• Title/Summary/Keyword: Genistin

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Bioconversion of Soybean Isoflavone by Lactobacillus plantarum and Bifidobacterium longum (Lactobacillus plantarum과 Bifidobacterium longum을 이용한 대두 이소플라본의 비배당체로의 전환)

  • Kim, In-Bok;Shin, Sun;Lim, Byung-Lak;Seong, Gem-Soo;Lee, Young-Eun
    • Korean journal of food and cookery science
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    • v.26 no.2
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    • pp.214-219
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    • 2010
  • In this study, phytoestrogen for the industrial production of soybean probiotics by lactic acid bacteria (LAB) was studied in a soybean extract. Soybean was fermented with LAB, Lactobacillus plantarum KCTC 3108 and Bifidobacterum longum ATCC 15707. The change in the content of various isoflavones (aglycone and glucoside) and the $\beta$-glucosidase activity in soybean during fermentation were investigated and shown to be dependent on the starter organism. Soybean extract powder fermented with L. plantarum showed the highest $\beta$-glucosidase activity and the greatest increase in the aglycone content. After 48h of fermentation, the contents of daidzin, genistin and glycitin in L. plantarum decreased from a mean initial levels of $83.03{\pm}2.17$, $168.13{\pm}8.17$ and $20.02{\pm}1.07$, respectively, to mean levels of $5.34{\pm}3.24$, $3.79{\pm}0.57$ and $1.87{\pm}1.09\;mg$/100 g. Whereas, after 48h fermentation, the contents of daidzein, genistein and glycitein increased from a mean initial levels of $8.09{\pm}0.78$, $11.20{\pm}0.84$ and $4.71{\pm}0.46$, respectively, to mean levels of $85.76{\pm}0.84$, $175.87{\pm}2.21$ and $22.41{\pm}0.91\;mg$/100 g. Taken together, these results suggested an increase of aglycones and decrease of glucoside in isoflavones occurred during fermentation, which coincided with an increase of $\beta$-glucosidase activity in the fermented soybean extract powder.

Isolation and Structural Determination of Free Radical Scavenging Compounds from Korean Fermented Red Pepper Paste (Kochujang)

  • Chung, Jin-Ho;Shin, Heung-Chule;Cho, Jeong-Yong;Kang, Seong-Koo;Lee, Hyoung-Jae;Shin, Soo-Cheol;Park, Keun-Hyung;Moon, Jae-Hak
    • Food Science and Biotechnology
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    • v.18 no.2
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    • pp.463-470
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    • 2009
  • Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

Component Changes in Antioxidant Activity and Isoflavones (β-glucoside & aglycone) Contents of Small Black Bean According to Different Cooking Methods (조리방법을 달리한 쥐눈이콩의 항산화력 및 이소플라본 배당체·비배당체 함량 비교)

  • Shin, Jihun;Joo, Nami
    • Korean journal of food and cookery science
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    • v.32 no.2
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    • pp.197-203
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    • 2016
  • Purpose: In this study, small black beans (Rhynchosia nulubilis) that were produced in the Jungsun province of South Korea were selected for use in various cooking recipes because they are known to contain higher isoflavones and excellent antioxidant effects, as compared to any other domestic soybeans. Methods: Physicochemical and antioxidant characteristics of small black beans were analyzed with uncooked beans and four other cooking methods of pan broiling, boiling, steaming, and pressure cooking. Results: Contents of ${\beta}$-glucosides (daidzin, glycitin, and genistin) and aglycone (daidzein, glycitein, and genistein) in small black beans were significantly different depending on the cooking methods (p<0.001). The results of the experiment indicated that the amount of total polyphenol in pressure cooked beans was highest, showing a value of 7.16 mg/g (p<0.001). Most contents of isoflavones (${\beta}$-glucoside, aglycone) in uncooked beans appeared to increase after cooking. In particular, the amount of glycitein was highest in pan broiled beans ($9.63{\mu}g/g$). The total isoflavone content differed among the different cooking methods, ranging from highest to lowest in the following order : pan broiled beans ($759.49{\mu}g/g$), pressure cooked beans ($725.12{\mu}g/g$), boiled beans ($591.05{\mu}g/g$), steamed beans ($511.61{\mu}g/g$), and uncooked beans ($180.80{\mu}g/g$) (p<0.001). Conclusion: Especially, the amount of isoflavones increased significantly in pan broiled beans and pressure cooked beans, suggestive of optimized cooking methods for increasing nutritional and functional contents in cooked food.

