• 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.

• 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.

• Food Science and Biotechnology
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• v.15 no.1
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• pp.96-101
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• 2006

Isoflavone distribution and ${\beta}$-glucosidase activity in cheonggukjang, a traditional Korean whole soybean-fermented food prepared with or without addition of Bacillus subtilis, were analyzed every 6 hr for 36 hr. Thermal cooking of raw-soaked soybeans significantly increased ${\beta}$-glucoside isoflavone level by 57.1 % and decreased malonyl-${\beta}$-glucosides by 57.6% (p<0.05). Consistent changes of isoflavone profiles in cheonggukjang without B. subtilis addition (COB) and samples with addition of B. subtilis (CWB) were not observed during 36 hr fermentation. ${\beta}$-Glucosides of isoflavones are major forms in both COB and CWB. ${\beta}$-Glucosidase activity in cheonggukjang decreased significantly compared to that of soaked soybeans due to thermal denaturation, while recovery of enzyme activity in COB was observed. Two new unidentified peaks were detected, and their relative peak areas in CWB were significantly larger than those in COB with increasing fermentation period (p<0.05), which indicates both peaks could be associated with fermentation metabolites.

• Korean Journal of Pharmacognosy
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• v.24 no.4
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• pp.309-312
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• 1993

A new method for separation and quantitative determination of isoflavone glucosides in rhizomes of Belamcanda chinensis (Iridaceae) by high performance liquid chromatography was elaborated. A reverse-phase system with a Spheri-5 RP-18 column using MeOH:HOAc:$H_2O$(24 : 5 : 71) as a mobile phase was developed. The isoflavonoids were detected at 268 nm and the analysis was successfully carried out within 15 min.

• Korean Journal of Food Science and Technology
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• v.39 no.3
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• pp.231-236
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• 2007

The isoflavone distributions of soy samples treated with soaking, oven-drying, and almond additions were determined by high performance liquid chromatography (HPLC). Oven-drying was performed to increase the amount of ${\beta}-glucoside$ isoflavones, and almonds were added to convert the ${\beta}-glucosides$ into their corresponding aglycones. Oven-drying at $100^{\circ}C$ for 4 hr significantly increased ${\beta}-glucoside$ levels and decreased $malonyl-{\beta}-glucosides$, while almond additions of 2.5% and 5.0% (w/w) significantly increased aglycone contents (p<0.05) for samples with 12 hr of drying. The rate of increase for genistein from genistin was faster than that of daidzein from daidzin with almond additions. The ${\beta}-glucosidase$ activity in the 5.0% added almond soybean samples was significantly higher than in the samples without added almond (p<0.05). The aglycone content increased from 1.62% in the raw soybeans to 61.55% in the 2.5% added almond soybean samples for 12 hr of incubation. The information from this study could be used to increase the isoflavone aglycone contents of soybeans by using natural products such as almonds, without organic solvent additions or microorganism fermentation.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.50 no.4
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• pp.291-300
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• 2005

This study was focuses on the variation of isoflavone contents during seed development and their interaction with major chemical components such as protein, amino acids, saccaharides, lipid and fatty acids. During maturing, lipid, protein, and amino acid contents in soybean seeds showed the highest values at R7 stages, but isoflavone contents were increased until R8 stage. It was noted that malonyl glucosides $(64.2\%)$ are predominant forms among conjugated isoflavones followed by glucosides $(30.7\%)$, acetyl glucosides $(4.1\%)$ and aglycones $(0.9\%)$. Sucrose and stachyose were presented as a major saccharide in soybean seeds. As maturing days progressed, they were constantly increased and the highest contents were observed at R8 stage. While small quantities of raffinose, fructose, glucose, maltose, DP3 (DP: degree of polymerization), DP6, and DP7 were detected. These results showed that saccharide composition at the beginning of seed development is primarily monosaccharides with little sucrose and oligosaccharides, but as maturing days proceeds, sucrose and starch increase with concomitant decrease in monosaccharides. Sucrose and stachyose were positively correlated with isoflavone (r=0.780, 0.764 at p<0.01, respectively), while fructose, glucose, maltose, and DP7 were negatively correlated (r=-0.651, -0.653, -0.602, and -0.586 at p<0.05, respectively). Soybeans at R8 stage were high in protein and amino acid, but low in free amino acid contents. Protein and amino acid contents showed positively significant correlations with isoflavone (r=0.571 and 0.599 at p<0.05, respectively), but free amino acid content were negatively correlation with isoflavone (r=-0.673, p<0.01). The lipid content reaches its final content relatively early stage of seed development and remains constant as compared with other chemical components. Among the fatty acids, although varietal difference was presented, stearic acid and linolenic acid were gradually decreased, while oleic and linoleic acid were increased as seed maturing progressed. Lipid was significantly correlated (r=0.754, p<0.01) with isoflavones. However, neither saturated fatty acid nor unsaturated fatty acids significantly affected the isoflavone contents of maturing soybean seeds.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.65 no.2
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• pp.84-92
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• 2020

