• The Korean Journal of Food And Nutrition
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• v.33 no.6
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• pp.655-665
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• 2020

In this study, chemical information on a total of 20 individual compounds was constructed to identify isoflavones from the previous reports related with used parts(seeds, leaves, stems, pods) and products of soybean(Glycine max L.). Through constructed library and UPLC-DAD-QToF/MS analysis, a total of 19 individual isoflavones including aglycones, glucosides, acetylglucosides and malonylglucosides as major compounds was identified and quantified from 14 selected soybean seeds. Among them, genistein 7-O-(2"-O-apiosyl)glucoside and genistein 7-O-(6"-O-apiosyl)glucoside(ambocin) were identified tentatively as novel compounds in soybean seeds. Besides, among malonylglucosides, glycitein 4'-O-(6"-O-malonyl)glucoside was estimated for the first time. Total isoflavone contents were distributed from 240.21 to 445.21(mg/100 g, dry matter) and 7-O-6"-O-malonylglucosides were composed of 77.8% on total isoflavone as well as genistein derivatives were confirmed as major class. It was considered importantly that the development of isoflavone-rich varieties was necessary to strengthen their effects such as anti-inflammation, anti-cancer and menopause mitigation. The qualitative and quantitative data presented precisely in this study could be help to select and breed isoflavone-rich varieties. Furthermore, their basic isoflavone profile is expected to be applied to estimate the change of isoflavone conjugates on bioavailability after soy food supplements.

• Korean Journal of Food Science and Technology
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• v.38 no.4
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• pp.461-468
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• 2006

콩가루 50, 75, 100% 첨가 콩 반죽에 0, 1, 3%의 아몬드 첨가와 0, 20, 40분의 반죽 정치시간을 통해 제조 된 콩 과자 반죽에서 ${\beta}-glucosidase$ 활성을 측정하였고 콩 과자에서의 이소플라본 함량 및 aglycone 이소플라본 변화를 연구하였다. 일반적으로 콩가루 첨가량이 증가 될수록, 아몬드 첨가량이 증가할수록 반죽의 ${\beta}-glucosidase$ 효소 활성도는 높았으며 반죽 정치시간 20분이 0분이나 40분 보다 효소 활성이 유의적으로 높았다. 콩 과자 반죽에 포함된 이소플라본 함량은 예상된 함량 보다 약 15.2-31.5% 가량 적게 검출 되었다. 콩가루의 이소플라본 분포에 비해 콩 과자는 aglycones과 $6@-O-{\beta}-glucosides$는 증가하였고 $6@-O-malonyl-{\beta}-glucosides$는 감소하였다. 콩 과자의 aglycone 함량 증가에는 아몬드 첨가 보다 반죽 정치시간 증가가 더 효율적이었다.

• Food Science and Preservation
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• v.24 no.1
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• pp.134-144
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• 2017

This study evaluated the changes of physiochemical properties, phytochemical compounds (isoflavones and phenolic acids), and biological activity during the fermentation of Doenjang without and with bitter melon powder (BMP). The pH decreased from 6.41-5.83 to 5.81-5.24, during the fermentation of Doenjang, while the acidity increased from 0.42-0.65% to 1.28-1.48%. The viable cell numbers of Bacillus and Yeast, salinity, and total amino acid contents increased at the end fermentation (60 day). Also, the fermented Doenjang (FD) with 10% BMP showed the highest ${\gamma}$-aminobutyric acid (GABA, 129.87 mg/100 g) contents, among all the Doenjang samples. The FD exhibited significantly higher inhibitory activities than unfermented Doenjang (UFD) on radicals and ${\alpha}$-glucosidase. The phytochemical compounds including isoflavone-aglycones and phenolic acids increased, whereas isoflavoneglycosides decreased in the BM following fermentative processing. Moreover, the total phenolic, isoflavone-aglycone, and phenolic acid contents were markedly increased, leading to a general increase in antioxidant and ${\alpha}$-glucosidase inhibition activities after fermentation. These results suggest that BMP may be used to prepare a new type of fermented Doenjang with improved antioxidant and antidiabetic activities.

• Korean Journal of Food Science and Technology
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• v.46 no.5
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• pp.556-565
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• 2014

In this study, we evaluated changes in physicochemical properties, total phenol and isoflavone contents, and antioxidant activity during soymilk fermentation by a potential probiotic Lactobacillus plantarum P1201. The P1201 strain showed survival rates of 58.14% and 62.22% after 4 h exposure to acid and artificial gastric acid conditions (pH 2.5), respectively. The optimal conditions for soy-yogurt fermentation by L. plantarum were determined to be as follows: temperature of $35^{\circ}C$, seed volume of 5.0%, and sucrose content of 10.0%. The total phenol and isoflavone contents and antioxidant activity were higher in soy-powder milk (SPM) yogurt than soymilk yogurt. In particular, the highest levels of isoflavone-aglycones, such as daidzein, glycitein, and genistein (91.50, 12.34, and $61.39{\mu}g/g$, respectively), were observed after 48 h of SPM fermentation. Thus, these results suggest that the soy-yogurt extract could be used as a potential source of natural antioxidants in food.

