Antioxidant Activity and Flavonoids Identification by LC-MS/MS Analysis in Leaf Extract from Trattinnickia rhoifolia Willd

  • Lilian Marigo Magalhaes Universidade Federal de Mato Grosso, UFMT, Brasil.; Faculdade FASIPE, FASIPE, Brasil.
  • Valeria Dornelles Gindri Sinhorin Universidade Federal de Mato Grosso, UFMT, Brasil.
  • Camila Cristina Pereira de Souza Universidade Federal de Mato Grosso, UFMT, Brasil.
  • Rogério de Campos Bicudo Embrapa Agrossilvipastoril, CPAMT, Brasil.
  • Adilson Paulo Sinhorin Universidade Federal de Mato Grosso, UFMT, Brasil.
Palavras-chave: Trattinnickia, Flavonoides, Antioxidante, Paracetamol

Resumo

Os objetivos deste trabalho foram avaliar as atividades antioxidante e hepatoprotetora no modelo de estresse oxidativo induzido por paracetamol em camundongos Swiss machos,avaliar a ação hipoglicemiante e hipolipidêmica e identificar flavonoides no extrato etanólico de folhas da Trattinnickia rhoifolia. Pelo método de LC-MS/MS foram identificados oito flavonoides nas frações hidrometanólica (HM) e acetato de etila (EA), com exceção da Amentoflavona, os flavonoides Apigenina, Canferol, Luteolina, Quercetina, Quercetina-3-β-d-glicosídeo, Rutina e Taxifolina, foram identificados pela primeira vez na espécie. Estas frações foram avaliadas quanto à capacidade antioxidante (teste de DPPH) e seu efeito protetor in vivo através das análises de superóxido dismutase, catalase, glutationa-s-transferase, tiois não-proteicos, ácido ascórbico, TBARS e proteínas carboniladas. Os dados mostraram que EA possui capacidade antioxidante e reparo do estresse oxidativo superior nas análises químicas e biológicas, além de ação hipoglicemiante e hipolipidêmica. Assim, o presente trabalho contribui significativamente para a literatura, uma vez que é o primeiro estudo que identifica os constituintes químicos e propriedades farmacológicas do extrato de folhas de T. rhoifolia.

Biografia do Autor

Lilian Marigo Magalhaes, Universidade Federal de Mato Grosso, UFMT, Brasil.; Faculdade FASIPE, FASIPE, Brasil.
Mestrado em Ciências Ambientais pela Universidade Federal de Mato Grosso, UFMT, Brasil. Professora na Faculdade FASIPE, FASIPE, Brasil.
Valeria Dornelles Gindri Sinhorin, Universidade Federal de Mato Grosso, UFMT, Brasil.
Doutorado em Bioquímica Toxicológica pela Universidade Federal de Santa Maria, UFSM, Brasil. Professora na Universidade Federal de Mato Grosso, UFMT, Brasil.
Camila Cristina Pereira de Souza, Universidade Federal de Mato Grosso, UFMT, Brasil.
Mestrado em Ciências Ambientais pela Universidade Federal de Mato Grosso, UFMT, Brasil.
Rogério de Campos Bicudo, Embrapa Agrossilvipastoril, CPAMT, Brasil.
Doutorado em Quimica Analitica pelo Instituto de Quimica de Sao Carlos-USP. Analista na Embrapa Agrossilvipastoril, CPAMT, Brasil.
Adilson Paulo Sinhorin, Universidade Federal de Mato Grosso, UFMT, Brasil.
Doutorado em Química pela Universidade Federal de Santa Maria, UFSM, Brasil. Professor na Universidade Federal de Mato Grosso, UFMT, Brasil.

Referências

Achat S, Rakotomanomana N, Madani, K Dangles O 2016. Antioxidant activity of olive phenols and other dietary phenols in model gastric conditions: Scavenging of the free radical DPPH and inhibition of the haem-induced peroxidation of linoleic acid. Food Chemistry 213:135-142.

Afanas’ev IB, Dcrozhko AI, Brodskii AV, Kostyuk VA, Potapovitch AI 1989. Biochemical Pharmacology. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochemical Pharmacology 38(11):1763-1769.

