Natural Compound α-PGG and Its Synthetic Derivative 6Cl-TGQ Alter Insulin Secretion: Evidence for Diminishing Glucose Uptake as a Mechanism

References

• Fu Z , Gilbert ER , Liu D . Regulation of insulin synthesis and secretion and pancreatic beta-cell dysfunction in diabetes. Curr Diabetes Rev . 2013;9(1):25–53. doi:10.2174/157339913804143225 22974359
   PubMedGoogle Scholar
• Rorsman P , Braun M . Regulation of insulin secretion in human pancreatic islets. Annu Rev Physiol . 2013;75(1):155–179. doi:10.1146/annurev-physiol-030212-183754 22974438
   PubMed Web of Science ®Google Scholar
• Saltiel AR , Kahn CR . Insulin signalling and the regulation of glucose and lipid metabolism. Nature . 2001;414(6865):799–806. doi:10.1038/414799a 11742412
   PubMed Web of Science ®Google Scholar
• Saltiel AR . Insulin signaling in the control of glucose and lipid homeostasis. Handb Exp Pharmacol . 2016;233:51–71.26721672
   PubMedGoogle Scholar
• MacDonald PE , Joseph JW , Rorsman P . Glucose-sensing mechanisms in pancreatic beta-cells. Philos Trans R Soc Lond B Biol Sci . 2005;360(1464):2211–2225. doi:10.1098/rstb.2005.1762 16321791
   PubMed Web of Science ®Google Scholar
• Jensen MV , Joseph JW , Ronnebaum SM , Burgess SC , Sherry AD , Newgard CB . Metabolic cycling in control of glucose-stimulated insulin secretion. Am J Physiol Endocrinol Metab . 2008;295(6):E1287–1297. doi:10.1152/ajpendo.90604.2008 18728221
   PubMed Web of Science ®Google Scholar
• Berger C , Zdzieblo D . Glucose transporters in pancreatic islets. Pflugers Arch . 2020;472(9):1249–1272. doi:10.1007/s00424-020-02383-4 32394191
   PubMed Web of Science ®Google Scholar
• Guillam MT , Hümmler E , Schaerer E , et al. Early diabetes and abnormal postnatal pancreatic islet development in mice lacking Glut-2. Nat Genet . 1997;17(3):327–3230. doi:10.1038/ng1197-327 9354799
   PubMed Web of Science ®Google Scholar
• Leary AC , Dowling M , Cussen K , O’Brien J , Stote RM . Pharmacokinetics and pharmacodynamics of intranasal insulin spray (Nasulin) administered to healthy male volunteers: influence of the nasal cycle. J Diabetes Sci Technol . 2008;2(6):1054–1060. doi:10.1177/193229680800200613 19885293
   PubMedGoogle Scholar
• Maltesen MJ , Bjerregaard S , Hovgaard L , Havelund S , van de Weert M . Quality by design - spray drying of insulin intended for inhalation. Eur J Pharm Biopharm . 2008;70(3):828–838. doi:10.1016/j.ejpb.2008.07.015 18755270
   PubMed Web of Science ®Google Scholar
• Arbit E , Kidron M . Oral insulin: the rationale for this approach and current developments. J Diabetes Sci Technol . 2009;3(3):562–567. doi:10.1177/193229680900300322 20144296
   PubMedGoogle Scholar
• Stote R , Marbury T , Shi L , Miller M , Strange P . Comparison pharmacokinetics of two concentrations (0.7% and 1.0%) of Nasulin, an ultra-rapid-acting intranasal insulin formulation. J Diabetes Sci Technol . 2010;4(3):603–609. doi:10.1177/193229681000400314 20513326
   PubMedGoogle Scholar
• He H , Ye J , Sheng J , Huang Y , Guanyi Chen WJ . Overcoming oral insulin delivery barriers: application of cell penetrating peptide and silica-based nanoporous composites. Front Chem Sci Eng . 2013;7(1):9–19. doi:10.1007/s11705-013-1306-9
   Web of Science ®Google Scholar
• Andreani T , de Souza ALR , Kiill CP , et al. Preparation and characterization of PEG-coated silica nanoparticles for oral insulin delivery. Int J Pharm . 2014;473(1–2):627–635. doi:10.1016/j.ijpharm.2014.07.049 25089510
   PubMed Web of Science ®Google Scholar
• Ramesan RM , Sharma CP . Recent advances in the oral delivery of insulin. Recent Pat Drug Deliv Formul . 2014;8(2):155–159. doi:10.2174/1872211308666140527143407 24867419
   PubMedGoogle Scholar
• Razavi Rohani SS , Abnous K , Tafaghodi M . Preparation and characterization of spray-dried powders intended for pulmonary delivery of insulin with regard to the selection of excipients. Int J Pharm . 2014;465(1–2):464–478. doi:10.1016/j.ijpharm.2014.02.030 24560646
   PubMed Web of Science ®Google Scholar
• Zijlstra E , Heinemann L , Plum-Morschel L . Oral insulin reloaded: a structured approach. J Diabetes Sci Technol . 2014;8(3):458–465. doi:10.1177/1932296814529988 24876606
