Formation of Succinyl Genistin and Succinyl Daidzin by Bacillus Species

• Published in: Journal of food science Vol. 75; no. 1; pp. C128 - C133
• Main Authors: Park, Chan Uk, Jeong, Min Kyu, Park, Min Hee, Yeu, JooDong, Park, Myeong Soo, Kim, Mi-Ja, Ahn, Seon Min, Chang, Pahn-Shick, Lee, JaeHwan
• Format: Journal Article
• Language: English
• Published: Malden, USA Blackwell Publishing Inc 2010; Wiley; Wiley Subscription Services, Inc
• Subjects: B. subtilis natto; Bacillus; Bacillus (bacteria); Bacillus subtilis; Bacillus subtilis - metabolism; Bacteria; Biological and medical sciences; cheonggukjang; Chromatography; Chromatography, High Pressure Liquid; daidzin; Doxorubicin - analogs & derivatives; Doxorubicin - metabolism; Enzymes; Fermentation; fermented foods; food analysis; food composition; Food industries; Food microbiology; Food science; Fundamental and applied biological sciences. Psychology; genistin; glucosides; Glucosides - analysis; isoflavones; Isoflavones - biosynthesis; Isoflavones - isolation & purification; Isoflavones - metabolism; natto; soybean products; Succinates - metabolism; succinyl genistin; succinyl-β-daidzin; succinyl-β-genistin; Isoflavone; B. subtilis natto; isoflavones; Bacillus subtilis; Natto; succinyl-β-daidzin; Bacillaceae; Flavonoid; Phytoestrogen; Polyphenol; Bacillales; succinyl-β-genistin; Bacteria; Species
• ISSN: 0022-1147; 1750-3841
• DOI: 10.1111/j.1750-3841.2009.01453.x

6″-O-Succinyl-4′-hydroxyisoflavone-7-O-β-D-glucopyranoside (succinyl-β-daidzin) and 6″-O-succinyl-6,4′-dihydroxyisoflavone-7-O-β-D-glucopyranoside (succinyl-β-genistin), 2 new isoflavone metabolites, are found in cheonggukjang or natto, traditional soy-based foods fermented with Bacillus species. Standard isoflavones including daidzin, genistin, daidzein, and genistein, and mixtures of isoflavones extracted from roasted soybeans were added to the medium growing Bacillus subtilis or B. subtilis natto and formation of succinyl-β-daidzin and succinyl-β-genistin were monitored by high-performance liquid chromatography (HPLC). Samples containing Bacillus with daidzin and genistin produced succinyl-β-daidzin and succinyl-β-genistin, respectively, while those with daidzein and genistein did not produce succinyl derivatives. Daidzin in samples with B. subtilis and B. subtilis natto decreased by 39.7% and 10.7%, respectively, for 4 h incubation while genistin decreased by 66.8% and 17.6%, respectively. Genistein decreased faster than daidzein during incubation with B. subtilis or B. subtilis natto without formation of succinyl derivatives. In the case of mixture of isoflavones, succinyl derivatives increased and β-glucosides and aglycones of isoflavones decreased significantly for 8 h incubation (P < 0.05).