Al-Saeedi AH, Hossain M 2015. Total phenols, total flavonoids contents and free radical scavenging activity of seeds crude extracts of pigeon pea traditionally used in Oman for the treatment of several chronic diseases. Asian Pacific Journal of Tropical Disease 5(4):316-321.

Aregullin M, Gompper ME, Rodriguez E 2002. Triterpenes and a sesquiterpene lactone in the resin of Trattinnickia aspera (Burseraceae). Biochemical Systematics and Ecology 30(2):187-188.

Behling EB, Sendão MC, Francescato HDC, Antunes LMG, Bianchi MDLP 2004. Flavonóide Quercetina: Aspectos Gerais E. Alimentos e Nutrição. Brazilian Journal of Food and Nutrition 15(3):285-292.

Biesaga M, Pyrzynska K 2009. Liquid chromatography/tandem mass spectrometry studies of the phenolic compounds in honey. Journal of Chromatography A 1216(38):6620-6626.

Bouterfas K, Mehdadi Z, Elaoufi MM, Latreche A, Benchiha W 2016. Antioxidant activity and total phenolic and flavonoids content variations of leaves extracts of white Horehound (Marrubium vulgare Linné) from three geographical origins. Annales Pharmaceutiques Françaises. http://dx.doi.org/10.1016/ j.pharma.2016.07.002.

Bradford MM 1976. A rapid and sensitive method for the quantitation of microgram quantities of proteína utilizing the principle of proteína-dye binding. Analytical Biochemistry 72(1-2):248-254.

Buege JA, Aust S 1978. Microsomal lipid peroxidation. Methods in Enzymology 52:302-310.

Carvalho NR, da Rosa EF, da Silva MH, Tassi CC, Corte CLD, Carbajo-Pescador S, Mauriz JL, González-Gallego J, Soares FA 2013. New therapeutic approach: diphenyl diselenide reduces mitochondrial dysfunction in acetaminophen-induced acute liver failure. PLoS ONE 8(12):1-13.

Coulibaly AY, Hashim R, Sulaiman SF, Sulaiman O, Ang LZP, Ooi KL 2014. Bioprospecting medicinal plants for antioxidant components. Asian Pacific Journal of Tropical Medicine 7(S1):S553-S559.

Coutinho MAS, Muzitano MF, Costa SS 2009. Flavonoids: potential therapeutic agents for the inflammatory process. Revista Virtual de Química 1(3):241-256.

Cuyckens F, Claeys M 2004. Special feature: mass spectrometry in the structural analysis of flavonoids. JournaL of Mass Spectrometry 39:1-15.

D’Andrea G 2015. Quercetin: A flavonol with multifaceted therapeutic applications. Fitoterapia 106:256-271.

Daly DC 1989. Studies in neotropical Burseraceae. II. Generic limits in New World Protieae and Canarieae. Brittonia 41:17-27.

Dhanya R, Arun KB, Syama HP, Nisha P, Sundaresan A, Santhosh Kumar TR, Jayamurthy P 2014. Rutin and quercetin enhance glucose uptake in L6 myotubes under oxidative stress induced by tertiary butyl hydrogen peroxide. Food Chemistry 158:546-54.

Dornas WC, Oliveira TT, Rodrigues-das-Dores RG, Santos AF, Nagem TJ 2007. Flavonoides: potencial terapêutico no estresse oxidativo. Revista de Ciências Farmacêuticas Básica e Aplicada 28(3):241-249.

Duan K, Yuan Z, Guo W, Meng Y, Cui Y, Kong D, Zhang L 2011. LC-MS/MS determination and pharmacokinetic study of five flavone components after solvent extraction/acid hydrolysis in rat plasma after oral administration of verbena officinalis L. extract. Journal of Ethnopharmacology 135(2):201-208.

Faccin H, Viana C, Nascimento PC, Bohrer D, Carvalho LM 2016. Study of ion suppression for phenolic compounds in medicinal plant extracts using liquid chromatography-electrospray tandem mass spectrometry. Journal of Chromatography A 1427:111-124.

