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.     

INFLUENCE OF HEAT TREATMENT AND GRAIN GERMINATION ON THE ISOFLAVONE PROFILE OF SOY MILK

Soy foods have attracted much attention for their possible effects on human health because of their phytochemical content, mainly isoflavones. Twelve forms of isoflavones have been identified in soybeans and soy products. Technological processes like heat treatment or fermentation can change the isoflavone profile of soy products. In this study, the effects of heat treatment and grain germination on isoflavone profile of soy milk prepared from BRS 213 soybean variety were evaluated. Isoflavone forms were separated and quantified by reversed‐phase high‐performance liquid chromatography. Heat treatment by autoclaving for 5 min did not affect the total isoflavone content, but led to a 90% decrease in malonyl forms, whereas β‐glycosides increased by 70%. Autoclaving for 15 min led to a 20% loss of total isoflavones. Germination for 3 days did not change the total isoflavone content, but changed the distribution profile (15% increase of malonyl forms and 30% decrease of β‐glycosides). Germination for 7 days increased the bioavailability of aglycone isoflavones in soy milk by seven times.     

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。     

Lesser in vitro anaerobic cecal isoflavone disappearance was associated with greater apparent absorption of daidzein and genistein in Golden Syrian hamsters

Our hypothesis in this study was that in vitro disappearance of isoflavones from fecal or cecal contents of Golden Syrian hamsters paralleled the apparent absorption of these compounds, comparable with previous findings from in vitro human fecal incubations. Two studies were conducted to test this idea: one on in vitro fecal (study 1, n = 20/sex) and the other on in vitro cecal contents (study 2, n = 10/sex) ability to degrade isoflavones. According to HPLC analysis, urinary isoflavone excretion was significantly less by 2-4 fold in males compared with females in both studies. Fecal isoflavone excretion was not significantly different between sexes or isoflavones (study 1) and was <0.5% of ingested dose. In vitro anaerobic fecal isoflavone degradation rate constants from study 1 were minimal with no significant correlation between urinary and fecal isoflavone excretion. However, in vitro anaerobic cecal isoflavone degradation rate constants (study 2) were greater and significantly correlated with urinary excretion of daidzein (R = 0.90; p = 0.01) and genistein (R = 0.93; p = 0.004), but not glycitein (R = 0.50; p = 0.3). Both male and female hamsters showed a pattern of urinary isoflavone excretion similar to that found in humans (daidzein > genistein). Hamster in vitro cecal isoflavone degradation rate constants seemed to be analogous to human in vitro fecal isoflavone degradation rate constants for genistein and daidzein. The sex difference in isoflavone excretion in hamsters and the instability in glycitein excretion across studies coupled with the paucity of human data on this isoflavone deserve further investigation.     

Bioavailability of Isoflavone Metabolites After Korean Fermented Soybean Paste (Doenjang) Ingestion in Estrogen‐Deficient Rats

Doenjang (DJ), a fermented soybean product used in soups, stews, and sauces, contains high quality proteins, fats, vitamins, minerals, and other functional ingredients, including isoflavones and saponins. This study investigated whether DJ improves the bioavailability of isoflavones compared to boiled soybean (BS) in sham‐operated or ovariectomized (OVX) rats. We also examined the effects of ovariectomy on the differences in bioavailability of isoflavones. BS and DJ were administered in sham‐operated and OVX rats, and blood samples were collected. Twenty‐six isoflavone‐derived metabolites were identified. Pharmacokinetic analysis revealed that T_1/2 values of the individual isoflavone metabolites were most different in sham and OVX rats, even after the same sample treatment; however, T_max values were significant different in a few metabolites such as daidzein 4′‐glucuronide, daidzein 4′‐sulfate, 2‐(4‐hydroxyphenyl)propionic acid, and benzoic acid. For most of the individual metabolites, C_max was higher in both sham and OVX rats administered BS than those administered DJ. The AUC was generally lower in OVX rats than in sham rats. The AUC of daidzein and genistein in BS‐fed sham rats was approximately 1.7‐fold higher than those administered DJ, whereas glycitein was detected only in the DJ group. No significant differences in AUC of daidzein and genistein were observed between BS and DJ administration in OVX rats, although the total isoflavone content of DJ was lower; thus, DJ‐mediated isoflavone bioavailability was more effective in OVX rats. Similar tendencies were observed for phase II and gut‐mediated metabolites. These results suggested that DJ enhanced isoflavone bioavailability under estrogen deficiency, even when the total isoflavone content was decreased by fermentation.     

