Inhibitory activity of corn-derived bisamide compounds against α-glucosidase

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 1, 2003, Pages 90-94

  Niwa, Toshio ^a   Doi, Umeyuki ^a   Osawa, Toshihiko ^b  

^a San ei Sucrochemical Co Ltd   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Glucosidase inhibitor; Amides; Corn; Ferulic acid

Indexed keywords

ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; ALPHA GLUCOSIDASES; AMIDE; COUMARIC ACID; DRUG DERIVATIVE; ENZYME INHIBITOR; FERULIC ACID; FERULOYLPUTRESCINE; HYDROXYL GROUP; N 4 COUMAROYL N' FERULOYLPUTRESCINE; N,N' DIFERULOYLPUTRESCINE; PUTRESCINE; STARCH; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CHEMISTRY; CORN; DRUG ACTIVITY; ENZYME INHIBITION; MAIZE; OXIDATION REDUCTION POTENTIAL; STRUCTURE ACTIVITY RELATION; ULTRAFILTRATION;

ALPHA-GLUCOSIDASES; COUMARIC ACIDS; ENZYME INHIBITORS; PUTRESCINE; STRUCTURE-ACTIVITY RELATIONSHIP; ULTRAFILTRATION; ZEA MAYS;

ZEA MAYS;

EID: 0037225782     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020758x     Document Type: Article

References (36)