Habig WH, Pabst MJ, Jacoby WB 1974. Glutathione S-transferase, the first enzymatic step in mercapturic acid formation. The Journal of Biological Chemistry 249:7130-7139.

Halliwell B 1999. Vitamin C: Poison, prophylactic or panacea? Trends in Biochemical Sciences 24(7):255-259.

Halliwell B, Whiteman M 2004. Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? British journal of pharmacology 142(2):231-255.

Heim KE, Tagliaferro AR, Bobilya DJ 2002. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem.13(10):572-584.

Hodgman MJ, Garrard AR 2012. A review of acetaminophen poisoning. Critical Care Clinics. 28(4):499-516.

Imessaoudene A, Merzouk H, Berroukeche F, Mokhtari N, Bensenane B, Cherrak S, Merzouk SA, Elhabiri M 2016. Beneficial effects of quercetin-iron complexes on serum and tissue lipids and redox status in obese rats. Journal of Nutritional Biochemistry 29:107-115.

La Cruz-Cañizares J, Doménech-Carbó MT, Gimeno-Adelantado JV, Mateo-Castro R, Bosch-Reig F 2005. Study of Burseraceae resins used in binding media and varnishes from artworks by gas chromatography-mass spectrometry and pyrolysis-gas chromatography-mass spectrometry. Journal of Chromatography 1093(1-2):177-194.

Lima MP, Braga PAC, Macedo ML, Silva MFGF, Ferreira AG, Fernandes JB, Vieira PC 2004. Phytochemistry of trattinnickia burserifolia, T. rhoifolia, and dacryodes hopkinsii: chemosystematic implications. Journal of the Brazilian Chemical Society 15(3):385-394.

Limón-Pacheco J, Gonsebatt ME 2009. The role of antioxidants and antioxidant-related enzymes in protective responses to environmentally induced oxidative stress. Mutation Research - Genetic Toxicology and Environmental Mutagenesis 674(1-2):137-47.

Marković JMD, Amić D, Lučić B, Marković ZS 2014. Oxidation of kaempferol and its iron (III) complex by DPPH radicals: spectroscopic and theoretical study. Monatshefte fur Chemie 145(4):557-563.

Marques MFS, Ribeiro MS 1994. Estudo dos constituintes químico das cascas da madeira de Trattinnickia peruviana. Acta Amazonica 24(1/2):49-52.

Mayne ST 2003. Antioxidant Nutrients and Chronic Disease: Use of Biomarkers of Exposure and Oxidative Stress Status in Epidemiologic Research. The Journal of Nutrition 133(3):933S-940S.

Mirochnitchenko O, Weisbrot-lefkowitz M, Reuhl K, Chen L, Yang C, Inouye M 1999. Acetaminophen toxicity. The journal of Biological Chemistry 274(15):10349-10355.

Misra HP, Fridovich I 1972. The role of superoxide anion in the autoxidation of epinephrine and a simple assay for superoxide dismutase. The Journal of Biological Chemistry 247(10):3170-3175

Nelson DP, Kiesow LA 1972. Enthalphy of decomposition of hydrogen peroxide by catalase at 25 °C (with molar extinction coefficients of H2O2 solution in the UV). Analytical Biochemistry 49:474-478

Nijveldt RJ 2001. Flavonoids: a review of probable mechanism of action and potential applications. Am J Clin Nutr 74:418-425.

Olaleye MT, Amobonye AE, Komolafe K, Akinmoladun AC 2014. Protective effects of parinari curatellifolia flavonoids against acetaminophen-induced hepatic necrosis in rats. Saudi Journal of Biological Sciences 21(5):486-492.

Olaleye MT, Rocha JBT 2008. Acetaminophen-induced liver damage in mice: effects of some medicinal plants on the oxidative defense system. Experimental and Toxicologic Pathology 59:319-327.

Orčić D, Francišković M, Bekvalac K, Svirčev E, Beara I, Lesjak M, Mimica-Dukić N 2014. Quantitative determination of plant phenolics in urtica dioica extracts by high-performance liquid chromatography coupled with tandem mass
spectrometric detection. Food Chemistry 143:48-53.

