, M.; HOSSAIN, C.F. Preliminary pharmacological studies on Piper chaba stem bark. Journal of Ethnopharmacology. 99(2), 203–209. 2005
MONZOTE, L.; GARCÍA, M.; MONTALVO, A.M.; SCULL, R.; MIRANDA, M. Chemist de outubro de ry, cytotoxicity and antileishmanial activity of the essential oil from Piper auritum. As Memórias do Instituto Oswaldo Cruz, 105(2), 168–173. 2010
MARQUES, A.M.; BARRETO, A.L.S.; CURVELO, J.A.R.; VELOZO, L.S.M.; MOREIRA, D.L.; GUIMARÃES, E.F.; SOARES, R.M.A.; KAPLAN, M.A.C. Biological activity and chemistry of essential oils from Piper claussenianum essential oil (Piperaceae). Nat Prod Commun. 11: 1837-1840. 2011
DO CARMO, D.F.M.; AMARAL, A.C.F.; MACHADO, G.M.C.; LEON, L.L.; DE ANDRADE SILVA Jr. Chemical and biological analyses of the essential oils and main constituents of Piper species. Molecules. 17(2), 1819–1829. 2012
DOS SANTOS, S.; MONTEIRO, A.B.; DELMONDES, G.A.; DO NASCIMENTO, E.P.; SOBREIRA DANTAS NÓBREGA DE FIGUÊIREDO, F.R.; DE SOUZA RODRIGUES, C.K.; EVANGELISTA DE LACERDA, J.F.; FERNANDES, C.N.; BARBOSA, M.O.; BRASIL, A.X.; TINTINO, S.R.; VEGA GOMEZ, M.C.; CORONEL, C.; MELO COUTINHO, H.D.; MARTINS, D.A.; COSTA, J.G.; BEZERRA FELIPE, C.F.; ALENCAR DE MENEZES, I.R.; KERNTOPF, M.R. Antiparasitic Activity and Essential Oil Chemical Analysis of the Piper Tuberculatum Jacq Fruit. Iran J Pharm Res. Winter. 17(1):268-275. 2018
CEOLE, L.F.; CARDOSO, M.D.G.; SOARES, M.J. Nerolidol, the main constituent of Piper aduncum essential oil, has anti-Leishmania braziliensis activity. Parasitology. 1-12. 2017
BERNUCI, K.Z.; IWANAGA, C.C.; FERNANDEZ-ANDRADE, C.M.M.; LORENZETTI, F.B.; TORRES-SANTOS, E.C.; FAIÕES, V.S.; GONÇALVES, J.E.; DO AMARAL, W.; DESCHAMPS, C.; SCODRO, R.B.L.; CARDOSO, R.F.; BALDIN, V.P.; CORTEZ, D.A.G.. Evaluation of Chemical Composition and Antileishmanial and Antituberculosis Activities of Essential Oils of Piper Species. Molecules. 21, 1698. 2016
VILLAMIZAR, L.H.; CARDOSO, M.D.G.; ANDRADE, J.D.; TEIXEIRA, M.L.; SOARES, M.J. Linalool, a Piper aduncum essential oil component, has selective activity against Trypanosoma cruzi trypomastigote forms at 4° C. Memórias do Instituto Oswaldo Cruz. 112(2), 131-139. 2017
MONZOTE, L.; SCULL, R.; COS, P.; SETZER, W.N. Essential oil from Piper aduncum: Chemical analysis, antimicrobial assessment, and literature review. Medicines. 4(3), 49. 2017
PÁJARO, C.; STASHENKO, E. Antiquorum sensing activity of essential oils isolated from different species of the genus piper. Vitae, Revista De La Facultad De Quimica Farmaceutica. 18, 77–82. 2011
SÁNCHEZ, Y.; CORREA, T.M.; ABREU, Y.; PINO, O. Effect of the essential Oil of Piper Marginatum Jacq . y sus componentes sobre xanthomonas albilineans (ASHBY) DAWSON. Revista de Proteccion Vegetal. 27(1), 39–44. 2012
WAN SALLEH, W.M.; AHMAD, F.; YEN, K.H. Chemical compositions and antimicrobial activity of the essential oils of Piper abbreviatum, P. erecticaule and P. lanatum (Piperaceae). Nat Prod Commun. Dec;9(12):1795-8. 2014
WAN SALLEH, M.N.H.W.; AHMAD, F.; SIRAT, H.M.; YEN, K.H. Original article: Chemical Compositions And Antibacterial Activity Of The Leaf And Stem Oils Of Piper Porphyrophyllum. Excli Journal. 11, 399–406. 2012
