Structures required of flavonoids for inhibiting digestive enzymes

Anti-Cancer Agents in Medicinal Chemistry

Volumn 12, Issue 8, 2012, Pages 929-939

  Cao, Hui ^a   Chen, Xiaoqing ^a  

^a CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

amylase; glucosidase; Aldose reductase; Flavonoids; Structure activity relationship

Indexed keywords

2' METHOXYKURARINNONE; 3 METHOXYAPIGENIN; 3,6 DIMETHOXYAPIGENIN; 5,7,3',4' TETRAMETHOXYFLAVONE; 5,7,4' TRIMETHOXYFLAVONE; 7 O ALPHA DEXTRO GLUCOPYRANOSYL 3,5 DIHYDROXY 3' (4''ACETOXY 3'' METHYLBUTYL) 6,4' DIMETHOXYFLAVONE AND 7 O ALPHA DEXTRO GLUCOPYRANOSYL 3, 4' DIHYDROXY3' (4'' ACETOXY 3'' METHYLBUTYL) 5,6 DIMETHOXYFLAVONE; 7 O METHYLLUTEONE; 8 PHENYLNARINGENIN; ALDEHYDE REDUCTASE; ALPHA GLUCOSIDASE; AMYLASE; APIGENIN; CHRYSOERIOL 7 O ALPHA DEXTRO GLUCOPYRANOSIDE; CHRYSOERIOL 7 O RUTINOSIDE; DAIDZEIN; FLAVANONE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL; FORMONONETIN; HYDROXYL GROUP; ISOANGUSTONE A; ISOFLAVONE; KURARINONE; KUSHENOL A; LUTEOLIN; LUTEOLIN 7 O ALPHA DEXTRO GLUCOPYRANOSIDE; LUTEOLIN 7 O RUTINOSIDE; SEMILICOISOFLAVONE B; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ENZYME INHIBITION; GLYCOSYLATION; HUMAN; HYDROGENATION; HYDROXYLATION; IC 50; IN VITRO STUDY; METHYLATION; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION;

ALDEHYDE REDUCTASE; ALPHA-AMYLASES; ALPHA-GLUCOSIDASES; BIOLOGICAL PRODUCTS; ENZYME INHIBITORS; FLAVONOIDS; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84866350396     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/187152012802650110     Document Type: Review

References (66)