Pereira RB, Sousa C, Costa A, Andrade PB, Valentão P 2013. Glutathione and the antioxidant potential of binary mixtures with flavonoids: synergisms and antagonisms. Molecules 18(8):8858-72.

Pollard SE, Kuhnle GGC, Vauzour D, Vafeiadou K, Tzounis X, Whiteman M, Rice-Evans C, Spencer JPE 2006. The reaction of flavonoid metabolites with peroxynitrite. Biochemical and Biophysical Research Communications 350(4):960-968.

Puntel RL, Roos DH, Paixão MW, Braga AL, Zeni G, Nogueira CW 2007. Oxalate modulates thiobarbituric acid reactive species (TBARS) production in supernatants of homogenates from rat brain, liver and kidney: effect of diphenyl diselenide and diphenyl ditelluride. Chemico-Biological Interactions 165(2):87-98.

Qiu JY, Chen X, Li Z, Wang SR, Wu XW, Li YJ, Yang DZ, Yu YY, Yin XX, Tang DQ 2015. LC-MS/MS method for the simultaneous quantification of 11 compounds of ginkgo biloba extract in lysates of mesangial cell cultured by high glucose. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 997:122-128.

Ramchoun M, Harnafi H, Alem C, Bücheleet B, Simmet T, Rouis M, Atmani F, Amrani S 2012. Hypolipidemic and antioxidant effect of polyphenol-rich extracts from moroccan thyme varieties. e-SPEN Journal 7(3):3-8.

Ramirez G, Zamilpa A, Zavala M, Perez J, Morales D, Tortoriello J 2016. Chrysoeriol and other polyphenols from tecoma stans with lipase inhibitory activity. Journal of Ethnopharmacology 185:1-8.

Ramos MFS, Guimarães AC, Siani AC 2003. Volatile monoterpenes from the oleoresin of Trattinnickia rhoifolia. Biochemical Systematics and Ecology 31(3):309-311.

Roe JH 1954. Methods of biochemical analysis. In D Glick (Ed). Interscience 1:115-139.

Rosquete C, Olmo ED, Corral JMMD, Lópea JL, Gordaliza M, Feliciano AS 2010. Eudesmanolides and other terpenoids from Trattinickia rhoifolia. Avances en Química 5(2):123-129.

Salazar-Silvera UJ, Rosquete C 2010. Chemical constituents of the leaves from Trattinickia rhoifolia. Avances en Química 5(1):63-65.

Salgueiro ACF, Folmer V, Rosa HS, Costa MT, Boligon AA, Paula FR, Roos DH, Puntel GO 2016. In vitro and in silico antioxidant and toxicological activities of Achyrocline satureioides. Journal of Ethnopharmacology 194:6-14.

Sánchez C 2016. Reactive oxygen species and antioxidant properties from mushrooms. Synthetic and Systems Biotechnology 2:13-22.

Sedlack J, Lindsay RH 1968. Estimation of total, proteína-bound, and nonproteína sulfhydryl groups in tissue with ellman’s reagent. Analytical Biochemistry 25:192-205.

Sentellas S, Morales-Ibanez O, Zanuy M, Albertí JJ 2014. GSSG/GSH ratios in cryopreserved rat and human hepatocytes as a biomarker for drug induced oxidative stress. Toxicology in Vitro 28(5):1006-1015.

Shanmugam G, Ayyavu M, Rao DM, Devarajan T, Subramaniam G 2013. Hepatoprotective effect of caralluma umbellate against acetaminophen induced oxidative stress and liver damage in rat. Journal of Pharmacy Research 6(3):342-345.

Shanmugam S, Thangaraj P, Lima BS, Chandran R, Souza de Araújo AA, Narain N, Serafini MR, Júnior LJQ 2016. Effects of luteolin and quercetin 3-β-D-Glucoside identified from passiflora subpeltata leaves against acetaminophen induced hepatotoxicity in rats. Biomedicine & Pharmacotherapy 83:1278-1285.

Shinagawa FB, Santana FC, Rabelo L, Torres O, Mancini-Filho J 2015. Grape seed oil: a potential functional food? Food Science and Technology 35(3):399-406.

