Functionalization of Isoflavones with Enzymes |
Lee, Jae-Hwan
(Department of Food Science and Technology, Seoul National University of Technology)
Doo, Eun-Hee (Department of Food Science and Technology, Ewha Womans University) Kwon, Dae-Yong (Food Functional Research Division, Korea Food Research Institute) Park, Jin-Byung (Department of Food Science and Technology, Ewha Womans University) |
1 | Hoeck J, Fehr W, Murphy P, Welke G. Influence of geneotype and environment on isoflavone contents of soybean. Crop Sci. 40: 48-51 (2000) DOI ScienceOn |
2 | Ishimi Y, Yoshida M, Wakimoto S, Wu J, Chiba H, Wang X, Takeda K, Miyaura C. Genistein, a soybean isoflavone, affects bone marrow lymphopoiesis and prevents bone loss in castrated male mice. Bone 31: 180-185 (2002) DOI ScienceOn |
3 | Jang C, Lim J, Kim J, Park C, Kwon D, Kim Y-S, Shin D, Kim J-S. Change of isoflavone content during manufacturing of cheonggukjang, a traditional Korean fermented soyfood. Food Sci. Biotechnol. 15: 643-646 (2006) 과학기술학회마을 |
4 | Esaki H, Watanabe R, Onozaki H, Kawakishi S, Osawa T. Formation mechanism for potent antioxidative O-dihydroxyisoflavones in soybeans fermented with Aspergillus saitoi. Biosci. Biotech. Bioch. 63: 851-858 (1999) DOI ScienceOn |
5 | Borriello SP, Setchell KDR, Axelson M, Lawson AM. Production and metabolism of lignans by the human fecal flora. J. Appl. Bacteriol. 58: 37-43 (1985) DOI |
6 | Sperry JF, Wilkins TD. Arginine, a growth-limiting factor for Eubacterium lentum. J. Bacteriol. 127: 780-784 (1976) |
7 | Winkel-Shirley B. Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol. 126: 485-493 (2001) DOI ScienceOn |
8 | Hagerman AE, Riedl KM, Jones GA, Sovik KN, Ritchard NT, Hartzfeld PW, Riechel TL. High molecular weight plant polyphenolics (tannins) as biological antioxidants. J. Agr. Food Chem. 46: 1887-1892 (1998) |
9 | Saito M, Hosoyama H, Ariga T, Kataoka S, Yamaji N. Antiulcer activity of grape seed extract and procyanidins. J. Agr. Food Chem. 46: 1460-1464 (1998) DOI ScienceOn |
10 | Yang S, Lee S, Lee S, Chang P-S, Choi S-S, Lee J. Succinyl daidzin and succinyl genistin are new isoflavone derivatives found in cheonggukjang. Food Sci. Biotechnol. 17: in press (2008) 과학기술학회마을 |
11 | Tsangalis D, Ashton JF, Stojanovska L, Wilcox G, Shah N. Development of an isoflavone aglycone-enriched soymilk using soy germ, soy protein isolate and bifidobacteria. Food Res. Int. 37: 301-312 (2004) DOI ScienceOn |
12 | Uzzan M, Labuza T. Critical issues in R&D of soy isoflavone enriched foods and dietary supplements. J. Food Sci. 69: 77-86 (2004) DOI ScienceOn |
13 | Esaki H, Kawakishi S, Morimitsu Y, Osawa T. New potent antioxidative O-dihydroxyisoflavones in fermented Japanese soybean products. Biosci. Biotech. Bioch. 63: 1637-1639 (1999) DOI ScienceOn |
14 | Shahidi F, Naczk M. Phenolic compounds of major oilseeds and plant oils. pp. 83-130. In: Phenolics in Food and Nutraceuticals. Shahidi F, Naczk M (eds). CRC Press, Inc., Boca Raton, FL, USA (2004) |
15 | Ariga T. The antioxidative function, preventive action on disease and utilization of proanthocyanidins. Biofactors 21: 197-201 (2004) DOI |
16 | Lee J, Renita M, Pioritto R, Martin S, Vodovotz Y. Isoflavone characterization and antioxidant activity of Ohio soybeans. J. Agr. Food Chem. 52: 2647-2651 (2004) DOI ScienceOn |
17 | Seeger M, Gonzalez M, Camara B, Munoz L, Ponce E, Mejias L, Mascayano C, Vasquez Y, Sepulveda-Boza S. Biotransformation of natural and synthetic isoflavonoids by two recombinant microbial enzymes. Appl. Environ. Microb. 69: 5045-5050 (2003) DOI |
18 | Desentis-Mendoza, Hernandez-Sanchez RMH, Moreno A, Emilio RDC, Chel-Guerrero L, Tamariz J, Jaramillo-Flores ME. Enzymatic polymerization of phenolic compounds using laccase and tyrosinase from Ustilago maydis. Biomacromolecules 7: 1845-1854 (2006) DOI ScienceOn |
19 | Mejias L, Reihmann MH, Sepulveda-Boza S, Ritter H. New polymers from natural phenols using horseradish or soybean peroxidase. Macromol. Biosci. 2: 24-32 (2002) DOI ScienceOn |
20 | Lozovaya V, Lygin A, Ulanov A, Nelson R, Dayde J, Widhohn J. Effect of temperature and soil moisture status during seed development on soybean seed isoflavone concentration and composition. Crop Sci. 45: 1934-1940 (2005) DOI ScienceOn |
21 | Klus K, Barz W. Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin A by bacteria isolated from tempe. Phytochemistry 47: 1045-1048 (1998) DOI |
22 | Kinoshita E, Ozawa Y, Aishima T. Novel tartaric acid isoflavone derivatives that play key roles in differentiating Japanese soy sauces. J. Agr. Food Chem. 45: 3753-3759 (1997) DOI ScienceOn |
