Change in isoflavone concentration of soybean (Glycine max L.) seeds at different growth stages

This study was conducted to determine the fluctuating levels of isoflavone in soybean (Glycine max L.) seeds of six varieties at different development stages. The average concentration of total isoflavone in the fully matured seed was 669 µg g^?1, whereas those in the seeds of the R5 (beginning), R6 (green full‐sized) and R7 (onset of physiological maturity) stages were 145, 296 and 611 µg g^?1, respectively. Sowonkong variety was highest in total isoflavone content of the fully matured and the R7 seed among all the varieties. In all six varieties, total isoflavone levels at the R7 stage were higher than those of R5 and R6 stages. Total isoflavone concentrations rapidly increased as growth stages transitioned from R5 to R7, as indicated by a positive correlation (r = 0.80***) between the total isoflavone and growth stages. Overall, total isoflavone levels were similar between R7 and the full maturity stages. Of the various isoflavone derivatives, acetylglucoside and aglycon were not significantly correlated with total isoflavone concentrations. However, glucoside (r = 0.97***), malonylglucoside (r = 0.99***), TGIN (genistein + genistin + malonylgenistin + acetylgenistin, r = 0.93***) and TDIN (daidzein + daidzin + malonyldaidzin + acetyldaidzin, r = 0.99***) were very highly correlated with total isoflavone concentrations. As a result, they constituted most of the total isoflavones in the soybean seeds at R5, R6, R7, and full maturity stages. Copyright © 2007 Society of Chemical Industry     

Functional attributes of soybean seeds and products,with reference to isoflavone content and antioxidant activity

The concentrations of isoflavones, especially daidzein and genistein, were determined by high performance liquid chromatography in 4 soybean cultivars and 26 soybean products. The total isoflavone content of the soybean cultivars was in the range of 525–986 mg per kg, and for soy products it was 32.9–795 mg per kg. Amongst the soybean products, the isoflavone content decreased in the order: soy sprouts, soy seeds, soy flour, soy milk, soy meals and soy sauce. Significant differences in the concentration of genistein and daidzein were observed between the commercial soy products and also within the soybean cultivars. The antioxidant activity of soybean and soy products correlated well with total phenolic content (TPC) and total isoflavones (TI), whereas TPC showed higher correlation with TI.     

Effect of soybean varieties on the content and composition of isoflavone in rice-koji miso

To clarify the effect of soybean varieties on isoflavone, a useful component for human health, in soybean products, we investigated changes in the isoflavone content and composition in rice-koji miso, after fermentation/aging for 6 or 12 months using varieties of soybeans (Tohoku-126, Tohoku-135, Tohoku-139, Suzuyutaka and Chinese soybeans), by high performance liquid chromatography. In soybeans, the total isoflavone content in Tohoku-126 was 444 mg/100 g, which was 1.2–2.0 times the content in the other soybean varieties. The malonyl glycosides and aglycones in soybeans accounted for more than 60% and only a few percent, respectively. As for rice-koji miso, the total isoflavone and aglycone contents were the highest in miso prepared from Tohoku-126. The ratios of glycosides to aglycones (80.1–92.6%) in miso were higher than those in the original soybeans. The time course of the isoflavone composition during the fermentation/aging process of rice-koji miso indicated that glycosides decreased from 86.4% to 44.9% after 6 months but aglycones increased from 9.6% to 53.3%.     

不同品种大豆异黄酮组分及体外抗氧化活性分析

为研究不同品种大豆异黄酮组分和含量以及抗氧化活性,测定了50个特色大豆品种的百粒重、色泽（L*、a*、b*）,通过高效液相色谱法（HPLC）测定异黄酮组分,评估不同品种大豆甲醇提取物的DPPH、ABTS自由基清除能力,并用相关性分析、主成分分析及聚类分析法对样品进行分析。结果表明:大豆的百粒重范围为7.05~47.46 g。不同种皮色大豆L*、a*和b*呈现显著差异（P<0.05）。HPLC分析结果发现糖苷型异黄酮含量是大豆中主要的异黄酮组分,占总异黄酮含量的90%以上。其中染料木苷含量最高。安豆115品种的大豆异黄酮的总含量最高,为2500.78 μg/g;靖江丝瓜青品种的大豆异黄酮含量最低,为888.86 μg/g。安豆115品种的DPPH和ABTS自由基清除能力较强,分别为（16.11±0.25）和（8.12±0.04）μmol V_C/g。糖苷型异黄酮含量与DPPH和ABTS自由基清除能力有较高的线性相关性（R2分别为0.903和0.867）。主成分分析表明6项指标可用2个主成分来表示（累计贡献率达66.3%）。聚类分析将50个品种的大豆分为4类:第一类中黄豆黄素和黄豆黄苷含量较高;第二类中大豆苷、大豆苷元、染料木苷和染料木素含量较高;第三类和第四类中其大豆异黄酮含量基本处于中等水平和较低含量。综上所述,不同大豆品种的异黄酮组成、含量和抗氧化能力存在较大差异,可为其进一步综合开发利用提供一定理论基础。     