Combination of low dose of genistein and daidzein has synergistic preventive effects on isogenic human prostate cancer cells when compared with individual soy isoflavone

The reduced incidence of prostate cancer (PCa) in Asia countries has been attributed to high soy diets, and major soy isoflavones, in particular daidzein and genistein, are thought to be the source of the beneficial and anti-cancer effects of soy foods. However, attention has been drawn to the safety of using high levels of soy isoflavones in humans, which is especially the concern for consumers taking regular soy isoflavone dietary supplements. The main objective of this study is thus to identify a soy isoflavone combination with lower levels of daidzein and genistein to be a more efficacious and safer chemo-preventive agent for PCa. The anticancer effects of daidzein and genistein, and their combinations on early-stage androgen-dependent PCa cells (LNCaP) and bone metastatic LNCaP-derivative PCa cells (C4-2B) were compared. Cells were treated with varying concentrations of daidzein, genistein (25–200 μM) or their combinations (25 or 50 μM) and cell proliferation, apoptosis, cell cycles and cellular uptakes of the isoflavones were measured after 48 h. Daidzein and genistein showed a synergistic effect on inhibiting cell proliferation and inducing apoptosis of both PCa cells. Twenty-five μM daidzein/50 μM genistein and 50 μM daidzein/50 μM genistein significantly increased the apoptotic effects on C4-2B cells although they did not show any effect when used individually. Except 50 μM daidzein/50 μM genistein, all other combinations had no impacts on cell cycles. For treatment with soy isoflavone combination, genistein was always better taken up than daidzein by both LNCaP and C4-2B cells.     

Effects of extraction temperature,ionic strength and contact time on efficiency of bis(2‐ethylhexyl) sodium sulfosuccinate (AOT) reverse micellar backward extraction of soy protein and isoflavones from soy flour

BACKGROUND: Soy protein enriched with isoflavones has been linked to various disease‐preventing and health‐promoting activities owing to the antihypertensive, hypocholesterolaemic, antiobesity and antioxidative properties of isoflavones. The isoflavone profiles of soy‐based products are known to be highly dependent on the various chemical and physical treatments to which the products have been subjected. The aim of this research was to increase the efficiency of backward extraction of soy protein and isoflavones from bis(2‐ethylhexyl) sodium sulfosuccinate (AOT) reverse micelles by studying the effects of extraction temperature, ionic strength of the aqueous stripping solution and contact time on the amounts of soy protein and isoflavones backward extracted from an AOT/H₂O/isooctane reverse micellar system. RESULTS: By modifying the extraction temperature, ionic strength and contact time, 47.0–60.2% of protein, 43.3–68.4% of daidzin, 43.8–74.6% of genistin, 39.0–88.8% of glycitin, 20.8–92.6% of malonyl genistin, 20.2–52.0% of malonyl glycitin, 32.7–75.6% of acetyl genistin, 49.7–76.8% of daidzein and 19.6–38.1% of genistein present in the AOT reverse micellar solution were backward extracted into the aqueous stripping phase. Statistical analysis showed that there were significant linear and interactive effects of temperature and contact time on the backward extraction of daidzin, genistin, glycitin and daidzein. Significant linear and interactive effects of ionic strength and contact time were found in the backward extraction of daidzin and genistin. The backward extraction of genistein was only influenced by contact time and its interaction with temperature. CONCLUSION: This study showed the potential of reverse micelles as a protocol for extracting isoflavones from soy samples for analytical purposes. By modifying the extraction temperature, contact time and ionic strength, soy protein enriched with daidzin, genistin, daidzein and genistein could be produced from soy flour. The results represent an important contribution to current knowledge on utilising reverse micellar extraction in food technology. Copyright © 2007 Society of Chemical Industry     

Relative antioxidant activity of soybean isoflavones and their glycosides

The present study compared the antioxidant potency of genistein and daidzein with their corresponding glycosides isolated from soybean seeds. The antioxidant activity was assessed using three methods, namely human low-density lipoprotein (LDL) oxidation, the ferric reducing-antioxidant power (FRAP) and the anti-DPPH free radical assays. It was found that soybean was rich in genistein and daidzein but they were present mainly in form of glycosides. Both the FRAP and the anti-DPPH assays demonstrated that these glycosides, as well as genistin, daidzein, glycitin, malonyl glycitin and malonyl genistein possessed similar antioxidant activities to their corresponding aglycones, genistein and daidzein. In contrast, the antioxidant potency of these glycosides was much weaker than their corresponding aglycones, genistein and daidzein, in the LDL oxidation assay. The present results demonstrate that genistein and daidzein were less effective, as antioxiants in the three assays, than two well-defined antioxidants, green tea epicatechin and -tocopherol. It is concluded that soybean isoflavones and their glycosides possess antioxidant activity but they are ineffective antioxidants compared with tea epicatechins and -tocopherol.     