1. Pan, M.H.; Lai, C.S.; Ho, C.T. Anti-inflammatory activity of natural dietary flavonoids. Food Funct., 2010, 1, 15-31.
2. Xiao, J.B.; Cao, H.; Wang, Y.F.; Yamamoto, K.; Wei, X.L. Structure-affinity relationship of flavones on binding to serum albumins: Effect of hydroxyl groups on ring A. Mol. Nutr. Food Res., 2010, 54, S253-S260.
3. Xiao, J.B.; Chen, T.T.; Cao, H.; Chen, L.; Yang, F. Molecular property-affinity relationship of flavanoids and flavonoids for human serum albumin in vitro. Mol. Nutr. Food Res., 2011, 55, 310-317.
4. Blade, C.; Arola, L.; Salvado, M.J. Hypolipidemic effects of proanthocyanidins and their underlying biochemical and molecular mechanisms. Mol. Nutr. Food Res., 2010, 54, 37-59.
5. Cheung, C.W.Y.; Gibbons, N.; Johnson, D.W.; Nicol, D.L. Silibinin -A promising new treatment for cancer. Aant-Cancer Agents ME., 2010, 10, 186-195.
6. Brand, W.; Padilla, B.; van Bladeren, P.J.; Williamson, G.; Rietjens, I.M.C.M. The effect of co-administered flavonoids on the metabolism of hesperetin and the disposition of its metabolites in Caco-2 cell monolayers. Mol. Nutr. Food Res., 2010, 54, 851-860.
7. Xiao, J.B.; Kai, G.Y.; Yang, F.; Liu, C.X.; Xu, X.C.; Yamamoto, K. Molecular structure-affinity relationship of natural polyphenols for bovine γ-globulin. Mol, Nutr, Food Res., 2011, 55, S86-S92.
8. Xiao, J.B.; Chen, T.T.; Cao, H.; Chen, L.S.; Yang, F. Molecular property-affinity relationship of flavanoids and flavonoids for human serum albumin in vitro. Mol. Nutr. Food Res., 2011, 55, 310-317.
9. Xiao, J.B.; Zhao, Y.R.; Wang, H.; Yuan, Y.M.; Yang, F.; Zhang, C.; Yamamoto, K. Non-covalent interaction of dietary polyphenols with common human plasma proteins. J. Agric. Food Chem., 2011, 59, 10747-10754.
10. Xiao, J.B.; Huo, J.L.; Yang, F.; Chen, X.Q. Non-covalent interaction of dietary polyphenols with bovine hemoglobin in vitro: Molecular structure/property-affinity relationship aspects. J. Agric. Food Chem., 2011, 59, 8484-8490.
11. Hirayama, F.; Lee, A.H.; Binns, C.W.; Hiramatsu, N.; Mori, M.; Nishimura, K. Dietary intake of isoflavones and polyunsaturated fatty acids associated with lung function, breathlessness and the prevalence of chronic obstructive pulmonary disease: Possible protective effect of traditional Japanese diet. Mol. Nutr. Food Res., 2010, 54, 909-917.
12. D'Archivio, M.; Filesi, C.; Varì R.; Scazzocchio B.; Masella, R. Bioavailability of the polyphenols: status and controversies. Int. J. Mol. Sci., 2010, 11, 1321-1342.
13. Azuma, T.; Kayano, S.; Matsumura, Y.; Konishi, Y.; Tanaka, Y.; Kikuzaki, H. Antimutagenic and α-glucosidase inhibitory effects of constituents from Kaempferia parviflora. Food Chem., 2011, 125, 471-475.
14. Hakamata, W.; Kurihara, M.; Okuda, H.; Nishio, T.; Oku, T. Design and screening strategies for α-glucosidase inhibitors based on enzymological information. Current Top. Med. Chem., 2009. 9, 3-12.
15. Yuk, H.J.; Lee, J.H.; Curtis-Long, M.J.; Lee, J.W.; Kim, Y.S.; Ryu, H.W., Park, C.G.; Jeong http://www.sciencedirect.com/science/article/pii/S030881461001544X-cor1#cor1, T.S.; Park, K.H. The most abundant polyphenol of soy leaves, coumestrol, displays potent α-glucosidase inhibitory activity. Food Chem., 2011, 126, 1057-1063.
