• 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%.

• Journal of Nutrition and Health
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• v.36 no.1
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• pp.32-39
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• 2003

Phytoestrogens, especially soy-derived isoflavones, are receiving great scrutiny as a food supplement for preventing hormone dependent disease such as postmenopausal osteoporosis. Their beneficial effects are derived from aglycone form of isoflavones, such as daidzein, genistein or glycitein. In contrast to the common usage of soybean, black bean (Rhynchosia Molubilis : Yak-kong) has been used as a supplement for preventing postmenopausal osteoporosis in oriental medicine. To investigate the effects of the saliva, artificial stomach fluid, and digestive enzymes on the conversion of glycosidic isoflavone to aglycone form, soybean and black bean were extracted with 70% methanol and freeze-dried. The recovery yield of methanol extracts of black bean was 14.1% which was higher than that of soybean, 13.5%. In terms of total isoflavones, we routinely obtained larger amount of isoflavones from black bean than those from soybean. By incubating methanol extracts of soybean and black bean with IN HCI for 180 min, the proportions of aglycones relative to the total isoflavone were significantly increased (32.4% and 52.4%, respectively). In vitro conversion, digestive enzymes ($\beta$-glucosidase and $\alpha$-glucosidase) may hydrolyze glycosidic bond of isoflavone more effectively than saliva or artificial stomach fluid did. It seems to say that the activity of $\beta$-glucosidase was higher than those of $\alpha$-glucosidase. The rate of conversion of glucoside form to aglycone form in black bean and soybean was low in physiological condition (pH) tested, although the enzymatic hydrolysis of glucoside was active. These results demonstrated that the composition of aglycone in food may be the important factors in terms of the bioavailability of isoflavones. (Korean J Nutrition 36(1): 32-39, 2003)

• Journal of the Korean Society of Food Science and Nutrition
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• v.35 no.10
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• pp.1420-1426
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• 2006

To establish a rapid and effective method for the analysis of soy isoflavone which is known to have lots of variation in derivatives of glucoside, conversion rate from isoflavone conjugates to its aglycones, and decomposition of conversed aglycones were investigated with various acid hydrolysis conditions. A number of heating conditions for acid hydrolysis including heating at convection oven $(105^{\circ}C)$, water bath $(95^{\circ}C)$, heating block $(120^{\circ}C)$, and hot plate $(120^{\circ}C)$ were applied. Acid hydrolysis in heating block with reflux was chosen as the best heating condition. From the stability test of isoflavone aglycone during acid hydrolysis, genistein, daidzein, and glycitein did not show any significant changes in their contents for 60 min of hydrolysis. Ten to thirty milligram of sample per 1 mL HCl was the best ratio of sample to acid. As conclusion, acid hydrolysis for 60 min after addition of 15 mL HCl solution to 0.5 g soybean, and then fill up to 50 mL with methanol, followed by HPLC analysis was set as a final analysis method. From this method, isoflavone contents expressed as total aglycone of feed meal was the highest with content of $1288.5{\mu}g/g$ followed by those of dehulled meal.

• The Korean Journal of Food And Nutrition
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• v.36 no.2
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• pp.87-92
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• 2023

Isoflavones found in soybeans are present as glycosides and aglycones, which differ according to their chemical structure. The absorption rate and bioavailability of aglycones are greater than those of glycosides. It is known that aglycone isoflavones in soybean was converted from glycoside isoflavones by activating of endogenous β-glucosidase under drying (40~60℃) conditions after soaking. In this study, we compared and analyzed the proximate composition and isoflavone contents of soybean powders prepared under dried after soaking were analyzed. In the comparison of the proximate compositions, the moisture contents of white soybean powder dried after soaking (WSPDS) and black soybean powder dried after soaking (BSPDS) were decreased as compared with those of the control white soybean powder (CWSP) and control black soybean powder (CBSP). Whereas the contents of other proximate compositions were increased. The aglycone isoflavone contents were higher in WSPDS than in CWSP. Whereas the aglycone isoflavone contents of BSPDS had a similar content those of CBSP because of the component characteristics of black soybean. In conclusion, we believe that it is appropriate to identify and utilize the component characteristics of soybean varieties in order to induce an increase in the functional component content of soybeans under drying conditions after soaking.

