Fenilpropanoides em espécies de plantas do gênero Duguetia: Uma revisão
DOI:
https://doi.org/10.33448/rsd-v11i4.27266Palavras-chave:
Duguetia; Fenilpropanoides; Atividade biológica; Extração.Resumo
O gênero Duguetia abrange 93 espécies, das quais 63 estão distribuídas no Brasil. No entanto, apenas dez espécies tiveram seus perfis químicos e biológicos investigados até agora. Embora os alcaloides sejam a classe de fitocompostos mais estudada, o interesse pelos fenilpropanoides está crescendo, uma vez que atividades biológicas distintas têm sido atribuídas a esses derivados ultimamente. Esta revisão reuniu estudos descrevendo a distribuição fitoquímica, métodos de extração e atividades biológicas dos fenilpropanoides da espécie Duguetia. Foi evidenciado que os solventes não-polares foram capazes de fornecer o maior rendimento de 2,4,5 trimetoxiestireno, γ-asarona, e asaraldeído localizados, principalmentes, nas cascas do caule moído. Por outro lado, a α-asarona, elimicina e (E)-metil-isoeugenol foram isolados dos extratos polares ou dos óleos essenciais das cascas e folhas. Os derivados 2,4,5 trimetoxiestireno e asarona foram eficazes como protetores de cultivares. A α- e γ-asarona, ácido 2,4,5-trimetoxicinâmico, asaraldeído, elemicina e (E)-metil-isoeugenol demonstraram atividades antiinflamatória, antidislipidêmica, antinocceptiva, antibacteriana, antidepressivo, ansiolítica, inseticida e larvicida. Plantas do gênero Duguetia podem ser uma fonte potencial de fenilpropanoides portanto, estudos futuros envolvendo sua extração, identificação e aplicação ainda são necessários e podem culminar na descoberta de novos candidatos a medicamentos ou defensivos agrícolas
Referências
Almeida, J. R. G. S., Araújo, E. C. C., Ribeiro, L. A. A., Lima, J. T., Nunes, X. P., Lúcio, A. S. S. C., & Filho, J. M. B. (2012). Antinociceptive activity of ethanol extract from Duguetia chrysocarpa Maas (Annonaceae). Sci. World J., 2012, 859210. https://doi.org/https://doi.org/10.1100/2012/859210
Almeida, J. R. G. S., De Lima, J. T., De Oliveira, H. R., De Oliveira, M. R., Meira, P. R. M., Lúcio, A. S. S. C., & Quintans Júnior, L. J. (2011). Antinociceptive activity of discretamine isolated from Duguetia moricandiana. Nat. Prod. Res., 25(20), 1908-1915. https://doi.org/https://doi.org/10.1080/14786419.2010.491227
Almeida, J. R. G. S., De Oliveira, M. R., Guimarães, A. L., De Oliveira, A. P., Ribeiro, L. A. A., Lúcio, A. S. S. C., & Quintans Júnior, L. J. (2011). Phenolic quantification and antioxidant activity of Anaxagorea dolichocarpa and Duguetia chrysocarpa (Annonaceae) Int. J. Pharma Bio Sci., 2(4), 367-374.
