JBM  Vol.7 No.3 , March 2019
UPLC-QTOF-MS Analysis of Extracts from the Leaves of Pouteria caimito (Sapotaceae) and Their Antioxidant Activity
Abstract: This study describes the phytochemical profile and antioxidant activity of an extract from the leaves of Pouteria caimito (Sapotaceae). The extract in ethanol was obtained by maceration at room temperature and subjected to the liquid-liquid partition to obtain fractions in hexane and ethyl acetate. Steroids, triterpenes, saponins, alkaloids and flavonoids were identified by the phytochemical prospection of extracts and fractions from the leaves. The analysis of the ethyl acetate fraction by UPLC-QTOF-MS allowed us to identify eight triterpenes, namely, euscaphic acid (1), hyptadienic acid (2), betulinic acid (3), oleanolic acid (4), ursolic acid (5), 3β-(O-p-coumaroyl)- alphitolic acid (6), 3β-(O-p-coumaroyl)-maslinic acid (7) and 3β-(O-p-coumaroyl)-2-hydroxy-urs-12-en-28-oic acid (8). The ethanol extract and ethyl acetate fraction presented total phenolic contents of 10.6 ± 0.1 and 11.4 ± 0.3 mg GAE g-1, respectively, and considerable antioxidant activity in the DPPH assay with EC50 values of 299.4 ± 1.5 and 391.8 ± 0.9 μg·ml-1, respectively.
Cite this paper: de Sousa, L. , de Carvalho Junior, A. , de Carvalho, M. , da Silva, T. and Ferreira, R. (2019) UPLC-QTOF-MS Analysis of Extracts from the Leaves of Pouteria caimito (Sapotaceae) and Their Antioxidant Activity. Journal of Biosciences and Medicines, 7, 92-101. doi: 10.4236/jbm.2019.73009.

[1]   Triono, T., Brown, A.H.D., West, J.G. and Crisp, M.D. (2007) A Phylogeny of Pouteria (Sapotaceae) from Malesia and Australasia. Australian Systematic Botany, 20, 107-118.

[2]   Pennington, T.D. (1990) Flora Neotropica: Sapotaceae. The New York Botanical Garden, New York.

[3]   Carneiro, C.E. and Almeida Junior, E.B. (2010) Sapotaceae. In: Lista de Espécies da Flora do Brasil, JardimBotanico do Rio de Janeiro, Rio de Janeiro.

[4]   Rodrigues, P.M., Dutra Gomes, J.V., Jamal, C.M., Cunha Neto, á., Santos, M.L., Fagg, C.W., Fonseca-Bazzo, Y.M., Magalhaes, P.O., de Sales, P.M. and Silveira, D. (2017) Triterpenes from Pouteria ramiflora (Mart.) Radlk. Leaves (Sapotaceae). Food and Chemical Toxicology, 109, 1063-1068.

[5]   Silva, C.A.M., Simeoni, L.A. and Silveira, D. (2009) Genus Pouteria: Chemistry and Biological Activity. Brazilian Journal of Pharmacognosy, 19, 501-509.

[6]   Fontes Junior, E.A., Souza, P.J.C., Nascimento, J.L.M., Santos, S.N., Espíndola, L.S. and Ferreira, V.M.M. (2009) Antinociceptive and Antiinflammatory Properties of the Ethanolic Extract of Pouteria ramiflora Roots. Latin American Journal of Pharmacy, 28, 812-818.

[7]   Sales, P.M., Souza, P.M., Dartora, M., Resck, I.S., Simeoni, L.A., Fonseca-Bazzo, Y. M., Magalhaes, P.O. and Silveira, D. (2017) Pouteria torta Epicarp as a Useful Source of α-Amylase Inhibitor in the Control of Type 2 Diabetes. Food and Chemical Toxicology, 109, 962-969.

[8]   Prabhu, S., Vinodhini, S., Elanchezhiyan, C. and Rajeswari, D. (2018) Evaluation of Antidiabetic Activity of Biologically Synthesized Silver Nanoparticles Using Pouteria sapota in Streptozotocin-Induced Diabetic Rats. Journal of Diabetes, 10, 28-42.

[9]   Gulyás-Fekete, G., Murillo, E., Kurtán, T., Papp, T., Illyés, T.-Z., Drahos, L., Visy, J., Agósc, A., Turcsi, E. and Deli, J. (2013) Cryptocapsi-nepoxide-Type Carotenoids from Red Mamey, Pouteria sapota. Journal of Natural Products, 76, 607-614.

[10]   Murillo, E., Mosquera, Y., Kurtán, T., Gulyás-Fekete, G., Nagy, V. and Deli, J. (2012) Isolation and Characterization of Novel Capsorubin-Like Carotenoids from the Red Mamey (Pouteria sapota). Helvetica Chimica Acta, 95, 983-988.

[11]   Boscolo, O.H. and Valle, L.S. (2008) Plantas de uso medicinal em Quissama, Rio de Janeiro, Brasil. Iheringia Série Botanica, 63, 263-277.