• Proceedings of the Korean Society for Food Science of Animal Resources Conference
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• 2004.10a
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• pp.371-374
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• 2004

본 연구는 식물성 에스트로겐인 isoflavone 배당체의 ${\beta}-1,4\;glycoside$ 결합을 ${\beta}-galactosidase$로 분해하여 그 생리적 작용이 더욱 효과적인 aglycone화 하기 위한 조건을 연구하여 기능성식품개발에 응용토록 하는데 목적이 있다. 실험 결과, 모든 ${\beta}-galactosidase$가 ${\beta}-1,4\;glycoside$ 결합의 분해력이 인정되지는 않았으며, 분해 가능성이 인정된 효소를 선택하여 실험한 결과 효소의 함량이 증가함에 따라 aglycone의 성분비율이 증대된 반면, 그 손실률 또한 증대되었고 배양시간이 길수록 aglycone의 성분비율이 증가하였으나 배양초기에 급격한 증가율을 보였으며, pH6과 7, 8에서 유사한 정도의 증가율을 보였고, 온도가 증가함에 따라 aglycone 성분비율이 증가되었지만 $40^{\circ}C$이상에서는 그 손실률이 크게 증가하였다. 결과적으로 판단해 볼 때, isoflavone을 aglycone화 하는데 있어 인체 내 유사조건에서 aglycone의 증가율이 높았으며 최적의 조건과 많은 차이를 나타내지 않았고 그 손실률 또한 최소화된 결과를 나타내어 isofalvone을 적용한 기능성 유제품을 연구하는데 있어 긍정적인 가능성을 보였다.

• Korean Journal of Microbiology
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• v.49 no.4
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• pp.391-397
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• 2013

Changes in ${\beta}$-glycosidase activity, total phenolic and isoflavone contents, and antioxidant activities during the fermentation of Korean black soybeans (Seoritae and Seomoktae) fermented food cheonggukjang by the potential probiotic Bacillus subtilis CSY191 were investigated. The levels of total phenolic and isoflavone-malonylglycoside and -aglycone contents increased, while 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) diammonium salt (ABTS) radical scavenging activity and ferric reducing/antioxidant power (FRAP) increased, but the isoflavone-glycoside contents decreased after cheonggukjang fermentation. The content of antioxidant compounds, including isoflavone-aglycones and -malonylglycosides, was increased by fermenting-processing, whereas the content of isoflavone-glycosides was decreased in the fermented soybeans. In particular, the Seoritae soybean fermented at 3 $7^{\circ}C$ for 48 h displayed the highest antioxidant activities, compared to those of the Seomoktae soybean and the fermented. The highest levels of daidzein, glycitein, and genistein were present at concentrations of 253.0 ${\mu}g/g$, 72.5 ${\mu}g/g$, and 114.1 ${\mu}g/g$ after 48 h of Seoritae soybean fermentation. From those results, we suggest that the high antioxidant activity of cheonggukjang of black soybeans might be related to the markedly higher levels of total phenolic and isoflavone-aglycone and -malonylglycoside contents achieved during fermentation.

• Journal of the East Asian Society of Dietary Life
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• v.20 no.4
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• pp.543-550
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• 2010

This study was conducted to determine the characteristics of chungkukjang with added isoflavone extracted from arrowroot and to determine its utility as a functional food substance. Crude isoflavone was prepared from arrowroot by the ethanol extraction method and frozen dried (AI). Samples of chungkukjang each had different amounts of isoflavone extracts added to them: 0 (control), 1.76 (AC1-chungkukjang), 3.52 (AC2-chungkukjang), and 7.11 (AC3-chungkukjang) g/kg. The pH, color, slime material content, calcium, and isoflavone of each sample were measured to investigate the quality and changes in isoflavone content. As AI increased, the pH of chungkukjang decreased to 7.46~7.53 compared to the pH of control (7.63). The slime material content range increased to 4.46~6.16%. However, there was no significant difference in the general components of chungkukjang between each of the groups (Con, AC1, AC2, AC3). In colors of chungkukjang, values for $L^*$, $a^*$, and $b^*$ decreased as AI increased. Meanwhile, the calcium content of AC1, AC2 and AC3 tended to increase by 11.18~12.82% compared to the control. This may be due to the influence of Ca in the arrowroot extract powder. There was a remarkable increase in total isoflavone content, by 30.81~130.66%, with an order of AC3>AC2>AC1. In all of the groups, the content of genistein and daidzein, aglycone form, increased dramatically, by 65.00~128.34%, and 89.38~142.91%, respectively, compared to the control. In AC3, in particular the genistin and daidzin content increased by 103.47% and 188.13%. These results showed that AI can be used as a source of isoflavone supplementation in chungkukjang.