Almeida, J. R. G. S., Facanali, R., Vieira, M. A. R. V., Marques, M. O. M., Lúcio, A. S. S. C., Lima, E. O., & Barbosa-Filho, J. M. (2010). Composition and antimicrobial activity of the leaf essential oils of Duguetia gardneriana Mart. and Duguetia moricandiana Mart. (Annonaceae). J. Essent. Oil Res., 22(3), 275-278. https://doi.org/https://doi.org/10.1080/10412905.2010.9700323
Almeida, J. R. G. S., Lúcio, A. S. S. C., Barbosa-Filho, J. M., Agra, M. F., Silva, M. S., Cunha, E. V. L., & Braz-Filho, R. (2007). Alkaloids and a new cinnamate derivative from Duguetia gardneriana. Biochem. Syst. Ecol., 35, 456-458. https://doi.org/https://doi.org/10.1016/j.bse.2006.12.011
Alves, D. S., Costa, V. A., Machado, A. R. T., Oliveira, D. F., & Carvalho, G. A. (2020). Duguetia lanceolata A. St.-Hil. Stem bark produces phenylpropanoids lethal to Spodoptera frugiperda (JE Smith) (Lepidoptera: Noctuidae) J. Crop Prot., 127, 104965. https://doi.org/https://doi.org/10.1016/j.cropro.2019.104965
Alves, D. S., Machado, A. R. T., Campos, V. A. C., Oliveira, D. F., & Carvalho, G. A. (2016). Selection of Annonaceae species for the control of Spodoptera frugiperda (Lepidoptera: Noctuidae) and metabolic profiling of Duguetia lanceolata using nuclear magnetic resonance spectroscopy J. Econ. Entomol., 109, 649-659. https://doi.org/https://doi.org/10.1093/jee/tov396
Alves, D. S., Morejón, R. C., Rodrigues, A. T. M., Carvalho, G. A., Oriela, P., & Oliveira, D. F. (2015). Acaricidal activity of Annonaceae fractions against Tetranychus tumidus and Tetranychus urticae (Acari: Tetranychidae) and the metabolite profile of Duguetia lanceolata (Annonaceae) using GC-M. Semina: Ciências Agrárias, 36(2), 4119-4132. https://doi.org/https://doi.org/10.5433/1679-0359.2015v36n6Supl2p4119
Antunez-Solis, J., Hernández-Derramadero, F., Aquino-Vega, M., Ibarra-Ramírez, S., Rodríguez-Páez, L., Baeza, I., & Wong, C. (2009). 2,4,5-trimethoxycinnamic acid: the major metabolite of a-asarone, retains most of the pharmacological properties of a-asarone. J. Enzyme Inhib. Med. Chem . 24(3), 903-909. https://doi.org/https://doi.org/10.1080/14756360802318902
Arora, D., Rani, A., & Sharma, A. (2013). A review on phytochemistry and ethnopharmacological aspects of genus Calendula. Pharmacogn. Rev., 7(14), 179-187. https://doi.org/https://doi.org/10.4103/0973-7847.120520
Bhardwaj, A., Kumar Tewary, D., Kumar, R., Kumar, V., Kumar Sinha, A., & Shanker, A. (2010). Larvicidal and structure-activity studies of natural phenylpropanoids and their semisynthetic derivatives against the tobacco armyworm Spodoptera litura (fab.) (lepidoptera: Noctuidae). Chem. Biodivers., 7(1), 168-177. https://doi.org/https://doi.org/10.1002/cbdv.200800345
Carollo, C. A., Hellmann-Carollo, A. R., Siqueira, J. M., & Albuquerque, S. (2006). Alkaloids and a flavonoid from aerial parts (leaves and twigs) of Duguetia furfuracea - Annonaceae. J. Chil. Chem. Soc., 51(2), 837-841. https://doi.org/https://doi.org/10.4067/S0717-97072006000200001
Carollo, C. A., Hellmann, A. R., & Siqueira, J. M. (2005). Sesquiterpenoids from the essential oil from leaves of Duguetia furfuracea (Annonaceae). Biochem. Syst. Ecol., 33, 647-649. https://doi.org/https://doi.org/10.1016/j.bse.2004.09.004
Casagrande, C., & Ferrari, G. (1970). Studies in aporphine alkaloids I. Alkaloids of a Brazilian Duguetia. Farmaco Sci., 25, 442-442.
Castoldi, L., Morales, R. L., Albiero, L. R., Nery, E. F., Kelly, T. O., Dalazen, J. C., & Andrighetti, C. R. (2020). In vitro cytotoxicity of Duguetia sp extracts on Ehrlich tumor cells. Sci. Elec. Arch., 13(2), 58-64. https://doi.org/https://doi.org/10.36560/13220201014
Chatrou, L. W., Rainer, H., & Maas, P. J. M. (2004). Annonaceae. In N. Smith, S. A. Mori, A. Henderson, D. W. Stevenson, & S. V. Heald (Eds.), Flowering plants of the neotropics. (pp. 18-20.). New York: Princeton University Press.