For humans, soybean and soybean products are the main dietary sources of isoflvones, which are polyphenolic compounds that represent one of the most common categories of phytoestrogens. The objective of this study was to determine isoflavone concentrations in soybean cultivars during germination when treated with some biotic substances. Three soybean cultivars were germinated in replicated trials in 2018/2019 and their individual and total isoflavone concentrations were determined using HPLC (High-Performance Liquid Chromatography). Significant differences were observed in total isoflavone content were observed among cultivars regardless of years and treatments. 'Daepung2-ho' and 'Uram' had significantly higher total isoflavones than 'Pungsannaul-kong'. Differences among treatments were also significant for total isoflavone content. In 2018, with chitosan treatment, total isoflavone concentration ranged from 551.15 to 7584.07 ㎍ g^-1, with an average of 2972.64 ㎍ g^-1 across cultivars. In 2019, there was no significant difference among treatments in total isoflavone content. Regarding individual isoflavone concentrations, the malonyl-glucoside groups accounted for over 85% of the total isoflavone content, which is indicated that these groups play an important role with regard to isoflavone components in soybean seeds. The individual proportions in the total concentrations of isoflavones varied according to germination period and seed tissues. Glucosides and malonyl-glucosides showed differences in concentrations among seed tissues, aglycones were further accumulated as germination period was progressed. This study suggests that biotic substances have an impact on seed isoflavone content during germination. However, cultivars with consistently high or low isoflavone concentrations across biotic substance treatments were identified desspite differences in germination period and seed tissues, demonstrating that the genetic factor plays the most important role in isoflavone accumulation.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.63 no.3
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• pp.239-247
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• 2018

Soybean produces three major types of isoflavones, daidzein, genistein, and glycitein aglycones and their glucosides and malonylglucosides. It has been known that malonylated glucosides are rapidly converted to their corresponding aglycones due to the unstable thermolabile glucoside malonates; therefore, the analytical study of malonylated glucosides has been insufficient. In this study, we analyzed the malonylglucoside content in soybean seeds. Isoflavone analysis of three soybean cultivars revealed that 81.5~90.0% of the total isoflavones were malonylglucosides, whereas aglycones were rarely detected. Moreover, the total isoflavone content increased during a 5-day germination period where growth regulators and coumaric acid treatments tended to yield higher isoflavone content than the normal germination treatment, however the differences were not significant; notably, the isoflavone accumulation trend continued with additional germination days. The content of malonylglucoside was higher than that of other isoflavones, which was 83.7~86.6% of the total isoflavone content in seeds with a 3-day germination period. Furthermore, isoflavones were significantly accumulated in the hypocotyl of seedlings with a 5-day germination period. The content of isoflavone in the hypocotyl of the Pungsannamul-kong was 10,240 ug/g when treated with coumaric acid, which was considerably higher than that of other cultivars and treatments. Additionally, soybean seeds heated at $60^{\circ}C$ for 1 hour produced higher isoflavone content than non-heated soybean seeds. Our results show that it is possible to increase the isoflavone content in soybean seeds through various treatments.

• Korean Journal of Food Science and Technology
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• v.34 no.5
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• pp.916-918
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• 2002

The effect of acid hydrolysis on isoflavone contents of defatted soybean flour (DSF) was investigated in this study. Isoflavone analyzed were daidzein, genistein, glycitein, daidzein, genistein and glycitein with using HPLC. The DSF suspension was heated at $95^{\circ}C$ for 4 hour with addition of HCl (0.25-3.00 N) and analyzed isoflavone. The results showed that the total isoflavone was increased as the HCl concentration increased up to 1.0 N HCl during heating, indicating conversion of glucoside isomers of isoflavone to its aglycons. However, higher concentration than 1.0 N HCl caused a relatively fast decrease in isoflavone after 4 hour of heating. These results were probably caused by degradation of isoflavone by high concentration of acid during heating. The glucosides of isoflavone were steadily decreased while its aglycons were rather increased during $1.0{\sim}2.0$ hour of heating.

• 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.