• Journal of the Korean Society of Food Science and Nutrition
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• v.35 no.3
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• pp.359-365
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• 2006

Changes in isoflavone and oligosaccharides, and some physicochemical properties of Chokong, a pickled and dried soybeans, were investigated during pickling in brewed vinegar at $20^{\circ}C$. The used soybeans were 24 hr germinated soybeans, which was maximumly increased in isoflavone content during germination. The isoflavone contents were significantly increased by approx. 80% in both glycosides and aglycone type of isoflavone after 20 day of pickling at $20^{\circ}C$. The isoflavone values of germinated Chokong were significantly higher than those of ungerminated ones. Pickling the soybeans in vinegar resulted in a rapid initial decrease in oligosaccharides, Particularly in raffinose and stachyose. The pH and soluble solids contents in vinegar increased markedly and L values decreased during initial pickling of 24 hr.

• Current Research on Agriculture and Life Sciences
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• v.12
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• pp.9-22
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• 1994

The changes of the time-dependent accumulation of isoflavone aglycones(daidzein, genistein) and their glucosides(daidzin, genistin) by various stress-inducing treatment on cotyledon of soybeans(Dankyungkong and Paldalkong) were investigated. Levels of isoflavone aglycones and their glucosides in soybeans treated with UDP-glucose, $MgSO_4$ and $HgCl_2$ and infected with phytopathogen appeared to be higher than those of treatment with distilled water. When compared with data for control, the levels of isoflavone glucosides in citrate-treated soybeans were increased but those of their aglycones did not appear appreciable differences. In Paldalkong treated with UDP-glucose, $MgSO_4$ and $HgCl_2$ the levels of isoflavone aglycones and their glucosides were higher than in Dankyungkong. In particular, the accumulation of daidzein in Paldalkong was significantly higher than in Dankyungkong. By infection with Botrytis cinerea, the maximum amount of accumulation of daidzein in two cultivar did not to be a large different, but accumulation time appeared more rapidly in Paldalkong than Dankyungkong. The accumulation amount of daidzein and genistein in Dankyungkong treated with elicitors appeared to be similar at initial stage, but the level of daidzein after 48hours appeared to be higher than that of genistein. In Paldalkong, the level of daidzein was higher than that of genistein at all stage. The level of daidzein in soybeans infected with phytopathogen appeared to be higher than that of genestein.

• Nutrition Research and Practice
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• v.7 no.5
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• pp.393-399
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• 2013

Asian populations are thought to receive significant health benefits from traditional diets rich in soybeans due to high isoflavone contents. However, available epidemiologic data only weakly support this hypothesis. The present study was carried out to assess the pharmacokinetics of isoflavones in South Korean women after ingestion of soy-based foods. Twenty-six healthy female volunteers (20-30 y old) consumed three different soy products (i.e., isogen, soymilk, and fermented soybeans) with different aglycone/glucoside ratios. Plasma and urine isoflavone concentrations were measured by high-performance liquid chromatography (HPLC) after ingestion of one of the soy products. Pharmacokinetic parameters were determined using the WinNonlin program. The area under the curve (AUC) for plasma daidzein levels of the soymilk group ($2,101{\pm}352ng{\cdot}h/mL$) was significantly smaller than those of the isogen ($2,628{\pm}573ng{\cdot}h/mL$) and fermented soybean ($2,593{\pm}465ng{\cdot}h/mL$) groups. The maximum plasma concentration ($C_{max}$) of daidzein for the soymilk group ($231{\pm}44$ ng/mL) was significantly higher than those of the isogen ($160{\pm}32$ ng/mL) and fermented soybean ($195{\pm}35$ ng/mL) groups. The half-lives of daidzein and genistein in the soymilk group (5.9 and 5.6 h, respectively) were significantly shorter than those in the individuals given isogen (9.6 and 8.5 h, respectively) or fermented soybean (9.5 and 8.2 h, respectively). The urinary recovery rates of daidzein and genistein were 42% and 17% for the isogen group, 46% and 23% for the fermented soybean group, and 33% and 22% for the soymilk group. In conclusion, our data indicated that soy products containing high levels of isoflavone aglycone are more effective for maintaining plasma isoflavone concentrations. Additional dose-response, durational, and interventional studies are required to evaluate the ability of soy-based foods to increase the bioavailability of isoflavones that positively affect human health.