Metabolism of Isoflavone Derivatives During Manufacturing of Traditional Meju and Doenjang

  • Jang, Chan-Ho (Department of Animal Science and Biotechnology, Kyungpook National University) ;
  • Park, Chun-Seok (Department of Food Science and Technology, Kyunghee University) ;
  • Lim, Jin-Kyu (Department of Animal Science and Biotechnology, Kyungpook National University) ;
  • Kim, Jeong-Hwan (Department of Food Science and Technology, Gyeongsang National University) ;
  • Kwon, Dae-Young (Korea Food Research Institute) ;
  • Kim, Yong-Suk (Research Center for Industrial Development of BioFood Materials and Faculty of Biotechnology, Chonbuk National University) ;
  • Shin, Dong-Hwa (Research Center for Industrial Development of BioFood Materials and Faculty of Biotechnology, Chonbuk National University) ;
  • Kim, Jong-Sang (Department of Animal Science and Biotechnology, Kyungpook National University)
  • Published : 2008.04.30

Abstract

Meju, a major ingredient of doenjang which is a popular Korean traditional fermented soyfood, was manufactured by fermenting steamed soybeans in natural environment in which steamed soy was exposed to airborne microorganism, in particular, fungi. Total isoflavone content was reduced from 1,849 mg/kg of cooked soy to 816 mg/kg of meju at the $90^{th}$ day of fermentation. Total glycosides and aglycones of isoflavones in meju were 1,827 and 22 mg/kg at 0 day and changed into 487 and 329 mg/kg at the 90th day of fermentation, respectively. Meanwhile, the ratio of glycosides to aglycones of isoflavones was not changed during aging of doenjang but remained relatively constant with 592 and 644 mg/kg aglycones at the 0 and $160^{th}$ day, respectively. When cooked soy was fermented with Aspergillus oryzae and Aspergillus flavus, isoflavone profiles were significantly different from each other while A. oryzae caused more extensive metabolism of isoflavones than A. flavus.

