• KOREAN JOURNAL OF CROP SCIENCE
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• v.66 no.4
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• pp.365-374
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• 2021

Soybean isoflavones are essential secondary metabolites synthesized through the phenylpropanoid pathway, and they play vital roles in human health. Isoflavone content is a complex quantitative trait controlled by multiple genes, and the genetic mechanisms underlying isoflavone biosynthesis remain largely unknown. Therefore, the present study analyzed the content of isoflavone and expression of six key genes involved in its biosynthesis (i.e., CHS6, HID, IF7GT, IF7MaT, GmIMaT1, and GmIMaT3) during soybean seed germination. Isoflavone content was quantified using high-performance liquid chromatography, and isoflavone biosynthetic gene expression was analyzed using quantitative real-time PCR. Two cultivars, namely 'Daepung2ho' and 'Pungsannamulkong', which are high- and low-isoflavone cultivars, respectively, were used. Isoflavone accumulation gradually increased with the progression of the germination period. As such, malonyl glucosides accounted for over 80% of the total content, whereas acetyl glucosides were present at trace amounts. Transcriptional analysis of isoflavone biosynthetic genes demonstrated expression patterns parallel to isoflavone content; however, there was no clear correlation between isoflavone content and gene expression. Moreover, most isoflavone biosynthetic genes showed different expression patterns depending on the individual gene or genotypes. Among the tested genes, HID showed consistently higher expression, except at 3 days after germination, and its expression was upregulated in 'Daepung2ho' but downregulated in 'Pungsannamulkong'. In addition, all tested genes exhibited different expression patterns between cotyledons and hypocotyls and responded differently to the germination period. These findings suggest that the expression levels of isoflavone biosynthetic genes are not consistent with the germination period and appear to be genotype-dependent.

• 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.

• Food Engineering Progress
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• v.15 no.4
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• pp.355-361
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• 2011

The separation conditions for the enhancement of isoflavone contents in soybean by soaking and germination were developed, and the fermentation conditions of Chungkukjang were optimized by using response surface methodology analysis. The high-yield of isoflavone production was obtained when the conditions of soaking and gemination were at 25.6$^{\circ}C$, 7 hr and 29.1$^{\circ}C$, 42.4 hr, respectively. Total isoflavone contents in soybean (Daepung) by treatment were increased from 1,012 ppm to 1,912 ppm. Also, the optimum fermentation conditions of Chungkukjang were determined 39.96$^{\circ}C$, 1.32% (inoulum size) and 42.4 hr, respectively. Isoflavone contents in Chungkugjang under the optimum fermentation conditions were 1.3 times higher than the control (1,960 ppm).

• Journal of Microbiology and Biotechnology
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• v.27 no.11
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• pp.1952-1960
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• 2017

Recently, soybean isoflavone aglycones (i.e., daidzein and genistein) and ${\gamma}-aminobutyric$ acid (GABA) have begun to receive considerable consumer attention owing to their potential as nutraceuticals. To produce these ingredients, multiple microorganisms and their enzymes are commonly used for catalysis in the nutraceutical industry. In this work, we introduce a novel fermentation process that uses whole-cell biocatalysis to accelerate GABA and isoflavone aglycone production in doenjang (a traditional Korean soybean paste). Microbial enzymes transform soybean isoflavone glycosides (i.e., daidzin and genistin) and monosodium glutamate into soybean isoflavone aglycones and GABA. Lactobacillus brevis GABA 100 and Aspergillus oryzae KACC 40250 significantly reduced the production time with the aid of a protease. The resulting levels of GABA and daidzein were higher, and genistein production resembled the levels in traditional doenjang fermented for over a year. Concentrations of GABA, daidzein, and genistein were measured as 7,162, 60, and $59{\mu}g/g$, respectively on the seventh day of fermentation. Our results demonstrate that the administration of whole-cell L. brevis GABA 100 and A. oryzae KACC 40250 paired with a protease treatment is an effective method to accelerate GABA, daidzein, and genistein production in doenjang.

