• Title/Summary/Keyword: isoflavone glycoside

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Hydrolysis of ${\beta}-glycosidic$ Bonds of Isoflavone Conjugates in the Lactic Acid Fermentation of Soy Milk (대두 요구르트 제조에서 이소플라본 배당체의 가수분해)

  • Choi, Yeon-Bae;Woo, Je-Gu;Noh, Wan-Seob
    • Korean Journal of Food Science and Technology
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    • v.31 no.1
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    • pp.189-195
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    • 1999
  • Isoflavones of soy milk were mainly present as sugar conjugates such as genistin and daidzin which a glucosyl residue was attached to their aglycones, genistein and daidzein through ${\beta}-glycosidic$ bond, respectively. When soy milk containing sucrose as a sugar source was fermented with lactic acid bacteria, small amount of lactic acid $(0.16{\sim}0.29%)$ was produced but isoflavone conjugates were fully hydrolyzed. Supplementation of glucose or lactose was required for normal lactic acid production and affected the hydrolysis of isoflavone conjugates in some lactic acid bacteria. In the case of Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047, glycosidic bond of isoflavone was fully hydrolyzed regardless of glucose supplementation. But only $25{\sim}40%$ of daidzin and $65{\sim}80%$ of genistin was hydrolyzed when glucose was added into soy milk in the other lactic acid bacteria, Lactobacillus bulgaricus KCTC 3188, Lactobacillus casei KCTC 3109, Lactobacillus delbrueckii subsp lactis KCTC 1058, Lactobacillus lactis KCTC 2181. The hydrolyzing enzyme, ${\beta}-glucosidase$ produced by lactic acid bacteria except Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047 could be considered as inducible in the fermentation of soy milk and its production was decreased when glucose was added.

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Bioactive compounds of Cheonggukjang prepared by different soybean cultivars with Bacillus subtilis HJ18-9 (Bacillus subtilis HJ18-9 이용하여 제조한 품종별 청국장의 품질특성과 isoflavone 함량의 변화)

  • Song, Jin;Lee, Kyung-Ha;Choi, Hye-Sun;Hwang, Kyung-A
    • Food Science and Preservation
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    • v.22 no.4
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    • pp.535-544
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    • 2015
  • This study was conducted to investigate the changes of isoflavone composition (glycoside and bio-active aglycone) in Cheonggukjang and to evaluate its quality characteristics depending on different soybean cultivars (Daewon, Daepoong, Wooram, Hwangkeumol and Saedanback). The bioactivity of Cheonggukjang was enhanced during fermentation at $37^{\circ}C$ for 48 h. Activities of ${\alpha}$-amylase, protease, and cellulase increased significantly after 48 h fermentation (p<0.05). In addition, amino-type nitrogen and reducing sugar contents in Cheonggukjang fermented with B. subtilis increased significantly after 48 h fermentation (p<0.05). Among the isoflavones, the content of $\beta$-glucosides and acetyl-glucosides decreased, while aglycone content increased during fermentation. Especially, Cheonggukjang fermented with Daepoong cultivars showed the greatest increase in daidzein, genistein and glycitein contents. After 48 h fermentation, the contents of daidzein, genistein and glycitein in the Cheonggukjang fermented with Daepoong cultivars increased significantly up to $503.65{\pm}2.76$, $111.40{\pm}0.42$, and $633.95{\pm}6.01{\mu}g/g$ (p<0.05), respectively. Total aerobic and anaerobic cell counts increased with increase in fermentation time. Therefore, it would be beneficial for the food industry if components of Cheonggukjang could be separated and used to develop functional products.

Functional and Chemical Composition of Hwanggumkong, Yakong and Huktae (국내산 황금콩, 약콩 및 흑태의 일반성분과 기능성 성분 분석)

  • Kim Min-Jung;Kim Kang-Sung
    • Korean journal of food and cookery science
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    • v.21 no.6 s.90
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    • pp.844-849
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    • 2005
  • The chemical composition of isoflavone, oligosaccharide and phytic acid content of three Korean soybeans, Hwanggumkong, Yakkong and Huktae cultivars, were examined. Moisture, crude fat, crude protein and ash content of soybean seeds were all in the ranges of 10.9-$12.5\%$, 15.8-$20.8\%$, 36.5-$41.1\%$ and 5.4-$5.6\%$ respectively, showing differences among the cultivars. Methionine, cystein and histidine were the minor components of soybean protein and ratio of methionine to the total proteins showed significant varietal differences. The main fatty acids of total lipids were linoleic, oleic and palmitic acids, which comprised over $80\%$ of the total fatty acids. Yakkong, Hwanggumkong and Hukae contained 2491.4 $\mu$g, 2176.8 $\mu$g and 1893.5$\mu$g of isoflavone in each gram of dry matter, respectively, and existed mainly as glycoside isomers. Oligosaccharide contents were similar among the cultivars. The total concentration of phytic acid was $2.63\%$ of Hwanggumkong, $2.12\%$ of Yakkong and $2.80\%$ of Huktae.