Chellian, R., Pandy, V., & Mohamed, Z. (2017). Pharmacology and toxicology of α- and β-Asarone: A review of preclinical evidence. Phytomed., 32, 41-58. https://doi.org/https://doi.org/10.1016/j.phymed.2017.04.003
Correa, M. P. (1978). Dicionário de Plantas Úteis do Brasil e das exóticas cultivadas (2nd ed. Vol. 6). Rio de Janeiro: Imprensa Nacional.
da Silva, D. B., Tulli, E. C. O., Garcez, W. S., Nascimento, E. A., & Siqueira, J. M. (2007). Chemical constituents of the underground stem bark of Duguetia furfuracea (Annonaceae). J. Braz. Chem. Soc., 18(8), 1560-1565. https://doi.org/https://doi.org/10.1590/S0103-50532007000800017
da Silva, D. B., Tulli, E. C. O., Militão, G. C. G., V., C.-L. L., Pessoa, C., Moraes, M. O., & Siqueira, J. M. (2009). The antitumoral, trypanocidal and antileishmanial activities of extract and alkaloids isolated from Duguetia furfuracea. Phytomed., 16(11), 1059-1063. https://doi.org/https://doi.org/10.1016/j.phymed.2009.03.019
de Sousa, F. D. M., Grossi, S. M., Monteiro, G. C., Demarque, D. P., & Espindola, L. S. (2020). Dereplication and isolation of larvicidal compounds from Annonaceae species against Aedes aegypti. Rev. Bras. Farmacogn., 30, 123-126. https://doi.org/https://doi.org/10.1007/s43450-020-00018-4
de Souza, C. A. S., Nardelli, V. B., Paz, W. H. P., Pinheiro, M. L. B., Rodrigues, A. C. B. C., Bomfim, L. M., & Costa, E. V. (2020). Asarone-derived phenylpropanoids and isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities. Quím. Nova, 43(10), 1397-1403. https://doi.org/https://doi.org/10.21577/0100-4042.20170617
Debourges, D., Roblot, F., Hocquemiller, R., & Cavé, A. (1987). Alcaloïdes des Annonacées, 77. Alcaloïdes de Duguetia spixiana. J. Nat. Prod., 50(4), 664-673. https://doi.org/https://doi.org/10.1021/np50052a015
Deng, Y., & Shanfa, L. (2017). Biosynthesis and regulation of phenylpropanoids in plants. Crit. Rev. Plant Sci., 36(4), 257-290. https://doi.org/https://doi.org/10.1080/07352689.2017.1402852
dos Santos, R. C., de Souza, A. V., Andrade-Silva, M., Cruz, K. C. V., Kassuya, C. A. L., Cardoso, C. A. L., & Formagio, A. S. N. (2018). Antioxidant, anti-rheumatic and anti-inflammatory investigation of extract and dicentrinone from Duguetia furfuracea (A. St.-Hil.) Benth. & Hook. f. J. Ethnopharmacol., 30(211), 9-16. https://doi.org/https://doi.org/10.1016/j.jep.2017.09.019
Fajemiroye, J. O., Galdino, P. M., De Paula, J. A. M., Rocha, F. F., Akanmu, M. A., Vanderlinde, F. A., & Costa, E. A. (2014). Anxiolytic and antidepressant like effects of natural food flavour (E)-methyl isoeugenol. Food Func., 5(8), 1819-1828. https://doi.org/https://doi.org/10.1039/c4fo00109e
Favareto, R., Teixeira, M. B., Soares, F. A. L., Belisário, C. M., Cabral, J. F., da Silva, E. A., & Cardozo-Filho, L. (2019). Extraction of bioactive compounds of leaves of Duguetia furfuracea (Annonaceae) using green and organic solvents. Braz. J. Chem. Eng., 36(01), 549-556. https://doi.org/10.1590/0104-6632.20190361s20170451
Fernandes, C. N., Sousa, H. H. F., Borges, M. C. M., Souza, C. E. S., Guedes, G. M. M., Figueredo, F. G., & Kerntopf, M. R. (2014). Evaluation of the modulatory and antibacterial activity of the ethanolic extract and fractions of Duguetia furfuracea A. St.-Hil. Afr. J. Pharmacy Pharmacol., 8(1), 16-20. https://doi.org/10.5897/AJPP2013.3707
Frausin, G., Lima, R. B. S., Hidalgo, A. F., Maas, P., & Pohlit, A. M. (2014). Plants of the Annonaceae traditionally used as antimalarials: a review. Rev. Bras. Frutic., 36(Spe 1), 315-336.