   PubMedGoogle Scholar
• Zhang B , Salituro G , Szalkowski D , et al. Discovery of a small molecule insulin mimetic with antidiabetic activity in mice. Science . 1999;284(5416):974–977. doi:10.1126/science.284.5416.974 10320380
   PubMed Web of Science ®Google Scholar
• Air EL , Strowski MZ , Benoit SC , et al. Small molecule insulin mimetics reduce food intake and body weight and prevent development of obesity. Nat Med . 2002;8(2):179–183. doi:10.1038/nm0202-179 11821903
   PubMed Web of Science ®Google Scholar
• Strowski MZ , Li Z , Szalkowski D , et al. Small-molecule insulin mimetic reduces hyperglycemia and obesity in a nongenetic mouse model of type 2 diabetes. Endocrinology . 2004;145(11):5259–5268. doi:10.1210/en.2004-0610 15297448
   PubMed Web of Science ®Google Scholar
• Srivastava AK , Mehdi MZ . Insulino-mimetic and anti-diabetic effects of vanadium compounds. Diabet Med J Br Diabet Assoc . 2005;22(1):2–13. doi:10.1111/j.1464-5491.2004.01381.x
   PubMed Web of Science ®Google Scholar
• Garcia-Vicente S , Yraola F , Marti L , et al. Oral insulin-mimetic compounds that act independently of insulin. Diabetes . 2007;56(2):486–493. doi:10.2337/db06-0269 17259395
   PubMed Web of Science ®Google Scholar
• Lin B , Li Z , Park K , et al. Identification of novel orally available small molecule insulin mimetics. J Pharmacol Exp Ther . 2007;323(2):579–585. doi:10.1124/jpet.107.126102 17687071
   PubMed Web of Science ®Google Scholar
• He K , Chan C-B , Liu X , et al. Identification of a molecular activator for insulin receptor with potent anti-diabetic effects. J Biol Chem . 2011;286(43):37379–37388. doi:10.1074/jbc.M111.247387 21908618
   PubMed Web of Science ®Google Scholar
• Jung D-W , Ha -H-H , Zheng X , Chang Y-T , Williams DR . Novel use of fluorescent glucose analogues to identify a new class of triazine-based insulin mimetics possessing useful secondary effects. Mol Biosyst . 2011;7(2):346–358. doi:10.1039/C0MB00089B 20927436
   PubMedGoogle Scholar
• Lee J , Jung D-W , Kim W-H , et al. Development of a highly visual, simple, and rapid test for the discovery of novel insulin mimetics in living vertebrates. ACS Chem Biol . 2013;8(8):1803–1814. doi:10.1021/cb4000162 23725454
   PubMed Web of Science ®Google Scholar
• Nankar RP , Doble M . Non-peptidyl insulin mimetics as a potential antidiabetic agent. Drug Discov Today . 2013;18(15–16):748–755. doi:10.1016/j.drudis.2013.04.005 23603635
   PubMed Web of Science ®Google Scholar
• Qiang G , Xue S , Yang JJ , et al. Identification of a small molecular insulin receptor agonist with potent antidiabetes activity. Diabetes . 2014;63(4):1394–1409. doi:10.2337/db13-0334 24651808
   PubMed Web of Science ®Google Scholar
• Alkhalidy H , Moore W , Zhang Y , et al. Small molecule kaempferol promotes insulin sensitivity and preserved pancreatic beta-cell mass in middle-aged obese diabetic mice. J Diabetes Res . 2015;2015:532984. doi:10.1155/2015/532984 26064984
   PubMed Web of Science ®Google Scholar
• Mukherjee S , Chattopadhyay M , Bhattacharya S , et al. Molecule also improves insulin sensitivity in diabetic mice. PLoS One . 2017;12(1):e0169809. doi:10.1371/journal.pone.0169809 28072841
   PubMed Web of Science ®Google Scholar
• Liu F , Kim J , Li Y , Chen X , Li J , Chen X . An extract of lagerstroemia speciosa L. has insulin-like glucose uptake-stimulatory and adipocyte differentiation-inhibitory activities in 3T3-L1 cells. J Nutr . 2001;131(9):2242–2247. doi:10.1093/jn/131.9.2242 11533261
   PubMed Web of Science ®Google Scholar
• Liu X , Kim J-K , Li Y , Li J , Liu F , Chen X . Tannic acid stimulates glucose transport and inhibits adipocyte differentiation in 3T3-L1 cells. J Nutr . 2005;135(2):165–171. doi:10.1093/jn/135.2.165 15671208
   PubMed Web of Science ®Google Scholar
• Li Y , Kim J , Li J , et al. Natural anti-diabetic compound 1,2,3,4,6-penta-O-galloyl-D-glucopyranose binds to insulin receptor and activates insulin-mediated glucose transport signaling pathway. Biochem Biophys Res Commun . 2005;336(2):430–437. doi:10.1016/j.bbrc.2005.08.103 16137651
   PubMed Web of Science ®Google Scholar
