Publicado

2023-03-23

Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec.

Aislamiento guiado por bioensayo de inhibidores de α-glucosidasa de Byrsonima garcibarrigae Cuatrec

Isolamento guiado por bioensaio de inibidores de α-glicosidase de Byrsonima garcibarrigae Cuatrec

DOI:

https://doi.org/10.15446/rcciquifa.v51n3.96982

Palavras-chave:

antidiabetic, oxidative stress, Byrsonima garcibarrigae (en)
antidiabético, estrés oxidativo, Byrsonima garcibarrigae (es)

Autores

  • Tallita Marques Machado Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Setor Sul, Coroado, 69067- 005 Manaus, Amazonas.
  • Carolina Queiroz Valentim Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Setor Sul, Coroado, 69067- 005 Manaus, Amazonas.
  • Leonard Domingo Rosales Acho Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Setor Sul, Coroado, 69067- 005 Manaus, Amazonas.
  • Emerson Silva Lima Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Setor Sul, Coroado, 69067- 005 Manaus, Amazonas.
  • Hector Henrique Ferreira Koolen DeMpSter Mass Spectrometry Group, Amazonas State University
  • Fernanda Guilhon-Simplicio Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Setor Sul, Coroado, 69067- 005 Manaus, Amazonas.

Introduction:Byrsonima garcibarrigae is an endemic tree of Amazonas state, Brazil, with pharmacological and chemical knowledge poorly understood. Aim: To investigate the antidiabetic potential of the B. garcibarrigae stem bark. Methods: The stem bark was sequentially extracted by maceration with hexane (EHBG), ethyl acetate (EABG), and methanol (EMBG). The antioxidant capacity, α-glucosidase inhibitory potentials and anti-glycation capacities were evaluated. A bio-guided fractionation gave compounds that were characterized by MS and NMR. Results: 8 compounds were identified by HPLC-MS. EMBG showed the highest α-glucosidase inhibitory activity (1.09±0.32 μg/mL), antioxidant activity (9.2±0.23 μg/mL) and phenolic compounds content (61.43±0.50%), thus was fractionated producing hexane (FHX), chloroform (FCL) and hydromethanolic (FHM) fractions. After additional anti-α-glucosidase assays, FHM (1.02±0.49 μg/mL) was fractionated giving quercitrin and epicatechin. The anti-glycation assay showed that EMBG, FHM and quercitrin presented higher activities in comparison to the positive control, aminoguanidine. Conclusions:B. garcibarrigae displayed antidiabetic potential since inhibited α-glucosidase, as well as presented expressive antioxidant and anti-glycation activities were recorded.

Introducción: Byrsonima garcibarrigae es un árbol endémico del estado de Amazonas, Brasil, con poco conocimiento farmacológico y químico. Objetivo: investigar el potencial antidiabético de la corteza del tallo de B. garcibarrigae. Métodos: la corteza del tallo se extrajo secuencialmente mediante maceración con hexano (EHBG), acetato de etilo (EABG) y metanol (EMBG). Se evaluó la capacidad antioxidante, los potenciales inhibidores de la α-glucosidasa y las capacidades anti-glicación. Un fraccionamiento bioguiado dio compuestos que se caracterizaron por MS y NMR. Resultados: se identificaron 8 compuestos mediante HPLC-MS. EMBG mostró la mayor actividad inhibidora de α-glucosidasa (1,09 ± 0,32 μg/mL), actividad antioxidante (9,2±0.23 μg/mL) y contenido de compuestos fenólicos (61,43 ± 0.50%), por lo que se fraccionó produciendo hexano (FHX), cloroformo (FCL) e hidrometanólicas (FHM). Después de ensayos adicionales de anti-α-glucosidasa, se fraccionó FHM (1,02 ± 0,49 μg/mL) dando quercitrina y epicatequina. El ensayo antiglicación mostró que EMBG, FHM y quercitrina presentaron actividades más altas en comparación con el control positivo, aminoguanidina. Conclusiones: B. garcibarrigae mostró potencial antidiabético ya que se registró una inhibición de la α-glucosidasa, así como también presentó actividades expresivas antioxidantes y antiglicación.