Content and Profile of Isoflavones in Soy-Based Foods as a Function of the Production Process

Soy has been traditionally incorporated in diet as processed foods, such as soymilk, tofu, miso, tempeh, etc., and the consumption is commonly associated with a reduction of the development of chronic diseases due to their antioxidant, anti-inflammatory, and anti-allergic properties, among others. Many of the health benefits of soy have been attributed to isoflavones. They comprise a group of naturally occurring flavonoids consisting of heterocyclic phenols. Soy contains three types of isoflavones in four chemical forms: the aglycones daidzein, genistein, and glycitein; the β-glucosides daidzin, genistin, and glycitin; their 6″-O-malonyl-β-glucosides (6OMalGlc); and their 6″-O-acetyl-β-glucosides (6OAcGlc) conjugates. Industrial processing methods of soy-based food products commonly lead to the loss of isoflavones through removal of undesirable fractions. On the other hand, isoflavones can be transformed into different conjugates, which may have significant effects on the food texture and on the bioavailability and pharmacokinetics of the isoflavones. This article reviews the effect of a number of soybean processing treatments on the isoflavone content and profile. The preparation and manufacturing of different soy-based food and food ingredients, fermented and non-fermented, has been analyzed in terms of content and distribution of the three major isoflavone derivatives, daidzein, genistein, and glycitein, and their respective conjugates.     

A new ultra-high pressure liquid chromatography method for the determination of total isoflavone aglycones after enzymatic hydrolysis: Application to analyze isoflavone levels in soybean cultivars

Since only isoflavone aglycones are considered to be bioactive, the determination of total aglycones that are released from conjugated isoflavones after hydrolytic treatment may facilitate an objective alternative for quantifying isoflavone contents in soy products. Given this major benefit, a new ultra-high pressure liquid chromatography (UV-UPLC?) method was developed for the fast and reliable determination of total aglycones in soybeans (daidzein, glycitein, and genistein) after enzymatic hydrolysis applying helix pomatia digestive juice. Capitalizing on the enhanced performance of UPLC?, aglycones were separated within 3 min only, with a total runtime of 8 min till the next injection. Thus, especially compared to HPLC protocols, UPLC? proved to be superior due to significantly shorter runtimes and accordingly increasing sample throughput. Additionally, regarding the performed validation (linearity, precision, recovery, selectivity, and robustness), the established method proved to be suitable for quantifying total aglycones in soybeans. Moreover, method applicability was demonstrated by analyzing 23 commercial soybean cultivars for their isoflavone contents. Cumulative aglycone levels ranged from 100 to 255 mg per 100 g, hence implying an average ratio of 52%, 41%, and 7% of total isoflavones for genistein, daidzein and glycitein, respectively. However, for some soybeans, other distinct aglycone distributions were observed as well.     

Isoflavone profiles,phenol content,and antioxidant activity of soybean seeds as influenced by cultivar and growing location in Ohio

Isoflavone levels and isoflavone chemical composition in soybeans vary between planting locations although the exact factors which control isoflavone biosynthesis are unclear. We compared levels of 12 isoflavones in soybean seeds of six cultivars grown in four different locations in Ohio in 2002 as determined by high‐performance liquid chromatography. Antioxidant activity contained in plant‐based foods can improve food oxidative stability and phenolics and isoflavones have proven active in food systems. Radical scavenging activity was assessed using the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical. Total phenolics (TPCs) were determined by using Folin–Ciocalteu reagent. Total isoflavones (TIs) varied five‐fold (1573–7710 nmol g^?1) between seeds from the various location–cultivar combinations. One location (Wooster, Ohio) produced seeds containing half the isoflavones as the other locations tested apparently due to poor growing conditions. The cultivars could be divided into two groups based on TI, one having approximately 50% more isoflavones. Surprisingly, across the entire data set, with increasing TI, the proportion of isoflavones accounted for by the daidzein family increased due primarily to malonyl daidzin. DPPH scavenging did not differ significantly by location or cultivar (P > 0.05) and did not correlate with TPC or TI. Profiling soybean isoflavones could help elucidate how isoflavone biosynthesis is regulated and lead to better disease resistance of soybean crops and soy foods with greater health benefits. Copyright © 2007 Society of Chemical Industry     

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。     

Profiling and quantification of isoflavones in soymilk from soy protein isolate using extracted ion chromatography and positive ion fragmentation techniques

