• Archives of Pharmacal Research
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• v.21 no.1
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• pp.17-23
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• 1998

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing ${\alpha}$-rhamnosidase, exo-${\beta}$-glucosidase, endo- ${\beta}$-glucosidase and/or ${\beta}$-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing ${\alpha}$-rhamnosidase and ${\beta}$-glucosidase or endo- ${\beta}$-glucosidase, and baicatin, puerarin and daidzin were transformed to their aglycones by the bacteria producing ${\beta}$glucuronidase, C-glycosidase and ${\beta}$-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaidehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

• The Korean Journal of Food And Nutrition
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• v.34 no.2
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• pp.187-195
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• 2021

This study was performed to investigate the antioxidant and antidiabetic activities of soybean fermented with Monascus. Also, the changes in the content of isoflavones and Monacolin K were analyzed. It was observed that the glycoside forms of daidzin and genistin were converted to aglycones of daidzein and genistein within 6 days of fermentation. The product can be used as a health functional material that can increase bioavailability. Monacolin K production was found to increase significantly with the progression of fermentation with an increase to 0.04 mg/g and 0.44 mg/g on 6 and 12 days of fermentation, respectively. The DPPH radical scavenging activity of soybean fermented with Monascus was significantly increased compared to that of soybean. The protein expression of inflammation-related genes (TNF-α, IL-6, and COX-2) in the MIN cell was significantly increased in the presence of alloxan compared to the normal group, but a decrease was observed in the presence of soybean fermented with Monascus. In conclusion, soybean fermented with Monascus showed the highest antidiabetic and antioxidant effects. These results suggest that soybean fermented with Monascus has the potential to be used as a beneficial ingredient with antidiabetic and antioxidant effects.

• Journal of Microbiology and Biotechnology
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• v.18 no.3
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• pp.573-578
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• 2008

Lactobacillus paraplantarum KM (Lp), Weissella sp. 33 (Ws), and Enterococcus faecium 35 (Ef) were used in single (Lp, Ws, Ef) or mixed cultures (Lp+Ws, Lp+Ef, Ws+Ef) for soy milk fermentation ($37^{\circ}C$, 12 h). After 12 h, the cell numbers, pH, and TA of soymilk were $7.4{\times}10^8-6.0{\times}10^9CFU/ml$, 3.8-4.5, and 0.59-0.70%, respectively. Changes in the contents of glycitin and genistin in soymilk fermented with Ef were not significant. The contents of isoflavone glucosides in soymilk fermented with the other cultures decreased significantly with an increase of aglycone contents (p<0.05). It corresponded well with a sharp increase in ${\beta}$-glucosidase activity during fermentation. About 92-100% of the daidzin and 98-100% of the genistin in soymilk were converted to corresponding aglycones by Lp, Ws, or Lp+Ef within 12 h.

• Korean Journal of Agricultural Science
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• v.43 no.5
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• pp.742-749
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• 2016

Boar taint, an unpleasant odor of pork, is associated with two substances including androstenone and skatole. Testosterone is a steroid hormone as well as a strong predictor for androstenone secretion. Isoflavones of soy origin play a role in modulating the metabolism of sex hormones. Although several methods responsible for reducing boar taint are under investigation, the precise mechanism by which isoflavones reduce testosterone has not yet been identified. The objective of the current study was to investigate the effects of isoflavones extracted from a soy by-product on the concentration of serum testosterone in mouse. A total of 24 mice were supplemented with basal diet (control), daidzin plus genistin mix (T1), or isoflavone extracts (T2). After 11 days of treatment, size and weight of testis, as well as the concentration of sex hormones, including testosterone and estrogen, were analyzed. There was no difference in size or weight of testis from mice among control, T1, and T2. Serum testosterone levels were significantly decreased (p < 0.05) both in T1 and T2 when compared with the control group. Furthermore, estrogen concentration in blood was increased (p < 0.05) in T2 (numerically increased in T1) compared with the control group. Taken together, the use of isoflavones extracted from soy by-products would be a plausible strategy for reducing testosterone level, ultimately reducing boar taint without castration of piglets.

