Biological and phytochemical study of the leaves of Verbesina macrophylla (Cass.) S.F. Blake (Asteraceae)
Estudo biológico e fitoquímico das folhas de Verbesina macrophylla (Cass.) SFBlake (Asteraceae)
DOI:
https://doi.org/10.53660/CLM-2666-23U61Palavras-chave:
Verbesina macrophylla; medicinal plant; sesquiterpenes; herbal medicine.Resumo
Verbesina macrophylla is used in folk medicine to treat infections, inflammation and fever. This work aimed to evaluate the biological activity and phytochemistry of the species. Extracts in hexane, ethyl acetate and ethanol from the leaves of V. macrophylla revealed, using the microdilution method, activity against Gram positive bacteria (B. cereus, S. aureus, B. subtilis and M. luteus), with Inhibitory Concentration Minimum (MIC) between 500 µg/mL and 7.81 µg/mL. Fractionation of the extract in ethyl acetate resulted in 51 samples, all inactive for Gram-negatives. Four fractions showed activity against C. albicans and two against A. niger, at a concentration of 1000 µg/mL. Analysis of NMR data from fraction 19-20 revealed the presence of two isomers: (6-O-b-E-p-coumaroyl-4a-hydroxyeudesmane and 6-O-b-Z-p-coumaroyl-4a-hydroxyeudesmane), active for all Gram positive bacteria, bactericidal for B. cereus and S. aureus, with MIC between 2.5 and 3.9 µg/mL. The cytotoxicity test on red blood cells of the extracts showed slight hemolysis only for the hexane extract. The kinetic study of microbial growth of the Vm F19-20 fraction using the time-kill method revealed a dose-dependent effect for the B. subtilis strain.
Downloads
Referências
Al-Dabbas MM, Hashinaga F, Abdelgaleil SA, Suganum T, Akiyama K, Hayashi H (2005). Antibacterial activity of an eudesmane sesquiterpene isolated from common Varthemia, Varthemia iphionoides. Journal of ethnopharmacology, 97(2), 237-240. https://doi.org/10.1016/j.jep.2004.11.007
Aligiannis N, Kalpoutzakis E, Mitaku S, Chinou IB (2001). Composition and antimicrobial activity of the essential oils of two Origanum species. Journal of agricultural and food chemistry, 49(9), 4168-4170. https://doi.org/10.1021/jf001494m
Bezerra LDA, Mangabeira PAO, de Oliveira RA, Costa LCDB, Da Cunha M (2018). Leaf blade structure of Verbesina macrophylla (Cass.) FS Blake (Asteraceae): ontogeny, duct secretion mechanism and essential oil composition. Plant Biology, 20(3), 433-443. https://doi.org/10.1111/plb.12700
Bohlmann F, Grenz M, Gupta RK, Dhar AK, Ahmed M, King RM, Robinson H (1980). Eudesmane derivatives from Verbesina species. Phytochemistry, 19(11), 2391-2397. https://doi.org/10.1016/S0031-9422(00)91034-3
BRASIL (2010). Farmacopeia Brasileira volume 1 / Agência Nacional de Vigilância Sanitária. Brasília: Anvisa, 546p.
Bresciania LFV, Yunes RA, Bürger C, De Oliveira LE, Bóf KL, Cechinel-Filho V (2004). Seasonal variation of kaurenoic acid, a hypoglycemic diterpene present in Wedelia paludosa (Acmela brasiliensis) (Asteraceae). Zeitschrift für Naturforschung C, 59(3-4), 229-232. https://doi.org/10.1515/znc-2004-3-419
Cantuária VL (2018). 200p. Estudo fitoquímico e atividades biológicas da espécie Eremanthus erythropappus (DC) MacLeish (Asteraceae). Dissertação (mestrado) – Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal dos Vales do Jequitinhonha e Mucuri, Diamantina.
Carvalho GJAD, Carvalho MGD, Ferreira DT, Faria TDJ, Braz-Filho R (2001). Diterpenos, triterpenos e esteróides das flores de Wedelia paludosa. Química Nova, 24, 24-26. https://doi.org/10.1590/S0100-40422001000100006
Cechinel V, Yunes RA (2001). Estudo químico de plantas medicinais orientado para análise biológica. Obtenção, determinação e modificação estrutural de compostos bioativos. Chapecó: Argos Editora Universitária. 523p.
