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1.
Isolation of human intestinal bacteria metabolizing the natural isoflavone glycosides daidzin and genistin 总被引:9,自引:0,他引:9
Fecal bacteria from a healthy individual were screened for the specific bacteria involved in the metabolism of dietary isoflavonoids. Two strains of bacteria capable of producing primary and secondary metabolites from the natural isoflavone glycosides daidzin and genistin were detected. The metabolites were identified by comparison of their HPLC/mass, 1H NMR and UV spectra with those of standard and synthetic compounds. Both Escherichia coli HGH21 and the gram-positive strain HGH6 converted daidzin and genistin to the their respective aglycones daidzein and genistein. Under anoxic conditions, strain HGH6 further metabolized the isoflavones daidzein and genistein to dihydrodaidzein and dihydrogenistein, respectively. The reduction of a double bond between C-2 and C-3 to a single bond was isoflavonoid-specific by strain HGH6, which did not reduce a similar bond in the flavonoids apigenin and chrysin. Strain HGH6 did not further metabolize dihydrodaidzein and dihydrogenistein. This is the first study in which specific colonic bacteria that are involved in the metabolism of daidzin and genistin have been detected. 相似文献
2.
S.-C. Hu K. Hong Y.-C. Song J.-Y. Liu R.-X. Tan 《World journal of microbiology & biotechnology》2009,25(1):115-121
A marine Streptomyces sp. 060524 capable of hydrolyzing the glycosidic bond of isoflavone glycosides, was isolated by detecting its β-glucosidase activity. 5 isoflavone aglycones were isolated from culture filtrates in soybean meal glucose medium. They were
identified as genistein (1), glycitein (2), daidzein (3), 3′,4′,5,7-tetrahydroxyisoflavone (4), and 3′,4′,7-trihydroxyisoflavone (5), based on UV, NMR and mass spectral analysis. The Streptomyces can selectively hydroxylate at the 3′-position in the daidzein and genistein to generate 3′-hydroxydaidzein and 3′-hydroxygenistein,
respectively. The Strain biotransformed more than 90% of soybean isoflavone glycosides into their aglycones within 108 h.
3′-hydroxydaidzein and 3′-hydroxygenistein exhibited stronger cytotoxicity against K562 human chronic leukemia than daidzein
and genistein. 相似文献
3.
In order to produce isoflavone aglycosides effectively, a process of isoflavone hydrolysis by Bacillus subtilis natto NTU-18 (BCRC 80390) was established. This process integrates the three stages for the production of isoflavone aglycosides in one single fermenter, including the growth of B. subtilis natto, production of β-glucosidase, deglycosylation of fed isoflavone glycosides. After 8 h of batch culture of B. subtilis natto NTU-18 in 2 L of soy medium, a total of 3 L of soy isoflavone glucoside solution containing 3.0 mg/mL of daidzin and 1.0 mg/mL of genistin was fed continuously over 34 h. The percentage deglycosylation of daidzin and genistin was 97.7% and 94.6%, respectively. The concentration of daidzein and genistein in the broth reached 1,066.8 μg/mL (4.2 mM) and 351 μg/mL (1.3 mM), respectively, and no residual daidzin or genistin was detected. The productivity of the bioconversion of daidzein and genistein over the 42 h of culture was 25.6 mg/L/h and 8.5 mg/L/h, respectively. This showed that this is an efficient bioconversion process for selective estrogen receptor modulator production. 相似文献
4.
《Journal of Fermentation and Bioengineering》1994,77(4):439-441
A novel isoflavone glycoside-hydrolyzing β-glucosidase produced by Lactobacillus casei subsp. rhamnosus IFO 3425 was solubilized by ultrasonic disruption of the cells in the presence of 2-mercaptoethanol and sorbitol as stabilizer. The β-glucosidase from L. casei subsp. rhamnosus specifically hydrolyzed soybean isoflavone glycosides, namely, daidzin and genistin, converting them to daidzein and genistein, respectively. By contrast, a commercial preparation of almond emulsin β-glucosidase could not hydrolyze these soybean isoflavone glycosides. The undesirably bitter and astringent isoflavone glycosides in soybean were decomposed for the first time with this novel β-glucosidase, an enzyme which has hitherto been considered difficult to solubilize, produced by a lactic acid bacterium. 相似文献
5.
Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047, grown in de Man, Rogosa and Sharpe (MRS) or soymilk media, completely hydrolyzed the isoflavone glucosides, genistin and daidzin at 50 g ml–1, into their respective aglycones, genistein and daidzein within 30 min. Other lactic acid bacteria did not produce -glucosidase, the enzyme responsible for the hydrolysis of isoflavone glucosides, when cultured in MRS medium. Glucoside-hydrolyzing activity was induced in some lactic acid bacteria when cultured in soymilk medium. These strains hydrolyzed 70–80% of genistin into genistein and 25–40% of daidzin into daidzein. 相似文献
6.
Kirakosyan A Kaufman PB Chang SC Warber S Bolling S Vardapetyan H 《Plant cell reports》2006,25(12):1387-1391
A mini-hydroponic growing system was employed for seedlings of kudzu vine (Pueraria montana) and contents of isoflavones (daidzein, genistein, daidzin, genistin, and puerarin) from shoot and root parts of seedlings were analyzed quantitatively. In addition, exogenous cork pieces, polymeric adsorbent, XAD-4, and universal elicitor, methyl jasmonate (MeJA), were used to regulate the production of these isoflavones. It was shown that cork pieces up-regulate the production of daidzein and genistein up to seven- and eight-fold greater than the levels obtained for control roots. In contrast, levels of glucosyl conjugates, daidzin and genistin, decrease up to five- and eight-fold, respectively. Cork treatment also induces the excretion of the root isoflavone constituents into the growth medium. Minimal levels of isoflavones are absorbed by the cork pieces. XAD-4 stimulates the production of glucosyl conjugates, daidzin and genistin, in root parts about 1.5-fold greater than that obtained in control roots. These are the highest amounts of daidzin and genistin that are observed (5.101 and 6.759 mg g−1 dry weight, respectively). In contrast to these two adsorbents, MeJA increases the accumulation of isoflavones in shoot rather than in root parts of seedlings, about three- to four-fold over control levels, with the exception of genistein. These studies reveal new observations on the regulation of isoflavone production in hydroponically grown Pueraria montana plants by two adsorbents (cork pieces and XAD-4) and MeJA elicitor. 相似文献
7.
The human intestinal microbiota may influence the fate of bioactive polyphenols, such as the isoflavone puerarin (daidzein 8-C-glucoside), following their oral intake. Faecal suspensions from 19 healthy subjects were tested for their ability to C-deglycosylate puerarin. Only one of these catalysed this reaction. A rod-shaped Gram-positive bacterium, strain CG19-1, capable of deglycosylating puerarin to daidzein was isolated from the corresponding suspension. However, the strictly anaerobic isolate was unable to utilize puerarin as sole carbon and energy source nor any of the tested carbohydrates. Comparative 16S rRNA gene sequence analysis indicated that strain CG19-1 is a new species of the Lachnospiraceae. Strain CG19-1 also converted other aromatic C-glucosides in addition to puerarin. The xanthone C-glucoside mangiferin was deglycosylated to norathyriol. The flavone C-glucosides homoorientin and vitexin were degraded to 3-(3,4-dihydroxyphenyl)propionic acid via luteolin and 3-(4-hydroxyphenyl)propionic acid respectively. In addition, strain CG19-1 converted flavonoid O-glucosides, but at rates that were lower than those of the C-glucosides tested. The isolate deglycosylated the isoflavone O-glucosides daidzin and genistin to daidzein and genistein respectively. Several O-glucosides of the flavones luteolin and apigenin undergoing deglycosylation were subsequently cleaved to 3-(3,4-dihydroxyphenyl)propionic acid and 3-(4-hydroxyphenyl)propionic acid respectively. Moreover, strain CG19-1 cleaved both O-desmethylangolensin and 6'-hydroxy-O-desmethylangolensin to yield 2-(4-dihydroxyphenyl)propionic acid. The corresponding cleavage product, resorcinol, was only observed for O-desmethylangolensin. 相似文献
8.