• Nutrition Research and Practice
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• v.9 no.6
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• pp.569-578
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• 2015

BACKGROUND/OBJECTIVES: Fermentation can increase functional compounds in fermented soybean products, thereby improving antioxidant and/or anti-inflammatory activities. We investigated the changes in the contents of phenolics and isoflavones, antioxidant activity and anti-inflammatory activity of Doenjang during fermentation and aging. MATERIALS/METHODS: Doenjang was made by inoculating Aspergillus oryzae and Bacillus licheniformis in soybeans, fermenting and aging for 1, 3, 6, 8, and 12 months (D1, D3, D6, D8, and D12). Doenjang was extracted using ethanol, and sequentially fractioned by hexane, dichloromethane (DM), ethylacetate (EA), n-butanol, and water. The contents of total phenolics, flavonoids and isoflavones, 2,2-diphenyl-1 picryl hydrazyl (DPPH) radical scavenging activity, and ferric reducing antioxidant power (FRAP) were measured. Anti-inflammatory effects in terms of nitric oxide (NO), prostaglandin (PG) E2 and pro-inflammatory cytokine production and inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 expressions were also measured using LPS-treated RAW 264.7 macrophages. RESULTS: Total phenolic and flavonoid contents showed a gradual increase during fermentation and 6 months of aging and were sustained thereafter. DPPH radical scavenging activity and FRAP were increased by fermentation. FRAP was further increased by aging, but DPPH radical scavenging activity was not. Total isoflavone and glycoside contents decreased during fermentation and the aging process, while aglycone content and its proportion increased up to 3 or 6 months of aging and then showed a slow decrease. DM and EA fractions of Doenjang showed much higher total phenolic and flavonoid contents, and DPPH radical scavenging activity than the others. At $100{\mu}g/mL$, DM and EA fractions of D12 showed strongly suppressed NO production to 55.6% and 52.5% of control, respectively, and PGE2 production to 25.0% and 28.3% of control with inhibition of iNOS or COX-2 protein expression in macrophages. CONCLUSIONS: Twelve month-aged Doenjang has potent antioxidant and anti-inflammatory activities with high levels of phenolics and isoflavone aglycones, and can be used as a beneficial food for human health.

• Journal of Microbiology and Biotechnology
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• v.25 no.4
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• pp.469-478
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• 2015

In spite of the reported probiotic effects, Bifidobacterium bifidum BGN4 (BGN4) showed no βglucosidase activity and failed to biotransform isoflavone glucosides into the more bioactive aglycones during soy milk fermentation. To develop an isoflavone-biotransforming BGN4, we constructed the recombinant B. bifidum BGN4 strain (B919G) by cloning the structural β-glucosidase gene from B. lactis AD011 (AD011) using the expression vector with the constitutively active promoter 919 from BGN4. As a result, B919G highly expressed β-glucosidase and showed higher β-glucosidase activity and heat stability than the source strain of the β-glucosidase gene, AD011. The biotransformation of daidzin and genistin compounds using the crude enzyme extract from B919G was completed within 4 h, and the bioconversion of daidzin and genistin in soy milk during fermentation with B919G also occurred within 6 h, which was much faster and higher than with AD011. The incorporation of this β-glucosidase-producing Bifidobacterium strain in soy milk could lead to the production of fermented soy milk with an elevated amount of bioavailable forms of isoflavones as well as to the indigenous probiotic effects of the Bifidobacterium strain.

• Journal of Microbiology and Biotechnology
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• v.22 no.7
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• pp.947-959
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• 2012

