Inhibition of α-glucosidase and α-amylase by flavonoid glycosides from Lu'an GuaPian tea: molecular docking and interaction mechanism.

Green tea may favorably modulate blood glucose homeostasis, and regular consumption of green tea can prevent the development of type 2 diabetes mellitus. In this study, α-glucosidase and α-amylase inhibitory effects of the novel acylated flavonol tetraglycoside (camellikaempferoside C, 1) and 14 other flavone and flavone glycosides (FGs) isolated from Lu'an GuaPian (Camellia sinensis L.O. Kuntze) were evaluated. The kaempferol monoglycoside (15) showed inhibitory activity against α-glucosidase with IC50 at 40.02 ± 4.61 μM, and kaempferol diglycoside (13) showed α-amylase inhibition with IC50 at 0.09 ± 0.02 μM. Further, inhibitory mechanisms of FGs 15 and 13 were studied by molecular docking analysis and fluorescence spectrometry. Molecular docking suggested that FG 15 interacted with α-glucosidase mainly by hydrogen bonding, which was the same interaction force between FG 13 and α-amylase. Intrinsic fluorescence of α-glucosidase and α-amylase was quenched by 15 and 13, respectively, through a static quenching mechanism. The spontaneous formation of 15-α-glucosidase and 13-α-amylase complexes was driven by van der Waals forces and hydrogen bonding. The present study provides new insight into the potential application of Lu'an GuaPian green tea as a functional food ingredient to regulate postprandial hyperglycemia through inhibition of α-glucosidase/α-amylase by FGs, particularly the mono- and di- glycosides of kaempferol.

[1]  Wei Zhang,et al.  Interaction between Ester-Type Tea Catechins and Neutrophil Gelatinase-Associated Lipocalin: Inhibitory Mechanism. , 2018, Journal of agricultural and food chemistry.

[2]  Z. Xiu,et al.  Pentacyclic triterpenes as α-glucosidase and α-amylase inhibitors: Structure-activity relationships and the synergism with acarbose. , 2017, Bioorganic & medicinal chemistry letters.

[3]  D. Ni,et al.  Effect of steeping temperature on antioxidant and inhibitory activities of green tea extracts against α-amylase, α-glucosidase and intestinal glucose uptake. , 2017, Food chemistry.

[4]  G. Williamson,et al.  Inhibition of Human and Rat Sucrase and Maltase Activities To Assess Antiglycemic Potential: Optimization of the Assay Using Acarbose and Polyphenols. , 2017, Journal of agricultural and food chemistry.

[5]  Mingzhu Zheng,et al.  Anti-obesity effects of zeaxanthin on 3T3-L1 preadipocyte and high fat induced obese mice. , 2017, Food & function.

[6]  N. P. Ulrih,et al.  An Overview of Herbal Products and Secondary Metabolites Used for Management of Type Two Diabetes , 2017, Front. Pharmacol..

[7]  T. Higgins,et al.  Heterologous expression of an α-amylase inhibitor from common bean (Phaseolus vulgaris) in Kluyveromyces lactis and Saccharomyces cerevisiae , 2017, Microbial Cell Factories.

[8]  M. Serafini,et al.  Antioxidants from black and green tea: from dietary modulation of oxidative stress to pharmacological mechanisms , 2017, British journal of pharmacology.

[9]  A. Gray,et al.  In vitro anti-diabetic activity of flavonoids and pheophytins from Allophylus cominia Sw . on PTP1B, DPPIV, alpha-glucosidase and alpha-amylase enzymes. , 2017, Journal of ethnopharmacology.

[10]  Weiqi Wang,et al.  Novel Acylated Flavonol Tetraglycoside with Inhibitory Effect on Lipid Accumulation in 3T3-L1 Cells from Lu'an GuaPian Tea and Quantification of Flavonoid Glycosides in Six Major Processing Types of Tea. , 2017, Journal of agricultural and food chemistry.

[11]  Ding Li,et al.  Inhibitory effect of phloretin on α-glucosidase: Kinetics, interaction mechanism and molecular docking. , 2017, International journal of biological macromolecules.

[12]  Guangcheng Wang,et al.  Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors. , 2017, European journal of medicinal chemistry.

[13]  Yonghong Meng,et al.  Evaluation of Total Flavonoids, Myricetin, and Quercetin from Hovenia dulcis Thunb. As Inhibitors of α-Amylase and α-Glucosidase , 2016, Plant Foods for Human Nutrition.

[14]  Zhi Yu,et al.  In vitro α-glucosidase inhibitory activity of isolated fractions from water extract of Qingzhuan dark tea , 2016, BMC Complementary and Alternative Medicine.

[15]  D. Gong,et al.  Inhibitory mechanism of morin on α-glucosidase and its anti-glycation properties. , 2016, Food & function.

[16]  Chongde Sun,et al.  Purification of Flavonoids from Chinese Bayberry (Morella rubra Sieb. et Zucc.) Fruit Extracts and α-Glucosidase Inhibitory Activities of Different Fractionations , 2016, Molecules.

[17]  Jingming Ning,et al.  Safety and anti-hyperglycemic efficacy of various tea types in mice , 2016, Scientific Reports.