Cockerill FR, Wikler MA, Alder J, Dudley MN, Eliopoulos GM, Ferraro MJ, Hardy DJ, Hecht DW, Hindler JA, Patel JB, Powell M, Swenson JM, Thomson RB, Traczewski MM, Turnidge JD, Weinstein, MP, Zimmer BL (2012). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard — ninth Edition. In: Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard- Ninth Edition, vol. 32. Issue 2
Contrucci BA, Silva R, Junior RA, Kozusny-Andreani DI (2019). Efeito de óleos essenciais sobre bactérias gram-negativas isoladas de alimentos. Ensaios e Ciência C Biológicas Agrárias e da Saúde, 23(3), 180-184. https://doi.org/10.17921/1415-6938.2019v23n3p180-184
Costa JGM, Rodrigues, FFG, Angélico EC, Silva MR, Mota ML, Santos NKA, Lemos, TLG (2005). Estudo químico-biológico dos óleos essenciais de Hyptis martiusii, Lippia sidoides e Syzigium aromaticum frente às larvas do Aedes aegypti. Revista Brasileira de Farmacognosia, 15, 304-309. https://doi.org/10.1590/S0102-695X2005000400008
Cowan MM (1999). Plant products as antimicrobial agents. Clinical microbiology reviews, 12(4), 564-582. https://doi.org/10.1128/cmr.12.4.564
Da Cunha Naghetini C (2006). Caracterização físico-química e atividade antifúngica dos óleos essenciais da cúrcuma. 61 p. Dissertação (mestrado). Programa de Pós-graduação em Ciência de Alimentos, Universidade Federal de Minas Gerais, Belo Horizonte, MG.
Da Silva Filho AA, Resende DO, Fukui MJ, Santos FF, Pauletti PM, Cunha WR, Nanayakkara NPD (2009). In vitro antileishmanial, antiplasmodial and cytotoxic activities of phenolics and triterpenoids from Baccharis dracunculifolia DC (Asteraceae). Fitoterapia, 80(8), 478-482. https://doi.org/10.1016/j.fitote.2009.06.007
Da Silva RZ, Da Silva MZ, Leal LDF, YUNES R, MIGUEL O, CECHINEL FILHO V (2002). Investigação fitoquímica e avaliação da atividade antibacteriana da Mikania lanuginosa DC (Asteraceae). Visão acadêmica, 3(2).
De Abreu PAP, Onofre SB (2010). Atividade antimicrobiana dos extratos de Baccharis dracunculifolia DC (Asteraceae). Sabios-Revista de Saúde e Biologia, 5(2).
De Haro Moreno A, Possebon L, Sant’ana M, Souza HR, Pilon MMI, Girol AP (2018). Avaliação da atividade antimicrobiana e citotoxicidade hemolítica em diferentes extratos vegetais. Arquivos de Ciências Da Saúde, 25(1), 11-12. https://doi.org/10.17696/2318-3691.25.1.2018.1172
De Matos Volpato AM, De Moura Rios E, Miguel MD, Sander PC, Miguel OG (2001). Investigação da atividade antibacteriana de Calendula officinalis L. (Asteraceae). Visão Acadêmica, 2(1).
de Veras BO, de Oliveira JRS, de Menezes Lima VL, Navarro DMDAF, de Oliveira Farias JCR, de Medeiros Moura GM, de Souza Lopes AC (2021). The essential oil of the leaves of Verbesina macrophylla (Cass.) SF Blake has antimicrobial, anti-inflammatory and antipyretic activities and is toxicologically safe. Journal of Ethnopharmacology, 265, 113248. https://doi.org/10.1016/j.jep.2020.113248
Dorman HD, Deans SG (2000). Antimicrobial agents from plants: antibacterial activity of plant volatile oils. Journal of applied microbiology, 88(2), 308-316. https://doi.org/10.1046/j.1365-2672.2000.00969.x
Duffy CF, Power RF (2001). Antioxidant and antimicrobial properties of some Chinese plant extracts. International journal of antimicrobial agents, 17(6), 527-530.
Dutra FSG, de Almeida Carlos L, da Motta OV, Vianna AP, Pereira SMF (2016). Atividade antimicrobiana de extratos vegetais frente à bactérias de importância médica. Biológicas & Saúde, 6(20).