This study was aimed at an evaluation of the potential inheritance of electroporation effects on Lactobacillus fermentum BT 8219 through to three subsequent subcultures, based on their growth, isoflavone bioconversion activities, and probiotic properties, in biotin-supplemented soymilk. Electroporation was seen to cause cell death immediately after treatment, followed by higher growth than the control during fermentation in biotin-soymilk (P<0.05). This was associated with enhanced intracellular and extracellular ${\beta}$-glucosidase specific activity, leading to increased bioconversion of isoflavone glucosides to aglycones (P<0.05). The growing characteristics, enzyme, and isoflavone bioconversion activities of the first, second, and third subcultures of treated cells in biotin-soymilk were similar to the control (P>0.05). Electroporation affected the probiotic properties of parent L. fermentum BT 8219, by reducing its tolerance towards acid (pH 2) and bile, lowering its inhibitory activities against selected pathogens, and reducing its ability for adhesion, when compared with the control (P<0.05). The first, second, and third subcultures of the treated cells showed comparable traits with that of the control (P>0.05), with the exception of their bile tolerance ability, which was inherited to the treated cells of the first and second subcultures (P<0.05). Our results suggest that electroporation could be used to increase the bioactivity of biotin-soymilk via fermentation with probiotic L. fermentum BT 8219, with a view towards the development of functional foods.

• Journal of the Korean Society of Food Science and Nutrition
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• v.45 no.5
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• pp.680-689
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• 2016

The present study evaluated the validation method for isoflavone contents of fermented soybean extracts by bioconversion as well as their antioxidant activities. Our results show that the total isoflavone contents of non-fermented and fermented soybean extract ranged between 119.8 to $637.7{\mu}g/g$ and between 567.3 to $2,074.6{\mu}g/g$, respectively. Moreover, fermented soybean extracts had higher contents of isoflavone aglycones, including daidzein, glycitein, and genistein than non-fermented soybean extracts as well as lower contents of isoflavone glucosides such as daidzin, glycitin, and genistin. FRAP and ORAC values ranged between 0.15 to 0.22 and between 195.24 to $753.79{\mu}M$ Trolox equivalents/g in non-fermented and fermented soybean extracts, respectively. These results indicate that fermented soybean extracts had higher total isoflavone contents and antioxidant activities than non-fermented soybean extracts. Bioconversion process in this study may have the potential to produce isoflavone-enriched natural antioxidant agents with high added value from soybean matrices.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.58 no.2
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• pp.149-160
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• 2013

The objective of present study was to simultaneously isolate of isoflavone and soyasaponin compounds from the germ of soybean seeds. Soy germ flours were defatted with hexane for 48h at room temperature, and methanolic extracts were prepared using reflux apparatus at $90^{\circ}C$ for 6h, two times. After extraction, extracts were separated with preparative RP-$C_{18}$ packing column ($125{\AA}$, $55-105{\mu}m$, $40{\times}150mm$), and collected 52 fractions were identified with TLC plate (Kieselgel 60 F-254) and HPLC, respectively. Among the identified isoflavone and soyasaponin fractions, isoflavone fractions were re-separated using a recycling HPLC with gel permeation column (Jaigel-W252, $20{\times}500mm$). Final fractions were air-dried, and the purified compounds of two isoflavones (ISF-1-1, ISF-1-2) and four soyasaponins (SAP-1, SAP-2, SAP-3, SAP-4) were obtained. Two isoflavone compounds (ISF-1-1, ISF-1-2) were acid-hydrolyzed for the identification of their aglycones, and confirmed by comparing with 12 types of isoflavone isomers. While the four kinds of soyasaponins were identified by using a micro Q-TOF mass spectrometer in the ESI positive mode with capillary voltage of 4.5kV, and dry temperature of $200^{\circ}C$. Base on the obtained results, it was conclude that ISF-1-1 is the mixture isomers of daidzin (43.4%), glycitin (47.0%), and genistin (9.6%), but ISF-1-2 is the single compound of genistin (99.8% <). On the other hand, soyasaponin SAP-1 is the mixture compounds of soyasaponin A-group (Aa, Ab, Ac, Ae, Af); SAP-2 is soyasaponin B-group (Ba, Bb, Bc) and E-group (Bd, Be); SAP-3 is soyasaponin B-group (Ba, Bb, Bc), E-group (Bd, Be), and DDMP-group (${\beta}g$); SAP-4 is soyasaponin B-group (Ba, Bb, Bc), E-group (Bd, Be), and DDMP-group (${\beta}g$, ${\beta}a$), respectively.

• Food Science and Biotechnology
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• v.17 no.2
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• pp.228-233
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• 2008

Considerable progress has been made in functionalization of the soy isoflavones through enzymatic modification of daidzin, genistin, and glycitin. After hydrolysis of $\beta$-glucosides into their corresponding aglycones, these compounds were structurally modified via biotransformations such as regioselective hydroxylation, enantioselective reduction, regioselective methylation, and polymerization. These reactions often resulted in an increase of the biological activities (e.g., anti oxidative activity, antiproliferative activity) and/or improvement of the physico-chemcial properties (e.g., water solubility, bioavailability). This review briefly summarizes on-going research activities on the biofunctionalization of the soy isoflavones.