Geethangili, M., & Ding, S.-T. (2018). A review of the phytochemistry and pharmacology of Phyllanthus urinaria L. Front. Pharmacol., 9(1109). https://doi.org/10.3389/fphar.2018.01109
Gonçalves, G. L. P., De Cássia Domingues, V., Do Prado Ribeiro, L., Fernandes, J. B., Das Graças Fernandes, M. D. F., Forim, M. R., & Vendramim, J. D. (2017). Compounds from Duguetia lanceolata St.-Hil.(Annonaceae) bioactive against Zabrotes subfasciatus (boheman)(Coleoptera: Chrysomelidae: bruchinae). Ind. Crops Prod., 97, 360-367. https://doi.org/https://doi.org/10.1016/j.indcrop.2016.12.032
Gottlieb, O. R., Magalhães, A. F., Magalhães, E. G., Maia, J. G. S., & Marsaioli, A. J. (1978). Oxoaporphine alkaloids from Duguetia eximia. Phytochem., 17(4), 837-838. https://doi.org/https://doi.org/10.1016/s0031-9422(00)94260-2
Huang, Y., Ho, S. H., & Kini, R. M. (1999). Bioactivities of safrole and isosafrole on Sitophilus zeamais (Coleoptera: Curculionidae) and Tribolium castaneum (Coleoptera: Tenebrionidae). J. Econ. Entomol., 92, 676-683. https://doi.org/https://doi.org/10.1093/jee/92.3.676
Ibrahim, R., & Barron, D. (1989). Phenylpropanoids. In J. B. Harborne (Ed.), Plant Phenolics (Vol. I, pp. 75-111). San Diego: Academic Press.
Ilijeva, R., & Buchbauer, G. (2016). Biological properties of some volatile phenylpropanoids. Nat. Prod. Comm., 11(10), 1619-1629. https://doi.org/https://doi.org/10.1177/1934578X1601101041
Jensen, R. A. (1986). Tyrosine and phenylalanine biosynthesis: relationship between alternative pathways, regulation and subcellular location. In E. E. Conn (Ed.), The shikimic acid pathway (pp. 57-81). Boston: Springer.
Koona, P., & Bouda, H. (2004). Activity of 2, 4, 5-trimethoxystyrene from Pachypodanthium staudtii against two stored product pests. Trop. Sci., 44(3), 120-123.
Koona, P., & Bouda, H. (2006). Biological activity of Pachypodanthium staudtii (Annonaceae) against the bean beetle Acanthoscelides obtectus Say (Coleoptera: Bruchidae). J. Appl. Sci. Res., 2(12), 1129-1131.
Korkina, L., Kostyuk, V., De Luca, C., & Pastore, S. (2011). Plant phenylpropanoids as emerging anti-inflammatory agents. Mini Rev. Med. Chem., 11, 823-835. https://doi.org/https://doi.org/10.2174/138955711796575489
Korkina, L. G. (2007). Phenylpropanoids as naturally occurring antioxidants: from plant defense to human health. Cell. Mol. Biol., 53(1), 15-25. https://doi.org/https://doi.org/10.1170/T772
Lee, J. Y., Lee, J. Y., Yun, B. S., & Hwang, B. K. (2004). Antifungal activity of β-asarone from rhizomes of Acorus gramineus. J. Agric. Food Chem., 52(4), 776-780. https://doi.org/https://doi.org/10.1021/jf035204o
Liu, X. C., Zhou, L. G., Liu, Z. L., & Du, S. S. (2013). Identification of insecticidal constituents of the essential oil of Acorus calamus rhizomes against Liposcelis bostrychophila Badonnel. Molecules, 18(5), 5684-5696. https://doi.org/https://doi.org/10.3390/molecules18055684
Łozowicka, B., & Kaczynski, P. (2013). Synthesis and antifeedant activity of novel alphaasarone derivatives against stored-product pests. Pest Manag. Sci., 69, 964-974. https://doi.org/https://doi.org/10.1002/ps.3461