1. Jenkins, D. J. A.; Wolever, T. M. S.; Taylor, R. H.; Barker, H.; Fielden, H.; Baldwin, J. M.; Bowling, A. C.; Newman, H. C.; Jenkins, A. L.; Goff, D. V. Glycemic index of foods: A physiological basis for carbohydrate exchange. Am. J. Clin. Nutr. 1981, 34, 362-366.
2. Jenkins, D. J. A.; Wolever, T. M. S.; Wong, G. S.; Kenshole, A.; Josse, R. G.; Thompson, L. U.; Lam, K. Y. Glycemic responses to foods: Possible differences between insulin-dependent and noninsulin-dependent diabetics. Am. J. Clin. Nutr. 1984, 40, 971-981.
3. Anderson, J. W.; Chen, W.-J. L. Plant fiber. Carbohydrate and lipid metabolism. Am. J. Clin. Nutr. 1979, 32, 346-363.
4. Heaton, K. W.; Marcus, S. N.; Emmett, P. M.; Bolton, C. H. Particle size of wheat, maize, and oat test meals: Effects on plasma glucose and insulin responses and on the rate of starch digestion in vitro. Am. J. Clin. Nutr. 1988, 47, 675-682.
5. Snow, P.; O'Dea, K. Factors affecting the rate of hydrolysis of starch in food. Am. J. Clin. Nutr. 1981, 34, 2721-2727.
6. Porte, D., Jr. β-Cells in type II diabetes mellitus. Diabetes 1991, 40, 166-180.
7. Taylor, S. I.; Accili, D.; Imai, Y. Insulin resistance or insulin deficiency. Which is the primary cause of NIDDM? Diabetes 1994, 43, 735-740.
8. O'Dea, K.; Turton, J. Optimum effectiveness of intestinal α-glucosidase inhibitors: Importance of uniform distribution through a meal. Am. J. Clin. Nutr. 1985, 41, 511-516.
9. Samad, A. H. B.; Willing, T. S. T.; Alberti, K. G. M. M.; Taylor, R. Effects of BAYm 1099, new α-glucosidase inhibitor, on acute metabolic responses and metabolic control in NIDDM over 1 mo. Diabetes Care 1988, 11, 337-344.
10. Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Inhibition of experimental metastasis by castanospermine in mice: Blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors. Cancer Res. 1986, 46, 5215-5222.
11. Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase. Nature 1987, 330, 74-77.
12. Trudel, G. C.; Holland, P. C. Effect of inhibitors of glycoprotein processing on integrin and the adhesion of myoblasts to extracellular matrix proteins. Biochem. Biophys. Res. Commun. 1989, 163, 1338-1343.
13. Block, T. M.; Lu, X.; Platt, F. M.; Foster, G. R.; Gerlich, W. H.; Blumberg, B. S.; Dwek, R. A. Secretion of human hepatitis B virus is inhibited by the imino sugar N-butyldeoxynojirimycin. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2235-2239.
14. Niwa, T.; Doi, U.; Kato, Y.; Osawa, T. Antioxidative properties of phenolic antioxidants isolated from corn steep liquor. J. Agric. Food Chem. 2001, 49, 177-182.
15. Crapo, P. A.; Insel, J.; Sperling, M.; Kolterman, O. G. Comparison of serum glucose, insulin, and glucagon responses to different types of complex carbohydrate in noninsulin-dependent diabetic patients. Am. J. Clin. Nutr. 1981, 34, 184-190.
16. Watanabe, J.; Kawabata, J.; Kurihara, H.; Niki, R. Isolation and identification of α-glucosidase inhibitors from Tochu-cha (Eucommia ulmoides). Biosci., Biotechnol., Biochem. 1997, 61, 177-178.
17. Mizusaki, S.; Tanabe, Y.; Noguchi, M.; Tamaki, E. p-Coumaroylputrescine, caffeoylputrescine and feruloylputrescine from callus tissue culture of Nicotiana tabacum. Phytochemistry 1971, 10, 1347-1350.
18. Rajan, P.; Vedernikova, I.; Cos, P.; Berghe, D. V.; Augustyns, K.; Haemers, A. Synthesis and evaluation of caffeic acid amides as antioxidants. Bioorg. Med. Chem. Lett. 2001, 11, 215-217.
19. Osawa, T.; Ide, A.; Su, J.-D.; Namiki, M. Inhibition of lipid peroxidation by ellagic acid. J. Agric. Food Chem. 1987, 35, 808-812.
20. Wu, T.-S.; Shi, L.-S.; Kuo, S.-C. Alkaloids and other constituents from Tribulus terrestris. Phytochemistry 1999, 50, 1411-1415.
21. Nishioka, T.; Watanabe, J.; Kawabata, J.; Niki, R. Isolation and activity of N-p-coumaroyltyramine, an α-glucosidase inhibitor in Welsh onion (Allium fistulosam). Biosci., Biotechnol., Biochem. 1997, 61, 1138-1141.
22. Castelluccio, C.; Paganga, G.; Melikian, N.; Bolwell, G. P.; Pridham, J.; Sampson, J.; Rice-Evans, C. Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett. 1995, 368, 188-192.
23. 2-dependent low density lipoprotein lipid peroxidation by naturally occurring phenolic acids. Biochem. Pharmacol. 1996, 51, 395-402.
24. Leaback, D. H. On the inhibition of β-N-acetyl-D-glucosaminidase by 2-acetamido-2-deoxy-D-glucono-(1 → 5)-lactone. Biochem. Biophys. Res. Commun. 1968, 32, 1025-1030.
25. Lai, H.-Y. L.; Axelrod, B. 1-Aminoglycosides, a new class of specific inhibitors of glycosidases. Biochem. Biophys. Res. Commun. 1973, 54, 463-468.
26. Harris, E. M. S.; Aleshin, A. E.; Firsov, L. M.; Honzatko, R. B. Refined structure for the complex of 1-deoxynojirimycin with glucoamylase from Aspergillus awamori var. X100 to 2.4-Å resolution. Biochemistry, 1993, 32, 1618-1626.
27. Legler, G. Active site directed inhibitors and mechanism of action of glycosidases. Mol. Cell. Biochem. 1973, 2, 31-38.
28. Marshall, P. J.; Sinnott, M. L.; Smith, P. J.; Widdows, D. Activesite-directed irreversible inhibition of glycosidases by the corresponding glycosylmethyl-(p-nitrophenyl)triazenes. J. Chem. Soc., Perkin Trans. 1 1981, 366-376.
29. Caron, G.; Withers, S. G. Conduritol aziridine: A new mechanism-based glucosidase inactivator. Biochem. Biophys. Res. Commun. 1989, 163, 495-499.
30. Moreau, R. A.; Nuñez, A.; Singh, V. Diferuloylputrescine and p-coumaroyl-feruloylputrescine, abundant polyamine conjugates in lipid extracts of maize kernels. Lipids 2001, 36, 839-844.
31. Martin-Tanguy, J.; Deshayes, A.; Perdrizet, E.; Martin, C. Hydroxycinnamic acid amides (HCA) in Zea mays. Distribution and changes with cytoplasmic male sterility. FEBS Lett. 1979, 108, 176-178.
32. Miller, J. D.; Miles, M.; Fielder, D. A. Kernel concentrations of 4-acetylbenzoxazolin-2-one and diferuloylputrescine in maize genotypes and gibberella ear rot. J. Agric. Food Chem. 1997, 45, 4456-4459.
33. Peipp, H.; Maier, W.; Schmidt, J.; Wray, V.; Strack, D. Arbuscular mycorrhizal fungus-induced changes in the accumulation of secondary compounds in barley roots. Phytochemistry 1997, 44, 581-587.
34. Lee, J.; Vogt, T.; Schmidt, J.; Parthier, B.; Löbler, M. Methyljasmonate-induced accumulation of coumaroyl conjugates in barley leaf segments. Phytochemistry 1997, 44, 589-592.
35. Ishihara, A.; Kawata, N.; Matsukawa, T.; Iwamura, H. Induction of N-hydroxycinnamoyltyramine synthesis and tyramine N-hydroxycinnamoyltransferase (THT) activity by wounding in maize leaves. Biosci., Biotechnol., Biochem. 2000, 64, 1025-1031.
36. Mehta, A.; Zitzmann, N.; Rudd, P. M.; Block, T. M.; Dwek, R. A. α-Glucosidase inhibitors as potential broad based anti-viral agents. FEBS Lett. 1998, 430, 17-22.