Bioactivity-guided isolation and purification of α-glucosidase inhibitor, 6-O-D-glycosides, from Tinta Cão grape pomace

Journal of Functional Foods

Volumn 23, Issue , 2016, Pages 573-579

  Sun, Shi ^a   Kadouh, Hoda Chaouki ^a   Zhu, Wenjun ^a   Zhou, Kequan ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

6 O p trans coumaroyl D glucopyranoside; Anti hyperglycaemic agents; Diabetes; Red wine grapes; Glucosidase

Indexed keywords

EID: 84962211295     PISSN: 17564646     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jff.2016.03.009     Document Type: Article

References (37)

1. Amarasinghe N.R., Jayasinghe L., Hara N., Fujimoto Y. Flacourside, a new 4-oxo-2-cyclopentenylmethyl glucoside from the fruit juice of Flacourtia indica. Food Chemistry 2007, 102(1):95-97.
2. Azmir J., Zaidul I.S.M., Rahman M.M., Sharif K.M., Mohamed A., Sahena F., Jahurul M.H.A., Ghafoor K., Norulaini N.A.N., Omar A.K.M. Techniques for extraction of bioactive compounds from plant materials: A review. Journal of Food Engineering 2013, 117(4):426-436.
3. Bell D.S. Importance of postprandial glucose control. Southern Medical Journal 2001, 94(8):804-809.
4. Casirola D.M., Ferraris R.P. α-Glucosidase inhibitors prevent diet-induced increases in intestinal sugar transport in diabetic mice. Metabolism: Clinical and Experimental 2006, 55(6):832-841.
5. Charbonnel B., Penfornis A., Varroud-Vial M., Kusnik-Joinville O., Detournay B. Insulin therapy for diabetes mellitus: Treatment regimens and associated costs. Diabetes & Metabolism 2012, 38(2):156-163.
6. Chiasson J.L., Josse R.G., Gomis R., Hanefeld M., Karasik A., Laakso M. Acarbose for prevention of type 2 diabetes mellitus: The STOP-NIDDM randomised trial. Lancet 2002, 359(9323):2072-2077.
7. Chung M.J., Lee Y.-S., Kim B.-C., Lee S.-B., Moon T.-H., Lee S.-J., Park K.-H. The hypoglycemic effects of acarviosine-glucose modulate hepatic and intestinal glucose transporters in vivo. Food Science and Biotechnology 2006, 15(6):851-855.
8. de Camargo A.C., Regitano-d'Arce M.A., Biasoto A.C., Shahidi F. Low molecular weight phenolics of grape juice and winemaking byproducts: Antioxidant activities and inhibition of oxidation of human low-density lipoprotein cholesterol and DNA strand breakage. Journal of Agricultural and Food Chemistry 2014, 62(50):12159-12171.
9. D'Abrosca B., Fiorentino A., Ricci A., Scognamiglio M., Pacifico S., Piccolella S., Monaco P. Structural characterization and radical scavenging activity of monomeric and dimeric cinnamoyl glucose esters from Petrorhagia velutina leaves. Phytochemistry Letters 2010, 3(1):38-44.
10. Deacon C.F. Dipeptidyl peptidase-4 inhibitors in the treatment of type 2 diabetes: A comparative review. Diabetes, Obesity and Metabolism 2011, 13(1):7-18.
11. Dehghan-Kooshkghazi M., Mathers J.C. Starch digestion, large-bowel fermentation and intestinal mucosal cell proliferation in rats treated with the alpha-glucosidase inhibitor acarbose. The British Journal of Nutrition 2004, 91(3):357-365.
12. Dormandy J.A., Charbonnel B., Eckland D.J., Erdmann E., Massi-Benedetti M., Moules I.K., Skene A.M., Tan M.H., Lefèbvre P.J., Murray G.D., Standl E., Wilcox R.G., Wilhelmsen L., Betteridge J., Birkeland K., Golay A., Heine R.J., Korányi L., Laakso M., Mokán M., Norkus A., Pirags V., Podar T., Scheen A., Scherbaum W., Schernthaner G., Schmitz O., Skrha J., Smith U., Taton J. Secondary prevention of macrovascular events in patients with type 2 diabetes in the PROactive Study (PROspective pioglitAzone Clinical Trial In macroVascular Events): A randomised controlled trial. Lancet 2005, 366(9493):1279-1289. PROactive Investigators.
13. Helm R.F., Ralph J., Hatfield R.D. Synthesis of feruloylated and p-coumaroylated methyl glycosides. Carbohydrate Research 1992, 229(1):183-194.
14. Hogan S., Canning C., Sun S., Sun X., Kadouh H., Zhou K. Dietary supplementation of grape skin extract improves glycemia and inflammation in diet-induced obese mice fed a Western high fat diet. Journal of Agricultural and Food Chemistry 2011, 59(7):3035-3041.
15. Hogan S., Zhang L., Li J., Sun S., Canning C., Zhou K. Antioxidant rich grape pomace extract suppresses postprandial hyperglycemia in diabetic mice by specifically inhibiting alpha-glucosidase. Nutrition and Metabolism 2010, 7:71.
16. Huang S.-X., Liao X., Nie Q.-J., Ding L.-S., Peng S.-L. Phenyl and phenylethyl glycosides from Picrorhiza scrophulariiflora. Helvetica Chimica Acta 2004, 87(3):598-604.
17. Inzucchi S.E., Bergenstal R.M., Buse J.B., Diamant M., Ferrannini E., Nauck M., Peters A.L., Tsapas A., Wender R., Matthews D.R. Management of hyperglycemia in type 2 diabetes: A patient-centered approach: position statement of the American Diabetes Association (ADA) and the European Association for the Study of Diabetes (EASD). Diabetes Care 2012, 35(6):1364-1379. American Diabetes Association (ADA), European Association for the Study of Diabetes (EASD)European Association for the Study of Diabetes (EASD).
