Comparison of inhibitory activities and mechanisms of five mulberry plant bioactive components against α-glucosidase

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 34, 2013, Pages 8110-8119

  He, Hao ^a   Lu, Yan Hua ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

glucosidase; 1 deoxynojirimycin; cyanidin 3 glucoside; cyanidin 3 rutinoside; interaction; oxyresveratrol; resveratrol

Indexed keywords

1-DEOXYNOJIRIMYCIN; CYANIDIN-3-GLUCOSIDE; CYANIDIN-3-RUTINOSIDE; GLUCOSIDASE; INTERACTION; OXYRESVERATROL;

HYDROGEN BONDS; HYDROPHOBICITY; LIGANDS; PLANTS (BOTANY); QUENCHING; RESVERATROL; SPECTROSCOPIC ANALYSIS;

CARBOHYDRATES;

ALPHA GLUCOSIDASE; ENZYME INHIBITOR; PLANT EXTRACT; SACCHAROMYCES CEREVISIAE PROTEIN;

ARTICLE; CHEMISTRY; CLASSIFICATION; COMPARATIVE STUDY; DRUG ANTAGONISM; ENZYMOLOGY; KINETICS; MORUS; SACCHAROMYCES CEREVISIAE;

ALPHA-GLUCOSIDASES; ENZYME INHIBITORS; KINETICS; MORUS; PLANT EXTRACTS; SACCHAROMYCES CEREVISIAE; SACCHAROMYCES CEREVISIAE PROTEINS;

EID: 84883384913     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4019323     Document Type: Article

References (44)