• Ren Y , Himmeldirk K , Chen X . Synthesis and structure−activity relationship study of antidiabetic penta-o-galloyl-d-glucopyranose and its analogues. J Med Chem . 2006;49(9):2829–2837. doi:10.1021/jm060087k 16640344
   PubMed Web of Science ®Google Scholar
• Cao Y , Li Y , Kim J , et al. Orally efficacious novel small molecule 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-α-D-glucopyranose selectively and potently stimulates insulin receptor and alleviates diabetes. J Mol Endocrinol . 2013;51(1):15–26. doi:10.1530/JME-12-0171 23549408
   PubMed Web of Science ®Google Scholar
• Hohmeier HE , Mulder H , Chen G , Henkel-Rieger R , Prentki M , Newgard CB . Isolation of INS-1-derived cell lines with robust ATP-sensitive K+ channel-dependent and -independent glucose-stimulated insulin secretion. Diabetes . 2000;49(3):424–430. doi:10.2337/diabetes.49.3.424 10868964
   PubMed Web of Science ®Google Scholar
• Slepchenko KG , Daniels NA , Guo A , Li YV . Autocrine effect of Zn (2)(+) on the glucose-stimulated insulin secretion. Endocrine . 2015;50(1):110–122. doi:10.1007/s12020-015-0568-z 25771886
   PubMed Web of Science ®Google Scholar
• Carter JD , Dula SB , Corbin KL , Wu R , Nunemaker CS . A practical guide to rodent islet isolation and assessment. Biol Proced Online . 2009;11(1):3–31. doi:10.1007/s12575-009-9021-0 19957062
   PubMed Web of Science ®Google Scholar
• Slepchenko KG , Corbin KL , Nunemaker CS . Comparing methods to normalize insulin secretion shows the process may not be needed. J Endocrinol . 2019;241(2):149–159. doi:10.1530/JOE-18-0542
   Web of Science ®Google Scholar
• Whitticar NB , Strahler EW , Rajan P , Kaya S , Nunemaker CS . An automated perifusion system for modifying cell culture conditions over time. Biol Proced Online . 2016;18(1):19. doi:10.1186/s12575-016-0049-7 27895534
   PubMed Web of Science ®Google Scholar
• Wu M , Neilson A , Swift AL , et al. Multiparameter metabolic analysis reveals a close link between attenuated mitochondrial bioenergetic function and enhanced glycolysis dependency in human tumor cells. Am J Physiol Cell Physiol . 2007;292(1):C125–136. doi:10.1152/ajpcell.00247.2006 16971499
   PubMed Web of Science ®Google Scholar
• Gohil VM , Sheth SA , Nilsson R , et al. Nutrient-sensitized screening for drugs that shift energy metabolism from mitochondrial respiration to glycolysis. Nat Biotechnol . 2010;28(3):249–255. doi:10.1038/nbt.1606 20160716
   PubMed Web of Science ®Google Scholar
• Liu Y , Cao Y , Zhang W , et al. A small-molecule inhibitor of glucose transporter 1 downregulates glycolysis, induces cell-cycle arrest, and inhibits cancer cell growth in vitro and in vivo. Mol Cancer Ther . 2012;11(8):1672–1682. doi:10.1158/1535-7163.MCT-12-0131 22689530
   PubMed Web of Science ®Google Scholar
• Qian Y , Wang X , Liu Y , et al. Extracellular ATP is internalized by macropinocytosis and induces intracellular ATP increase and drug resistance in cancer cells. Cancer Lett . 2014;351(2):242–251. doi:10.1016/j.canlet.2014.06.008 24973521
   PubMed Web of Science ®Google Scholar
• Cieniewicz AM , Kirchner T , Hinke SA , et al. Novel monoclonal antibody is an allosteric insulin receptor antagonist that induces insulin resistance. Diabetes . 2017;66(1):206–217. doi:10.2337/db16-0633 27797911
   PubMed Web of Science ®Google Scholar
• Schaffer L , Brand CL , Hansen BF , et al. A novel high-affinity peptide antagonist to the insulin receptor. Biochem Biophys Res Commun . 2008;376(2):380–383. doi:10.1016/j.bbrc.2008.08.151 18782558
   PubMed Web of Science ®Google Scholar
• Ramadan JW , Steiner SR , O’Neill CM , Nunemaker CS . The central role of calcium in the effects of cytokines on beta-cell function: implications for type 1 and type 2 diabetes. Cell Calcium . 2011;50(6):481–490. doi:10.1016/j.ceca.2011.08.005 21944825
   PubMed Web of Science ®Google Scholar
• Straub SG , James RF , Dunne MJ , Sharp GW . Glucose activates both K(ATP) channel-dependent and K(ATP) channel-independent signaling pathways in human islets. Diabetes . 1998;47(5):758–763. doi:10.2337/diabetes.47.5.758 9588447
   PubMed Web of Science ®Google Scholar
• Choi BY . Biochemical basis of anti-cancer-effects of phloretin-a natural dihydrochalcone. Mol Basel . 2019;24:278.