Many beneficial effects of probiotics have been reported; however, few have focussed on the effects of Lactobacillus, a probiotic, on the bioconversion of isoflavonoids. We hypothesized that Lactobacillus rhamnosus will modify the metabolism of isoflavone. In an in vitro incubation, L. rhamnosus JCM 2771 produced daidzein from daidzin along with genistein. However, daidzin and genistein were not detected in the incubation
solution of daidzein with L. rhamnosus. In the fecal suspension from a male equol producer with daidzein, equol was detected in the presence of a low or high concentration
of L. rhamnosus. In the fecal incubation with daidzin, the equol concentration increased with an increasing concentration of L. rhamnosus JCM 2771. L. rhamnosus affected the equol production in the in vitro incubation of daidzein with fecal flora from a male equol producer. We demonstrated
for the first time that L. rhamnosus JCM 2771 could produce genistein from daidzin and affect the equol production of fecal flora from a male equol producer in
vitro. 相似文献
9.
Kouji Miyazaki 《Pigment cell & melanoma research》2004,17(4):407-412
The effects of soy isoflavones, genistein and daidzein, which exhibit estrogenic, anti‐estrogenic and/or tyrosine kinase inhibitory activity, on the dendritic morphology of B16 mouse melanoma cells were quantitatively evaluated and compared with those of 17β‐estradiol (Est) and tyrphostin, a tyrosine kinase inhibitor. Dendricity was significantly stimulated in the order of Est >> genistein > daidzein = tyrphostin, but not by glycosides of genistein and daidzein. In competition experiments, Est counteracted the stimulatory activity of genistein and daidzein, but enhanced the activity of tyrphostin additively, suggesting that genistein and daidzein agonized Est. In addition, when the concentration ratios of genistein/Est and daidzein/Est were higher than 5000 and 50 000, respectively, genistein and daidzein agonized Est. In contrast, when the ratio of daidzein/Est was lower than 500, daidzein antagonized Est. Furthermore, genistein and daidzein competed with each other in stimulatory activity. These observations suggest that: 1) dendricity is stimulated by agonists (genistein and daidzein) of Est and tyrosine kinase inhibitors (genistein and tyrphostin), 2) the concentration ratio of isoflavone aglycone/Est is very important as one regulatory factor for estrogenic and/or anti‐estrogenic activity, and 3) daidzein antagonizes not only Est but also genistein. It is concluded that a quantitative and simple dendricity assay using B16 mouse melanoma cells is available to evaluate estrogenic and anti‐estrogenic activity in vitro. 相似文献
10.
Soygerm isoflavones were subjected to fermentation by Bifidobacterium breve. Most of isoflavone glycosides (daidzin, glycitin and genistin) in soygerms were deglycosylated to their corresponding isoflavone aglycones (daidzein, glycitein and genistein) within 24 h fermentation. Fermented isoflavones significantly inhibited pancreatic lipase activity in fermentation-time and dosage dependant manner. When fermented isoflavones were orally administered with olive oil to SD rats, the triglyceride (TG) level in plasma after 2 h of ingestion was significantly lower than the control of only olive oil administered group whereas no such significant decrease in plasma TG was observed in unfermented isoflavone administered group. This result indicates that oral administration of fermented isoflavones effectively suppressed absorption of excessive lipid into a body. Addition of either unfermented or fermented soygerm isoflavones effectively inhibited adipocyte differentiation from 3T3-L1 in a dose dependent manner. In conclusion, B. breve successfully converted soygerm isoflavones into their aglycones, and these aglycones were more effective in suppressing lipid absorption as well as adipocytes differentiation than their glycosides. 相似文献
11.