Dietary supplements on soy based foods and beverages are increasingly gaining prominence all over the world. In this study, liquid chromatography coupled with positive electrospray ionisation tandem mass spectrometry (LC-ESI-MS) and diode array detection was used for the quantitation and characterisation of isoflavones in fermented and unfermented soymilk made from soy protein isolate SUPRO 590. Bifidobacterium animalis ssp. lactis Bb12 was used for the fermentation of soymilk. The isoflavones were found to produce characteristic radical ions as well as molecules of H₂O, CO₂, a sugar unit, and an alcohol through collision-induced fragmentation. Product ion fragments revealed unique fragmentation pathways for each isoflavone compound. Characteristic fragmentation of different isoflavones were unequivocally identified and differentiated. The occurrence of aldehydes such as pentanal, ethanal and methanal was shown to be specifically linked with isoflavone aglycones, daidzein, genistein and glycitein, respectively. Main glycosides such as genistin, daidzin and glycitin as well as the acetyl-, and malonyl forms also showed respective aglycone ions in their spectra fragmentation. Thus positive ion fragmentation was important in the absolute confirmation of isoflavones and to reveal the occurrence of other related compounds such as aldehydes in soymilk.     

中国大豆制品中异黄酮含量测定和分析研究

对中国几种有代表性的大豆制品进行了异黄酮含量测定。测定结果表明 :中国的大豆制品中含有一定量的异黄酮 ,其中非发酵制品中的异黄酮只有极少量以游离形式存在 ,大部分以 β 葡萄糖苷的形式存在 ,主要是黄豆苷 (daidzin)和染料木素 (genistin) ;而在发酵大豆制品中 ,由于酶的作用 ,部分黄豆苷和染料木素转化成黄豆苷原 (daidzein)和染料木因 (genis tein) ,因此 ,游离态的异黄酮比例增加。中国大豆制品中异黄酮含量随大豆品种和加工工艺而异 ,含量范围在 1 1 2 82～ 1 871 6 1 μg/ g ,这个结果表明中国的大豆制品对人体的健康具有重要作用。     

Changes of isoflavone in soybean cotyledons soaked in different volumes of water

Soybean cotyledons, recently dehulled, were soaked at 50 °C for 12 h as a pre treatment to obtain defatted soy flour enriched in aglycones. Grains of cultivar BRS 213 from the crop years 2004 and 2005 were used and initially had 1.4 and 1.2 mg g⁻¹ of total isoflavones, respectively. The molar mass of malonyl and β-glycosides decreased after soaking (33% and 56.5%, in grains from the crop years 2004 and 2005, respectively), while the aglycones daidzein and genistein, that were previously undetectable, increased to 0.5 and 0.8 μmol g⁻¹ in grains from the crop years 2004 and 2005, respectively. Cotyledons treated with the reduced volume of water had a reduction of 4% of the total isoflavone molar mass while, for the cotyledons treated with higher volume of water, there was a reduction of 14%, due to the leaching of isoflavones to the soaking water.     

Nutrikinetics of Isoflavone Metabolites After Fermented Soybean Product (Cheonggukjang) Ingestion in Ovariectomized Mice

1 Scope

Cheonggukjang (CGJ) is a soybean‐based quick‐fermented food popular in Korea that contains a variety of biologically active compounds including isoflavones and saponins. Isoflavone bioavailability may be important for the bone health of postmenopausal women; therefore, the aim of this study is to evaluate the influence of fermentation on the isoflavone metabolite nutrikinetic profile after single dose CGJ or unfermented soybean administration in ovariectomized (OVX) and sham mice.

2 Methods and results

We identify 34 isoflavone metabolites using UPLC–QTOF‐MS and analyze their nutrikinetics at different time points (0.25, 0.5, 1, 2, 4, 8, 16, and 24 h) to understand their fermentation‐ and OVX‐mediated time‐dependent concentration changes. Nutrikinetics analysis shows that genistein, daidzein, genistein 4′‐sulfate, dihydrodaidzein sulfate, equol 4′‐sulfate, and equol‐7‐glucuronide are present at high concentrations in all groups based on area‐under‐the‐curve analysis. OVX mice appear to show lower isoflavone bioavailability than mice in the sham group. CGJ enhances various isoflavone metabolite bioavailability including genistein, 3‐hydroxygenistein, and equol 7‐glucuronide, compared to the unfermented soybean‐treated group. Among these metabolites, intact isoflavones, 3‐hydroxygenistein, genistein 4′‐sulfate, and equol 7‐glucuronide promote osteoblastogenesis and inhibit osteoclast formation.