Composition of Isoflavone, Phytic Acid, and Saponins in Hypocotyls and Cotyledons of Six Traditional Korean Soybeans

  • Kim, Kang-Sung
    • Journal of Environmental Health Sciences
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    • v.33 no.3
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    • pp.195-201
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    • 2007
  • The objective of present study was to examine the composition of functional components (isoflavones, phytic acid, and saponin) in hypocotyls and cotyledons of six traditional Korean soybeans, namely Cheongtae, Seoritae, Jinjoori, Subaktae, Yutae, and Huktae. Three 'family' of isoflavones, as four chemical structures were present in hypocotyls and cotyledons of six soybean cultivars: the aglycones genistein, daidzein, and glycitein; the glycosides genistin, daidzin, and glycitin; the acetylglycosides 6"-O-acetylgenistin, 6"-O-acetyldaidzin, and 6"-O-acetylglycitin; and the malonylglycosides 6"-O-malonylgenistin, 6"-O-malonyldaidzin, and 6"-O-malonylglycitin. Isoflavone contents of hypocotyls and cotyledons differed among the cultivars, and glucosides and malonylglucosides accounted for more than 90% of the total phytoestrogens, with the remaining $1\sim7%$ taken up by aglycones. Concentrations of isoflavones in cotyledons were approximately about $10\sim20%$ of respective hypocotyls. Contents of phytic acids in hypocotyls and cotyledons of the selected soybean cultivars were $1.21\sim1.70%$ and $2.59\sim3.01%$, respectively. Hypocotyls of Seoritae showed the lowest content of phytic acid with 1.21%, while cotyledons of Cheongtae showed the highest content with 3.01%. The sapogenol concentrations ranged from $13.58mg/100g\sim20.82mg/100g$ for hypocotyls and $0.95mg/100g\sim2.55mg/100g$ for cotyledons showing that concentrations of saponin are $7\sim10$ times higher in hypocotyls than in cotyledons of respective soybeans. For both hypocotyls and cotyledons the sapogenol A were present in higher concentrations than soyasapogenol B.

Antioxidant Activities and Quality Characteristics of Tofu Supplemented with Chinese Artichoke Powder (초석잠 분말을 첨가한 두부의 항산화 활성 및 품질 특성)

  • Lee, Ji Eun;Jin, So Yeon;Han, Young Sil
    • The Korean Journal of Food And Nutrition
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    • v.27 no.1
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    • pp.10-21
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    • 2014
  • This study is conducted to investigate the effects of Chinese artichoke powder on the antioxidant activities and the quality characteristics of tofu. Tofus are being prepared with different amounts of Chinese artichoke powder in ratios of 0, 0.2, 0.4, 0.6 and 0.8% according to the soy milk quantity. According to the increasing contents of Chinese artichoke powder, the yield and turbidity of tofus are significantly increased (p<0.001) whereas the pH levels of tofus are significantly decreased (p<0.001). In terms of color, the L, a and b values are significantly decreased with increasing Chinese artichoke powder concentrations (p<0.001). From the texture profile analysis of the tofus, the chewiness, gumminess and cohesiveness of tofus are significantly decreased (p>0.01) according to the levels of added Chinese artichoke powder content. The contents of isoflavones such as daidzin and genistin are significantly increased with increasing concentrations of Chinese artichoke powder (p<0.001). The microstructure of tofus is being examined by SEM (Scanning Electron Microscope). In the sensory test, the sample which contains 0.4% of Chinese artichoke powder is ranked significantly higher (p>0.001) than the other groups according to several sensory parameters such as appearance, color, flavor, taste, texture and the overall preferences.