Goes VFF (2009). 141p. Ação de extratos, óleos essenciais e frações isoladas de plantas Medicinais sobre a formação do biofilme em Candida ssp (Doctoral dissertation, tese de doutorado]. São Paulo (SP): Unicamp).
Guarim Neto G, Morais RGD (2003). Recursos medicinais de espécies do Cerrado de Mato Grosso: um estudo bibliográfico. Acta Botanica Brasilica, 17, 561-584. https://doi.org/10.1590/S0102-33062003000400009
Kabara, JJ (2008). Fats are good for you and other secrets: how saturated fat and cholesterol actually benefit the body. North Atlantic Books. p.16.
Karis PO, Ryding O (1994). Tribe heliantheae.. In: BREMER, K. (ed.) Asteraceae. Cladistics and Classification. Portland: Timber Press. p. 559-625.
Kato T, Frei B, Heinrich M, Sticher O (1996). Sesquiterpenes with antibacterial activity from Epaltes mexicana. Planta medica, 62(01), 66-67. https://doi.org/10.1055/s-2006-957803
Kim MK, Choi GJ, Lee HS (2003). Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. Journal of agricultural and food chemistry, 51(6), 1578-1581. https://doi.org/10.1021/jf0210369
Klepser ME, Ernst EJ, Lewis RE, Ernst ME, Pfaller MA (1998). Influence of test conditions on antifungal time-kill curve results: proposal for standardized methods. Antimicrobial agents and chemotherapy, 42(5), 1207-1212. https://doi.org/10.1128/aac.42.5.1207
Lorenzi H, Matos FJDA (2021). Plantas medicinais no Brasil: nativas e exóticas. Nova Odessa: Instituto Plantarum, São Paulo, p. 544
Maddila S, Hemalatha KPJ (2017). Phytochemical screening and in vitro antimicrobial properties of crude leaf extracts of Wrightia tinctoria R. Br. International Journal of Current Microbiology and Applied Sciences, 6(1), 707-720.
Maia GLDA, Sousa FHT, Costa VCDO, Tavares JF, Barbosa Filho JM (2011). p-Coumarate of borneol isolated of verbesina macrophylla; p-Ccumaratos de borneol isolados de Verbesina macrophylla. Sociedade Brasileira de Química (SBQ)
Malheiro A, Peres MTLP (2001). Alelopatia: interações químicas entre espécies. Yunes RA, Calixto JB. Plantas medicinais sob a ótica da química medicinal moderna. Chapecó: Argos, 503-523.
Martinez LN, Rodrigues SFL, Silva NB, Santos EV, Costa JDAN (2020). Avaliação etnobotânica das espécies das famílias Asteraceae e Lamiaceae utilizadas com potencial medicinal na região de Porto Velho–Rondônia. Interfaces Científicas-Saúde e Ambiente, 8(2), 431-445. https://doi.org/10.17564/2316-3798.2020v8n2p431-445
Mora FD, Alpan L, McCracken VJ, Nieto M (2013). Chemical and biological aspects of the genus Verbesina. The natural products journal, 3(2), 140-150. https://doi.org/10.2174/2210315511303020009
Mora FD, Rojas YL, González V, Velasco J, Díaz T, Ríos N, Nieto M (2015). Chemical Composition and in vitro Antibacterial Activity of the Essential Oil of Verbesina negrensis from the Venezuelan Andes. Natural product communications, 10(7). https://doi.org/10.1177/1934578X1501000743.
Moreno RBDSP (2013). 87p. Caracterização do potencial biotecnológico do Crambe abyssinica na alimentação de ruminante. Dissertação (Mestrado em Ciência e Tecnologia Ambiental) – Faculdade de Ciências Exatas e Tecnologia, Universidade Federal da Grande Dourados, Dourado.