Introdução:Byrsonima garcibarrigae é uma árvore endêmica do estado do Amazonas, Brasil, com pouco conhecimento farmacológico e químico. Objetivo: investigar o potencial antidiabético da casca do caule de B. garcibarrigae. Métodos: a casca do caule foi extraída sequencialmente por maceração com hexano (EHBG), acetato de etila (EABG) e metanol (EMBG). A capacidade antioxidante, potencial inibibitório de α-glicosidase e capacidade antiglicação foram avaliadas. Um fracionamento bioguiado isolou compostos que foram caracterizados por MS e RMN. Resultados: 8 compostos foram identificados por HPLC-MS. O EMBG apresentou a maior atividade inibitória de α-glicosidase (1,09 ± 0,32 μg/mL), atividade antioxidante (9,2±0,23 μg/mL) e teor de compostos fenólicos (61,43 ± 0,50%), por isso foi fracionado produzindo hexano (FHX), clorofórmio (FCL) e hidrometanólico (FHM). Após ensaios anti-α-glicosidase adicionais, FHM (1,02 ± 0,49 μg/mL) foi fracionado, originando a quercitrina e epicatequina. O ensaio de antiglicação mostrou que EMBG, FHM e quercitrina exibiram atividades mais altas em comparação com o controle positivo, aminoguanidina. Conclusões:B. garcibarrigae apresentou potencial antidiabético, uma vez que foi registrada inibição da α-glicosidase, bem como expressiva atividade antioxidante e antiglicação.

Referências

M.P. Czech, Insulin action and resistance in obesity and type 2 diabetes, Nat. Med., 23, 804-814 (2017).

M. Saraswat, P.Y. Reddy, P. Muthenna, G.B. Reddy, Prevention of non-enzymic glycation of proteins by dietary agents: prospects for alleviating diabetic complications, Br. J. Nutr., 101, 1714 (2009).

K.A. Adeshara, A.G. Diwan, T.R. Jagtap, K. Advani, A. Siddiqui, R.S. Tupe, Relationship between plasma glycation with membrane modification, oxidative stress and expression of glucose trasporter-1 in type 2 diabetes patients with vascular complications, J. Diabetes Complications, 31, 439-448 (2017).

N. Thomford, D. Senthebane, A. Rowe, D. Munro, P. Seele, A. Maroyi, K. Dzobo, Natural products for drug discovery in the 21st century: Innovations for novel drug discovery, Int. J. Mol. Sci., 19, 1578 (2018).

C.M. Dobson, Chemical space and biology, Nature, 432, 824-828 (2004).

J. Hong, Role of natural product diversity in chemical biology, Curr. Opin. Chem. Biol., 15, 350-354 (2011).

C. Lankatillake, T. Huynh, D.A. Dias, Understanding glycaemic control and current approaches for screening antidiabetic natural products from evidencebased medicinal plants, Plant Methods, 15, 105 (2019).

D. Giles-Rivas, S. Estrada-Soto, A.B. Aguilar-Guadarrama, J. Almanza-Pérez, S. García-Jiménez, B. Colín-Lozano, G. Navarrete-Vázquez, R. Villalobos-Molina, Antidiabetic effect of Cordia morelosana, chemical and pharmacological studies, J. Ethnopharmacol., 251, 112543 (2020).

F. Guilhon-Simplicio, M.d.M. Pereira, Aspectos químicos e farmacológicos de Byrsonima (Malpighiaceae), Quim. Nova, 34, 1032-1041 (2011).

M.C.d.S. Verdam, F. Guilhon-Simplicio, K.C. de Andrade, K.L.M. Fernandes, T.M. Machado, F.M.A. da Silva, M.P. de Souza, H.H.F. Koolen, C.S. Paula, B.C.K. Hirota, V.B. de Oliveira, C.M.S. Miyazaki, M. Kalegari, M.D. Miguel, P.M. Stuelp-Campelo, O.G. Miguel, et al., Analgesic, anti-inflammatory, and antioxidant activities of Byrsonima duckeana W. R. Anderson (Malpighiaceae), Sci. World J., 2017, 8367042 (2017).