Maas, P. J. M., Westra, L. Y. T., & Chatrou, L. W. (2003). Duguetia (Annonaceae). Flora Neotrop., 88, 1-274. https://doi.org/https://doi.org/10.2307/4393920
Maia, J. G. S., Andrade, E. H. A., Carreira, L. M. M., & Oliveira, J. (2006). Essential oil composition from Duguetia species (Annonaceae). J. Essent. Oil Res., 18, 60-63. https://doi.org/https://doi.org/10.1080/10412905.2006.9699386
Mathouet, H., Elomri, A., Lameiras, P., Daıch, A., & Vérité, P. (2007). An alkaloid, two conjugate sesquiterpenes and a phenylpropanoid from Pachypodanthium confine Engl. and Diels. Phytochem., 68, 1813-1818. https://doi.org/https://doi.org/10.1016/j.phytochem.2007.04.001
Matos, M. F. C., eite, L. I. S. P., Brustolim, D., De Siqueira, J. M., Carollo, C. A., Hellmann, A. R., & Da Silva, D. B. (2006). Antineoplastic activity of selected constituents of Duguetia glabriuscula. Fitoter., 77(3), 227-229. https://doi.org/https://doi.org/10.1016/j.fitote.2006.01.013
Mello-Silva, R., Lopes, J. C., & Pirani, J. R. (2012). Flora da Serra do Cipó, Minas Gerais: Annonaceae. Bol. Bot. Univ. São Paulo, 30(1), 37-56. https://doi.org/https://doi.org/10.11606/issn.2316-9052.v30i1p23-35
Muhammad, I., Dunbar, D. C., Takamatsu, S., Walker, L. A., & Clark, A. M. (2001). Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha. J. Nat. Prod., 64, 559-562. https://doi.org/https://doi.org/10.1021/np000436s
Nahar, L., & Sarker, S. D. (2006). Isolation and characterization of 2,4,5-trimethoxybenzaldehyde and 1-(2,4,5-trimethoxyphenyl)-ethanone from Pachypodanthium staudtii, and their general toxicity towards Brine shrimps. Nat. Prod. Comm., 1(5), 377-380. https://doi.org/https://doi.org/10.1177/1934578X0600100506
Nardelli, V. B., De Souza, C. A. S., Chaar, J. S., Koolen, H. H. F., Da Silva, F. M. A., & Costa, E. V. (2021). Isoquinoline-derived alkaloids and one terpene lactone from the leaves of Duguetia pycnastera (Annonaceae). Biochem. Syst. Ecol., 94, 104206. https://doi.org/https://doi.org/10.1016/j.bse.2020.104206
Ngouonpe, A. W., Mbobda, A. S. W., Happi, G. M., Mbiantcha, M., Tatuedom, O. K., Ali, M. S., & Kouam, S. F. (2019). Natural products from the medicinal plant Duguetia staudtii (Annonaceae). Biochem. Syst. Ecol., 83, 22-25. https://doi.org/https://doi.org/10.1016/j.bse.2018.12.015
Pares, R. B., Alves, D. S., Alves, L. F. A., Godinho, C. C., Neto, L. G., Ferreira, T. T., & Oliveira, D. F. (2021). Acaricidal activity of Annonaceae plants for Dermanyssus gallinae (Acari: Dermanyssidae) and metabolomic profile by HPLC-MS/MS. Neotrop. Entomol., 50(4), 662-672. https://doi.org/https://doi.org/10.1007/s13744-021-00885-z
Pérez, E., Sáez, J., Blair, S., Franck, X., & Figadère, B. (2004). Isoquinoline alkaloids from Duguetia vallicola stem bark with antiplasmodial activity. Lett. Org. Chem., 1, 102-104. https://doi.org/https://doi.org/10.2174/1570178043488743
Perez, E. G., & Cassels, B. K. (2010). Alkaloids from the Genus Duguetia. In G. A. Cordell (Ed.), The alkaloids: Chemistry and biology (Vol. 68, pp. 83-156). London: Academic Press.