Mosmann T (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of immunological methods, 65(1-2), 55-63. https://doi.org/10.1016/0022-1759(83)90303-4
Newman DJ, Cragg GM (2012). Natural products as sources of new drugs over the 30 years from 1981 to 2010. Journal of natural products, 75(3), 311-335. https://doi.org/10.1021/np200906s
Paula CS, Canteli VCD, Verdam MCS, Kalegari M, Campos R, Hirota BCK, Miguel MD (2014). Atividade antioxidante e toxicidade preliminar do extrato e frações obtidas das folhas e cascas do caule de Dasyphyllum tomentosum (Spreng.) Cabrera. Revista Brasileira de Plantas Medicinais, 16, 189-195. https://doi.org/10.1590/S1516-05722014000200004
Pereira MET, Pereira CT, Medeiros CIS, Barbosa-Filho JM, de Azevedo Maia GL, de Sousa AP, de Oliveira Filho AA (2022). Avaliação da citotoxicidade em hemácias de humanos do extrato etanólico de Praxelis clematidea (Griseb.). Revista Colombiana de Ciencias Químico-Farmacéuticas, 51(2). https://doi.org/10.15446/rcciquifa.v51n2.98326
Pradeepa S, Subramanian S, Kaviyarasan V (2014). Evaluation of antimicrobial activity of Pithecellobium dulce pod pulp extract. Asian Journal of Pharmaceutical and Clinical Research, 7(1), 32-37.
Sacchetti G, Maietti S, Muzzoli M, Scaglianti M, Manfredini S, Radice M, Bruni R (2005). Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food chemistry, 91(4), 621-632. https://doi.org/10.1016/j.foodchem.2004.06.031
Saroglou V, Karioti A, Demetzos C, Dimas K, Skaltsa H (2005). Sesquiterpene Lactones from Centaurea s pinosa and their antibacterial and cytotoxic activities. Journal of natural products, 68(9), 1404-1407. https://doi.org/10.1021/np058042u
Sartori MR, Pretto JB, Cruz AB, Bresciani LFV, Yunes RA, Sortino M, Cechinel Filho V. (2003). Antifungal activity of fractions and two pure compounds of flowers from Wedelia paludosa (Acmela brasiliensis) (Asteraceae). Pharmazie, 58(8), 567-569.
Silva DDF (2016). Avaliação da atividade biológica de β-Citronelol sobre Candida albicans. 62f. Dissertação (Mestrado em Produtos Naturais Sintéticos e Bioativos – Farmacologia) – Universidade Federal da Paraíba.
Singh S, Sobel JD, Bhargava P, Boikov D, Vazquez JA (2002). Vaginitis due to Candida krusei: epidemiology, clinical aspects, and therapy. Clinical infectious diseases, 35(9), 1066-1070. https://doi.org/10.1086/343826
Stefanovic OD, Stanojevic DD, Comic LR (2012). Synergistic antibacterial activity of Salvia officinalis and Cichorium intybus extracts and antibiotics. Acta Pol Pharm, 69(3), 457-463.
Toribio MS, Oriani DS, Fernández JG, Skliar MI (2005). Actividad antimicrobiana de Verbesina encelioides. InVet, 7(1), 41-45.
Toribio MS, Riesco S, Oriani DS, Tortone C, Fernández JG (2012). Actividad biológica de los extractos metanólicos de Verbesina encelioides frente a aislamientos clínicos de Staphylococcus aureus resistentes a meticilina. Ars Pharmaceutica (Internet), 53(2), 45-47. https://doi.org/10.30827/ars
Walsh C. 2003. Antibiotics: actions, origins, resistance. American Society for Microbiology (ASM).
Wang B, Deng J, Gao Y, Zhu L, He R, Xu Y (2011). The screening toolbox of bioactive substances from natural products: A review. Fitoterapia, 82(8), 1141-1151. https://doi.org/10.1016/j.fitote.2011.08.007
Webster D, Taschereau P, Belland, RJ, Sand, C, Rennie RP (2008). Antifungal activity of medicinal plant extracts; preliminary screening studies. Journal of ethnopharmacology, 115(1), 140-146. https://doi.org/10.1016/j.jep.2007.09.014
Wilkens M, Alarcón C, Urzúa A, Mendoza L (2002). Characterization of the bactericidal activity of the natural diterpene kaurenoic acid. Planta medica, 68(05), 452-454. https://doi.org/10.1055/s-2002-32086
Xu WH, Liang Q, Liang ZS, Li XC (2010). Two new eudesmane derivatives from Verbesina virginica. Chinese Chemical Letters, 21(6), 693-695. https://doi.org/10.1016/j.cclet.2010.01.009
Yang R, Yuan BC, Ma YS, Zhou S, Liu Y (2017). The anti-inflammatory activity of licorice, a widely used Chinese herb. Pharmaceutical biology, 55(1), 5-18. https://doi.org/10.1080/13880209.2016.1225775