SANTOS, T.G.; REBELO, R.A.; DALMARCO, E.M.; GUEDES, A.; GASPER, A.L.D.; CRUZ, A.B.; NUNES, R.K. Chemical composition and antimicrobial activity of leaf essential oil from Piper malacophyllum (C. Presl.) C.D.C. Química Nova. v.35, n.3, p.477-481. 2012
RESTREPO, J.; MORA, L.E. Extraction, Chemical Composition And Antimicrobial Activity Of The Essential Oils Of Pipilongo (Piper Tuberculatum) Using Supercritical Carbon Dioxide. Universidad del Valle. (October), 45–56. 2013
SINGH, S.; KAPOOR, I.P.S, SINGH, G.; SCHUFF, C.; DE LAMPASONA, M.P.; CATALAN, C.A.N. Chemistry, antioxidant and antimicrobial potentials of white pepper (Piper nigrum L.) essential oil and oleoresins. Proceedings of the National Academy of Sciences India Section B - Biological Sciences. 83(3), 357–366. 2013
MORALES, A.; ROJAS, J.; MOUJIR, L.M.; ARAUJO, L.; RONDÓN, M. Chemical composition, antimicrobial and cytotoxic activities of Piper hispidum SW. Essential oil collected in Venezuela. Journal of Applied Pharmaceutical Science. 3(6), 16–20. 2013
DE OLIVEIRA, R.A.; DE ASSIS, A.M.A.D.; DA SILVA, L.A.M.; ANDRIOLI, J.L.; DE OLIVEIRA, F.F. Chemical Profile and Antimicrobial Activity of Essential Oil of Piper ilheusense. Chemistry of Natural Compounds. 52(2), 331–333. 2016
MOTHANA, R.; ALSAID, M.; KHALED, J.M.; ALHARBI, N.S.; ALATAR, A.; RAISH, M.; AHAMAD, S.R. Assessment of antinociceptive, antipyretic and antimicrobial activity of Piper cubeba L. Essential oil in animal models. Pakistan Journal of Pharmaceutical Sciences. 29(2), 671–677. 2016
ALHARBI NS, KHALED JM, ALZAHARNI KE, MOTHANA RA, ALSAID MS, ALHOSHAN M, DASS LA, KADAIKUNNAN S, ALOBAIDI AS. Effects of Piper cubeba L. essential oil on methicillin‐resistant Staphylococcus aureus: an AFM and TEM study. Journal of Molecular Recognition. January, Vol.30(1). 2017
HASHIM, N.A.; AHMAD, F.; JANI, N.A.; SUSANTI, D. In vitro Antioxidant, Antityrosinase, Antibacterial and Cytotoxicity Activities of the Leaf and Stem Essential Oil from Piper magnibaccum C. DC. Journal of Essential Oil Bearing Plants. 20(1), 223-232. 2017
ISMAIL, M.; KEMEGNE, G.A.; NJAYOU, F.N.; PENLAP, V.; MBACHAM, W.F.; KAMDEM, S.L.S. Chemical composition, antibiotic promotion and in vivo toxicity of Piper nigrum and Syzygium aromaticum essential oil. African Journal of Biochemistry Research. 11(10), 58-71. 2017
WAN SALLEH, M.N.H.W.; AHMAD, F.; KHONG, H.Y. Essential oil compositions and antimicrobial activity of Piper arborescens roxb. Marmara Pharmaceutical Journal. March 20(2):111-115. 2016
ABREU, O.A.; SÁNCHEZ, I.; PINO, J.; BARRETO, G. Antimicrobial Activity of Piper aduncum subsp ossanum Essential Oil. International Journal of Phytomedicine, 7(2), 205-208. 2015
RATNAM, K.V.; BHAKSHU, L.M.; RAJU RV. Phytochemical Composition and In vitro Antimicrobial Activity of Essential Oil of Piper hymenophyllum Miq.: A Rare Wild Betel. Int J Pharmacognosy Phytochem Res. 7(1), 68-71. 2015
WAN SALLEH, M.N.H.W.; AHMAD, F.; SIRAT, H.M.. Chemical compositions, antioxidant and antimicrobial activities of essential oils of Piper caninum Blume. International journal of molecular sciences. V. 12, n. 11, p. 7720-7731. 2011