3 Conclusions

CGJ has good isoflavone bioavailability and may be beneficial for the bone health of postmenopausal women.     

Higher bioavailability of isoflavones after a single ingestion of aglycone-rich fermented soybeans compared with glucoside-rich non-fermented soybeans in Japanese postmenopausal women

BACKGROUND: There have been conflicting study results concerning how the food matrix affects the bioavailability of isoflavone aglycone and glucoside. In this study the bioavailability of isoflavones after a single ingestion of aglycone‐rich fermented soybeans (Fsoy) and glucoside‐rich non‐fermented soybeans (Soy) was compared. Eleven healthy postmenopausal Japanese women were recruited for a randomised, double‐blind, crossover trial and consumed Fsoy or Soy powder dissolved in hot water. Blood samples were collected 0, 1, 2, 3, 4, 6, 8, 12 and 24 h and urine samples from 0 to 48 h after ingestion of the powders. The Fsoy and Soy powders ingested had the same total isoflavone content (95 µmol), but the former was rich in aglycone (90.6 µmol) while the latter was rich in glucoside (81.9 µmol). RESULTS: Serum concentrations of total isoflavones after 1–4 h were significantly higher in the Fsoy group than in the Soy group. The Fsoy group showed significantly higher maximum concentration (Cmax: 2.79 ± 0.13 vs 1.74 ± 0.13 µmol L^?1) and area under the curve (AUC_{0–24 h}: 23.78 ± 2.41 vs 19.95 ± 2.03 µmol day L^?1) and lower maximum concentration time (Tmax: 1.00 ± 0.00 vs 5.00 ± 0.67 h) compared with the Soy group. The cumulative urinary excretion of total isoflavones after 2 h was significantly higher in the Fsoy group than in the Soy group. Individual isoflavones (daidzein, genistein and glycitein) showed similar trends to total isoflavones. Equol (a metabolite from daidzein) did not differ between the two groups. CONCLUSION: The results of this study demonstrated that the isoflavones of aglycone‐rich Fsoy were absorbed faster and in greater amounts than those of glucoside‐rich Soy in postmenopausal Japanese women. Copyright © 2010 Society of Chemical Industry     

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.     

Isoflavone phytoestrogen degradation in fermented soymilk with selected beta-glucosidase producing L. acidophilus strains during storage at different temperatures

Soymilk fermented with 3 selected Lactobacillus acidophilus strains were stored at various temperatures (-80 degrees C, 4 degrees C, 25 degrees C and 37 degrees C) for 8 weeks and the concentration of isoflavones determined weekly using RP-HPLC. The decreasing concentration of isoflavones in soymilk during storage due to degradation was found to fit the first order kinetics model. Isoflavone aglycones as well as isoflavone glucosides largely appeared to be stable during storage (P<0.01). Interestingly, the aglycone forms showed much smaller degradation as compared to glucoside forms at all the storage temperatures studied. Of the isoflavone aglycones, daidzein was found to be the most stable followed by genistein, while glycitein was least stable. Isoflavone aglycones such as glycitein, daidzein and genistein showed smaller degradation constants in fermented soymilk at lower storage temperatures (-80 degrees C and 4 degrees C) and higher degradation constants at higher storage temperatures (25 degrees C and 37 degrees C) with each strain. In contrast, glucosides glycitin and daidzin showed higher degradation at lower storage temperatures (-80 degrees C and 4 degrees C) and lower degradation at higher storage temperatures (25 degrees C and 37 degrees C). Storage temperature was therefore found to be very important in regulating the rate of degradation soy isoflavones in fermented soymilk.     

Concentration of phytoestrogens in soybeans and soybean products in Korea

Concentrations of total isoflavones in soybean varieties of different origins and soybean products were determined by high performance liquid chromatography. Wild soybeans showed the trend to have more isoflavone content than cultivars or landraces, showing mean value of 1528, 1265 and 1249 mg kg⁻¹, respectively. There were no meaningful differences in the ratio of genistein and daidzein among the modern variety groups. Korean varieties including South Korea and North Korea seemed to have total isoflavone content more than Chinese varieties, although samples of Chinese varieties were limited. In a dried basis of soyfoods, total isoflavone contents were in order of soybean sprout, chungkukjang, soymilk, soybean curd, denjang, kochujang, respectively. Five soybean foods contributed 96% of total genistein and daidzein intake in Korea: soybean sprout, soybean curd, denjang, chungkukjang and soybean seed itself. According to a Korean National Survey Report and our data, the average Korean daily intake of isoflavone from soybean foods can be estimated as 21 mg day⁻¹. © 2000 Society of Chemical Industry