Calisteginas, alcalóides polihidroxilados inibidores de glicosidases presentes em Solanum crinitum / Calistegines, polyhydroxylated alkaloids that inhibit glycosidases present in Solanum crinitum

Authors

  • Luís Fernando Lira Souto
  • Antonio Jorge Ribeiro da Silva

DOI:

https://doi.org/10.34117/bjdv6n8-079

Keywords:

calisteginas, análise fitoquímica, inibidores de glicosidases, alcaloides.

Abstract

Calisteginas são um grupo de alcaloides polihidroxilados que apresentam atividade de inibição de glicosidases e têm ampla ocorrência em plantas do gênero Solanum (Solanaceae). Nesse sentido, o presente trabalho tem como objetivo determinar a concentração de calisteginas em frutos de S. crinutum e avaliar a atividade de inibição enzimática  in vitro do extrato hidroalcoólico desses frutos. O IC50 foi calculado por regressão logística de quatro parâmetros. As análises qualitativas foram realizadas por cromatografia em fase gasosa acoplada à espectrometria de massas (GC-EM). Cromatografia em fase gasosa com detector de ionização em chama (GC-FID) foi utilizada na análise quantitativa. O extrato dos frutos de S. crinitum apresentou atividade inibitória da ?-glicosidase de Saccharomyces cerevisiae. A análise dos frutos indicou a presença das calisteginas A3, B1 e B2. Os resultados evidenciam que calisteginas tem contribuição na atividade antidiabética e hipoglicemiante atribuída aos frutos de S. crinitum.

References

AGRA, M. F. A New Species of Solanum subgenus Leptostemonum (Solanaceae) from Chapada da Diamantina, Bahia, Brazil. Novon, p. 292-295, 1999.

ANDRADE, L. E. et al. Brazilian Flora 2020: innovation and collaboration to meet target 1 of the global strategy for plant conservation (GSPC). 2018.

APOSTOLIDIS, E.; LEE, C. M. In vitro potential of Ascophyllum nodosum phenolic antioxidant?mediated ??glucosidase and ??amylase inhibition. Journal of Food Science, v. 75, n. 3, p. H97-H102, 2010.

ARAÚJO, N. D.; COELHO, V. P. M.; AGRA, M. F. Estudo farmacobotânico comparativo de folhas de Solanum crinitum Lam., Solanum gomphodes Dunal e Solanum lycocarpum

A. St.-Hil., Solanaceae. Revista Brasileira de Farmacognosia, v. 20, n. 5, p. 666-674, 2010.

ASANO, N. et al. Calystegin N1, a novel nortropane alkaloid with a bridgehead amino group from Hyoscyamus niger: Structure determination and glycosidase inhibitory activities. Carbohydrate Research, v. 284, n. 2, p. 169-178, 1996.

ASANO, N. et al. N-containing sugars from Morus alba and their glycosidase inhibitory activities. Carbohydrate Research, v.259, n.2, p.243-255, 1994b.

ASANO, N. et al. Polyhydroxylated alkaloids isolated from mulberry trees (Morus alba L.) and silkworms (Bombyx mori L.). Journal of Agricultural and Food Chemistry, v. 49, n. 9, p. 4208-4213, 2001.

ASANO, N. et al. Specific ??galactosidase inhibitors, N?methylcalystegines structure/activity relationships of calystegines from Lycium Chinense. European Journal of Biochemistry, v. 248, n. 2, p. 296-303, 1997a.

ASANO, N. et al. The effects of calystegines isolated from edible fruits and vegetables on mammalian liver glycosidases. Glycobiology, v.7, n.8, p.1085-1088, out. 1997b.

BEKKOUCHE, K. et al. Calystegine distribution in some solanaceous species. Phytochemistry, v. 58, n. 3, p. 455-462, 2001.

BIASTOFF, S.; DRÄGER, B. Calystegines. In: CORDELL, G. A. (Org.). The Alkaloids: Chemistry and Biology. San Diego: Academic Press, 2007, Cap.2, p.49-52.

BOUREBABA, L. et al. Evaluation of antidiabetic effect of total calystegines extracted from Hyoscyamus albus. Biomedicine & Pharmacotherapy, v. 82, p. 337-344, 2016.

CORNELIUS, M. T. F. et al. Other chemical constituents isolated from Solanum crinitum Lam.(Solanaceae). Journal of the Brazilian Chemical Society, v. 21, n. 12, p. 2211 2219, 2010.

CORNELIUS, M. T. F. et al. Solasonina e flavonóides isolados de Solanum crinitum Lam. Rev Bras Farm, v. 85, p. 57-59, 2004.

DE MENDONCA, J. L.; LOPES, J. F. Coleção de germoplasma de espécies silvestres de Solanum da Embrapa. Brasília: Embrapa, 2019.

DOS SANTOS, K. A. Estudo etnobotânico de plantas medicinais utilizadas como hipoglicemiantes por usuários do Programa de Fitoterapia da Universidade Federal do Maranhão, Brasil. Scientia Plena, v. 13, n. 3, 2017.

DRÄGER, B. Identification and quantification of calystegines, polyhydroxyl nortropane alkaloids. Phytochemical Analysis, v. 6, n. 1, p. 31-37, 1995.

DUCROT, P.-H.; LALLEMAND, J. Y. Structure of the Calystegines: New alkaloids of the nortropane family. Tetrahedron Letters, v. 31, n. 27, p. 3879-3882, 1990.