Bioconversion of Isoflavone and Soyasaponin in the Fermentation of Soy Embryo Using Lactic Acid Bacteria (콩배아의 Lactobacillus plantarum 발효에 의한 이소플라본과 소야사포닌 변화)

  • Lee, Mi Ja;Park, Song Yi;Lee, Kwang sik;Kim, Hyun young;Ra, Ji Eun;Ham, Hyeon Mi
    • Food Engineering Progress
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    • v.23 no.3
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    • pp.209-216
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    • 2019
  • The effects of fermentation on soy embryo have been investigated using lactic acid bacteria, Lactobacillus acidophilus (LA), Lactobacillus bulgaricus (LB), Streptococcus thermophilussei (ST), and Lactobacillus plantarum (LP). As a result of the fermentation test of the isoflavone conversion by strain type, inoculation content, and fermentation time, the optimum conditions were LP bacterium, an inoculum amount of 5%, and a fermentation time of 24 hours. The composition of the isoflavone glycosides in the control was the highest in the order of glycitin> daidzin> genistin. When fermented with lactic acid bacteria, glycoside content decreased, and aglycone content increased. The order of composition was daidzein>glycitein>genistein. In the fermentation with LP bacterium, soyasaponin Ab content decreased and Ba and Bb content increased. Upon assessing the result of the experiment, it was found that the pH of the fermentation broth had a great influence in the bioconversion of isoflavone and soyasaponin. In the case of fermentation by pH 6 broth, aglycone and Bb content was the highest. The increase of aglycone content by fermentation reaction with the LP bacterium can increase the physiological activity and functionalization of soy embryo, which is a byproduct of processing.

Quality Characteristics and Composition Profile of Traditional Doenjang and Manufactured Doenjang during Storage Time (저장기간에 따른 전통된장과 개량식된장의 이화학적 특성, 기능성분 및 대사체 분석)

  • Kang, Hee-Joo;Kim, Jin-Hee;Kim, Ri-Rang;Kim, Kang Sung;Hong, Sang-Phi;Kim, Min-Jung;Yang, Hye Jeong
    • The Korean Journal of Food And Nutrition
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    • v.29 no.5
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    • pp.785-794
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    • 2016
  • This research was conducted to evaluate quality changes in traditional Doenjang and manufactured Doenjang during a storage period of 8 weeks. Low-salt Doenjang and commercial Doenjang were purchased from different manufacturers and proximate analysis as well as changes in isoflavone, polyphenol, flavonoid contents of the samples were investigated using a mass spectrophotometer. The salinity of traditional Doenjang, low salt Doenjang, and commercial Doenjang were $13.2{\pm}1.15$, $7.17{\pm}2.74$, $10.67{\pm}0.35%$, respectively and the salt concentrations of the soybean pastes did not change during storage. After 8 weeks at $35^{\circ}C$, chromatic values of all the paste samples decreased somewhat, with traditional Doenjang exhibiting fewer changes as compared to manufactured Doenjang. Amino acid nitrogen, acidity, microbial population all tended to increase with time, although some samples showed fluctuations during the test period. Moreover, the total isoflavone contents of traditional Doenjang increased with storage time while that of manufactured Doenjang tended to decrease. The isoflavone aglycone was shown to be the highest in traditional Doenjang, while isoflavone glycoside was abundant in manufactured Doenjang. Total flavonoid contents showed similar trends regardless of samples; initial contents of total flavonoid was 0.6 mg/g which increased to more than twice to 1.4 mg/g at the end of storage period. Composition profile of Doenjang extracts was analyzed using UPLC-Q-ToF.

Enhanced biological effect of fermented soy-powder milk with Lactobacillus brevis increasing in γ-aminobutyric acid and isoflavone aglycone contents (가바와 비당체 이소플라본이 증가된 Lactobacillus brevis 발효 콩-분말 두유의 생리활성 증진 효과)