Pinho, F. V., Da Cruz, L. C., Rodrigues, N. R., Waczuk, E. P., Souza, C. E., Coutinho, H. D., & De Menezes, I. R. (2016). Phytochemical composition, antifungal and antioxidant activity of Duguetia furfuracea A.St.-Hill. Oxid. Med. Cell. Longev., 2016, 7821051. https://doi.org/https://doi.org/10.1155/2016/7821051
Popławski, J., Łozowicka, B., Dubis, A. T., Lachowska, B., Winiecki, Z., & Nawrot, J. (2000). Feeding-deterrent activity of α-asarone isomers against some stored Coleoptera. . Pest Manag. Sci., 56, 560-564. https://doi.org/https://doi.org/10.1002/(SICI)1526-4998(200006)56:6<560::AID-PS171>3.0.CO;2-X
Prates, L. V., Luciana, S., Almeida, J. R. G. S., & Scotti, M. T. (2020). Annonaceae family alkaloids as agents against leishmaniasis: A review and molecular docking evaluation. Curr. Drug Metab., 21(7), 482-492. https://doi.org/https://doi.org/10.2174/1389200221666200702124046
Ribeiro, L. P., Vendramim, J. D., Gonçalves, G. L. P., Ansante, T. F., Gloria, E. M., Lopes, J. C., & Fernandes, J. B. (2016). Searching for promising sources of grain protectors in extracts from Neotropical Annonaceae. Bol. Latinoam. Caribe Plantas Med. Aromát., 15(4), 215-232.
Rodrigues, A. C. B. C., Bomfim, L. M., Neves, S. P., A., M. L. R., Dias, R. B., Soares, M. B. P., & Bezerra, D. P. (2015). Antitumor properties of the essential oil from the leaves of Duguetia gardneriana. Planta Med., 81, 798-803. https://doi.org/https://doi.org/10.1055/s-0035-1546130
Rodrigues, A. M. S., De Paula, J. E., Degallier, N., Molez, J. F., & Espíndola, L. S. (2006). Larvicidal activity of some Cerrado plant extracts against Aedes aegypti. J. Am. Mosq. Control Assoc., 22(2), 314-317. https://doi.org/https://doi.org/10.2987/8756-971X(2006)22[314:LAOSCP]2.0.CO;2
Rodrigues, R. P., Baroni, A. C. M., Carollo, C. A., Demarque, D. P., Pardo, L. F. L., Rezende, L. M. P., & Siqueira, J. M. (2020). Synthesis, phytotoxic evaluation and in silico studies for the development of novel natural products-inspired herbicides Biocatal. Agric. Biotechnol., 25, 101559. https://doi.org/https://doi.org/10.1016/j.bcab.2020.101559
Rodrigues, V. E. G., & Carvalho, D. A. (2001). Levantamento etnobotânico de plantas medicinais no domínio do cerrado na região do Alto Rio Grande –Minas Gerais. Ciên. Agrotec., 25(1), 102-123.
Rossi, P. G., BAO, L., Luciani, A., Panighi, J., Desjobert, J. M., Costa, J., & Bert, L. (2007). (E)-methylisoeugenol and elemicin: Antibacterial components of Daucus carota l. Essential oil against Campylobacter jejuni. J. Agric. Food Chem., 55, 7332−7336. https://doi.org/https://doi.org/10.1021/jf070674u
Salazar, M., Salazar, S., Ulloa, V., Mendoza, T., & Chamoro, G. (1992). Teratogenic action of alpha-asarone in the mouse. J. Toxicol. Clin. Exp., 12(3), 149-154.