16. Brayer, G.D.; Sidhu, G.; Maurus, R.; Rydberg, E.H.; Braun, C.; Wang, Y.; Nguyen, N.T.; Overall, C.M.; Withers, S.G. Subsite mapping of the human pancreatic alpha-amylase active site through structural, kinetic and mutagenesis techniques. Biochemistry, 2000, 39, 4778-4791.
17. de la Fuente, J.A.; Manzanaro, S. Aldose reductase inhibitors from natural sources. Nat. Prod. Rep., 2003, 20, 243-251.
18. Lim, S.S.; Jung, S.H.; Ji, J.; Shin, K.H.; Keum, S.R. Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues. J. Pharm. Pharmacol., 2001, 53, 653-668.
19. Gao, H.; Nishioka, T.; Kawabata, J.; Kasai, T. Structure-activity relationships for alpha-glucosidase inhibition of baicalein, 5,6,7-trihydroxyflavone: the effect of A-ring substitution. Biosci. Biotechnol. Biochem., 2004, 68, 369-375.
20. Gao, H.; Kawabata, J. Importance of the B ring and its substitution on the alpha-glucosidase inhibitory activity of baicalein, 5,6,7-trihydroxyflavone. Biosci. Biotechnol. Biochem., 2004, 68, 1858-1864.
21. Tadera, K.; Minami, Y.; Takamatsu K.; Matsuoka T. Inhibition of α-glucosidase and α-amylase by flavonoids. J. Nutr. Sci. Vitaminol., 2006, 5, 149-153.
22. Lee, E.H.; Song, D.G.; Lee, J.Y.; Pan, C.H.; Um, B.H.; Jung, S.H. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation end products. Biol. Pharm. Bull., 2008, 31, 1626-1630.
23. Matsuda, H.; Asao, Y.; Nakamura, S.; Hamao, M.; Sugimoto, S.; Hongo, M.; Pongpiriyadacha, Y.; Yoshikawa, M. Antidiabetogenic constituents from the Thai traditional medicine cotylelobium melanoxylon. Chem. Pharm. Bull., 2009, 57, 487-494.
24. Li, H.; Song, F.; Xing, J.; Tsao, R.; Liu, Z.; Liu, S. Screening and structural characterization of α-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS. J. Am. Soc. Mass Spectrom., 2009, 20, 1496-1503.
25. Wang, H.; Du, Y.J.; Song, H.C.α-Glucosidase and α-amylase inhibitory activities of guava leaves. Food Chem., 2010, 123, 6-13.
26. Yoshida, K.; Hishida, A.; Iida, O.; Hosokawa, K.; Kawabata, J. Flavonol caffeoylglycosides as α-glucosidase inhibitors from Spiraea cantoniensis flower. J. Agric. Food Chem., 2008, 56, 4367-4371.
27. Lee, E.H.; Song, D.G.; Lee, J.Y.; Pan, C.H.; Um, B.H.; Jung, S.H. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation end products. Biol. Pharm. Bull., 2008, 31, 1626-1630.
28. Matsuda, H.; Wang, T.; Managi, H.; Yoshikawa, M. Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. Bioorg. Med. Chem., 2003, 11, 5317-5323.
29. Ishikawa, A.; Yamashita, H.; Hiemori, M.; Inagaki, E.; Kimoto, M.; Okamoto, M.; Tsuji, H.; Memon, A.N.; Mohammadi, A.; Natori, Y. Characterization of inhibitors of postprandial hyperglycemia from the leaves of Nerium indicum. J. Nutr. Sci. Vitaminol., 2007, 53, 166-173.
30. Gao, H.; Kawabata, J. α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as a-glucosidase inhibitors. Bioorg. Med. Chem., 2005, 13, 1661-1671.
31. Kim, J.K.; Lee, Y.S.; Kim, S.H.; Bae, Y.S.; Lim, S.S. Inhibition of aldose Reductase by phenylethanoid Glycoside isolated from the Seeds of Paulownia coreana. Biol. Pharm. Bull., 2011. 34, 160-163.
32. Xie, H.H.; Wang, T.; Matsuda, H.; Morikawa, T.; Yoshikawa, M.; Tani, T. Bioactive constituents from Chinese natural medicines. XV.1) Inhibitory effect on aldose reductase and structures of sussureosides A and B from Saussurea medusa. Chem. Pharm. Bull., 2005, 53, 1416-1422.