ELYA, B. et al. Antidiabetic activity and phytochemical screening of extracts from Indonesian plants by inhibition of alpha amylase, alpha glucosidase and dipeptidyl peptidase IV. Pakistan Journal of Biological Sciences, v. 18, n. 6, p. 279, 2015.

FRIEDMAN, M.; ROITMAN, J. N.; KOZUKUE, N. Glycoalkaloid and calystegine contents of eight potato cultivars. Journal of Agricultural and Food Chemistry, v. 51, n. 10, p. 2964-2973, 2003.

GRIFFITHS, D. W.; SHEPHERD, T.; STEWART, D. Comparison of the calystegine composition and content of potato sprouts and tubers from Solanum tuberosum group Phureja and Solanum tuberosum group Tuberosum. Journal of Agricultural and Food Chemistry, v. 56, n. 13, p. 5197-5204, jun. 2008.

JOCKOVIC?, N. Biological role of calystegines: isolation from potato sprouts, analysis and dietary perspectives. 2014. 164f. Tese (Doutorado) - Faculty of Sciences I, Martin Luther University Halle-Wittenberg, Halle, 2014.

JOCKOVIC?, N. et al. Inhibition of human intestinal ?-glucosidases by calystegines. Journal of Agricultural and Food Chemistry, v.61, n.23, p.5550-5557, maio 2013.

KAUNDA, J. S.; ZHANG, Y.-J. The Genus Solanum: An Ethnopharmacological, Phytochemical and Biological Properties Review. Natural Products and Bioprospecting, v. 9, n. 2, p. 77-137, 2019.

LIMA, R. A.; dos SANTOS, M. R. A.; SMOZINSKI, C. V. (Orgs.). Flora de Rondônia, Brasil: Solanum L. (Solanaceae). Porto Velho-RO: EDUFRO, 2014.102 p.

MLA. Quest Graph™ IC50 Calculator. AAT Bioquest, Inc. 2020. Disponível em: https://www.aatbio.com/tools/ic50-calculator. Acesso em: 15 maio 2020.

MULDER, P. P. J. et al. Occurrence of tropane alkaloids in food. EFSA Supporting Publications, v.13, n.12, p.1140E, dez. 2016.

NASH, R. J. et al. Calystegines in Solanum and Datura species and the death's-head hawk-moth (Acherontia atropus). Phytochemistry, v. 34, n. 5, p. 1281-1283, 1993.

PIZZUTTI, I. R. et al. A multi-residue method for pesticides analysis in green coffee beans using gas chromatography–negative chemical ionization mass spectrometry in selective ion monitoring mode. Journal of Chromatography A, v. 1251, p. 16-26, 2012.

RIBANI, M. et al. Validação em métodos cromatográficos e eletroforéticos. Química nova, v. 27, n. 5, p. 771-780, 2004.

RICHTER, U.; SONNEWALD, U.; DRÄGER, B. Calystegines in potatoes with genetically engineered carbohydrate metabolism. Journal of Experimental Botany, v.58, n.7, p.1603-1615, 2007.

RIVERA-CHÁVEZ, J. et al. Thielavins A, J and K: ?-Glucosidase inhibitors from MEXU 27095, an endophytic fungus from Hintonia latiflora. Phytochemistry, v. 94, p. 198-205, 2013.

ROSAK, C.; MERTES, G. Critical evaluation of the role of acarbose in the treatment of diabetes: patient considerations. Diabetes, metabolic syndrome and obesity: targets and therapy, v. 5, p. 357, 2012.

SANTOS, M. M.; NUNES, M. G. S.; MARTINS, R. D. Uso empírico de plantas medicinais para tratamento de diabetes. Revista Brasileira de Plantas Medicinais, v. 14, n. 2, p. 327-334, 2012.

SCHIMMING, T. et al. Calystegines as chemotaxonomic markers in the Convolvulaceae. Phytochemistry, v. 66, n. 4, p. 469-480, 2005.

SOUTO, L. F. L.; SILVA, A. J. R. Calisteginas, alcalóides polihidroxilados presentes em hortaliças: frutos e tuberosas. Química Nova, v. 43, n. 1, p. 37-43, 2020.

VARROT, A. et al. Direct observation of the protonation state of an imino sugar glycosidase inhibitor upon binding. Journal of the American Chemical Society, v. 125, n. 25, p. 7496-7497, 2003.

VOLPE, D. A.; HAMED, S. S.; ZHANG, L. K. Use of different parameters and equations for calculation of IC 50 values in efflux assays: potential sources of variability in IC50 determination. The AAPS journal, v. 16, n. 1, p. 172-180, 2014.

WATSON, A. A. et al. Calystegine alkaloids in the potato and other food plants. In: Tu, A.T.; Gaffield, W. (Org.). Natural and Selected Synthetic Toxins, Washington: American Chemical Society, 2007, p. 129-139.

ZHANG, B.-W. et al. Dietary flavonoids and acarbose synergistically inhibit ?-glucosidase and lower postprandial blood glucose. Journal of Agricultural and Food Chemistry, v. 65, n. 38, p. 8319-8330, 2017.

Published

2020-08-10

How to Cite

Lira Souto, L. F., & da Silva, A. J. R. (2020). Calisteginas, alcalóides polihidroxilados inibidores de glicosidases presentes em Solanum crinitum / Calistegines, polyhydroxylated alkaloids that inhibit glycosidases present in Solanum crinitum. Brazilian Journal of Development, 6(8), 55202–55215. https://doi.org/10.34117/bjdv6n8-079

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Original Papers