Saldanha, A. A., Letícia Vieira, L., Ribeiro, R. I. M. A., Thomé, R. G., Dos Santos, H. B., Silva, D. B., & Soares, A. C. (2019). Chemical composition and evaluation of the anti-inflammatory and antinociceptive activities of Duguetia furfuracea essential oil: Effect on edema, leukocyte recruitment, tumor necrosis factor alpha production, iNOS expression, and adenosinergic and opioidergic systems. J. Ethnopharmacol., 231(325-336). https://doi.org/https://doi.org/10.1016/j.jep.2018.11.01
Saldanha, A. A., Vieira, L., De Oliveira, F. M., De Oliveira Lopes, D., De Azambuja Ribeiro, R. I. M., Thomé, R. G., & Soares, A. C. (2020). Anti-inflammatory and central and peripheral anti-nociceptive activities of α-asarone through the inhibition of TNF-α production, leukocyte recruitment and iNOS expression, and participation of the adenosinergic and opioidergic systems. Inflammopharmacol., 28(4), 1039-1052. https://doi.org/https://doi.org/10.1007/s10787-019-00679-1
Saldanha, A. A., Vieira, L., Oliveira, F. M., Lopes, D. O., Ribeiro, R. I. M. A., Thomé, R. G., & Soares, A. C. (2021). Anti‑infammatory and antinociceptive activities of a phenylpropanoid‑enriched fraction of Duguetia furfuracea. Inflammopharmacol., 29, 409-422. https://doi.org/https://doi.org/10.1007/s10787-020-00775-7
Santana, H. T., Trindade, F. T. T., Stabelli, R. G., Silva, A. A. E., Militão, J. S. L. T., & Facundo, V. A. (2015). Essential oils of leaves of Piper species display larvicidal activity against the dengue vector, Aedes aegypti (Diptera: Culicidae). Rev. Bras. Plantas Med., 17(1), 105-111. https://doi.org/https://doi.org/10.1590/1983-084X/13_052
Santos, D. Y. A. C., & Salatino, M. L. F. (2000). Foliar flavonoids of Annonaceae from Brazil: taxonomic significance. Phytochem., 55(6), 567-573. https://doi.org/https://doi.org/10.1016/S0031-9422(00)00227-2
Santos, T. C. B., Oliveira, R. C., Vasconcelos, L. G., Sousa Jr., P. T., Silva, V. C. P., Carvalho, M. G., & Ribeiro, T. A. N. (2019). Chemical constituents from roots of Duguetia furfuracea (A. St.-Hil.) Saff. (Annonaceae). Biochem. Syst. Ecol., 87, 103951. https://doi.org/https://doi.org/10.1016/j.bse.2019.103951
Silberbauer-Gottsberger, I. (1981). O cerrado como potencial de plantas medicinais e tóxicas. Oréades, 8(14), 15-30.
Silveira e Sá, R. C., Andrade, L. N., de Oliveira, R. R. B., & de Sousa, D. P. (2014). A review on anti-inflammatory activity of phenylpropanoids found in essential oils. Molecules, 19, 1459-1480. https://doi.org/https://doi.org/10.3390/molecules19021459
Simpson, M. G. (2010). Diversity and classification of flowering plants. In M. G. Simpson (Ed.), Plant Systematics (2nd ed., pp. 181-274). Burlington: Academic Press.
Singh, S., Kaur, I., & Kariyat, R. (2021). The multifunctional roles of polyphenols in plant-herbivore interactions. Int. J. Mol. Sci., 22, 1442. https://doi.org/https://doi.org/10.3390/ijms22031442
Siqueira, J. M., Ziminiani, M. G., Resende, U. M., & Boaventura, M. A. D. (2001). Estudo fitoquímico das cascas do caule de Duguetia glabriuscula - Annonaceae, biomonitorado pelo ensaio de toxicidade frente a Artemia Salina Leach. Quím. Nova, 24(2), 185-187. https://doi.org/https://doi.org/10.1590/S0100-40422001000200006
Sousa, O. V., Del-Vechio-Vieira, G., Alves, M. S., Araújo, A. A. L., Pinto, M. A. O., Amaral, M. P. H., & Kaplan, M. A. C. (2012). Chemical composition and biological activities of the essential oils from Duguetia lanceolata St. Hil. Barks. Molecules, 17, 1056-1066. https://doi.org/https://doi.org/10.3390/molecules170911056
Sousa, O. V., Del-Vechio-Vieira, G., Santos, B. C. S., Yamamoto, C. H., Araújo, A. L. S. M., Araújo, A. L. A., & Alves, M. S. (2016). In- vivo and vitro bioactivities of the essential oil of Duguetia lanceolata branches. Afr. J. Pharmacy Pharmacol., 10(14), 298-310. https://doi.org/https://doi.org/10.5897/AJPP2015.4497
Sousa, O. V., Del-Vechio, G., Amaral, M. P. H., Pinho, J. J. R. G., Yamamoto, C. H., & Alves, M. S. (2008). Efeitos antinociceptivo e antiinflamatório do extrato etanólico das folhas de Duguetia lanceolata St.-Hil. (Annonaceae). Lat. Am. J. Pharm., 27(3), 398-402.