酱油渣异黄酮抗氧化功效成分纯化研究

以酱油渣为原料,采用乙醇提取法提取酱油渣中大豆异黄酮,对提取条件进行了优化。比较了醇沉法、等电点沉淀法、浓缩离心法、正丁醇法、二氯甲烷法、乙酸乙酯萃取法等6种方法对异黄酮粗提物的纯化效果。通过高效液相鉴定了纯化产物的异黄酮单体组成,并采用邻苯三酚氧化法和DPPH法评价了异黄酮纯化物的体外抗氧化活性。结果表明：优化条件下提取的异黄酮粗提物中异黄酮质量分数为1.21%、提取率为（85.36±0.09）%。6种纯化方法中,浓缩离心法所得异黄酮产物中异黄酮纯度为7.75%,去除蛋白质效果最佳;二氯甲烷萃取法所得异黄酮产物中异黄酮纯度为27.74%,去除总糖和灰分效果最佳;两者联用后所得纯化产物的异黄酮纯度为44.88%,其主要由染料木素、大豆黄素和大豆素组成,质量分数分别为67.37%、9.33%、23.30%。在质量浓度为1 mg/mL时,异黄酮纯化物对超氧阴离子、DPPH自由基的清除率分别为67.65%、89.18%,显著高于异黄酮粗提物（P＜0.05）,其IC50分别为0.34、0.26 mg/mL,说明异黄酮纯化物具有一定的抗氧化活性,有望作为一种潜在的天然抗氧化剂应用于功能性食品中。     

Potential risk and sodium content of children’s ready-to-eat foods distributed at major amusement parks in Korea

This study was conducted to help better understand the current sodium intake of Korean children and to establish children’s good eating habits through investigation of the sodium content of ready-to-eat foods collected from nine major amusement parks in Korea. The sodium content of a total of 322 products was analysed by using ICP and then the potential risk based on the recommended daily intake of sodium as described in the Korean dietary reference intakes was determined. The results showed that sodium content was the lowest in muffins (245 mg/100 g) and the highest in seasoned dried filefish (1825 mg/100 g). The average amounts of sodium per serving of seasoned dried filefish, tteokbokki and fish paste were 1150, 1248 and 1097 mg, respectively. The values were above 50% of the daily intake of sodium recommended by the Korean dietary reference intake. The ready-to-eat foods were also classified into high, medium and low sodium content on the basis of standards recommended by the Korean Food and Drug Administration. Most snacks were classified as high sodium foods because they exceeded “300 mg (84.5% of the total daily allowance)”. Furthermore, the meal substitution foods such as kimbab, tteokbokki, mandus, sandwiches and hamburgers exceeded “600 mg (90.3% of the total daily allowance)” and were also classified as high sodium foods. In addition, ready-to-eat foods in amusement parks are similar to foods eaten on streets and foods around school zones, which contain high sodium content; thus, the intake frequency might be high, which would induce high risk to children health. Koreans already consume a high amount of sodium daily via their usual diets. So, the sodium content in snacks and substitution foods needs to be reduced. Consequently, this study noted that parents and guardians should carefully consider their children’s consumption of ready-to-eat foods from Korean amusement parks.     