• Journal of the Korean Society of Food Culture
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• v.31 no.3
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• pp.213-219
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• 2016

Analysis of nutritional compositions of soybean sprouts cultivated with bamboo ash was carried out. Bamboo ash was utilized as sprouting water of soybeans and adjusted to 0.2, 0.6, 1.0, 1.4, 2.0, 6.0 and 10.0 g/L. Stem length and contents of isoflavone (daidzin, glycitin, genestin, daidzein, glycitein, and genestein) and vitamin C in soybean sprouts cultivated with 0.2 g/L were higher than those in soybean sprouts cultivated with only water. Potassium, magnesium, and calcium of all cultivation methods were detected in higher contents than others. In particular, potassium showed a high absorption rate in the soybean sprouts. The major amino acid was asparagine (616.05~849.15 mg/100 g, soybean eq.), and contents of lysine, leucine, and ornithine in soybean sprouts cultivated at 0.2 g/L were higher than those of methods by only water and addition of 6-benzylaminopurine. According to the results, soybean sprouts cultivated with 0.2 g/L of bamboo ash were effective for increasing nutritional compositions.

• Korean Journal of Medicinal Crop Science
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• v.19 no.6
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• pp.446-455
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• 2011

Galgeun-tang (GGT) is a traditional medicinal formula that is widely prescribed to treat cold, asthma, and hives in Korea. Fermented herbal medicines can be made more effective than normal herbal medicines by increasing the absorption and bioavailability of the active compounds. In this study, we fermented Galgeun-tang to produce bioconversion constituents using Lactobacillus plantarum (GGT144), and found that four peaks were decreased, three peaks were increased and two new peaks appeared in the HPLC-DAD chromatogram. After HPLC-DAD-guided fractionation of the newly-appearing compounds (1 and 5) and the increased (6, 7, and 9) compounds, the structure of the compounds was determined using NMR and MS. Using this approach the compounds were identified to be pyrogallol (1), daidzein (5), liquiritigenin (6), cinnamyl alcohol (7), and formononetin (9), respectively. In addition, the decreased compounds were identified to be daidzin (2), liquiritin (3), ononin (4), and cinnam aldehyde (8) using HPLC-DAD analysis with standard compounds. The high performance liquid chromatography method was used to quantify the nine constituents in GGT and GGT144. All calibration curves of the standard compounds displayed excellent linearity with a $R^2$ > 0.9968.

• Journal of Applied Biological Chemistry
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• v.52 no.4
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• pp.163-169
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• 2009

A total of 155 microbial strains were isolated from the Korean traditional soybean paste based on their morphological features on the growth of agar plate. Among the isolated strains, a total of 28 strains were capable of hydrolyzing isoflavone glycoside to isoflavone aglycone efficiently in the soybean paste. Finally, two strains, K123-1 and SI, were selected because of their resistance to 15% NaCl and ability to convert isoflavone glycoside to isoflavone aglycone efficiently during the fermentation of soybean paste. The isolated strains K123-1 and SI were identified to be Pichia guilliermondii and Candida fermentati, respectively, using the partial 26S rDNA sequence analysis and phylogenic analysis. Pichia guilliermondii K123-1 and Candida fermentati SI converted daidzin to daidzein up to 96% and 95%, respectively, and genistin to genistein up to 92% when soybean pastes were fermented at $30^{\circ}C$ for 20 days with a single isolated strain. Pichia guilliermondii K123-1 and Candida fermentati SI were able to grow in the presence of 15% NaCl on both liquid medium and agar plate. We think that Pichia guilliermondii K123-1 and Candida fermentati SI might be one of good candidates for making functional soybean paste because they are isolated from the Korean traditional soybean paste and have a good ability to convert isoflavone glycosides to isoflavone aglycones and a high salt tolerance.