23 | Yang S, Chang P-S, Lee J. Isoflavone distribution and betaglucosidase activity in cheonggukjang, a traditional Korean whole soybean-fermented food. Food Sci. Biotechnol. 15: 96-101 (2006) 과학기술학회마을 |
24 | Wang XL, Kim HJ, Kang SI, Kim SI, Hur HG. Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria. Arch. Microbiol. 187: 155-160 (2007) DOI ScienceOn |
25 | Sathyamoorthy N, Wang TTY. Differential effects of dietary phytooestrogens daidzein and equol on human breast cancer MCF-7 cells. Eur. J. Cancer. 33: 2384-2389 (1997) DOI ScienceOn |
26 | Ibrahim RK, Bruneau A, Bantignies B. Plant O-methyltransferases: Molecular analysis, common signature, and classification. Plant Mol. Biol. 36: 1-10 (1998) DOI ScienceOn |
27 | Toda T, Uesugi T, Hirai K, Nukaya H, Tsuji K, Ishida H. New 6-Oacyl isoflavone glycosides from soybeans fermented with Bacillus subtilis (natto). I. 6-O-Succinylated isoflavone glycosides and their preventive effects on bone loss in ovariectomized rats fed a calciumdeficient diet. Biol. Pharm. Bull. 22: 1193-1201 (1999) DOI ScienceOn |
28 | Hendrich S, Wang G, Lin H, Xu X, Tew B, Wang H, Murphy P. Isoflavone metabolism and bioavailability. pp. 211-230. In: Antioxidant Status, Diet, Nutrition, and Health. Papas A (ed). CRC Press, Inc., Boca Raton, FL, USA (1999) |
29 | Shimoni E. Stability and shelf life of bioactive compounds during food processing and storage: Soy isoflavone. J. Food Sci. 69: 160-166 (2004) DOI ScienceOn |
30 | Izumi T, Piskula M, Osawa S, Obata A, Tobe K, Saito M, Kataoka S, Kubota Y, Kikuchi M. Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucoside in humans. J. Nutr. 130: 1695-1699 (2000) |
31 | Minamida K, Tanaka M, Abe A, Sone T, Tomita F, Hara H, Asano K. Production of equol from daidzein by Gram-positive rod-shaped bacterium isolated from rat intestine. J. Biosci. Bioeng. 102: 247-250 (2006) DOI ScienceOn |
32 | Kim BG, Jung BR, Lee Y, Hur HG, Lim Y, Ahn JH. Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli. J. Agr. Food Chem. 54: 823-828 (2006) DOI ScienceOn |
33 | Esaki H, Osawa T, Kawakishi S. Potent antioxidative O-dihydroxyisoflavones in soy sauces and their antioxidative activities. J. Jpn. Soc. Food Sci. Technol. 49: 476-483 (2002) DOI ScienceOn |
34 | Hirota A, Inaba M, Chen YC, Abe N, Taki S, Yano M, Kawaii S. Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso. Biosci. Biotech. Bioch. 68: 1372-1374 (2004) DOI ScienceOn |
35 | Yang S, Chang P-S, Baek B, Hong S, Lee J. Changes of isoflavone distribution in soybeans using almond powder. Korean J. Food Sci. Technol. 39: 231-236 (2007) 과학기술학회마을 |
36 | Eldridge A, Kwolek W. Soybean isoflavones: Effect of environment and variety on composition. J. Agr. Food Chem. 31: 394-396 (1983) DOI |
37 | Zheng G, Zhu S. Antioxidant effects of soybean isoflavones. pp. 123-130. In: Antioxidants in Human Health and Disease. Basu T, Temple N, Garg M (eds). CABI Publishing, Wallingford, UK (1999) |
38 | Kataoka S. Functional effects of Japanese style fermented soy sauce (shoyu) and its components. J. Biosci. Bioeng. 100: 227-234 (2005) DOI ScienceOn |
39 | Kim DH, Kim BG, Lee Y, Ryu JY, Lim Y, Hur HG, Ahn JH. Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. J. Biotechnol. 119: 155-162 (2005) DOI ScienceOn |
40 | Kwon D, Jang J, Lee J, Kim Y-S, Shin D-H, Park S. The isoflavonoid aglycone-rich fractions of cheonggukjang, fermented unsalted soybeans, enhance insulin signaling, and peroxisome proliferator-activated activity in vitro. Biofactors 26: 245-258 (2006) DOI |
41 | Klus K, Barz W. Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe. Arch. Microbiol. 164: 428-434 (1995) DOI |
42 | He XZ, Reddy JT, Dixon RA. Stress responses in alfalfa (Medicago sativa L). XXII. cDNA cloning and characterization of an elicitorinducible isoflavone 7-O-methyltransferase. Plant Mol. Biol. 36: 43-54 (1998) DOI ScienceOn |
43 | French CE, Bruce NC. Bacterial morphinone reductase is related to old yellow enzyme. Biochem. J. 312: 671-678 (1995) DOI |
44 | Shimakage A, Shinbo M, Yamada S, Ito H. Changes in isoflavone content in soybeans during the manufacturing processes of tubunatto and hikiwari-natto. J. Jpn. Soc. Food Sci. Technol. 53: 185-188 (2006) DOI |
45 | Ismail B, Hayes K. activity toward different glycosidic forms of isoflavones. J. Agr. Food Chem. 53: 4918-4924 (2005) DOI ScienceOn |
46 | Kim BG, Kim H, Hur HG, Lim Y, Ahn JH. Regioselectivity of 7-Omethyltransferase of poplar to flavones. J. Biotechnol. 126: 241-247 (2006) DOI ScienceOn |