F. Guilhon-Simplicio, T.M. Machado, L.F. do Nascimento, R.D.S. Souza, H.H.F. Koolen, F.M.A. da Silva, L.D.R. Acho, A.R.S. dos Santos, P. Cos, M.d.M. Pereira, E.S. Lima, Chemical composition and antioxidant, antinociceptive, and anti-inflammatory activities of four Amazonian Byrsonima species, Phytother. Res., 31, 1686-1693 (2017).

V.L. Singleton, J.A. Rossi, Colorimetry of total phenolics with phosphomolybdic- phosphotungstic acid reagents, Am. J. Enol. Vitic., 16, 144-158 (1965).

P. Molyneux, The use of the stable free radical diphenylpicryl- hydrazyl (DPPH) for estimating antioxidant activity, Songklanakarin J. Sci. Technol., 26, 211-219 (2004).

A. Andrade-Cetto, J. Becerra-Jiménez, R. Cárdenas-Vázquez, Alfa-glucosidaseinhibiting activity of some Mexican plants used in the treatment of type 2 diabetes, J. Ethnopharmacol., 116, 27-32 (2008).

R.M.P. Gutierrez, L.B.F. Cotera, A.M.N. Gonzalez, Evaluation of the antioxidant and anti-glication effects of the hexane extract from Piper auritum leaves in vitro and beneficial activity on oxidative stress and advanced glycation endproduct- mediated renal injury in streptozotocin-treated diabetic rats, Molecules, 17, 11897-11919 (2012).

O. Trott, A.J. Olson, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31, 455-461 (2010).

B. Zhang, X. Li, W. Sun, Y. Xing, Z. Xiu, C. Zhuang, Y. Dong, Dietary flavonoids and acarbose synergistically inhibit α-glucosidase and lower postprandial blood glucose, J. Agric. Food Chem., 65, 8319-8330 (2017).

U. Asmat, K. Abad, K. Ismail, Diabetes mellitus and oxidative stress-A concise review, Saudi Pharm. J., 24, 547-553 (2016).

S. Felhi, A. Daoud, H. Hajlaoui, K. Mnafgui, N. Gharsallah, A. Kadri, Solvent extraction effects on phytochemical constituents profiles, antioxidant and antimicrobial activities and functional group analysis of Ecballium elaterium seeds and peels fruits, Food Sci. Technol., 37, 483-492 (2017).

A. Thouri, H. Chahdoura, A. El Arem, A.O. Hichri, R.B. Hassin, L. Achour, Effect of solvents extraction on phytochemical components and biological activities of Tunisian date seeds (var. Korkobbi and Arechti), BMC Complement. Altern. Med., 17, 248 (2017).

F. Carmona, A.M.S. Pereira, Herbal medicines: Old and new concepts, truths and misunderstandings, Brazilian J. Pharmacogn., 23, 379-385 (2013).

L.K. Caesar, N.B. Cech, Synergy and antagonism in natural product extracts: When 1 + 1 does not equal 2, Nat. Prod. Rep., 36, 869-888 (2019).

F.A. Ashu, J. Na-Iya, B.E.N. Wamba, J. Kamga, P. Nayim, B. Ngameni, V.P. Beng, B.T. Ngadjui, V. Kuete, Antistaphylococcal activity of extracts, fractions and compounds of Acacia polyacantha wild (Fabaceae), Evidence-Based Complement. Altern. Med., 2020, 2654247 (2020).

J.B.D.F. Tostes, A.J.R. da Silva, R.M. Kuster, Isolation and characterization of polyphenols from Euphorbia heterophylla L. (Euphorbiaceae) leaves, Rev. Fitos, Rio de Janeiro, 13, 49-60 (2019).

M.C.d.S. Verdam, F. Guilhon-Simplicio, K.C. de Andrade, K.L.M. Fernandes, T.M. Machado, F.M.A. da Silva, M.P. de Souza, H.H.F. Koolen, C.S. Paula, B.C.K. Hirota, V.B. de Oliveira, C.M.S. Miyazaki, M. Kalegari, M.D. Miguel, P.M. Stuelp-Campelo, O.G. Miguel, Analgesic, Anti-inflammatory, and antioxidant activities of Byrsonima duckeana W. R. Anderson (Malpighiaceae), Sci. World J., 2017, 8367042 (2017).

