Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 16, 2005, Pages 6516-6524

  Li, Dan ^a   Roh, Sun Ah ^a   Shim, Jae Hoon ^a   Mikami, Bunzo ^b   Baik, Moo Yeol ^c   Park, Cheon Seok ^c   Park, Kwan Hwa ^a  

^a Seoul National University   (South Korea)

^b Kyung Hee University   (South Korea)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

4 glucanotransferase; CGTase; Cyclization; Cycloamylose; Genistin; Isoflavone; Solubility; Transglycosylation

Indexed keywords

4 ALPHA GLUCANOTRANSFERASE; 4 ALPHA-GLUCANOTRANSFERASE; CYCLOMALTODEXTRIN GLUCANOTRANSFERASE; GENISTEIN; GLUCAN; GLUCOSYLTRANSFERASE; GLYCOGEN DEBRANCHING ENZYME; STARCH;

ARTICLE; BACILLUS; CHEMICAL STRUCTURE; ENZYMOLOGY; GLYCOSYLATION; MASS SPECTROMETRY; METABOLISM; SOLUBILITY; THERMUS;

BACILLUS; GENISTEIN; GLUCANS; GLUCOSYLTRANSFERASES; GLYCOGEN DEBRANCHING ENZYME SYSTEM; GLYCOSYLATION; MOLECULAR STRUCTURE; SOLUBILITY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STARCH; THERMUS;

BACILLUS SP.; THERMUS; THERMUS SCOTODUCTUS;

EID: 23844520610     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050732g     Document Type: Article

References (35)