1. Bastyr, E. J.; Stuart, C. A.; Brodows, R. G.; Schwartz, S.; Graf, C. J.; Zagar, A.; Kenneth, R. Therapy Focused on Lowering Postprandial Glucose, Not Fasting Glucose, May Be Superior for Lowering Diabetes Care 2000, 23, 1236-1241
2. American Diabetes Assocition Postprandial Blood Glucose. Diabetes Care 2001, 24, 775-778.
3. Trial, T. S.; Josse, R. G.; Gomis, R. Acarbose Treatment and the Risk of Cardiovascular Disease and Hypertension J. Am. Med. Assoc. 2003, 290, 486-494
4. 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, 1607-1614
5. Hsiao, S.-H.; Liao, L.-H.; Cheng, P.-N.; Wu, T.-J. Hepatotoxicity associated with acarbose therapy Ann. Pharmacother. 2006, 40, 151-154
6. Tao, W.; Deqin, Z.; Yuhong, L.; Hong, L.; Zhanbiao, L.; Chunfeng, Z.; Limin, H.; Xiumei, G. Regulation effects on abnormal glucose and lipid metabolism of TZQ-F, a new kind of Traditional Chinese Medicine J. Ethnopharmacol. 2010, 128, 575-582
7. Kim, G.-N.; Kwon, Y.-I.; Jang, H.-D. Mulberry leaf extract reduces postprandial hyperglycemia with few side effects by inhibiting α-glucosidase in normal rats J. Med. Food 2011, 14, 712-717
8. Park, J. M.; Bong, H. Y.; Jeong, H. I.; Kim, Y. K.; Kim, J. Y.; Kwon, O. Postprandial hypoglycemic effect of mulberry leaf in Goto-Kakizaki rats and counterpart control Wistar rats Nutr. Res. Pract. 2009, 3, 272-278
9. Nakagawa, K.; Kubota, H.; Kimura, T.; Yamashita, S.; Tsuzuki, T.; Oikawa, S.; Miyazawa, T. Occurrence of orally administered mulberry 1-deoxynojirimycin in rat plasma J. Agric. Food Chem. 2007, 55, 8928-8933
10. Kimura, T.; Nakagawa, K.; Kubota, H.; Kojima, Y.; Goto, Y.; Yamagishi, K.; Oita, S.; Oikawa, S.; Miyazawa, T. Food-grade mulberry powder enriched with 1-deoxynojirimycin suppresses the elevation of postprandial blood glucose in humans J. Agric. Food Chem. 2007, 55, 5869-5874
11. Nuengchamnong, N.; Ingkaninan, K.; Kaewruang, W.; Wongareonwanakij, S.; Hongthongdaeng, B. Quantitative determination of 1-deoxynojirimycin in mulberry leaves using liquid chromatography-tandem mass spectrometry J. Pharm. Biomed. Anal. 2007, 44, 853-858
12. Yasuda, K.; Kizu, H.; Yamashita, T.; Kameda, Y.; Kato, A.; Nash, R. J.; Fleet, G. W. J.; Molyneux, R. J.; Asano, N. New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii J. Nat. Prod. 2002, 65, 198-202
13. Kuriyama, C.; Kamiyama, O.; Ikeda, K.; Sanae, F.; Kato, A.; Adachi, I.; Imahori, T.; Takahata, H.; Okamoto, T.; Asano, N. In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures Bioorg. Med. Chem. 2008, 16, 7330-7336
14. Palsamy, P.; Subramanian, S. Chemico-Biological Interactions Modulatory effects of resveratrol on attenuating the key enzymes activities of carbohydrate metabolism in streptozotocin -nicotinamide-induced diabetic rats Chem.-Biol. Interact. 2009, 179, 356-362
15. Kerem, Z.; Bilkis, I.; Flaishman, M.; Sivan, L. Antioxidant Activity and Inhibition of α-Glucosidase by trans-Resveratrol, Piceid, and a Novel trans-Stilbene from the Roots of Israeli Rumex bucephalophorus L J. Agric. Food Chem. 2006, 54, 1243-1247
16. Song, W.; Wang, H.-J.; Bucheli, P.; Zhang, P.-F.; Wei, D.-Z.; Lu, Y.-H. Phytochemical profiles of different mulberry (Morus sp.) species from China J. Agric. Food Chem. 2009, 57, 9133-9140
17. Akkarachiyasit, S.; Charoenlertkul, P.; Yibchok-Anun, S.; Adisakwattana, S. Inhibitory Activities of Cyanidin and Its Glycosides and Synergistic Effect with Acarbose against Intestinal α-Glucosidase and Pancreatic α-Amylase Int. J. Mol. Sci. 2010, 11, 3387-3396
18. Sirichai, A.; Sirintorn, Y.-A.; Piyawan, C.; Natthakan, W. Cyanidin-3-rutinoside alleviates postprandial hyperglycemia and its synergism with acarbose by inhibition of intestinal α-glucosidase J. Clin. Biochem. Nutr. 2011, 49, 36-41
19. Chen, W.-P.; Chi, T.-C.; Chuang, L.-M.; Su, M.-J. Resveratrol enhances insulin secretion by blocking K(ATP) and K(V) channels of beta cells Eur. J. Pharmacol. 2007, 568, 269-277
20. Bharatham, K.; Bharatham, N.; Park, K. H.; Lee, K. W. Binding mode analyses and pharmacophore model development for sulfonamide chalcone derivatives, a new class of α-glucosidase inhibitors J. Mol. Graphics Modell. 2008, 26, 1202-1212
21. Yao, X.; Mauldin, R.; Byers, L. Multiple sugar binding sites in α-glucosidase Biochim. Biophys. Acta 2003, 1645, 22-29
22. Liu, M.; Zhang, W.; Qiu, L.; Lin, X. Synthesis of butyl-isobutyl- phthalate and its interaction with α-glucosidase in vitro J. Biochem. 2011, 149, 27-33
