Formation of Succinyl Genistin and Succinyl Daidzin by Bacillus Species

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. St...

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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
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Abstract	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).
AbstractList	6-O-Succinyl-4'-hydroxyisoflavone-7-O-b-D-glucopyranoside (succinyl-b-daidzin) and 6-O-succinyl-6,4'-dihydroxyisoflavone-7-O-b-D-glucopyranoside (succinyl-b-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-b-daidzin and succinyl-b-genistin were monitored by high-performance liquid chromatography (HPLC). Samples containing Bacillus with daidzin and genistin produced succinyl-b-daidzin and succinyl-b-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 b-glucosides and aglycones of isoflavones decreased significantly for 8 h incubation (P < 0.05). 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). 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). [PUBLICATION ABSTRACT] 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). 6''-O-Succinyl-4'-hydroxyisoflavone-7-O-beta-D-glucopyranoside (succinyl-beta-daidzin) and 6''-O-succinyl-6,4'-dihydroxyisoflavone-7-O-beta-D-glucopyranoside (succinyl-beta-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-beta-daidzin and succinyl-beta-genistin were monitored by high-performance liquid chromatography (HPLC). Samples containing Bacillus with daidzin and genistin produced succinyl-beta-daidzin and succinyl-beta-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 beta-glucosides and aglycones of isoflavones decreased significantly for 8 h incubation (P < 0.05). 6''-O-Succinyl-4'-hydroxyisoflavone-7-O-beta-D-glucopyranoside (succinyl-beta-daidzin) and 6''-O-succinyl-6,4'-dihydroxyisoflavone-7-O-beta-D-glucopyranoside (succinyl-beta-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-beta-daidzin and succinyl-beta-genistin were monitored by high-performance liquid chromatography (HPLC). Samples containing Bacillus with daidzin and genistin produced succinyl-beta-daidzin and succinyl-beta-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 beta-glucosides and aglycones of isoflavones decreased significantly for 8 h incubation (P < 0.05).
Author	Park, Chan Uk Jeong, Min Kyu Park, Min Hee Lee, JaeHwan Kim, Mi-Ja Park, Myeong Soo Yeu, JooDong Chang, Pahn-Shick Ahn, Seon Min
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Keywords	Isoflavone B. subtilis natto isoflavones Bacillus subtilis Natto succinyl-β-daidzin Bacillaceae Flavonoid Phytoestrogen Polyphenol Bacillales succinyl-β-genistin Bacteria Species
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Snippet	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... 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... 6''-O-Succinyl-4'-hydroxyisoflavone-7-O-beta-D-glucopyranoside (succinyl-beta-daidzin) and 6''-O-succinyl-6,4'-dihydroxyisoflavone-7-O-beta-D-glucopyranoside... 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... 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... 6-O-Succinyl-4'-hydroxyisoflavone-7-O-b-D-glucopyranoside (succinyl-b-daidzin) and 6-O-succinyl-6,4'-dihydroxyisoflavone-7-O-b-D-glucopyranoside...
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SubjectTerms	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
Title	Formation of Succinyl Genistin and Succinyl Daidzin by Bacillus Species
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