1. Setchell, K. D. R.; Cassidy, A. Dietary isoflavones: biological effects and relevance to human health. J. Nutr. 1999, 129, 758S-767S.
2. McCue, P.; Shetty, K. Health benefits of soy isoflavonoids and strategies for enhancement: a review. Crit. Rev. Food Sci. Nutr. 2004, 44, 361-367.
3. Sarkar, F. H.; Li, Y. Soy isoflavones and cancer prevention. Cancer Invest. 2003, 21, 744-757.
4. Li, D.; Park, J. H.; Park, J. T.; Park, C. S.; Park, K. H. Biotechnological production of highly soluble daidzein glycosides using Thermotoga maritima maltosyltransferase. J. Agric. Food Chem. 2004, 52, 2561-2567.
5. Kometani, T.; Nishimura, T.; Nakae, T.; Okada, S. Synthesis of neohesperidin glycosides and naringin glycosides by cyclodextrin glucanotransferase from an alkalophilic Bacillus species. Biosci., Biotechnol., Biochem. 1996, 60, 645-649.
6. Lee, S. J.; Kim, J.; Kim, M. J.; Kitaoka, M.; Park, C. S.; Lee, S. Y.; Ra, M.; Moon, T. W.; Robyt, J. F.; Park, K. H. Transglycosylation of naringin by Bacillus stearothermophilus maltogenic amylase to give glycosylated naringin. J. Agric. Food Chem. 1999, 47, 3669-3674.
7. Kim, Y. K.; Kim, M. J.; Park, C. S.; Park, K. H. Modification of sorbitol by transglycosylation using Bacillus stearothermophilus maltogenic amylase. Food Sci. Biotechnol. 2002, 11, 401-406.
8. Svasti, J.; Phongsak, T.; Sarnthima, R. Transglucosylation of tertiary alcohols using cassava β-glucosidase. Biochem. Biophys. Res. Commun. 2003, 305, 470-475.
9. Ducret, A.; Trani, M.; Lortie, R. Screening of various glycosidases for the synthesis of octyl glucoside. Biotechnol. Bioeng. 2002, 77, 752-757.
10. Spangenberg, P.; Andre, C.; Dion, M.; Rabiller, C.; Mattes, R. Comparative study of new α-galactosidases in transglycosylation reactions. Carbohydr. Res. 2000, 329, 65-73.
11. Zeng, X.; Yoshino, R.; Murata, T.; Ajisaka, K.; Usui, T. Regioselective synthesis of p-nitrophenyl glycosides of β-D-galactopyranosyl-disaccharides by transglycosylation with β-D-galactosidases. Carbohydr. Res. 2000, 325, 120-131.
12. Li, D.; Park, S. H.; Shim, J. H.; Lee, H. S.; Tang, S. Y.; Park, C. S.; Park, K. H. In vitro enzymatic modification of puerarin to puerarin glycosides by maltogenic amylase. Carbohydr. Res. 2004, 339, 2789-2797.
13. Kim, T. J.; Kim, M. J.; Kim, B. C.; Kim, J. C.; Cheong, T. K.; Kim, J. W.; Park, K. H. Modes of action of acarbose hydrolysis and transglycosylation catalyzed by a thermostable maltogenic amylase, the gene for which was cloned from a Thermus strain. Appl. Environ. Microbiol. 1999, 65, 1644-1651.
14. Van der Veen, B. A.; Uitdehaag, J. C.; Dijkstra, B. W.; Dijkhuizen, L. Engineering of cyclodextrin glycosyltransferase reaction and product specificity. Biochim. Biophys. Acta 2000, 1543, 336-360.
15. Yoon, S. H.; Bruce Fulton, D.; Robyt, J. F. Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and Leuconostoc mesenteroides B-742CB dextransucrase. Carbohydr. Res. 2004, 339, 1517-1529.
16. Shibuya, T.; Aga, H.; Watanabe, H.; Sonoda, T.; Kubota, M.; Fukuda, S.; Kurimoto, M.; Tsujisaka, Y. Transglycosylation of glycosyl residues to cyclic tetrasaccharide by Bacillus stearothermophilus cyclomaltodextrin glucanotransferase using cyclomaltodextrin as the glycosyl donor. Biosci., Biotechnol., Biochem. 2003, 67, 1094-1100.
17. Takata, H.; Takaha, T.; Okada, S.; Hizukuri, S.; Takagi, M.; Imanaka, T. Structure of the cyclic glucan produced from amylopectin by Bacillus stearothermophilus branching enzyme. Carbohydr. Res. 1996, 295, 91-101.
18. Takata, H.; Takaha, T.; Okada, S.; Takagi, M.; Imanaka, T. Cyclization reaction catalyzed by branching enzyme. J. Bacteriol. 1996, 178, 1600-1606.
19. Yanase, M.; Takata, H.; Takaha, T.; Kuriki, T.; Smith, S. M.; Okada, S. Cyclization reaction catalyzed by glycogen debranching enzyme (EC 2.4.1.25/EC 3.2.1.33) and its potential for cycloamylose production. Appl. Environ. Microbiol. 2002, 68, 4233-4239.
20. Takaha, T.; Smith, S. M. The functions of 4-α-glucanotransferases and their use for the production of cyclic glucans. Biotechnol. Genet. Eng. Rev. 1999, 16, 257-280.
21. Takaha, T.; Yanase, M.; Takata, H.; Okada, S.; Smith, S. M. Cyclic glucans produced by the intramolecular transglycosylation activity of potato D-enzyme on amylopectin. Biochem. Biophys. Res. Commun. 1998, 247, 493-497.
22. Shim, J. H.; Kim, Y. W.; Kim, T. J.; Chae, H. Y.; Park, J. H.; Cha, H.; Kim, J. W.; Kim, Y. R.; Schaefer, T.; Spendler, T.; Moon, T. W.; Park, K. H. Improvement of cyclodextrin glucanotransferase as an antistaling enzyme by error-prone PCR. Protein Eng. Design Sel. 2004, 17, 205-211.
23. Bradford, M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
24. Laemmli, U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970, 227, 680-685.
25. Lee, H. S.; Auh, J. H.; Yoon, H. G.; Kim, M. J.; Park, J. H.; Hong, S. S.; Kang, M. H.; Kim, T. J.; Moon, T. W.; Kim, J. W.; Park, K. H. Cooperative action of α-glucanotransferase and maltogenic amylase for an improved process of isomaltooligosaccharide (IMO) production. J. Agric. Food Chem. 2002, 50, 2812-2817.
26. Wang, J.; Sporns, P. MALDI-TOF MS analysis of isoflavones in soy products. J. Agric. Food Chem. 2000, 48, 5887-5892.
27. Kurimoto, M.; Tabuchi, A.; Mandai, T.; Shibuya, T.; Chaen, H.; Fukuda, S.; Sugimoto, T.; Tsujisaka, Y. Synthesis of glycosyl-trehaloses by cyclomaltodextrin glucanotransferase through the transglycosylation reaction. Biosci., Biotechnol., Biochem. 1997, 61, 1146-1149.
28. Jeon, B. S.; Taguchi, H.; Sakai, H.; Ohshima, T.; Wakagi, T.; Matsuzawa, H. 4-α-glucanotransferase from the hyperthermophilic archaeon Thermococcus litoralis - enzyme purification and characterization, and gene cloning, sequencing and expression in Escherichia coli. Eur. J. Biochem. 1997, 248, 171-178.
29. Terada, Y.; Yanase, M.; Takata, H.; Takaha, T.; Okada, S. Cyclodextrins are not the major cyclic α-1,4-glucans produced by the initial action of cyclodextrin glucanotransferase on amylose. J. Biol. Chem. 1997, 272, 15729-15733.
30. The Amylase Research Society of Japan. Cyclomaltodextrin glucanotransferase In Enzyme Chemistry and Molecular Biology of Amylase and Related Enzymes, 1st ed.; CRC Press: Boca Raton, FL, 1995; pp 8-9.
31. Bender, H. An improved method for the preparation of cyclooctaamylose, using starches and the cyclodextrin glycosyltransferase of Klebsiella pneumoniae M 5 al. Carbohydr. Res. 1983, 124, 225-233.
32. Bertoft, E. Partial characterization of amylopectin α-dextrins. Carbohydr. Res. 1989, 189, 181-193.
33. Ravindranath, M. H.; Muthugounder, S.; Presser, N.; Viswanathan, S. Anticancer therapeutic potential of soy isoflavone, genistein. Adv. Exp. Med. Biol. 2004, 546, 121-165.
34. Federici, E.; Touche, A.; Choquart, S.; Avanti, O.; Fay, L.; Offord, E.; Courtois, D. High isoflavone content and estrogenic activity of 25-year-old Glycine max tissue cultures. Phytochemistry 2003, 64, 717-724.
35. Steer, T. E.; Johnson, I. T.; Gee, J. M.; Gibson, G. R. Metabolism of the soybean isoflavone glycoside genistin in vitro by human gut bacteria and the effect of prebiotics. Br. J. Nutr. 2003, 90, 635-642.