Keywords

References

  1. Messina M. Modern applications for an ancient bean: Soybeans and the prevention and treatment of chronic disease. J. Nutr. 125: 567S-569S (1995)
  2. Allred CD, Allred KF, Ju YH, Goeppinger TS, Doerge DR, Helferich WG. Soy processing influences growth of estrogendependent breast cancer tumors. Carcinogenesis 25: 1649-1657 (2005)
  3. Kim JH, Lim HA, Lee JS, Sung MK, Kim YK, Yu RN, Kim JS. Effect of low doses of genistein and equol on protein expression profile in MCF-7 cells. Food Sci. Biotechnol. 14: 854-859 (2005)
  4. Zubik L, Meydani M. Bioavailability of soybean isoflavones from aglycone and glucoside forms in American women. Am. J. Clin. Nutr. 77: 1459-1465 (2003) https://doi.org/10.1093/ajcn/77.6.1459
  5. Watkins BA, Reinwald S, Li Y, Seifert MF. Protective actions of soy isoflavones and n-3 PUFAs on bone mass in ovariectomized rats. J. Nutr. Biochem. 16: 479-488 (2005) https://doi.org/10.1016/j.jnutbio.2005.01.019
  6. Omoni AO, Aluko RE. Soybean foods and their benefits: Potential mechanisms of action. Nutr. Rev. 63: 272-283 (2005) https://doi.org/10.1111/j.1753-4887.2005.tb00141.x
  7. Bingham SA, Atkinson C, Liggins J, Bluck L, Coward A. Phytooestrogens: Where are we now? Brit. J. Nutr. 79: 393-406 (1998) https://doi.org/10.1079/BJN19980068
  8. Park KY, Jung KO, Rhee SH, Choi YH. Antimutagenic effects of doenjang (Korean fermented soypaste) and its active compounds. Mutat. Res. 523-524: 43-53 (2003) https://doi.org/10.1016/S0027-5107(02)00320-2
  9. Omoni AO, Aluko RE. Soybean foods and their benefits: Potential mechanisms of action. Nutr. Rev. 63: 272-283 (2005) https://doi.org/10.1111/j.1753-4887.2005.tb00141.x
  10. Cornwell T, Cohick W, Raskin I. Dietary phytoestrogens and health. Phytochemistry 65: 995-1016 (2004) https://doi.org/10.1016/j.phytochem.2004.03.005
  11. Ososki AL, Kennelly EJ. Phytoestrogens: A review of the present state of research. Phytother. Res. 17: 845-869 (2003) https://doi.org/10.1002/ptr.1364
  12. Choi YB, Rhee, JS, Lee YB, Nam SY, Kim KS. Extraction of isoflavones from soybean hypocotyls using aqueous ethanol. Food Sci. Biotechnol 13: 719-723 (2004)
  13. Murphy PA, Song T, Buseman G, Barua K, Beecher GR, Trainer D, Holden J. Isoflavones in retail and institutional soy foods. J. Agr. Food Chem. 47: 2697-2704 (1999) https://doi.org/10.1021/jf981144o
  14. Coward L, Smith M, Kirk M, Barnes S. Chemical modification of isoflavones in soyfoods during cooking and processing. Am. J. Clin. Nutr. 68 (6 Suppl): 1486S-1491S (1998) https://doi.org/10.1093/ajcn/68.6.1486S
  15. Murphy PA, Song T, Buseman G, Barua K. Isoflavones in soy-based infant formula. J. Agr. Food Chem. 45: 4635-4638 (1997) https://doi.org/10.1021/jf970590t
  16. Lee IH, Chou CC. Distribution profiles of isoflavone isomers in black bean kojis prepared with various filamentous fungi. J. Agr. Food Chem. 54: 1309-1314 (2006) https://doi.org/10.1021/jf058139m
  17. Steensma A, Faassen-Peters MA, Noteborn HP. Rietjens IM. Bioavailability of genistein and its glycoside genistin as measured in the portal vein of freely moving unanesthetized rats. J. Agr. Food Chem. 54: 8006-8012 (2006) https://doi.org/10.1021/jf060783t
  18. Kano M, Takayanagi T, Harada K, Sawada S, Ishikawa F. Bioavailability of isoflavones after ingestion of soy beverages in healthy adults. J. Nutr. 136: 2291-2296 (2006) https://doi.org/10.1093/jn/136.9.2291
  19. Setchell KDR, Brown NM, Zimmer-Nechemias L, Brashear WT, Wolfe BE, Kirschner AS, Heubi JE. Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability. Am. J. Clin. Nutr. 76: 447-453 (2002) https://doi.org/10.1093/ajcn/76.2.447
  20. Brown JP. Hydrolysis of glycosides and esters. pp. 109-144. In: Role of the Gut Flora in Toxicity and Cancer. Rowland I (ed). Academic Press, San Diego, CA, USA (1988)
  21. Cassidy A, Brown JE, Hawdon A, Faughnan MS, King LJ, Millward J, Zimmer-Nechemias L, Wolfe B, Setchell KD. Factors affecting the bioavailability of soy isoflavones in humans after ingestion of physiologically relevant levels from different soy foods. J. Nutr. 136: 45-51 (2006) https://doi.org/10.1093/jn/136.1.45
  22. Jang CH, Lim JK, Kim JH, Park CS, Kwon DY, Kim YS, Shin DH, Kim JS. Change of isoflavone content during manufacturing of cheonggukjang, a traditional Korean fermented soyfood. Food Sci. Biotechnol. 15: 643-646 (2006)
  23. Jung KO, Park SY, Park KY. Longer aging time increases the anticancer and antimetastatic properties of doenjang. Nutrition 22: 539-545 (2006) https://doi.org/10.1016/j.nut.2005.11.007
  24. Choi UK, Jeong Y-S, Kim M-H, Lee NH, Hwang Y-H. Quality charactistics of meju according to germination time of raw soybean (Glycine max: 'Hwanggeumkong'). Food Sci. Biotechnol. 16: 386-391 (2007)
  25. Choi UK, Kim M-H, Lee NH, Hwang Y-H. The characteristics of cheonggukjang, a fermented soybean product by the degree of germination of raw soybeans. Food Sci. Biotechnol. 16: 734-739 (2007)