QIN, W.; HUANG, S.; LI, C.; CHEN, S.; PENG, Z. Biological activity of the essential oil from the leaves of Piper sarmentosum Roxb. (Piperaceae) and its chemical constituents on Brontispa longissima (Gestro) (Coleoptera: Hispidae). Pesticide Biochemistry and Physiology. 96(3), 132–139. 2010
MATASYOH, J.C.; WATHUTA, E.M.; KARIUKI, S.T.; CHEPKORIR, R. Chemical composition and larvicidal activity of Piper capense essential oil against the malaria vector, Anopheles gambiae. Journal of Asia-Pacific Entomology. 14(1), 26–28. 2011
OLIVEIRA, G.L.; VIEIRA, T.M.; NUNES, V.F.; RUAS, M.D.; DUARTE, E.R.; MOREIRA, D.D.; KAPLAN, M.A.C.. Chemical composition and efficacy in the egg-hatching inhibition of essential oil of Piper aduncum against Haemonchus contortus from sheep. Rev Bras Farmacognosia. 24(3): 288-292. 2014
DO NASCIMENTO, J.C.; DAVID, J.M.; BARBOSA, L.C.; DE PAULA, V.F.; DEMUNER, A.J.; DAVID, J.P.; GUIMARÃES, E.F. Larvicidal activities and chemical composition of essential oils from Piper klotzschianum (Kunth) C. DC. (Piperaceae). Pest Management Science. 69(11), 1267–1271. 2013
OBEN, E.O.; MCCONCHIE, R.; PHAN-THIEN, K.; NTONIFOR, N.N. Essential oil composition of different fractions of Piper guineense Schumach. et Thonn from Cameroon using gas chromatography-mass spectrometry and their insecticidal effect on Sitophilus oryzae (L.). African Journal of Biotechnology. 14(36), 2662-2671. 2015
CRUZ, G.S.; WANDERLEY-TEIXEIRA, V.; OLIVEIRA, J.V.; CORREIA, A.A.; BREDA, M.O.; ALVES, T.J.S.; NAVARRO, D.M.A.F. Bioactivity of Piper hispidinervum (Piperales: Piperaceae) and Syzygium aromaticum; (Myrtales: Myrtaceae) Oils, With or Without Formulated Bta on the Biology and Immunology of Spodoptera frugiperda. Journal of Economic Entomology. 107(1), 144–153. 2014
SANTANA, H.T.; TRINDADE, F.T.T.; STABELI, R.G.; SILVA, A.A.E.; MILITÃO, J.; FACUNDO, V.A. Essential oils of leaves of Piper species display larvicidal activity against the dengue vector, Aedes aegypti (Diptera: Culicidae). Revista Brasileira de Plantas Medicinais. 17(1), 105–111. 2015
SANTANA, A.I.; VILA, R.; CANIGUERAL, S.; GUPTA, M.P. Chemical Composition and Biological Activity of Essential Oils from Different Species of Piper from Panama. Planta Medica. 82(11–12), 986–991. 2016
DA SILVA, M.F.R.; BEZERRA-SILVA, P.C.; DE LIRA, C.S.; DE LIMA, A.B.N.; AGRA NETO, A.C.; PONTUAL, E.V.; MACIEL Jr PAIVA, P.M.G.; NAVARRO, D.M.A.F. Composition and biological activities of the essential oil of Piper corcovadensis (Miq.) C. DC (Piperaceae). Experimental Parasitology. June, Vol.165, pp.64-70. 2016
SANINI, C.; MASSAROLLI, A.; KRINSKI, D.; BUTNARIU, A.R. Essential oil of spiked pepper, Piper aduncum L.(Piperaceae), for the control of caterpillar soybean looper, Chrysodeixis includens Walker (Lepidoptera: Noctuidae). Brazilian Journal of Botany. 40(2), 399-404. 2017
VOLPE, H.X.; FAZOLIN, M.; GARCIA, R.B.; MAGNANI, R.F.; BARBOSA, J.C.; MIRANDA, M.P. Efficacy of essential oil of Piper aduncum against nymphs and adults of Diaphorina citri. Pest management Science. 72(6), 1242-1249. 2016
MAMOOD, S.N.H.; HIDAYATULFATHI, O.; BUDIN, S.B.; ROHI, G.A.; ZULFAKAR, M.H. The formulation of the essential oil of Piper aduncum Linnaeus (Piperales: Piperaceae) increases its efficacy as an insect repellent. Bulletin of entomological research. 107(1), 49-57. 2017