The original bovine rumen bacterial strain Niu-O16, capable of anaerobically bioconverting isoflavones daidzein and genistein
to dihydrodaidzein (DHD) and dihydrogenistein (DHG), respectively, is a rod-shaped obligate anaerobic bacterium. After a long-term
domestication, an oxygen-tolerant bacterium, which we named Aeroto-Niu-O16 was obtained. Strain Aeroto-Niu-O16, which can
grow in the presence of atmospheric oxygen, differed from the original obligate anaerobic bacterium Niu-O16 by various characteristics,
including a change in bacterial shape (from rod to filament), in biochemical traits (from indole negative to indole positive
and from amylohydrolysis positive to negative), and point mutations in 16S rRNA gene (G398A and G438A). We found that strain
Aeroto-Niu-O16 not only grew aerobically but also converted isoflavones daidzein and genistein to DHD and DHG in the presence
of atmospheric oxygen. The bioconversion rate of daidzein and genistein by strain Aeroto-Niu-O16 was 60.3% and 74.1%, respectively.
And the maximum bioconversion capacity for daidzein was 1.2 and 1.6 mM for genistein. Furthermore, when we added ascorbic
acid (0.15%, m/v) in the cultural medium, the bioconversion rate of daidzein was increased from 60.3% to 71.7%, and that of genistein from
74.1% to 89.2%. This is the first reported oxygen-tolerant isoflavone biotransforming pure culture capable of both growing
and executing the reductive activity under aerobic conditions. 相似文献
12.
Yemin Xue Jinjin Yu Xiangfei Song 《Journal of industrial microbiology & biotechnology》2009,36(11):1401-1408
A recombinant Thermotoga maritima β-glucosidase A (BglA) was purified to homogeneity for performing enzymatic hydrolysis of isoflavone glycosides from soy
flour. The kinetic properties K
m, k
cat, and k
cat/K
m of BglA towards isoflavone glycosides, determined using high-performance liquid chromatography, confirmed the higher efficiency
of BglA in hydrolyzing malonylglycosides than non-conjugated glycosides (daidzin and genistin). During hydrolysis of soy flour
by BglA at 80°C, the isoflavone glycosides (soluble form) were extracted from soy flour (solid state) into the solution (liquid
state) in thermal condition and converted to their aglycones (insoluble form), which mostly existed in the pellet to be separated
from BglA in the reaction solution. The enzymatic hydrolysis in one-step and two-step approaches yielded 0.38 and 0.35 mg
genistein and daidzein per gram of soy flour, respectively. The optimum conditions for conversion of isoflavone aglycones
were 100 U per gram of soy flour, substrate concentration 25% (w/v), and incubation time 3 h for 80°C. 相似文献
13.
Miyazaki K 《Pigment cell research / sponsored by the European Society for Pigment Cell Research and the International Pigment Cell Society》2004,17(4):407-412
The effects of soy isoflavones, genistein and daidzein, which exhibit estrogenic, anti-estrogenic and/or tyrosine kinase inhibitory activity, on the dendritic morphology of B16 mouse melanoma cells were quantitatively evaluated and compared with those of 17 beta-estradiol (Est) and tyrphostin, a tyrosine kinase inhibitor. Dendricity was significantly stimulated in the order of Est > genistein > daidzein = tyrphostin, but not by glycosides of genistein and daidzein. In competition experiments, Est counteracted the stimulatory activity of genistein and daidzein, but enhanced the activity of tyrphostin additively, suggesting that genistein and daidzein agonized Est. In addition, when the concentration ratios of genistein/Est and daidzein/Est were higher than 5000 and 50,000, respectively, genistein and daidzein agonized Est. In contrast, when the ratio of daidzein/Est was lower than 500, daidzein antagonized Est. Furthermore, genistein and daidzein competed with each other in stimulatory activity. These observations suggest that: 1) dendricity is stimulated by agonists (genistein and daidzein) of Est and tyrosine kinase inhibitors (genistein and tyrphostin), 2) the concentration ratio of isoflavone aglycone/Est is very important as one regulatory factor for estrogenic and/or anti-estrogenic activity, and 3) daidzein antagonizes not only Est but also genistein. It is concluded that a quantitative and simple dendricity assay using B16 mouse melanoma cells is available to evaluate estrogenic and anti-estrogenic activity in vitro. 相似文献
14.