• Proceedings of the Korean Society of Plant Biotechnology Conference
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• 2003.04a
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• pp.77-84
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• 2003

Metabolic engineering for production of isoflavones in non-legume plants could distribute the health benefits of these phytoe-strogens in more widely-consumed grains. We investigate the ability of the heterologous isoflavone synthase enzyme to interact with the endogenous phenylpropanoid pathway. Overall, results provide possibility of production of isoflavonoids in several plant tissue systems including soybean and non-legumes. In tissue that undergoes naturally enhanced synthesis of anthocyanins, genistein production was enhanced. In a monocot cell system, introduced expression of a transcription factor regulating genes of the antho-cyanin pathway was effective in conferring the ability produce genistein in the presence of the isoflavone synthase gene. However, in this case the intermediate accumulated to high levels indicating an inefficiency in its conversion. Introduction of a third gene, chalcone reductase, provided the ability to synthesize an additional substrate of isoflavone synthase resulting in production of the isoflavone daidzein. These research efforts provide insight into requirements for metabolic engineering for isoflavone production in non-legume dicot and monocot tissues.

• Food Science and Biotechnology
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• v.15 no.1
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• pp.24-27
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• 2006

A simple HPLC quantification method was developed for genistein, genistin, daidzein, and daidzin in soybeans and soybean products. The procedure used a $4.6{\times}100\;mm$ $Chromolith^{(R)}$ RP-18e column with a mobile phase of 1% HOAc in 20% MeOH to 1% HOAc in 80% MeOH for 10 min. The injection volume was $2\;{\mu}L$ at a flow rate of 2 mL/min. Detection was carried out under UV at 254 nm. Under these conditions, the major isoflavones daidzein, daidzin, genistein, and genistin in soybean and soybean pastes were eluted within 7 min with baseline separation. Optimal extraction of the above four major isoflavones was achieved when 40 g of soybean or soybean paste was refluxed in 100 mL of 95% ethanol for 2 hr. Ten different soybean cultivars and nine commercial soybean pastes were analyzed by this method. The total isoflavone content was highest in the cultivar Somyung ($2,497\;{\mu}g/g$ dry weight). The isoflavone content in soybean pastes varied widely from manufacturer to manufacturer (an almost five-fold difference between the highest and lowest values). Such variations were presumably due to differences in fermentation conditions, type of soybeans used, and levels of such additives as starch and salt.

• Korean journal of food and cookery science
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• v.26 no.4
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• pp.441-449
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• 2010

The objective of this study was to investigate the physicochemical characteristics of soybeans cultivated in different regions and the accompanying soybean curd properties. To produce soybeans with regional competitiveness and demonstrate the distinctiveness of the soybean product, four regions(Paju, Andong, Muju, Hadong) and four varieties of soybean(Daewonkong, Daepungkong, Seonyukong, Cheogja 2) were selected for these experiments. There was a significant difference in the isoflavone content of soybeans and soybean curds(p<0.05). Soybeans from Andong had the highest content of genistein, daidzein and total isoflavone and soybeans from Hadong had the lowest content of these compound. Fatty acid composition of soybeans demonstrated a significant difference according to region(p<0.05). In particular, soybeans grown under adverse environmental conditions, such as high temperature and low latitude, contained the highest composition of oleic acid and the lowest composition of linoleic acid and linolenic acid. Although fatty acid content of soybean curd had a third of the fatty acid concentration of soybean, the same characteristic was observed in the fatty acid composition of soybean curd. In addition, both soybean and soybean curd had more than 80% unsaturated fatty acids and 50% of the unsaturated fatty acid content was linoleic acid. In conclusion, these results demonstrate the significant difference of soybean and soybean curd originating from different regions and showed the transition of nutritional constituents from soybean to soybean curd as a function of environmental factors. Therefore, we must consider these factors when manufacturing soy products.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.56 no.1
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• pp.64-71
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• 2011