P.A. Rodrigues, S.M. de Morais, L.A. Aguiar, N.S. Vila-Nova, S.R. Benjamin, Effect of Byrsonima sericea DC. leaf extracts on mice gastrointestinal tract, Toxicol. Reports, 6, 1182-1187 (2019).

K. Nowotny, T. Jung, A. Höhn, D. Weber, T. Grune, Advanced glycation end products and oxidative stress in type 2 Diabetes Mellitus, Biomolecules, 5, 194- 222 (2015).

R. Testa, A.R. Bonfigli, F. Prattichizzo, L.L. Sala, V. de Nigris, A. Ceriello, The “Metabolic Memory” theory and the early treatment of hyperglycemia in prevention of diabetic complications, Nutrients, 9, 437 (2017).

J. Uribarri, M.D. del Castillo, M.P. de la Maza, R. Filip, A. Gugliucci, C. Luevano-Contreras, M.H. Macías-Cervantes, D.H.M. Bastos, A. Medrano, T. Menini, M. Portero-Otin, A. Rojas, G.R. Sampaio, K. Wrobel, K. Wrobel, M.E. Garay-Sevilla, Dietary advanced glycation end products and their role in health and disease, Adv. Nutr., 6, 461-473 (2015).

S. Meng, J. Cao, Q. Feng, J. Peng, Y. Hu, Roles of chlorogenic acid on regulating glucose and lipids metabolism: A review, Evidence-Based Complement. Altern. Med., 2013, 801457 (2013).

J. Santana-Gálvez, L. Cisneros-Zevallos, D.A. Jacobo-Velázquez, Chlorogenic acid: Recent advances on its dual role as a food additive and a nutraceutical against metabolic syndrome, Molecules, 22, 358 (2017).

Y. Yamashita, L. Wang, F. Nanba, C. Ito, T. Toda, H. Ashida, Procyanidin promotes translocation of glucose transporter 4 in muscle of mice through activation of insulin and AMPK signaling pathways, PLoS One, 11, e0161704 (2016).

D.K. Choudhary, N. Chaturvedi, A. Singh, A. Mishra, Characterization, inhibitory activity and mechanism of polyphenols from faba bean (gallic-acid and catechin) on α-glucosidase: insights from molecular docking and simulation study, Prep. Biochem. Biotechnol., 50, 123-132 (2020).

N. Pujirahayu, D.K. Bhattacharjya, T. Suzuki, T. Katayama, α-Glucosidase inhibitory activity of cycloartane-type triterpenes isolated from Indonesian stingless bee propolis and their structure–activity relationship, Pharmaceuticals (Basel), 12, 102 (2019).

S. Chen, H. Jiang, X. Wu, J. Fang, Therapeutic effects of quercetin on inflammation, obesity, and type 2 diabetes, Mediators Inflamm., 2016, 9340637 (2016).

G.J. Shi, Y. Li, Q.H. Cao, H.X. Wu, X.Y. Tang, X.H. Gao, J. Yu, Z. Chen , Y. Yang, In vitro and in vivo evidence that quercetin protects against diabetes and its complications: A systematic review of the literature, Biomed. Pharmacother., 109, 1085-1099 (2019).

S.B. Nimse, D. Pal, Free radicals, natural antioxidants, and their reaction mechanisms, RSC Adv., 5, 27986-28006 (2015).

E.B. Kurutas, The importance of antioxidants which play the role in cellular response against oxidative/nitrosative stress: current state, Nutr. J., 15, 71 (2016).

B.F. García, A. Torres, F.A. Macías, Synergy and other interactions between polymethoxyflavones from citrus byproducts, Molecules, 20, 20079-20106 (2015).

L. Sanhueza, R. Melo, R. Montero, K. Maisey, L. Mendoza, M. Wilkens, Synergistic interactions between phenolic compounds identified in grape pomace extract with antibiotics of different classes against Staphylococcus aureus and Escherichia coli, PLoS One, 12, e0172273 (2017).