Chang-Won Cho Hyun-Cheol Jeong Hee-Do Hong Young-Chan Kim Sang Yoon Choi Kyungtack Kim Jin Yeul Ma Young-Chul Lee 《Biotechnology and Bioprocess Engineering》2012,17(5):1062-1067
In this study, the possible application of Lactobacillus strains as a functional starter culture to ferment Samso-Eum (SE), an oriental herbal medicine formula, and the production of bioactive isoflavones (daidzein, genistein) were investigated. Four strains of Lactobacillus (Lactobacillus plantarum KFRI 144, L. amylophilus KFRI 161, L. curvatus KFRI 166, and L. bulgaricus KFRI 344) were used for SE fermentation. Declines in pH and in viable cell counts during fermentation were investigated and the quantification of isoflavones using HPLC were performed after fermentation at 37°C for 48 h. All the tested Lactobacillus strains lowered the pH level to approximately 3.6 after 48 h and showed the highest level of growth at 24 h during SE fermentation. During the SE fermentation of the four Lactobacillus strains, the conversion of isoflavone glycosides (daidzin, genistin) into bioactive aglycones (daidzein, genistein) was observed in all of the fermentations, but with different rates depending on the strains. L. plantarum KFRI 144 and L. amylophilus KFRI 161 exhibited the highest bioconversion rate of isoflavone glycosides into their bioactive aglycones. These results demonstrate that L. plantarum KFRI 144 and L. amylophilus KFRI 161 have potentials as functional starter cultures for manufacturing fermented SE with higher isoflavone bioavailability. 相似文献
15.
《Bioscience, biotechnology, and biochemistry》2013,77(12):2626-2631
Soybean extracts (SBE) containing isoflavone glycosides were cultured with Ganoderma lucidum mycelia producing β-glucosidase. The anti-angiogenic effects of the cultivated product, containing rich in genistein, named GCP (genistein combined polysaccharide), were assessed with chick chorioallantoic membranes (CAM) and a mouse dorsal air-sac model. β-Glucosidase produced by the mycelia converted the isoflavone glycosides into aglycons. A test of volunteers showed that serum concentrations of genistein in the subjects treated with GCP (n=4) at 3 h after administration were significantly higher than those in the subjects treated with SBE (n=4).GCP inhibited angiogenesis in CAM, and the activity of GCP was greater than that of SBE. GCP inhibited the formation of new vessels induced by colon carcinoma cells in vivo. 相似文献
16.
Hydrolysis of isoflavone glycosides by Bacillus subtilis natto NTU-18 in black soymilk is reported. At the concentration of 3–5% (w/v), black soymilk in flask cultures, the isoflavones, daidzin, and genistin were highly deglycosylated within 24 h. Deglycosylation of isoflavones was further carried out in a 7-l fermenter with 5% black soymilk. During the fermentation, viable cells increased from 103 to 109 CFU ml−1 in 15 h, and the activity of β-glucosidase appeared at 8 h after inoculation and reached a maximum (3.3 U/ml) at 12 h, then decreased rapidly. Deglycosylation of isoflavone glycosides was observed at the same period, the deglycosylation rate of daidzin and genistin at 24 h was 100 and 75%, respectively. It is significantly higher than the previous reports of fermentation with lactic acid bacteria. In accordance with the deglycosylation of isoflavone glycosides, the estrogenic activity of the 24 h fermented black soymilk for ERβ estrogen receptor increased to threefold; meanwhile, the fermented broth activated ERα estrogen receptor to a less extent than ERβ. These results suggest that this fermentation effectively hydrolyzed the glycosides from isoflavone in black soymilk and the fermented black soymilk has the potential to be applied to selective estrogen receptor modulator products. 相似文献
17.