Comparison of nutritional components (isoflavone,protein, oil,and fatty acid) and antioxidant properties at the growth stage of different parts of soybean [<Emphasis Type="Italic">Glycine max</Emphasis> (L.) Merrill]

This is the first study to investigate antioxidant capacities of isoflavones prepared using microwave-assisted hydrolysis method from different parts (seeds, leaves, leafstalks, pods, stems and roots) of soybean at growth stages. In addition, the fluctuations in the isoflavone, protein, fatty acid, and oil contents in R6-R8 (R6: beginning; R7: beginning maturity; R8: full maturity) seeds were confirmed. The R7 seeds exhibited the most predominant contents of isoflavones (1218.1±7.3 μg/g) in the following order: daidzein (48%)>genistein (35%)>glycitein (17%). The second highest isoflavone content was found in the leaves (1052.1±10.4 μg/g), followed by R8 seeds>roots>R6 seeds>leafstalks> pods; the stems exhibited the lowest isoflavone content (57.2±1.7 μg/g). Interestingly, daidzein showed the highest individual isoflavone content with remarkable variations (57.2-766.8 μg/g), representing 46-100% of the total isoflavone content. R8 exhibited higher protein, fatty acid, and oil contents than R6 or R7. Moreover, the antioxidant capacities against two radicals in different parts of soybean plant showed considerable differences depending upon the isoflavone content. Our results suggested that soybean leaves and seeds might be useful materials for functional foods.     

不同大豆制品中大豆异黄酮含量的比较研究

大豆异黄酮是一类具有重要生物活性的化合物,在大豆及其制品中含量丰富。本实验采用乙醇热回流提取法研究大豆及其制品中异黄酮含量。结果表明:样品加标回收率大于99%,说明该方法适用于大豆样品异黄酮含量的测定;大豆及其制品中异黄酮含量的大小顺序依次为:大豆>豆浆>豆腐脑>卤水豆腐>腐竹>白豆干>豆腐皮>油豆腐>脆豆皮,表明加工工艺会影响大豆异黄酮的含量。     

Daidzein and genestein contents in tempeh and selected soy products

The total isoflavones in tempeh and selected local soy products was determined. Raw tempeh contained 26 ± 6 mg daidzein (Da) and 28 ± 11 mg genestein (Ge) while fried tempeh contained 35 ± 11 mg Da and 31 ± 11 mg Ge in 100 g (wet basis). Total isoflavone content in 100 g of raw tempeh, based on a dry weight, was 205 ± 56 mg and significantly reduced to 113 ± 41 mg in 100 g of fried tempeh. Tempeh in batter was deep-fried for 30 min which reduced 45% of the total isoflavone content compared to the raw one. Raw tempeh contained the highest total content of isoflavone among the studied local soy products. Total isoflavone content in processed soy foods like egg tofu and home made soybean drink were significantly lower than other soy products studied.     

大豆异黄酮组分在腐乳后酵过程中的变化

研究腐乳后酵过程中大豆异黄酮组成和含量的变化。结果表明：在腐乳后酵过程中,大豆异黄酮总含量呈下降趋势;当食盐含量较低时,糖苷(daidzin 和genistin)分解较快;大豆异黄酮糖苷形式(daidzin 和genistin)转化为苷元形式(daidzein 和genistein)。说明腐乳后酵有效提高了大豆异黄酮的生物活性。     

Isoflavone Profile in Soymilk as Affected by Soybean Variety,Grinding, and Heat‐Processing Methods

Isoflavones impart health benefits and their overall content and profile in foods are greatly influenced at each step during processing. In this study, 2 soybean varieties (Prosoy and black soybean) were processed with 3 different grinding (ambient, cold, and hot grinding) and heating methods (traditional stove cooking, 1‐phase UHT, and 2‐phase UHT) for soymilk making. The results showed after cold, ambient, and hot grinding, the total isoflavones were 3917, 5013, and 5949 nmol/g for Prosoy; the total isoflavones were 4073, 3966, and 4284 nmol/g for black soybean. Grinding could significantly increase isoflavone extraction. The grinding process had a destructive effect on isoflavones and this effect varied with grinding temperature. Different heating methods had different effects on different isoflavone forms. Two soybean varieties showed distinct patterns with respect to the change of isoflavone profile during processing.     