Isoflavone Content in Korean Fermented and Unfermented Soybean Foods (대두 가공 식품 중의 이소플라본 함량)

  • Choi, Yeon-Bae;Sohn, Heon-Soo
    • Korean Journal of Food Science and Technology
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    • v.30 no.4
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    • pp.745-750
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    • 1998
  • Soybean isoflavones known as an anticarcinogenic factor were evaluated in some Korean soybean foods by high performance liquid chromatography. Unfermented soybean foods contained predominantly isoflavone ${\beta}-glycosides$ (genistin and daidzin), but in the fermented soybean foods isoflavones were present mainly as aglycones (genistein and daidzein). Average contents of isoflavones of tofu, soymilk and soy sprout were 1, 151, 676 and 424 mg/kg, respectively. Among the fermented soybean products, soybean paste (Chongkukjang) was highest in the isoflavone content (920 mg/kg) and the degree of hydrolysis of ${\beta}-glycosidic$ bonds was ranged from 30 to 100%. Doenjang, Chunjang and Kanjang contained lesser amounts of isoflavones and their contents were 627, 291 and 10 mg/kg, respectively. Korean traditional fermented foods, Chongkukjang and Doenjang could be regarded as the excellent sources of soy isoflavone aglycones.

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Change of Isoflavone Content during Manufacturing of Cheonggukjang, a Traditional Korean Fermented Soyfood

  • Jang, Chan-Ho;Lim, Jin-Kyu;Kim, Jeong-Hwan;Park, Cheon-Seok;Kwon, Dae-Young;Kim, Yong-Suk;Shin, Dong-Hwa;Kim, Jong-Sang
    • Food Science and Biotechnology
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    • v.15 no.4
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    • pp.643-646
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    • 2006
  • Cheonggukjang, a popular Korean traditional fermented soyfood, was manufactured by fermenting steamed soybeans in a temperature-controlled room by traditional methods in which steamed soy was exposed to rice straw naturally rich in Bacillus species. B. subtilus and B. licheniformis were found to be the major microorganisms present in cheonggukjang made by the traditional method. We analyzed the composition of 12 kinds of isoflavones and their glycosides present in cheonggukjang collected at various fermentation times. Total isoflavone content in raw soybeans was 2,867 mg/kg and this decreased by about 50% during cooking prior to cheonggukjang preparation. However, total isoflavone content changed slightly during 45 hr of fermentation. Total content of isoflavone glycosides, consisting mainly of daidzin, glycitein, and genistin, decreased by about 40% during 45 hr of fermenting cooked soybeans. The contents of tree isoflavones including daidzein, glycitein, and genistein showed a dramatic increase during fermentation in cheonggukjang preparation, with a 2.9-, 54.0-, and 20.6-fold increase in concentration, respectively, by the end of fermentation (45 hr). In conclusion, short-term fermentation of cooked soybeans with Bacillus species caused conspicuous changes in the composition of isoflavone derivatives, and its implication in terms of health benefits deserves further study.

Antioxidant Property of Genistein: Inhibitory Effect on HOCI Induced Protein Degradation, DNA Cleavage, and Cell Death

  • Choi, Je-Min;Ryu, Hyun-Jin;Chung, Jae-Hwan;Park, Jae-Chul;Hwang, Jae-Kwan;Shin, Dong-Bum;Lee, Sang-Kyou;Ryang, Ryung
    • Food Science and Biotechnology
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    • v.14 no.3
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    • pp.399-404
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    • 2005
  • The aim of this study was to investigate the in vitro antioxidant profiles of genistein and other isoflavonoids. The reactivity of genistein towards stable radical and reactive oxygen species including ${\bullet}\;ABTS^+$, ${\bullet}{O_2}^-$, $H_2O_2$ and HOCl has been investigated, and the effects were compared with other isoflavonoids and antioxidants. All the tested isoflavonoids showed remarkable ${\bullet}\;ABTS^+$ scavenging activity and genistein was more potent than BHT and ascorbic acid. Genistein was more effective in scavenging hypochlorous acid than superoxide and hydrogen peroxide. At $10\;{\mu}M$ concentrations of genistein and genistin showed about 90% inhibitory effect on HOCl, while BHT and ascorbic acid showed lower than 50% inhibitory effect. Moreover, genistein could inhibit plasmid DNA cleavage, protein degradation and cell death from HOCl attack, while daidzein, BHT and ascorbic acid could not protect them effectively. These results suggest that genistein is a more potent radical scavenger than other isoflavonoids, and it can remarkably reduce cellular damage induced by HOCl.