33. Walle, T. Methylation of dietary flavones greatly improves their hepatic metabolic stability and intestinal absorption. Mol. Pharmaceut., 2007, 4, 826-832.
34. Walle, T. Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? Semin. Cancer Biol., 2007, 17, 354-362.
35. Shibano, M.; Kakutani, K.; Taniguchi, M.; Yasuda, M.; Baba, K. Antioxidant constituents in the dayflower (Commelina communis L.) and their α-glucosidase-inhibitory activity. J. Nat. Med., 2008, 62, 349-353.
36. Iqbal, K.; Malik, A.; Mukhtar, N.; Anis, I.; Khan, S.N.; Choudhary, M.I. α-Glucosidase inhibitory constituents from Duranta repens. Chem. Pharm. Bull., 2004, 52, 785-789.
37. Al-Dabbas, M.M.; Kitahara, K.; Suganuma, T.; Hashimoto, F.; Tadera, K. Antioxidant and α-amylase inhibitory compounds from aerial parts of Varthemia iphionoides Boiss. Biosci. Biotechnol. Biochem., 2006, 70, 2178-2184.
38. Kim, J.H.; Ryu, Y.B.; Kang, N.S.; Lee, B.W.; Heo, J.S.; Jeong, I.Y.; Park, K.H. Glycosidase inhibitory flavonoids from Sophora flavescens. Biol. Pharm. Bull., 2006, 29, 302-305.
39. Piparo, E.L.; Scheib, H.; Frei, N.; Williamson, G.; Grigorov, M.; Chou, C.J. Flavonoids for controlling starch digestion: structural requirements for inhibiting human α-amylase. J. Med. Chem., 2008, 51, 3555-3561.
40. Lee, Y.S.; Kim, S.H.; Jung, S.H.; Kim, J.K.; Pan, C.H.; Lim, S.S. Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. Biol. Pharm. Bull., 2010, 33,917-921.
41. Park, C.H.; Lim, S.S.; Lee, D.U. Structure-activity relationships of components from the roots of Pueraria thunbergiana having aldose reductase inhibitory and antioxidative activity. Bull. Korean Chem. Soc., 2007, 28, 493-495.
42. Güvenç, A.; Okada, Y.; Akkol, E.K.; Duman, H.; Okuyama, T.; Çaliş, I. Investigations of anti-inflammatory, antinociceptive, antioxidant and aldose reductase inhibitory activities of phenolic compounds from Sideritis brevibracteata. Food Chem., 2010, 118, 686-692.
43. Yawadio, R.; Tanimori, S.; Morita, N. Identification of phenolic compounds isolated from pigmented rices and their aldose reductase inhibitory activities. Food Chem., 2007, 101, 1616-1625.
44. Day, A.J.; DuPont, M.S.; Ridley, S.; Rhodes, M.; Rhodes, M.J.C.; Williamson, G. Deglycosylation of favonoid and isofavonoid glycosides by human small intestine and liver L-glucosidase activity. FEBS Lett., 1998, 436, 71-75.
45. Fossen, T.; Pedersen, A.T.; Anderson, O.M. Flavonoids from red onion (Allium cepa). Phytochemistry, 1998, 47, 281-285.
46. Jung, H.A.; Kim, Y.S.; Choi, J.S. Quantitative HPLC analysis of two key flavonoids and inhibitory activities against aldose reductase from different parts of the Korean thistle, Cirsium maackii. Food Chem. Toxicol., 2009, 47, 2790-2797.
47. Kim, J.; Kwon, C.; Son, K. Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid. Biosci. Biotechnol. Biochem., 2000, 64, 2458-2461.
48. Fan, P.; Terrier, L.; Hay, A.E.; Marston, A.; Hostettmann, K. Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F. Schmidt ex Maxim (Polygonaceae). Fitoterapia, 2010, 81, 124-131.
49. Phuwapraisirisan, P.; Puksasook, T.; Kokpol, U.; Suwanborirux, K. Corchorusides A and B, new flavonol glycosides as α-glucosidase inhibitors from the leaves of Corchorus olitorius. Tetrahedron Lett., 2009, 50, 5864-5867.