Health beneficial properties of soybean [Glycine max (L.) Merr.] isoflavones are well known. The objectives of this study were to determine and compare the isoflavone composition and concentrations of soybean varieties grown in different cultivated regions of Vietnam (i.e., upland and lowland). Total and individual isoflavone composition and concentrations were determined by high-performance liquid chromatography (HPLC). Total isoflavone concentrations varied from 1153 to $6604{\mu}g\;g^{-1}$ and averaging $3354{\mu}g\;g^{-1}$ across environments and varieties. In the lowland region, the highest total isoflavones concentration was observed in M103 cultivar ($5653{\mu}g\;g^{-1}$) and the lowest in VX9-3 ($1153{\mu}g\;g^{-1}$), whereas in the upland region the highest and lowest concentrations were in M103 ($6604{\mu}g\;g^{-1}$) and DT93 ($1938{\mu}g\;g^{-1}$), respectively. Across varieties, average total isoflavones concentration was higher in the upland than lowland region (3728 vs. $2980{\mu}g\;g^{-1}$). The malonylglucosides and acetylglucosides concentrations in upland soybean varieties were higher than those from the lowland region. Despite the presence of Genotype (G) x Environment (E) interactions, varieties with consistently high (M103) and low (VX9-3, DT93) isoflavone concentrations across environments were identified. This is the first report of isoflavones in Vietnamese soybean varieties, revealing large variation in isoflavones concentration and profile among different varieties and cultivated regions. Results will be useful in selecting high-isoflavones soybean varieties for growth in tropical regions.

• Food Science and Biotechnology
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• v.16 no.1
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• pp.83-89
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• 2007

In our study, lactic acid bacteria (LAB)-fermented whey solutions were applied in the soybean soaking process to minimize bacterial contamination and to enrich the biologically functional components of isoflavone and $\gamma$-aminobutyric acid (GABA). Among the 11 LAB tested, Bifidobacteria infantis and a mixed culture (Lactobacillus acidophilus, Bifidobacteria lactis, and Streptococcus thermophilus; ABT-3) displaying the greatest $\beta$-glucosidase activity were selected to produce improved biologically functional soybean preparations. In the soybean soaking processing (without water spraying), the LAB-cultured 10% whey solution was used to soak and to ferment the soybeans and the fermented soybeans were finally dried by heat-blowing at $55^{\circ}C$. The processing conditions used in this study demonstrated that the final soybean product had a reduced contamination by aerobic and coliform bacteria, compared to raw soybeans, likely due to the decrease in pH during LAB fermentation. The aglycone content of the isoflavone increased up to 44.6 mg per 100 g of dried soybean by the processing method, or approximately 8-9 times as much as their initial content. The GABA contents in the processed samples increased as the processing time of soaking-fermentation proceeded as well. The soybean sample that fermented by ABT-3 culture for 24 hr showed the greatest increase in GABA content (23.95 to 97.79 mg/100 g), probably as a result of the activity of glutamate decarboxylases (GAD) released from the soybean or produced by LAB during the soaking process.

• Food Science and Biotechnology
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• v.14 no.4
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• pp.498-502
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• 2005

Three Korean soybean varieties - Shinpaldal-2, Seomoktae and Seoritae - were investigated for changes in their physical properties and the amount of functional components (i.e. isoflavones and oligosaccharides), during germination. Soybeans were germinated at $20^{\circ}C$ for 96 hr in complete darkness. The dry weights of cotyledone, hypocotyl, seed coat, and hilum of Seoritae were heavier than those of other varieties. The dry weights of the three bean varieties decreased steadily in spite of root growth. The largest amount of isoflavone content was observed from Shinpaldal-2 (1.824 mg/g), followed by Seoritae (1.216 mg/g) and Seomoktae (1.125 mg/g). Total isoflavone content increased by 13% during initial germination, and then decreased thereafter. Aglycone types such as daidzein and genistein dominated the increase in isoflavone contents. The increase in genistein content of Shinpaldal-2 was 17.5 fold compared with ungerminated soybean, while the amount of daidzein was 6.7 times as much as ungerminated Shinpaldal-2 over an 18-hr germination period. Oligosaccharide contents such as raffinose (Raf) and stachyose (Sta) rapidly decreased during germination, while the sucrose (Sue) content remained constant until 36-48 hr of germination. From these results, it was clearly shown that the germination process significantly changed the contents of functional nutrients in soybeans. Therefore, the optimization of germination process should be considered to improve the biological functionality of soybeans in food processing.