Como Citar

APA

Marques Machado, T., Queiroz Valentim, C., Domingo Rosales Acho, L., Silva Lima, E., Ferreira Koolen, H. H. e Guilhon-Simplicio, F. (2023). Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec. Revista Colombiana de Ciencias Químico-Farmacéuticas, 51(3). https://doi.org/10.15446/rcciquifa.v51n3.96982

ACM

[1]
Marques Machado, T., Queiroz Valentim, C., Domingo Rosales Acho, L., Silva Lima, E., Ferreira Koolen, H.H. e Guilhon-Simplicio, F. 2023. Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec. Revista Colombiana de Ciencias Químico-Farmacéuticas. 51, 3 (mar. 2023). DOI:https://doi.org/10.15446/rcciquifa.v51n3.96982.

ACS

(1)
Marques Machado, T.; Queiroz Valentim, C.; Domingo Rosales Acho, L.; Silva Lima, E.; Ferreira Koolen, H. H.; Guilhon-Simplicio, F. Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec. Rev. Colomb. Cienc. Quím. Farm. 2023, 51.

ABNT

MARQUES MACHADO, T.; QUEIROZ VALENTIM, C.; DOMINGO ROSALES ACHO, L.; SILVA LIMA, E.; FERREIRA KOOLEN, H. H.; GUILHON-SIMPLICIO, F. Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec. Revista Colombiana de Ciencias Químico-Farmacéuticas, [S. l.], v. 51, n. 3, 2023. DOI: 10.15446/rcciquifa.v51n3.96982. Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/96982. Acesso em: 22 jan. 2025.

Chicago

Marques Machado, Tallita, Carolina Queiroz Valentim, Leonard Domingo Rosales Acho, Emerson Silva Lima, Hector Henrique Ferreira Koolen, e Fernanda Guilhon-Simplicio. 2023. “Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec”. Revista Colombiana De Ciencias Químico-Farmacéuticas 51 (3). https://doi.org/10.15446/rcciquifa.v51n3.96982.

Harvard

Marques Machado, T., Queiroz Valentim, C., Domingo Rosales Acho, L., Silva Lima, E., Ferreira Koolen, H. H. e Guilhon-Simplicio, F. (2023) “Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec”., Revista Colombiana de Ciencias Químico-Farmacéuticas, 51(3). doi: 10.15446/rcciquifa.v51n3.96982.

IEEE

[1]
T. Marques Machado, C. Queiroz Valentim, L. Domingo Rosales Acho, E. Silva Lima, H. H. Ferreira Koolen, e F. Guilhon-Simplicio, “Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec”., Rev. Colomb. Cienc. Quím. Farm., vol. 51, nº 3, mar. 2023.

MLA

Marques Machado, T., C. Queiroz Valentim, L. Domingo Rosales Acho, E. Silva Lima, H. H. Ferreira Koolen, e F. Guilhon-Simplicio. “Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec”. Revista Colombiana de Ciencias Químico-Farmacéuticas, vol. 51, nº 3, março de 2023, doi:10.15446/rcciquifa.v51n3.96982.

Turabian

Marques Machado, Tallita, Carolina Queiroz Valentim, Leonard Domingo Rosales Acho, Emerson Silva Lima, Hector Henrique Ferreira Koolen, e Fernanda Guilhon-Simplicio. “Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec”. Revista Colombiana de Ciencias Químico-Farmacéuticas 51, no. 3 (março 23, 2023). Acessado janeiro 22, 2025. https://revistas.unal.edu.co/index.php/rccquifa/article/view/96982.

Vancouver

1.
Marques Machado T, Queiroz Valentim C, Domingo Rosales Acho L, Silva Lima E, Ferreira Koolen HH, Guilhon-Simplicio F. Bioassay-guided isolation of α-glucosidase inhibitors from Byrsonima garcibarrigae Cuatrec. Rev. Colomb. Cienc. Quím. Farm. [Internet]. 23º de março de 2023 [citado 22º de janeiro de 2025];51(3). Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/96982

Baixar Citação

CrossRef Cited-by

CrossRef citations0

Dimensions

PlumX

Acessos à página de resumo

282

Downloads

Não há dados estatísticos.