50. Kawabata, J.; Mizuhata, K.; Sato, E.; Nishioka, T.; Aoyama, Y.; Kasai, T. 6-Hydroxyflavonoids as α-glucosidase inhibitors from Marjoram (Origanum majorana) leaves. Biosci. Biotechnol. Biochem., 2003, 67, 445-447.
51. Jung, H.A.; Islam, N.; Kwon, Y.S.; Jin, S.E.; Son, Y.K.; Park, J.J.; Sohn, H.S.; Choi, J.S. Extraction and identification of three major aldose reductase inhibitors from Artemisia Montana. Food Chem. Toxicol., 2011, 49, 376-384.
52. Liu, H.B.; Wang, Z.L.; Qiao, Y.X.; Zhou, J.J. Flavonoids with aldose reductase inhibiting activity: Pharmacophore modeling and implications for mechanism. Acta Phys. Chim. Sin., 2007, 23, 1059-1064.
53. Yoshikawa, M.; Morikawa, T.; Murakami, T.; Toguchida, I.; Harima, S.; Matsuda, H. Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L. Chem. Pharm. Bull., 1999, 47, 340-345.
54. Jung, S.H.; Kang, S.S.; Shin, K.H.; Kim, Y.S. Inhibitory effects of naturally occurring flavonoids on rat lens aldose reductase. Nat. Prod. Sci., 2004, 10, 35-39.
55. Park, H.Y.; Kim, S.H.; Kim, G.B.; Sim, J.Y.; Lim, S.S.; Kim, M.J.; Chun, W.; Kwon, Y.S. A new isoflavone glycoside from the stem bark of Sophora japonica. Arch. Pharm. Res., 2010, 33, 1165-1168.
56. Shin, K.H.; Kang, S.S.; Seo, E.A.; Shin, S.W. Isolation of aldose reductase inhibitors from the flowers of Chrysanthemum boreale. Arch. Pharm. Res., 1995, 18, 65-68.
57. Haraguchi, H.; Ohmi, I.; Sakai, S.; Fukuda, A. Effect of Polygonum hydropiper sulfated flavonoids on lens aldose reductase and related enzymes. J. Nat. Prod., 1996, 59, 443-445.
58. Park, H.Y.; Kim, H.K.; Jeon, S.H.; Kim, S.H.; Chun, W.J.; Lim, S.S.; Kim, M.J.; Kwon, Y.S. Aldose reductase inhibitors from the leaves of Salix hulteni. J. Korean Soc. Appl. Biol. Chem., 2009, 52, 493-497.
59. Yoo, N.H.; Jang, D.S.; Yoo, J.L.; Lee, Y.M.; Kim, Y.S.; Cho, J.H.; Kim, J.S. Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity. J. Nat. Prod., 2008, 71, 713-715.
60. Al-Yahya, M.A.; El-Sayed, A.M.; Mossa, J.S.; Kozlowski, J.F.; Antoun, M.D.; Ferin, M.; Baird, W.M.; Cassady, J.M. Potential cancer chemopreventive and cytotoxic agents from Pulicaria crispa. J. Nat. Prod., 1988, 51, 621-624.
61. Okuda, J.; Miwa, I.; Inagaki, K.; Horie, T.; Nakayama, M. Inhibition of aldose reductases from rat and bovine lenses by flavonoids. Biochem. Pharmacol., 1982, 31, 3807-3822.
62. Lim, S.S.; Jung, Y.J.; Hyun, S.K.; Lee, Y.S.; Choi J.S. Rat lens aldose reductase inhibitory constituents of Nelumbo nucifera stamens. Phytother. Res., 2006, 20, 825-830.
63. Ye, X.P.; Song, C.Q.; Yuan, P.; Mao, R.G.α-Glucosidase and α-amylase inhibitory activity of common constituents from traditional Chinese medicine used for diabetes mellitus. Chin. J. Natural Med., 2010, 8, 349-352.
64. Komaki, E.; Yamaguchi, S.; Maru, I.; Kinnoshita, M.; Kakehi, K.; Ohta, Y.; Tsukada, Y. Identification of anti-amylase components from olive leaf extracts. Food Sci. Technol. Res., 2003, 9, 35-39.
65. Kumar, V.; Kumar, S.; Rani, P. Pharmacophore modeling and 3D-QSAR studies on flavonoids as α-glucosidase inhibitors. Der Pharma Chem., 2010, 2, 324-335.
66. Xiao, J.B.; Kai, G.Y.; Ni, X.L.; Yang, F., Chen, X.Q. Interaction of natural polyphenols with human α-amylase in vitro: Molecular property-affinity relationship aspect. Mol. BioSyst., 2011, 7, 1883-1890.