Formation of succinyl genistin and succinyl daidzin by Bacillus species.
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).
Park
Chan Uk
CU
Dept. of Food Science and Technology, Seoul Natl. Univ. of Technology, Seoul, Republic of Korea.
Jeong
Min Kyu
MK
Park
Min Hee
MH
Yeu
JooDong
J
Park
Myeong Soo
MS
Kim
Mi-Ja
MJ
Ahn
Seon Min
SM
Chang
Pahn-Shick
PS
Lee
JaeHwan
J
D001412:Bacillus subtilis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004317:Doxorubicin / Q000031:analogs & derivatives / Q000378:metabolism; D005285:Fermentation; D005960:Glucosides / Q000032:analysis; D007529:Isoflavones / Q000096:biosynthesis* / Q000302:isolation & purification / Q000378:metabolism; D013386:Succinates / Q000378:metabolism
D005960:Glucosides; D007529:Isoflavones; D013386:Succinates; C074869:7-deoxy-13-dihydroadriamycinone; C040641:genistin; C013908:daidzin; D004317:Doxorubicin