  • Hwang, Chung Eun;Kim, Su Cheol;Lee, Jin Hwan;Hong, Su Young;Cho, Kye Man
    • Journal of Applied Biological Chemistry
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    • v.61 no.3
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    • pp.245-255
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    • 2018
  • The research was aimed to analyze the functional constituents (GABA and isoflavone), radical (2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and hydroxyl) scavenging activities and enzyme (${\alpha}-glucosidase$ and lipase) inhibitory effects of soypowder milk (SPM) and fermented soy-powder milk (FSPM) with varied Lactobacillus brevis. Ten ${\gamma}-aminobutyric$ acid (GABA) producing lactic acid bacteria that showed 96-99% similarity with L. brevis, according to 16S rRNA gene sequence analysis, were isolated from fermented kimchi. The conversion rates of GABA were obtained 66.96-93.51, 63.76-84.58, and 57.05-69.75% in monosodium glutamate, gluten and soy protein, respectively. The levels of pH and glutamic acid of FSPM were found lower than those of SPM, but the acidity and GABA contents were higher. The GABA conversion rate of FSPM with BMK484 strain was attained the highest 69.97%. The contents of isoflavone glycoside ($1290.93{\mu}g/g$) was higher in SPM, but the content of isoflavone aglycone ($287.27-501.9{\mu}g/g$) was higher in FSPM. The levels of isoflavone aglycone such as daidzein, glycitein and genistein, were found as the highest 240.2, 61.24 and $200.45{\mu}g/g$, respectively, when FSPM was made with BMK484 strain. The DPPH, ABTS and hydroxyl radical scavenging and ${\alpha}-glucosidase$ and pancreatic lipase inhibitory activities of FSPM made with BMK484 strain were the relatively higher 60.31, 88.10, 61.25, 52.71, and 39.37%, respectively. Therefore, the L. brevis can be used as a material capable of simultaneously enhanced GABA and isoflavone aglycone in FSPM.

Comparison of γ-aminobutyric acid and isoflavone aglycone contents, to radical scavenging activities of high-protein soybean sprouting by lactic acid fermentation with Lactobacillus brevis (발아 고단백 콩의 Lactobacillus brevis 젖산발효에 의한 가바와 이소플라본 함량 및 라디칼 소거활성의 비교)

  • Hwang, Chung Eun;Haque, Md. Azizul;Lee, Jin Hwan;Joo, Ok Soo;Kim, Su Cheol;Lee, Hee Yul;Um, Bong Sik;Park, Kyung Sook;Cho, Kye Man
    • Food Science and Preservation
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    • v.25 no.1
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    • pp.7-18
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    • 2018
  • In this study, soy-powder yogurt (SPY) with enhanced levels of ${\gamma}$-aminobutyric acid (GABA) and isoflavone aglycone was produced from sprouting high-protein soybeans (HPSs). The fermented steam-HPS sprouts (0 to 4 cm) were fermented (72 h) with Lactobacillus brevis, and the total free amino acids (FAAs) of the formed mixtures were determined to be 79.53, 489.93, 877.55, 780.53, and 979.97 mg/100 mL in the fermented HPS (FHPS), and the fermented steam-HPS with 0 cm (FSHPS-0), 1 cm (FSHPS-1), 2 cm (FSHPS-2), and 4 cm sprouting lengths (FSHPS-4), respectively. The levels of glutamic acid (GA) and GABA were observed to be the highest, 100.31 and 101.60 mg/100 mL, respectively, in the unfermented HPS (UFSHPS-1, 1 cm) and FSHPS-1 sprouts, respectively. Moreover, the total contents of the isoflavone glycoside form decreased proportionally to the increasing total levels of isoflavone aglycones after fermentation in FSHPS-0, FSHPS-1, FSHPS-2, and FSHPS-4. The levels of isoflavone aglycones were detected as 350.34, 289.15, 361.61, 445.05, and $491.25{\mu}g/g$ in FHPS, FSHPS-0, FSHPS-1, FSHPS-2, and FSHPS-4, respectively. While FSHPS-1 exhibited the highest DPPH (63.28%) and ABTS (73.28%) radical scavenging activities, FSHPS-4 contained the highest isoflavone aglycone ratio (81.63%). All in all, the FSHPS-1 mixture prepared in this study exhibited high GABA content and functional prosperity, thereby making it suitable for potential applications in the soy-dairy industry.

Changes in phytoestrogen contents and antioxidant activities during fermentation of soybean-powder milks prepared from different soybean cultivars by Lactobacillus plantarum P1201 (Lactobacillus plantarum P1201에 의한 콩 품종별 콩-분말 두유 발효 과정에서의 식물성 에스트로젠 함량과 항산화 활성의 변화)