VASANTHA-SRINIVASAN, P.; SENTHIL-NATHAN, S.; PONSANKAR, A.; THANIGAIVEL, A.; EDWIN, E.S.; SELIN-RANI, S.; CHELLAPPANDIAN, M.; PRADEEPA, V.; LIJA-ESCALINE, J.; KALAIVANI, K.; HUNTER, W.B.; DURAIPANDIYAN, V.; AL-DHABI, N.A. Comparative analysis of mosquito (Diptera: Culicidae: Aedes aegypti Liston) responses to the insecticide Temephos and plant derived essential oil derived from Piper betle L. Ecotoxicology and Environmental Safety. 139, 439-446. 2017
WAGAN, T.A.; CHAKIRA, H.; HUA, H.; HE Y, Z.H.A.O. J. Biological Activity of Essential Oil from Piper nigrum Against Nymphs and Adults of Blattella germanica (Blattodea: Blattellidae). Journal of the Kansas Entomological Society. 90(1), 54-62. 2017
ANDRÉS, M.F.; ROSSA, G.E.; CASSEL, E.; VARGAS, R.M.F.; SANTANA, O.; DÍAZ, C.E.; GONZÁLEZ-COLOMA, A. Biocidal effects of Piper hispidinervum (Piperaceae) essential oil and synergism among its main components. Food and Chemical Toxicology. Nov;109(Pt 2):1086-1092. 2017
CHAABAN, A.; SANTOS, V.M.C.S.; GOMES, E.N.; MARTINS, C.E.N.; AMARAL, W.D.; DESCHAMPS, C.; MOLENTO, M.B. Chemical composition of Piper gaudichaudianum essential oil and its bioactivity against Lucilia cuprina (Diptera: Calliphoridae). Journal of Essential Oil Research. 1-8. 2018
SALGADO, D.; D'ANTONINO FARONI, L.R.; SOTO, G. Essential Oil Of Piper Crassinervum To Control Of Sitophilus Zeamais (Coleoptera: Curculionidae). Boletín Científico. Centro de Museos. Museo de Historia Natural. 16(1), 99-107. 2012
PRAKASH, B.; SHUKLA, R.; SINGH, P.; KUMAR, A.; MISHRA, P.K.; DUBEY, N.K. Efficacy of chemically characterized Piper betle L. essential oil against fungal and aflatoxin contamination of some edible commodities and its antioxidant activity. International Journal of Food Microbiology. 142(1–2), 114–119. 2010
VIEIRA, S.C.H. Antifungal activity of Piper diospyrifolium Kunth (Piperaceae) essential oil. Braz. J. Microbiol. [online], vol.42, n.3, pp.1001-1006. ISSN 1517-8382. 2011
DA SILVA, J.K.R.; PINTO, L.C.; BURBANO, R.M.R.; MONTENEGRO, R.C.; GUIMARÃES, E.F.; ANDRADE, E.H.A.; MAIA, J.G.S. Essential oils of Amazon Piper species and their cytotoxic, antifungal, antioxidant and anti-cholinesterase activities. Industrial Crops and Products. 58, 55–60. 2014
SCALVENZI, L.; YAGUACHE, B.; CABRERA, P.; GUERRINI, A. Actividad Antifúngica in vitro de aceites. Bioagro. 28(1), 39–46. 2016
BASAK, S.; GUHA, P. Betel leaf (Piper betle L.) essential oil microemulsion: Characterization and antifungal activity on growth, and apparent lag time of Aspergillus flavus in tomato paste. LWT-Food Science and Technology. 75, 616-623. 2017a
BASAK, S.; GUHA, P. Use of predictive model to describe sporicidal and cell viability efficacy of betel leaf (Piper betle L.) essential oil on Aspergillus flavus and Penicillium expansum and its antifungal activity in raw apple juice. LWT-Food Science and Technology. 80, 510-516. 2017b
MAKKAR, N.; PRASANNA, S.B.; SINGLA, H. Comparative Evaluation of Antifungal Activity of Piper Betel Leaf Oil, Origanum vulgare Essential Oil and Fluconazole Suspension on Candida albicans− An in vitro Study. Journal of Indian Association of Public Health Dentistry. 15(1), 89. 2017