Sousa, O. V., Soares Júnior, D. T., Del-Vechio, G., Mattosinhos, R. G., Gattass, C. R., & Kaplan, M. A. C. (2004). Atividades antinociceptiva e antiinflamatória do óleo essencial de cascas de Duguetia lanceolata St. Hil., Annonaceae. Rev. Bras. Farmacogn., 14(Supl 01), 11-14. https://doi.org/https://doi.org/10.1590/S0102-695X2004000300005
Tsabang, N., Fokou, P. V. T., Tchokouaha, L. R. Y., Noguem, B., Bakarnga-Via, I., Nguepi, M. S. D., & Boyom, F. F. (2012). Ethnopharmacological survey of Annonaceae medicinal plants used to treat malaria in four areas of Cameroon. J. Ethnopharmacol., 139, 171-180. https://doi.org/https://doi.org/10.1016/j.jep.2011.10.035
Valter, J. L., Alencar, K. M. C., Sartori, A. L. B., Nascimento, E. A., Chang, R., de Morais, S. A. L., & Siqueira, J. M. (2008). Variação química no óleo essencial das folhas de seis indivíduos de Duguetia furfuracea (Annonaceae). Rev. Bras. Farmacogn., 18(3), 373-378. https://doi.org/https://doi.org/10.1590/S0102-695X2008000300011
van Zuilen, C. M., Koek-Noorman, J., & Maas, P. J. M. (1995). A phylogenetic analysis of Duguetia (Annonaceae) based on morphological data. Plant Syst. Evol., 194(3/4), 173-188. https://doi.org/https://doi.org/10.1007/BF00982854
Vidotto, C., Da Silva, D. B., Patussi, R., Brandão, L. F. G. B., Tibúrcio, J. D., Alves, S. N., & De Siqueira, J. M. (2013). Brine shrimp lethality test as a biological model for preliminary selection of pediculicidal components from natural source. Biosci. J., 29(1), 255-263. https://doi.org/https://doi.org/10.13140/2.1.4422.5929
Vogt, T. (2010). Phenylpropanoid biosynthesis. Mol. Plant, 3(1), 2-20. https://doi.org/https://doi.org/10.1093/mp/ssp106
Wang, Z. J., Zhu, Y. Y., Yi, X., Zhou, Z. S., He, Y. J., Zhou, Y., & Luo, X. D. (2020). Bioguided isolation, identification and activity evaluation of antifungal compounds from Acorus tatarinowii Schott. J. Ethnopharmacol., 261, 113119. https://doi.org/https://doi.org/10.1016/j.jep.2020.113119
Wang, Z. W., Ma, W. W., McLaughlin, J. L., & Gupta, M. P. (1988). 2,4,5-trimethoxystyrene, a bioactive component of the bark of Duguetia panamensis. J. Nat. Prod., 51(2), 382-384. https://doi.org/https://doi.org/10.1021/np50056a041
Waterman, P. G. (1976). 2,4,5-Trimethoxystyrene from Pachypodanthium staudtii. Phytochem., 15(2), 347. https://doi.org/https://doi.org/10.1016/s0031-9422(00)89033-0
Downloads
Publicado
Como Citar
Edição
Seção
Licença
Copyright (c) 2022 Gleydiane Marcelle da Silva Nascimento; Aline Aparecida Saldanha; Mariana de Lima Nascimento; Whocely Victor de Castro
Este trabalho está licenciado sob uma licença Creative Commons Attribution 4.0 International License.
Autores que publicam nesta revista concordam com os seguintes termos:
1) Autores mantém os direitos autorais e concedem à revista o direito de primeira publicação, com o trabalho simultaneamente licenciado sob a Licença Creative Commons Attribution que permite o compartilhamento do trabalho com reconhecimento da autoria e publicação inicial nesta revista.
2) Autores têm autorização para assumir contratos adicionais separadamente, para distribuição não-exclusiva da versão do trabalho publicada nesta revista (ex.: publicar em repositório institucional ou como capítulo de livro), com reconhecimento de autoria e publicação inicial nesta revista.
3) Autores têm permissão e são estimulados a publicar e distribuir seu trabalho online (ex.: em repositórios institucionais ou na sua página pessoal) a qualquer ponto antes ou durante o processo editorial, já que isso pode gerar alterações produtivas, bem como aumentar o impacto e a citação do trabalho publicado.