Siani AC, Ribeiro SMN 1995. Podocarpus flavone A from the leaves of Trattinnickia glaziovii. Biochemical Systematics and Ecology 23(7-8):879.

Silva ER, Oliveira DR, Melo FF, Bizzo HR, Leitão SG 2016. Oriximiná, Brazil. Part I: Is there a difference between black and white Breu? Brazilian Journal of Pharmacognosy 26(5):647-656.

Silva MH, Rosa EJF, Carvalho NR, Dobrachinski F, Rocha JBT, Mauriz JL, Gonzalez-Gallego J, Soares FAA 2012. Acute brain damage induced by acetaminophen in mice: effect of diphenyl diselenide on oxidative stress and mitochondrial dysfunction. Neurotoxicity Research 21(3):334-344.

Simões CMO, Schenkel EP, Gosmann G, Mello JCP, Mentz LA, Petrovick PR, 2004. Farmacognosia: da planta ao medicamento. 5. ed. Porto Alegre: UFSC, 1102.

Singh H, Atish P, Kalia AN, Majeed ABA 2015. Synergistic hepatoprotective potential of ethanolic extract of solanum xanthocarpum and juniperus communis against paracetamol and azithromycin induced liver injury in rats. Journal of Traditional and Complementary Medicine ():1-7.

Srinivasan R, Chandrasekar MJN, Nanjan MJ, Suresh B 2007. Antioxidant activity of caesalpinia digyna root. Journal of Ethnopharmacology 113(2):284-291.

Suke SG, Shukla A, Mundhada D, Banerjee BD, Mediratta PK 2013. Effect of phosphamidon on cognition and oxidative stress and its modulation by ascorbic acid and 4′-chlorodiazepam in rats. Pharmacology Biochemistry and Behavior 103(3):637-642.

Tang D, Yu Y, Zheng X, Wu J, Li Y, Wu X, Du Q, Yin X 2014. Comparative investigation of in vitro biotransformation of 14 components in Ginkgo biloba extract in normal, diabetes and diabetic nephropathy rat intestinal bacteria matrix. Journal of Pharmaceutical and Biomedical Analysis. 2014(100):1-10.

Teixeira S, Siquet C, Alves C, Boal I, Marques MP, Borges F, Lima JLFC, Reis S 2005. Structure-property studies on the antioxidant activity of flavonoids present in diet. Free Radical Biology and Medicine 39(8):1099-1108.

Touati R, Santos SAO, Rocha SM, Belhamel K, Silvestre AJD 2017. Phenolic composition and biological prospecting of grains and stems of retama sphaerocarpa. Industrial Crops and Products 95:244-255.

Urso ML, Clarkson PM 2003. Oxidative stress, exercise, and antioxidant supplementation. Toxicology 189:41-54.
Woisky RG, Salatino A 1998. Analysis of própolis: Some parameters and procedures for chemical quality control. Journal of Apicultural Research 37(2):99-105.

Xie J, Zhang Y, Kong D, Rexit M 2011. Rapid identification and determination of 11 polyphenols in Herba lycopi by HPLC-MS/MS with multiple reactions monitoring mode (MRM). Journal of Food Composition and Analysis 24(7):1069 -1072.

Yan LJ, Traber MG, Packer L 1995. Spectrophotometric method for determination of carbonyls in oxidatively modified apolipoproteína B of human low-density lipoproteínas. Analytical Biochemistry 228:349 - 351.
Publicado
2019-05-01
Como Citar
Magalhaes, Lilian Marigo, Valeria Dornelles Gindri Sinhorin, Camila Cristina Pereira de Souza, Rogério de Campos Bicudo, e Adilson Paulo Sinhorin. 2019. Antioxidant Activity and Flavonoids Identification by LC-MS/MS Analysis in Leaf Extract from Trattinnickia Rhoifolia Willd. Fronteiras: Journal of Social, Technological and Environmental Science 8 (2), 13-34. https://doi.org/https://doi.org/10.21664/2238-8869.2019v8i2.p13-34.
Seção
Dossiê - Tecnologias, Inovação e Sustentabilidade