MAGALHÃES, L.G.; DE SOUZA, J.M.; WAKABAYASHI, K.A.L.; DA S.; LAURENTIZ, R.; VINHÓLIS, A.H.C.; REZENDE, K.C.S.; E SILVA, M.L.A. In vitro efficacy of the essential oil of Piper cubeba L. (Piperaceae) against Schistosoma mansoni. Parasitology Research. 110(5), 1747–1754. 2012
TEIXEIRA, L. Antioxidant activity and characterization of the essential oil from the roots of Piper marginatum jacq. Ciência e Natura. 38(3), 1504-1511. 2016
LIMA, D.K.; BALLICO, L.J.; ROCHA LAPA, F.; GONÇALVES, H.P.; DE SOUZA, L.M.; IACOMINI, M.; WERNER, M.F.; BAGGIO, C.H.; PEREIRA, I.T.; DA SILVA, L.M.; FACUNDO, V.A.; SANTOS, A.R. Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C. DC in rodents. Journal of Ethnopharmacology. 142(1), 274-282. 2012
OYEMITAN, I.A.; KOLAWOLE, F.; OYEDEJI, A.O. Acute toxicity, antinociceptive and anti-inflammatory activity of the essential oil of fresh fruits of Piper guineense Schum Thonn (Piperaceae) in rodents. Journal of Medicinal Plants Research. 8(40), 1191-1197. 2014
HOFF BRAIT, D.R.; MATTOS VAZ, M.S.; DA SILVA ARRIGO, J.; BORGES DE CARVALHO, L.N.; SOUZA DE ARAÚJO, F.H.; VANI, J.M.; DA SILVA MOTA, J.; CARDOSO, C.A.; OLIVEIRA, R.J.; NEGRÃO, F.J.; KASSUYA, C.A.; ARENA, A.C. Toxicological analysis and anti-inflammatory effects of essential oil from Piper vicosanum leaves. Regulatory Toxicology and Pharmacology. 73(3), 699-705. 2015
PINO, O.; SÁNCHEZ, Y.; RODRÍGUEZ, H.; CORREA, T.M.; DEMEDIO, J.; SANABRIA, J.L. Caracterización Química Y Actividad Acaricida del Aceite Esencial de Piper aduncum subsp. ossanum frente Varroa destructor. Rev. Protección Veg. Abr, 26, n.1, p.52-61. 2011
ARAÚJO, M.J.C.; CÂMARA, C.A.G.; BORN, F.S.; MORAES, M.M.; BADJI, C.A. Acaricidal activity and repellency of essential oil from Piper aduncum and its components against Tetranychus urticae. Experimental and Applied Acarology. 57(2), 139–155. 2012
GIROLA, N.; FIGUEIREDO, C.R.; FARIAS, C.F.; AZEVEDO, R.A.; FERREIRA, A.K.; TEIXEIRA, S.F.; LAGO, J.H.G. Camphene isolated from essential oil of Piper cernuum (Piperaceae) induces intrinsic apoptosis in melanoma cells and displays antitumor activity in vivo. Biochemical and Biophysical Research Communications. 467(4), 928–934. 2015
DE SOUZA, S.P.; VALVERDE, S.S.; COSTA, N.F.; CALHEIROS, A.S.; LIMA, K.S.; FRUTUOSO, V.S.; LIMA, A.L. Chemical composition and antinociceptive activity of the essential oil of Piper mollicomum and Piper rivinoides. Journal of Medicinal Plants Research. 8(22), 788-793. 2014
RAMESHKUMAR, K.B.; NANDU, T.G.; ANU ARAVIND, A.P.; MATHEW, S.P.; SHIBURAJ, S. Chemical composition and FtsZ GTPase inhibiting activity of the essential oil of Piper sarmentosum from Andaman Islands, India. Journal of Essential Oil Research, 1-6. 2017
JIMÉNEZ DASILBA, A.P.; PILLCO TITO, A.; FLORES QUISBERT, N.; GONZÁLES DAVALOS, E.; BERMEJO BENITO, P. Genotoxic evaluation of essential oil and ethanolic extract of Piper elongatum Vahl. BIOFARBO. 19(2): 13-20. 2011
DOS SANTOS; P.R.D.; GOMES PEREIRA, F.; MARQUES FREITAS, J.C.; MELO DOS SANTOS, N.; DE ALBUQUERQUE FARINELLE. C.; BOSCO DE SALLES, J.; VON SOHSTEN DE SOUZA MEDEIROS, E.; GUIMARÃES, E.F.; COELHO KAPLAN, M.A. Effect of Essential Oil of Piper tuberculatum var. minus C. DC. Leaves on the Hepatic. Journal of Essential Oil Bearing Plants. 18: Issue 2. 2015.