• Molecules and Cells
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• v.37 no.2
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• pp.172-177
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• 2014

A glycosyltransferase, YjiC, from Bacillus licheniformis has been used for the modification of the commercially available isoflavonoids genistein, daidzein, biochanin A and formononetin. The in vitro glycosylation reaction, using UDP-${\alpha}$-D-glucose as a donor for the glucose moiety and aforementioned four acceptor molecules, showed the prominent glycosylation at 4' and 7 hydroxyl groups, but not at the $5^{th}$ hydroxyl group of the A-ring, resulting in the production of genistein 4'-O-${\beta}$-D-glucoside, genistein 7-O-${\beta}$-D-glucoside (genistin), genistein 4',7-O-${\beta}$-D-diglucoside, biochanin A-7-O-${\beta}$-D-glucoside (sissotrin), daidzein 4'-O-${\beta}$-D-glucoside, daidzein 7-O-${\beta}$-D-glucoside (daidzin), daidzein 4', 7-O-${\beta}$-D-diglucoside, and formononetin 7-O-${\beta}$-D-glucoside (ononin). The structures of all the products were elucidated using high performance liquid chromatography-photo diode array and high resolution quadrupole time-of-flight electrospray ionization mass spectrometry (HR QTOF-ESI/MS) analysis, and were compared with commercially available standard compounds. Significantly higher bioconversion rates of all four isoflavonoids was observed in both in vitro as well as in vivo bioconversion reactions. The in vivo fermentation of the isoflavonoids by applying engineered E. coli $BL21(DE3)/{\Delta}pgi{\Delta}zwf{\Delta}ushA$ overexpressing phosphoglucomutase (pgm) and glucose 1-phosphate uridyltransferase (galU), along with YjiC, found more than 60% average conversion of $200{\mu}M$ of supplemented isoflavonoids, without any additional UDP-${\alpha}$-D-glucose added in fermentation medium, which could be very beneficial to large scale industrial production of isoflavonoid glucosides.

• Korean Journal of Food Science and Technology
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• v.31 no.5
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• pp.1254-1261
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• 1999

The influence of addition of arrow(Pueraria hirsuta Matsum) root flour and its fractions by ultrafiltration on the flow properties of the rice flour-water systems were investigated. The flow properties of rice flour pastes during cold storage$(5^{\circ}C)$ were measured and the components from arrow root flour responsible for changes of flow properties were screened. Addition of arrow root flour significantly changed the flow properties of rice flour pastes. Permeate fractions by ultrafiltration, representing low molecular weight component fraction, significantly affected the flow property of rice flour paste stored at $5^{\circ}C$. Addition of permeate fraction to rice flour pastes rapidly decreased the consistency index, yield stress and pseudoplasticity, and showed a stability of flow property during storage suggesting the retardation of rice starch retrogradation. Permeate fractions of ultrafiltration were identified as puerarin, daidzein and daidzin known to representive isoflavonoid from arrow root.

• Food Science of Animal Resources
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• v.27 no.3
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• pp.329-336
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• 2007

This study was designed to find the optimum conditions for converting isoflavone glycoside to aglycone by ${\beta}-galactosidase$. Three different forms of the enzyme were tested and the optimum enzyme concentration, incubation temperature, pH, and incubation time were determined. Before treatment with enzyme, isoflavone contained 89.4% glycoside including daidzin, glycitin and genistin, and only 10.6% aglycone including daidzein, glycitein and genistein. Among the enzymes tested, the highest rate of isoflavone hydrolysis to aglycone, 35%, was observed when 3 unit/g Fungal Lactase (Amano Enzyme) was used. Higher incubation temperatures resulted in a higher rate of hydrolysis along with a greater loss of isoflavone mass. Therefore, body temperature $(37^{\circ}C)$ may be adequate for isoflavone conversion, with 44.9% hydrolysis and less than 10% loss of mass. As expected, a higher amount of aglycone was produced at pH 7 compared with other pH values. During 5hr of incubation, the conversion of glycoside to aglycone increased dramatically from 0 to 1hr, and plateaued thereafter. In addition, commercial soy-based milk was hydrolyzed more effectively with ${\beta}-galactosidase$ when incubated for 5hr. Based on the above results, the optimum conditions for isoflavone hydrolysis by ${\beta}-galactosidase$ were for 3 hr at $37^{\circ}C$, pH 7 with 3 unit/g Fungal Lactase (Amano Lactase), yielding an average total amount of aglycone ranging from 40 to 47%.