[18]  L. Milella,et al.  α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium. , 2016, Journal of natural products.

[19]  H. Wahab,et al.  Synthesis, In vitro and Docking Studies of New Flavone Ethers as α‐Glucosidase Inhibitors , 2016, Chemical biology & drug design.

[20]  Syed Muhammad Kashif,et al.  Synthesis of novel flavone hydrazones: in-vitro evaluation of α-glucosidase inhibition, QSAR analysis and docking studies. , 2015, European journal of medicinal chemistry.

[21]  Jie‐Hua Shi,et al.  Binding interaction of sorafenib with bovine serum albumin: Spectroscopic methodologies and molecular docking. , 2015, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[22]  H. Mo,et al.  Comparative evaluation of tannic acid inhibiting α-glucosidase and trypsin. , 2015, Food research international.

[23]  Young-In Kwon,et al.  Selected Tea and Tea Pomace Extracts Inhibit Intestinal α-Glucosidase Activity in Vitro and Postprandial Hyperglycemia in Vivo , 2015, International journal of molecular sciences.

[24]  Rongjin Sun,et al.  Disposition of flavonoids impacts their efficacy and safety. , 2015, Current drug metabolism.

[25]  Jianbo Xiao,et al.  Advance in Dietary Polyphenols as Aldose Reductases Inhibitors: Structure-Activity Relationship Aspect , 2015, Critical reviews in food science and nutrition.

[26]  F. Facchinetti,et al.  Dietary Interventions, Lifestyle Changes, and Dietary Supplements in Preventing Gestational Diabetes Mellitus: A Literature Review , 2014, Obstetrical & gynecological survey.

[27]  Ye-Gao Chen,et al.  Isolation of α-glucosidase inhibitors including a new flavonol glycoside from Dendrobium devonianum , 2014, Natural product research.

[28]  G. McDougall,et al.  Phenolic-rich extracts from the edible seaweed, ascophyllum nodosum, inhibit α-amylase and α-glucosidase: Potential anti-hyperglycemic effects , 2014 .

[29]  P. Labute,et al.  Assessment of fully automated antibody homology modeling protocols in molecular operating environment , 2014, Proteins.

[30]  Guowen Zhang,et al.  α-Glucosidase inhibition by luteolin: kinetics, interaction and molecular docking. , 2014, International journal of biological macromolecules.

[31]  Qing-Wen Zhang,et al.  α-Glucosidase Inhibitory Effect and Simultaneous Quantification of Three Major Flavonoid Glycosides in Microctis folium , 2013, Molecules.

[32]  Jianbo Xiao,et al.  A Review on Structure–Activity Relationship of Dietary Polyphenols Inhibiting α-Amylase , 2013, Critical reviews in food science and nutrition.

[33]  G. Derosa,et al.  α-Glucosidase inhibitors and their use in clinical practice , 2012, Archives of medical science : AMS.

[34]  B. Frei,et al.  Grape seed and tea extracts and catechin 3-gallates are potent inhibitors of α-amylase and α-glucosidase activity. , 2012, Journal of agricultural and food chemistry.

[35]  Guowen Zhang,et al.  Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques. , 2012, Journal of agricultural and food chemistry.

[36]  Jianbo Xiao,et al.  Interaction of natural polyphenols with α-amylase in vitro: molecular property-affinity relationship aspect. , 2011, Molecular bioSystems.

[37]  Zhiwei Yang,et al.  Sugar compositions, α-glucosidase inhibitory and amylase inhibitory activities of polysaccharides from leaves and flowers of Camellia sinensis obtained by different extraction methods. , 2010, International journal of biological macromolecules.

[38]  K. Poutanen,et al.  Impact of Dietary Polyphenols on Carbohydrate Metabolism , 2010, International journal of molecular sciences.

[39]  F. Gao,et al.  Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase. , 2009, Journal of agricultural and food chemistry.

[40]  R. Strong,et al.  The siderocalin/enterobactin interaction: a link between mammalian immunity and bacterial iron transport. , 2008, Journal of the American Chemical Society.

[41]  H. Iso,et al.  Randomized controlled trial for an effect of green tea-extract powder supplementation on glucose abnormalities , 2008, European Journal of Clinical Nutrition.

[42]  D. Panagiotakos,et al.  Effects of black and green tea consumption on blood glucose levels in non-obese elderly men and women from Mediterranean Islands (MEDIS epidemiological study) , 2008, European journal of nutrition.

[43]  Hai-zhuan Lin,et al.  Nitroaniline Isomers Interaction with Bovine Serum Albumin and Toxicological Implications , 2007, Journal of Fluorescence.

[44]  S. Louro,et al.  Chlorpromazine interactions to sera albumins. A study by the quenching of fluorescence. , 2004, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[45]  Jong-Sang Kim,et al.  Inhibition of Alpha-glucosidase and Amylase by Luteolin, a Flavonoid , 2000, Bioscience, biotechnology, and biochemistry.

[46]  Wenhang Wang,et al.  Transglutaminase-induced crosslinking of gelatin-calcium carbonate composite films. , 2015, Food chemistry.

[47]  G. Williamson.  Possible effects of dietary polyphenols on sugar absorption and digestion. , 2013, Molecular nutrition & food research.