Macronutrients,Phytochemicals, and Antioxidant Activity of Soybean Sprout Germinated with or without Light Exposure

This study examined the macronutrients, phytochemicals, and antioxidant activities of yellow soybean sprout (YSS) and green soybean sprout (GSS) with different germination days. YSS and GSS were obtained by sprouting soybean in darkness or with light exposure at 21 °C. Lipid, protein, carbohydrate, and ash contents were analyzed before and after soybean germination. Phytochemicals (total phenolic compounds, saponin, and isoflavone) were also determined. DPPH, ferric reducing antioxidant power (FRAP), and oxygen radical absorbance capacity (ORAC) were determined to examine the antioxidant activities of soybean sprout. Results showed YSS had a higher yield than GSS. Based on dry mass composition, 7‐d germination of GSS decreased 14% protein, 37% lipid, 22% carbohydrate, and 16% ash, whereas 7‐d germination of YSS decreased 6% protein and 47% lipid. Carbohydrate did not change and ash significantly increased for the 7‐d germinated YSS. Lipid was greatly metabolized in germination, which explained why the protein relative percentage in dried soybean sprout was higher than that in the corresponding soybean. Total phenolic compounds and saponin (mg/g soybean sprout, dry basis) had the same accumulation trend in soybean sprout with the increases in germination days. Aglycone isoflavones (genistein, glycitein, and daidzein) and daidzin showed an increased trend, whereas malonylgenistin and malonylglycitin showed a decreased trend with germination days for both GSS and YSS. The change in other isoflavones did not show definite trends. GSS had 20% more antioxidant activities than YSS (7‐d germinated soybean sprout). The increases in ORAC antioxidant activity suggest eating GSS may be more beneficial than GSS for promoting human health.     

Analysis of biotin in Korean representative foods and dietary intake assessment for Korean

Biotin is an important vitamin functioning as coenzyme in several carboxylase-mediated metabolic reactions. Total 105 foods were selected as the target samples, of those 75 samples were highly and frequently consumed by Korean and the others were potently high biotin content foods. HPLC with the triple column system had been optimized and applied for the analysis of biotin in various food samples. The foods with the biotin concentration over 0.10 μg/g were 13 kinds of foods such as soybean (2.037 μg/g), soy milk (0.591 μg/g), pork liver (0.455 μg/g), etc. The total daily biotin exposure per person via average and the 95^th percentile food intake was 44.656 and 169.416 μg, respectively. The Korean staple food, rice contributed as fifth diet for biotin intake (3.433 μg/person/day) following soybean (9.167 μg/person/day) > milk (6.018 μg/person/day) > soy milk (4.433 μg/person/day) > beer (4.428 μg/person/day).     

Isoflavone content in soy germ flours prepared from two drying methods

Isoflavone glucosides and aglucons in various soybean varieties (Chiang Mai‐60, S.J.‐5, Chiang Mai‐2, Srisumrong‐1, and Nakhonsawan‐1) harvested from dry vs. rainy seasons were quantified. Isoflavone contents of all soy germs ranged from 16.5 to 30.6 μmol g^?1. Regardless of varieties, isoflavone contents in germ of seeds from dry season were higher (P < 0.05) than those from rainy season. The Chiang Mai‐60 germ, having the highest isoflavone content (30.6 μmol g^?1), was selected for germ flour production. Freeze‐dried germ flour contained higher isoflavone aglucons (17.72 μmol g^?1 daidzein; 6.48 mg g^?1 glycitein; 4.28 μmol g^?1 genistein) than those (15.07; 5.59; 3.41) of drum‐dried germ flour. However, isoflavone glucoside contents in freeze‐dried germ flour (3.27 μmol g^?1 daidzin; 1.86 μmol g^?1 glycitin; 1.41 μmol g^?1 genistin) were lower than those (5.22; 3.15; 1.89) of drum‐dried germ flour. Total isoflavone contents of drum‐dried and freeze‐dried germ flours were comparable (34.32 vs. 35.02 μmol g^?1) but more than that (30.16 μmol g^?1) of unprocessed germ flour.     

Urinary isoflavone excretion in Korean adults: comparisons of fermented soybean paste and unfermented soy flour

BACKGROUND: This study compared the 24 h urinary excretion of isoflavone algycones after the consumption of fermented soybean paste or unfermented soy flour in a population of healthy Koreans (four males and five females). An equivalent amount (20 mg) of total isoflavone was consumed as either 52 g of soybean paste or 12.2 g of soy flour in a randomised, crossover trial consisting of two single‐time‐point feedings and having 3 day run‐in and washout periods between feedings. RESULTS: Analysis of starting materials indicated that daidzein (1.4%) and genistein (1.4%) constituted a smaller proportion of the total isoflavones in soy flour as compared with soybean paste (55.3% daidzein and 45.7% genistein). Free and glycosidic forms of isoflavones differed significantly between the two soy products. Levels of β‐glycosides as well as total glycosides (β‐glycosides, malonyl and acetyl forms) were two‐fold higher in soy flour as compared with soybean paste. Malonyl forms predominated in soy flour. CONCLUSIONS: The consumption of soybean paste resulted in significantly higher urinary excretion of both daidzein and genistein as compared with soy flour (P < 0.05 and P < 0.01 respectively). Copyright © 2007 Society of Chemical Industry     