   Google Scholar
• Cao Y , Himmeldirk KB , Qian Y , Ren Y , Malki A , Chen X . Biological and biomedical functions of penta-o-galloyl-d-glucose and its derivatives. J Nat Med . 2014;68(3):465–472. doi:10.1007/s11418-014-0823-2 24532420
   PubMed Web of Science ®Google Scholar
• Leibiger IB , Leibiger B , Berggren P-O . Insulin feedback action on pancreatic beta-cell function. FEBS Lett . 2002;532(1–2):1–6. doi:10.1016/S0014-5793(02)03627-X
   PubMed Web of Science ®Google Scholar
• Khan FA , Goforth PB , Zhang M , Satin LS . Insulin activates ATP-sensitive K(+) channels in pancreatic beta-cells through a phosphatidylinositol 3-kinase-dependent pathway. Diabetes . 2001;50(10):2192–2198. doi:10.2337/diabetes.50.10.2192 11574397
   PubMed Web of Science ®Google Scholar
• Persaud SJ , Asare-Anane H , Jones PM . Insulin receptor activation inhibits insulin secretion from human islets of Langerhans. FEBS Lett . 2002;510(3):225–228. doi:10.1016/S0014-5793(01)03268-9 11801259
   PubMed Web of Science ®Google Scholar
• Nunemaker CS , Zhang M , Satin LS . Insulin feedback alters mitochondrial activity through an ATP-sensitive K+ channel-dependent pathway in mouse islets and beta-cells. Diabetes . 2004;53(7):1765–1772. doi:10.2337/diabetes.53.7.1765 15220200
   PubMed Web of Science ®Google Scholar
• Hee-Park S , Lim B , Baek W-K , Bae J-H , Song D-K . Negative and positive feedback regulation of insulin in glucose-stimulated Ca2+ response in pancreatic beta cells. Diabetes Res Clin Pract . 2007;77(3):S143–149. doi:10.1016/j.diabres.2007.02.023 17467844
   PubMed Web of Science ®Google Scholar
• Ohsugi M , Cras-Meneur C , Zhou Y , et al. Reduced expression of the insulin receptor in mouse insulinoma (MIN6) cells reveals multiple roles of insulin signaling in gene expression, proliferation, insulin content, and secretion. J Biol Chem . 2005;280(6):4992–5003. doi:10.1074/jbc.M411727200 15546857
   PubMed Web of Science ®Google Scholar
• Jimenez-Feltstrom J , Lundquist I , Obermuller S , Salehi A . Insulin feedback actions: complex effects involving isoforms of islet nitric oxide synthase. Regul Pept . 2004;122(2):109–118. doi:10.1016/j.regpep.2004.06.004 15380928
   PubMedGoogle Scholar
• Aspinwall CA , Lakey JR , Kennedy RT . Insulin-stimulated insulin secretion in single pancreatic beta cells. J Biol Chem . 1999;274(10):6360–6365. doi:10.1074/jbc.274.10.6360 10037726
   PubMed Web of Science ®Google Scholar
• Andrali SS , Sampley ML , Vanderford NL , Ozcan S . Glucose regulation of insulin gene expression in pancreatic beta-cells. Biochem J . 2008;415(1):1–10. doi:10.1042/BJ20081029 18778246
   PubMed Web of Science ®Google Scholar
• Pang K , Mukonoweshuro C , Wong GG . Beta cells arise from glucose transporter type 2 (Glut2)-expressing epithelial cells of the developing rat pancreas. Proc Natl Acad Sci U S A . 1994;91(20):9559–9563. doi:10.1073/pnas.91.20.9559 7937805
   PubMed Web of Science ®Google Scholar