18. Jenkins D.J., Kendall C.W., Augustin L.S., Franceschi S., Hamidi M., Marchie A., Jenkins A.L., Axelsen M. Glycemic index: Overview of implications in health and disease. The American Journal of Clinical Nutrition 2002, 76(1):266S-273S.
19. Jovanovic L. Rationale for prevention and treatment of postprandial glucose-mediated toxicity. The Endocrinologist 1999, 9(2):87-92.
20. Kahn S.E., Haffner S.M., Heise M.A., Herman W.H., Holman R.R., Jones N.P., Kravitz B.G., Lachin J.M., O'Neill M.C., Zinman B., Viberti G. Glycemic durability of rosiglitazone, metformin, or glyburide monotherapy. New England Journal of Medicine 2006, 355(23):2427-2443. ADOPT Study Group.
21. Kawamori R., Tajima N., Iwamoto Y., Kashiwagi A., Shimamoto K., Kaku K. Voglibose for prevention of type 2 diabetes mellitus: A randomised, double-blind trial in Japanese individuals with impaired glucose tolerance. Lancet 2009, 373(9675):1607-1614.
22. Kim M.-J., Lee S.-B., Lee H.-S., Lee S.-Y., Baek J.-S., Kim D., Moon T.W., Robyt J.F., Park K.-H. Comparative study of the inhibition of α-glucosidase, α-amylase, and cyclomaltodextrin glucanosyltransferase by acarbose, isoacarbose, and acarviosine-glucose. Archives of Biochemistry and Biophysics 1999, 371(2):277-283.
23. Majumdar S.K., Inzucchi S.E. Investigational anti-hyperglycemic agents: The future of type 2 diabetes therapy?. Endocrine 2013, 44(1):47-58.
24. Mata R., Cristians S., Escandon-Rivera S., Juarez-Reyes K., Rivero-Cruz I. Mexican antidiabetic herbs: Valuable sources of inhibitors of alpha-glucosidases. Journal of Natural Products 2013, 76(3):468-483.
25. McAdam Marx C. Economic implications of type 2 diabetes management. The American Journal of Managed Care 2013, 19(Suppl. 8):s143-s148.
26. Molitch M.E. Current state of type 2 diabetes management. The American Journal of Managed Care 2013, 19(Suppl. 8):s136-s142.
27. Obiro W.C., Zhang T., Jiang B. The nutraceutical role of the Phaseolus vulgaris alpha-amylase inhibitor. The British Journal of Nutrition 2008, 100(1):1-12.
28. Pieters L., Vlietinck A.J. Bioguided isolation of pharmacologically active plant components, still a valuable strategy for the finding of new lead compounds?. Journal of Ethnopharmacology 2005, 100(1-2):57-60.
29. Rengasamy K.R.R., Aderogba M.A., Amoo S.O., Stirk W.A., Van Staden J. Potential antiradical and alpha-glucosidase inhibitors from Ecklonia maxima (Osbeck) Papenfuss. Food Chemistry 2013, 141(2):1412-1415.
30. Sales P.M., Souza P.M., Simeoni L.A., Silveira D. α-Amylase inhibitors: A review of raw material and isolated compounds from plant source. Journal of Pharmacy and Pharmaceutical Sciences: A Publication of the Canadian Society for Pharmaceutical Sciences, Societe Canadienne Des Sciences Pharmaceutiques 2012, 15(1):141-183.
31. Sasidharan S., Chen Y., Saravanan D., Sundram K.M., Yoga Latha L. Extraction, isolation and characterization of bioactive compounds from plants' extracts. African journal of traditional, complementary, and alternative medicines: AJTCAM 2011, 8(1):1-10.
32. Shimomura H., Sashida Y., Adachi T. Phenylpropanoid glucose esters from Prunus buergeriana. Phytochemistry 1988, 27(2):641-644.
33. van de Laar F.A., Lucassen P.L., Akkermans R.P., van de Lisdonk E.H., Rutten G.E., van Weel C. Alpha-glucosidase inhibitors for patients with type 2 diabetes: Results from a Cochrane systematic review and meta-analysis. Diabetes Care 2005, 28(1):154-163.
34. Wang L., Cui Q., Hou Y., Bai F., Sun J., Cao X., Liu P., Jiang M., Bai G. An integrated strategy of ultra-high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry and virtual screening for the identification of α-glucosidase inhibitors in acarviostatin-containing complex. Journal of Chromatography. A 2013, 1319:88-96.
35. Yamagishi S., Nakamura K., Takeuchi M. Inhibition of postprandial hyperglycemia by acarbose is a promising therapeutic strategy for the treatment of patients with the metabolic syndrome. Medical Hypotheses 2005, 65(1):152-154. 10.1016/j.mehy.2004.12.008.
36. Zhang L., Hogan S., Li J.R., Sun S., Canning C., Zheng S.J., Zhou K.Q. Grape skin extract inhibits mammalian intestinal alpha-glucosidase activity and suppresses postprandial glycemic response in streptozocin-treated mice. Food Chemistry 2011, 126(2):466-471.
37. Zhou K., Hogan S., Canning C., Sun S. Inhibition of intestinal α-glucosidases and anti-postprandial hyperglycemic effect of grape seed extract. ACS Symposium Series 2012, 1093:431-441. Emerging Trends in Dietary Components for Preventing and Combating Disease.