Raimondi S Roncaglia L De Lucia M Amaretti A Leonardi A Pagnoni UM Rossi M 《Applied microbiology and biotechnology》2009,81(5):943-950
Twenty-two strains of Bifidobacterium, representative of eight major species of human origin, were screened for their ability to transform the isoflavones daidzin
and daidzein. Most of the strains released the aglycone from daidzin and 12 gave yields higher than 90%. The kinetics of growth,
daidzin consumption, and daidzein production indicated that the hydrolytic activity occurred during the growth. The supernatant
of the majority of the strains did not release the aglycone from daidzin, suggesting that cell-associated β-glucosidases (β-Glu)
are mainly responsible for the metabolism of soybean glyco-conjugates. Cell-associated β-Glu was mainly intracellular and
significantly varied among the species and the strains. The lack of β-Glu was correlated with the inability to hydrolyze daidzin.
Although S-equol production by anaerobic intestinal bacteria has been established, information on S-equol-producing bifidobacteria
is contradictory. In this study, 22 bifidobacteria failed to transform daidzein into reduced metabolites under all the experimental
conditions, excluding any role in the reductive pathway of daidzein toward the production of S-equol. These results suggest
that selected probiotic strains of Bifidobacterium can be used to speed up the release of daidzein, improving its bioavailability for absorption by colonic mucosa and/or biotransformation
to S-equol by other intestinal microorganisms. 相似文献
18.
Release of Flavonoids by the Soybean Cultivars McCall and Peking
and Their Perception as Signals by the Nitrogen-Fixing Symbiont
Sinorhizobium fredii 总被引:1,自引:0,他引:1
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Steven G. Pueppke Maria Cristina Bola?os-Vásquez Dietrich Werner Marie-Pierre Bec-Ferté Jean-Claude Promé Hari B. Krishnan 《Plant physiology》1998,117(2):599-606
Sinorhizobium fredii strain USDA191 forms N-fixing nodules on the soybean (Glycine max L. Merr.) cultivars (cvs) McCall and Peking, but S. fredii strain USDA257 nodulates only cv Peking. We wondered whether specificity in this system is conditioned by the release of unique flavonoid signals from one of the cultivars or by differential perception of signals by the strains. We isolated flavonoids and used nodC and nolX, which are nod-box-dependent and -independent nod genes, respectively, to determine how signals activate genes in the microsymbionts. Seeds of cv McCall and cv Peking contain the isoflavones daidzein, genistein, and glycitein, as well as their glucosyl and malonylglucosyl glycosides. Roots exude picomolar concentrations of daidzein, genistein, glycitein, and coumestrol. Amounts are generally higher in cv Peking than in cv McCall, and the presence of rhizobia markedly influences the level of specific signals. Nanomolar concentrations of daidzein, genistein, and coumestrol induce expression of nodC and nolX in strain USDA257, but the relative nolX-inducing activities of these signals differ in strain USDA191. Glycitein and the conjugates are inactive. Strain USDA257 deglycosylates daidzin and genistin into daidzein and genistein, respectively, thereby converting inactive precursors into active inducers. Although neither soybean cultivar contains unique nod-gene-inducing flavonoids, strain- and cultivar-specific interactions are characterized by distinct patterns of signal release and response. 相似文献
19.
20.
Ajdžanović V Spasojević I Sošić-Jurjević B Filipović B Trifunović S Sekulić M Milošević V 《The Journal of membrane biology》2011,239(3):131-135
A decrease of erythrocyte membrane fluidity can contribute to the pathophysiology of hypertension. Soy products, which are
used as alternative therapeutics in some cardiovascular conditions, contain various isoflavones (genistein, daidzein, and
their glucosides, genistin and daidzin), which can incorporate cellular membrane and change its fluidity. The aim of this
study was to examine the effects of soy extract (which generally corresponds to the soy products of isoflavone composition)
on erythrocyte membrane fluidity at graded depths. We used electron paramagnetic resonance spectroscopy and fatty acid spin
probes (5-DS and 12-DS), the spectra of which are dependent on membrane fluidity. After being treated with soy extract, erythrocytes
showed a significant (P = 0.016) decrease of membrane fluidity near the hydrophilic surface, while there were no significant changes of fluidity
in deeper hydrophobic membrane regions. These results suggest that soy products containing high levels of genistein and isoflavone
glucosides may not be suitable for use in hypertension because they decrease erythrocyte membrane fluidity. 相似文献