Variation of Major Isoflavone Contents in Soybeans (Glycine max (L.) Merill.) of Collection Area, Diversity, and Seed Coat Color

  • Yu-Mi Choi;Hyemyeong Yoon;Sukyeung Lee;Ho-Cheol Ko;Myoung-Jae Shin;Myung-Chul Lee;On sook Hur;Na young Ro;Kebede Taye Desta
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2020.08a
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    • pp.96-96
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    • 2020
  • Soybean seeds are important sources of non-nutritive health promoting metabolites. The contents of these metabolites are affected by both genetic and environmental factors. In the present study, the contents of five common isoflavones including daidzin, genistin, glycitin, malonyldaidzin, and malonylgenistin were analyzed in 72 soybeans of different seed coat colors, diversity, and of different origins including China (22), Japan (9), USA (12), India (4), and Korea (25). The average total isoflavone content (TIC) was maximum in Indian soybeans (3302.36 ㎍/g) and minimum in Chinese landraces (1214.95 ㎍/g). The Korean landraces had higher average TIC (2148.05 ㎍/g) than the USA genetic materials (1580.23 ㎍/g) and Japanese landraces (1485.99 ㎍/g). The content of malonylgenistin was in the range of 54.31 - 2385.68 ㎍/g in the entire population, and was the most abundant isoflavone irrespective of origin although there was content variation among individual soybeans. Besides, glycitin was the least concentrated isoflavone, and its content ranged from 0.00 to 79.79 ㎍/g. With respect to seed coat color, green soybeans from all countries displayed the maximum malonylgenistin and TIC contents. Exceptions were those of Korean and Indian origins where black and yellowish-green soybeans presented the highest malonylgenistin and TIC contents, respectively. In multivariate analysis, 92.72% of the variance was explained by the first two principal components, and the soybeans were grouped in to three clusters based on isoflavone contents. Overall, our findings signify the importance of seed coat color and origin as discriminant parameters, and provide wide spectrum of routes for breeding soybean cultivars.

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Cloning of $\beta$-Glucosidase Gene from Streptomyces coelicolor A3(2) and Characterization of the Recombinant $\beta$-Glucosidase Expressed in Escherichia coli (Streptomyces coelicolor A3(2)로 부터 $\beta$-Glucosidase 유전자 클로닝 및 재조합 효소의 특성)

  • Kim, Jae-Young;Kim, Bong-Kyu;Yi, Yong-Sub;Kang, Chang-Soo;Ahn, Joong-Hoon;Lim, Yoong-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.2
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    • pp.99-104
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    • 2009
  • The $\beta$-glucosidase gene from Streptomyces coelicolor A3(2) was cloned and expressed in Escherichia coli. The ORF consisted of 1377 nucleotides encoding 51 kDa in a predicted molecular weight. Effects of pH indicated that the $\beta$-glucosidase showed similar activity using $\alpha$-pNPG($\rho$-nitrophenyl-$\alpha$-D-glucopyranoside), $\beta$-pNPG($\rho$-nitrophenyl-$\beta$-D-glucopyranoside), and $\beta$-pNPF($\rho$-nitrophenyl-$\beta$-D-fucopyranoside) at range of pH 3 to 10, and high activity using $\beta$-pNPGA ($\rho$-nitrophenyl-$\beta$-D-galactopyranoside) from pH 5 to 10, especially, 3.3 times higher activity at pH 9. Effects of temperature indicated that the $\beta$-glucosidase showed low activity using $\alpha$-pNPG, $\beta$-pNPG, and $\beta$-pNPF from $20^{\circ}C$ to $70^{\circ}C$, and increased activity using $\beta$-pNPGA from $30^{\circ}C$ to $50^{\circ}C$, 1.8 times higher activity at $50^{\circ}C$ than at $30^{\circ}C$. According to activity determination of other substrates, the enzyme was active on daidzin, genistin, and glycitin, inactive on esculin and apigenin-7-glucose. The EDTA and DTT as reducing agents inhibited $\beta$-glucosidase activity, but SDS and mercaptoethanol did not inhibit. Monovalent or divalent metal ions such as $MnSO_4$, $CaCl_2$, KCl, and $MgSO_4$ did not inhibited $\beta$-glucosidase activity. $CuSO_4$ and NaCl showed low inhibition, and $ZnSO_4$ inhibited 3.3 times higher than control.