23. Liu, M.; Zhang, W.; Wei, J.; Lin, X. Synthesis and α-glucosidase inhibitory mechanisms of bis(2,3-dibromo-4,5-dihydroxybenzyl) ether, a potential marine bromophenol α-glucosidase inhibitor Mar. Drugs. 2011, 9, 1554-1565
24. You, Q.; Chen, F.; Wang, X.; Luo, P. G.; Jiang, Y. Inhibitory effects of muscadine anthocyanins on α-glucosidase and pancreatic lipase activities J. Agric. Food Chem. 2011, 59, 9506-9511
25. Li, Y. Q.; Zhou, F. C.; Gao, F.; Bian, J. S.; Shan, F.; Zhao, C. Study on the interaction between 3 flavonoid compounds and α-amylase by fluorescence spectroscopy J. Food Sci. 2009, 74, C199-C203
26. Eftink, Maurice R.; Camillo, A. Ghiron Fluorescence Quenching Studies with Proteins Anal. Biochem. 1981, 114, 199-227
27. Unneberg, P.; Merelo, J. J.; Chacón, P.; Morán, F. SOMCD: method for evaluating protein secondary structure from UV circular dichroism spectra Proteins: Struct., Funct., Genet. 2001, 42, 460-470
28. Li, Y. Q.; Zhou, F. C.; Gao, F.; Bian, J. S.; Shan, F. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase J. Agric. Food Chem. 2009, 57, 11463-11468
29. Hawe, A.; Sutter, M.; Jiskoot, W. Extrinsic fluorescent dyes as tools for protein characterization Pharm. Res. 2008, 25, 1487-1499
30. Park, J. H.; Ko, S.; Park, Hw. Toward the Virtual Screening of α-Glucosidase Inhibitors with the Homology-Modeled Protein Structure Bull. Korean Chem. Soc. 2008, 29, 921-927
31. Park, H.; Hwang, K. Y.; Oh, K. H.; Kim, Y. H.; Lee, J. Y.; Kim, K. Discovery of novel α-glucosidase inhibitors based on the virtual screening with the homology-modeled protein structure Bioorg. Med. Chem. 2008, 16, 284-292
32. Yoshimizu, M.; Tajima, Y.; Matsuzawa, F.; Aikawa, S.-I.; Iwamoto, K.; Kobayashi, T.; Edmunds, T.; Fujishima, K.; Tsuji, D.; Itoh, K.; Ikekita, M.; Kawashima, I.; Sugawara, K.; Ohyanagi, N.; Suzuki, T.; Togawa, T.; Ohno, K.; Sakuraba, H. Binding parameters and thermodynamics of the interaction of imino sugars with a recombinant human acid α-glucosidase (alglucosidase alfa): insight into the complex formation mechanism Clin. Chim. Acta 2008, 391, 68-73
33. Chiba, S. Molecular mechanism in α-glucosidase and Glucoamylase Biotechnol., Biochem. 1997, 61, 1233-1239
34. Jiang, X. Y.; Li, W. X.; Cao, H. Study of the Interaction between Trans-resveratrol and BSA by the Multi-spectroscopic Method J. Solution Chem. 2008, 37, 1609-1623
35. Li, J.; Ren, C.; Zhang, Y.; Liu, X.; Yao, X.; Hu, Z. Spectroscopic studies on binding of Puerarin to human serum albumin J. Mol. Struct. 2008, 885, 64-69
36. Shang, Q.; Xiang, J.-F.; Tang, Y.-L. Screening α-glucosidase inhibitors from mulberry extracts via DOSY and relaxation-edited NNR Talanta 2012, 97, 362-367
37. Liu, X.-H.; Xi, P.-X.; Chen, F.-J.; Xu, Z.-H.; Zeng, Z.-Z. Spectroscopic studies on binding of 1-phenyl-3-(coumarin-6-yl)sulfonylurea to bovine serum albumin J. Photochem. Photobiol., B 2008, 92, 98-102
38. Du, Z.; Liu, R.; Shao, W.; Mao, X.; Ma, L.; Gu, L.; Huang, Z.; Chan, A. S. C. α-Glucosidase inhibition of natural curcuminoids and curcumin analogs Eur. J. Med. Chem. 2006, 41, 213-218
39. Wang, Y.; Ma, L.; Li, Z.; Du, Z.; Liu, Z.; Qin, J.; Wang, X.; Huang, Z.; Gu, L.; Chen, A. S. C. Synergetic inhibition of metal ions and genistein on α-glucosidase FEBS Lett. 2004, 576, 46-50
40. Tsujimoto, Y.; Tanaka, H.; Takemura, R.; Yokogawa, T.; Shimonaka, A.; Matsui, H.; Kashiwabara, S.; Watanabe, K.; Suzuki, Y. Molecular Determinants of Substrate Recognition in Thermostable α-glucosidases Belonging to Glycoside Hydrolase Family 13 J. Biochem. 2007, 142, 87-93
41. Bharatham, K.; Bharatham, N.; Park, K. H.; Lee, K. W. Binding mode analyses and pharmacophore model development for sulfonamide chalcone derivatives, a new class of α-glucosidase inhibitors J. Mol. Graphics Modell. 2008, 26, 1202-1212
42. Hansawasdi, C.; Kawabata, J. α-Glucosidase inhibitory effect of mulberry (Morus alba) leaves on Caco-2 Fitoterapia 2006, 77, 568-573
43. Francis, F. J.; Markakis, P. C. Food colorants: anthocyanins Crit. Rev. Food Sci. Nutr. 1989, 28, 273-314
44. Mei, M.; Ruan, J.-Q.; Wu, W.-J.; Zhou, R.-N.; Lei, J. P.-C.; Zhao, H.-Y.; Yan, R.; Wang, Y.-T. In vitro pharmacokinetic characterization of mulberroside A, the main polyhydroxylated stilbene in mulberry (Morus alba L.), and its bacterial metabolite oxyresveratrol in traditional oral use J. Agric. Food Chem. 2012, 60, 2299-2308