  • Hwang, Chung Eun;Haque, Md. Azizul;Lee, Jin Hwan;Ahn, Min Ju;Lee, Hee Yul;Lee, Byong Won;Lee, Yu-Young;Lee, Choonwo;Kim, Byung Joo;Park, Ji-Yong;Sim, Eun-Yeong;Lee, Dong Hoon;Ko, Jong Min;Kim, Hyun Tae;Cho, Kye Man
    • Korean Journal of Microbiology
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    • v.52 no.2
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    • pp.202-211
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    • 2016
  • This study evaluated the changes of phytoestrogen contents and antioxidant activities of soybean-powder milk (SPM) prepared from yellow soybean during fermentation with Lactobacillus plantarum P1201. In consequence, the levels of total phenolic and isoflavone-aglycone contents, ABTS and DPPH radical-scavenging activities, and FRAP assay values increased, while isoflavone-glycoside contents decreased during fermentation. The highest levels of daidzein, glycitein, and genistein were present in the Daepung SPM at concentrations of 177.92, 20.64, and $106.14{\mu}g/g$, respectively after 60 h of fermentation. Moreover, Daepung SPM showed the highest DPPH radical-scavenging activity of 48.54%, an ABTS radical-scavenging activity of 99.25%, and a FRAP assay value of 0.84 at the end of fermentation. The fermented Daepung SPM possessed highest isoflavone aglycone contents and antioxidant activities, which can be utilized for the development of functional foods.

Changes in isoflavone content and quality characteristics of Cheonggukjang prepared with Bacillus subtilis HJ18-3 and KACC 15935 (Bacillus subtilis HJ18-3과 KACC 15935를 이용하여 제조한 청국장의 품질특성과 isoflavone 함량의 변화)

  • Lee, Kyung Ha;Choi, Hye Sun;Choi, Yoon Hee;Park, Shin Young;Song, Jin
    • Food Science and Preservation
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    • v.21 no.1
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    • pp.121-128
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    • 2014
  • This study was conducted in order to investigate the change of isoflavone composition (glycoside and bio-active aglycone), and to evaluate the quality characteristics of Cheonggukjang, which was prepared by different bacillus strains. After the 48-hour fermentation, the contents of daidzein, genistein, and glycitein in the Bacillus subtilis HJ18-3 have significantly increased up to approximately $89.06{\pm}3.59$, $10.36{\pm}0.28$, and $101.37{\pm}3.67ug/g$, respectively. The contents of daidzein, genistein, and glycitein in the Bacillus subtilis KACC 15935 were $38.88{\pm}5.39$, $12.58{\pm}2.14$, and $80.13{\pm}0.71ug/g$, respectively. The original content of daidzein was 3.96 ug/g, while genistein and glycitein were not measured. However, the contents of daidzen and genistein in HJ18-3 and in KACC 15935 were decreased. The ${\alpha}$-Amylase and cellulase activities of Chungkookjang in HJ18-3 were higher than in the KACC 15935. The contents of Chungkookjang in HJ18-3 were $29.70{\pm}11.66$ and $4861.3{\pm}388.07unit/g$, respectively. The amino type nitrogen contents and ammonia type nitrogen contents of Chungkookjang in KACC 15935 were higher than in the HJ18-3. These results suggested that it could be used to increase the bioactivity via fermentation with the Bacillus subtilis possessing a ${\beta}$-glucosidase activity with a view towards the development of functional foods.

Changes in nutritional components and antioxidant activities from soybean leaves containing high isoflavone contents according to different storage temperatures and periods (고 이소플라본 함유 콩잎의 저장 온도와 기간에 따른 영양학적 성분과 항산화 활성 변화)

  • Lee, Hee Yul;Lee, Dong Hee;Kim, Su Cheol;Cho, Du Yong;Cho, Kye Man
    • Journal of Applied Biological Chemistry
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    • v.63 no.4
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    • pp.305-317
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    • 2020
  • This study investigated that change of the nutrients (including fatty acids, amino acids, and minerals) and total phenolic (TP), total flavonoid (TF), and isoflavone contents and antioxidant activities during the storage of soybean leaves containing high isoflavone contents at 5, 25, and 55 ℃ for 180 days. The contents of free amino acids were increased from 1313.81 mg/100 g at 0 day to 1776.15, 1693.93 and 1551.18 mg/100 g at 5, 25, and 55 ℃ storage for 180 days, respectively, but the values of fatty acids were little unchanged. The contents of minerals were detected from 51.65 mg/100 g (0 day) to 49.93 (5 ℃), 50.20 (25 ℃), and 61.21 (55 ℃) mg/100 g at 180 days, respectively. The levels of total isoflavones did not change during the storage periods. In case of storage at 55 ℃, the contents of glycosides (1347.78→2195.13 ㎍/g) and aglycones (342.79→480.61 ㎍/g) increased during storage, while the levels of malonylglycosides (2209.22→1289.48 ㎍/g) decreased. Also, the TP and TF contents were slightly increased from 9.31 and 8.61 mg/g at 0 day to 9.97 and 9.3 mg/g at 180 days, corresponding to the radical scavenging activities of 2,2-diphenyl-1-picrydrazyl, 2,4,6-azino-bis (3-ethylbenzthiazoline-6-sulphnoic acid), and hydroxyl increased from 30.91, 55.98 and 23.27% from 37.10, 62.54, and 30.95%, respectively.