[12]   Virgolin, L.B., Seixas, F.R.F. and Janzantti, N.S. (2017) Composition, Content of Bioactive Compounds, and Antioxidant Activity of Fruit Pulps from the Brazilian Amazon Biome. Revista Agropecuária Brasileira, 52, 933-941.

[13]   Souza, P.M., Sales, P.M., Simeoni, L.A., Silva, E.C., Silveira, D. and Magalhaes, P.O. (2012) Inhibitory Activity of Alpha-Amylase and Alpha-Glucosidase by Plant Extracts from the Brazilian Cerrado. Planta Medica, 78, 393-399.

[14]   Pellicciari, R., Ardon, A. and Bellavita, V. (1972) Triterpenes from Pouteria caimito. Planta Medica, 22, 196-200.

[15]   Carvalho Junior, A.R., Gomes, G.A., Ferreira, R.O. and Carvalho, M.G. (2014) Constituintesquímicos e atividadeantioxidante de folhas e galhos de Eugenia copacabanensis Kiaersk (Myrtaceae). Química Nova, 37, 477-482.

[16]   Ferreira, R.O., Carvalho Junior, A.R., Silva, T.M.G., Castro, R.N., Silva, T.M.S. and Carvalho, M.G. (2014) Distribution of Metabolites in Galled and Non-Galled Leaves of Clusialanceolata and Its Antioxidant Activity. Brazilian Journal of Pharmacognosy, 24, 617-625.

[17]   Ferreira, R.O., Carvalho Junior, A.R., Riger, C.J., Castro, R.N., Silva, T.M.S. and Carvalho, M.G. (2016) Constituintesquímicos e atividadeantioxidante in Vivo de flavonoidesisolados de Clusialanceolata (Clusiaceae). Química Nova, 39, 1093-1097.

[18]   Matos, F.J. (1997) Introducao à fitoquímica experimental. 2nd Edition, Edicoes UFC, Fortaleza.

[19]   Singleton, V.L., Orthorfer, R. and Lamuela-Raventós, R.M. (1999) Analysis of Total Phenols and Other Oxidation Substrates and Antioxidants by Means of Follin-Ciocateu Reagent. Methods in Enzimology, 299, 152-178.

[20]   Zhang, D. and Hamauzu, Y. (2004) Phenolics, Ascorbic Acid, Carotenoids and Antioxidant Activity of Broccoli and Their Changes during Conventional and Microwave Cooking. Food Chemistry, 88, 503-509.

[21]   Wu, L., Jiang, X., Huang, L. and Chen, S. (2013) Processing Technology Investigation of Loquat (Eriobotrya japonica) Leaf by Ultra-Performance Liquid Chromatography-Quadrupole Time-of-Flight Mass Spectrometry Combined with Chemometrics. PLoS ONE, 8, e64178.

[22]   Lee, S.-M., Park, J.-G., Lee, Y.-H., Lee, C.-G., Min, B.-S., Kim, J.-H. and Lee, H.-K. (2004) Anti-Complementary Activity of Triterpenoides from Fruits of Zizyphusjujuba. Biological Pharmaceutical Bulletin, 27, 1883-1886.

[23]   Rocha, G.G., Simoes, M., Lúcio, K.A., Oliveira, R.R., Kaplan, M.A.C. and Gattass, C.R. (2007) Natural Triterpenoids from Cecropialyratiloba Are Cy Totoxic to Both Sensitive and Multidrug Resistant Leukemia Cell Lines. Bioorganic Medicinal Chemistry, 15, 7355-7360.

[24]   Mitsuhashi, Y., Furusawa, Y., Aradate, T., Zhao, Q.-L., Moniruzzaman, R., Kanamori, M., Noguchi, K. and Kondo, T. ((2017) 3-O-Trans-p-Coumaroyl Alphitolic Acid, a Triterpenoid from Zizyphus jujuba, Leads to Apoptotic Cell Death in Human Leukemia Cells through Reactive Oxygen Species Production and Activation of the Unfolded Protein Response. PLoS ONE, 12, e0183712.

[25]   Vechia, L.D., Gnoatto, S.C.B. and Gosmann, G. (2009) Derivadosoleananos e ursanos e suaimportancianadescoberta de novosfármacos com atividadeantitumoral, anti-inflamatória e antioxidante. Química Nova, 32, 1245-1252.

[26]   Fuentealba, C., Gálvez, L., Cobos, A., Olaeta, J.A., Defilippi, B.G., Chirinos R, Campos, D. and Pedreschi, R. (2016) Characterization of Main Primary and Secondary Metabolites and in Vitro Antioxidant and Antihyperglycemic Properties in the Mesocarp of three Biotypes of Pouterialucuma. Food Chemistry, 190, 403-411.

[27]   Yahia, E.M., Gutiérrez-Orozco, F. and Arvizude Leon, C. (2011) Phytochemical and Antioxidant Characterization of Mamey (Pouteria sapota Jacq. H.E. Moore & Stearn) Fruit. Food Research International, 44, 2175-2181.

[28]   Pavithra, K. and Vadivuk-karasi, S. (2015) Evaluation of Free Radical Scavenging Activity of Various Extracts of Leaves from Kedrostis foetidissima (Jacq.) Cogn. Food Science and Human Wellness, 4, 42-46.