青方腐乳发酵过程中大豆异黄酮的转化研究

本文比较了青方、红方、白方和低盐红腐乳中大豆异黄酮组成和含量差异,并对青方腐乳发酵过程中大豆异黄酮含量和构型变化规律进行研究。结果表明,四种类型腐乳中大豆异黄酮基本以苷元形式存在,青方腐乳大豆异黄酮含量明显低于其他类型腐乳,仅为红方腐乳的33.01%,从单一异黄酮来看,大豆苷元和染料木素在四种类型腐乳中的含量明显高于黄豆黄素;青方腐乳发酵过程中大豆异黄酮转化研究发现,白坯中大豆异黄酮以糖苷型为主,染料木苷含量高于大豆苷和黄豆黄苷,前酵过程中糖苷型大豆异黄酮转化为苷元型大豆异黄酮,盐腌过程中糖苷型大豆异黄酮含量有轻微降低,发酵过程中苷元型大豆异黄酮总量在后酵前30 d显著下降,其中大豆苷元可能部分转化为雌马酚,导致青方腐乳大豆异黄酮含量明显低于其他类型腐乳,对其转化物质需进一步鉴定。     

常见大豆类制品中金雀花素相对含量比较

金雀花素(5,7,4'-三羟基异黄酮,genistein,也称之为染料木素)是一种植物雌激素,目前发现在豆类作物中含量最高。近十几年的研究表明,金雀花素在防治多种癌症和疾病方面具有非常大的潜力。本文选择国内市场上常见大豆类制品作为实验材料,从中提取出金雀花素并进行分离纯化,测定其含量,以大豆作为基准,确定了在上述豆制品中,豆腐金雀花素含量比例为83.44%,而豆芽和醋大豆中分别为65.60%和47.67%。这表明,经过简单加工的大豆制品中金雀花素损失最少,因此豆腐、豆芽等大豆制品可作为中老年人群日常补充植物雌激素的推荐食品。     

大豆发芽期异黄酮含量变化的研究及其促进剂的影响

本文研究了以不同促进剂浸泡大豆发芽，对异黄酮含量变化的影响，HPLC测定结果表明以0．05％的硫酸铵为促进剂浸泡发芽的大豆，异黄酮含量提高率的最大，比未发芽大豆的异黄酮的含量提高了53．6％，而且产量也提高了13．2％。本法生产豆芽不但简单易行，便于推广，而且提高了营养品质，具有重要的实际应用价值。     

大豆异黄酮作为大豆溯源特征指标的筛选北大核心CSCD

采用高效液相色谱法对黑龙江省不同产地、不同品种大豆中大豆异黄酮含量进行测定,利用不同品种和产地大豆中大豆异黄酮单体含量的不同对大豆异黄酮溯源特征指标进行筛选。结果表明:同一产地不同品种之间大豆异黄酮单体含量总体差异显著(p<0.05),不同产地不同品种之间大豆异黄酮单体含量总体没有显著差异(p>0.05)。因此,可以利用不同品种大豆中大豆异黄酮单体含量作为对大豆异黄酮溯源特征指标实现品种溯源。     

永川豆豉传统发酵过程中的大豆异黄酮变化

为了探明永川豆豉在传统发酵过程中大豆异黄酮总含量和构成变化,采用高效液相色谱技术对永川豆豉传统发酵过程中大豆异黄酮总量和构成进行测定。结果表明：永川豆豉在发酵加工过程中大豆异黄酮总含量由发酵起始的3117mg/kg下降到豆豉成熟时的1754mg/kg;大豆异黄酮构成变化显著,游离苷元型大豆异黄酮含量迅速增加由发酵起始的3.2%上升到豆豉成熟时的95.7%,同时结合糖苷型大豆异黄酮含量迅速降低。