glycitein and genistin

Isoflavone supplements, consumed by women experiencing menopausal symptoms, are suggested to have positive effects on menopause-related adiposity and cardiovascular disease risk profile, but discussions about their safety are still ongoing.. The objective was to study the effects of an 8-wk consumption of 2 different isoflavone supplements compared with placebo on whole-genome gene expression in the adipose tissue of postmenopausal women.. This double-blind, randomized, placebo-controlled crossover intervention consisted of 2 substudies, one with a low-genistein (LG) supplement (56% daidzein + daidzin, 16% genistein + genistin, and 28% glycitein + glycitin) and the other with a high-genistein (HG) supplement (49% daidzein + daidzin, 41% genistein + genistin, and 10% glycitein + glycitin). Both supplements provided ∼ 100 mg isoflavones/d (aglycone equivalents). After the 8-wk isoflavone and placebo period, whole-genome arrays were performed in subcutaneous adipose tissue of postmenopausal women (n = 26 after LG, n = 31 after HG). Participants were randomized by equol-producing phenotype, and data analysis was performed per substudy for equol producers and nonproducers separately.. Gene set enrichment analysis showed downregulation of expression of energy metabolism-related genes after LG supplementation (n = 24) in both equol-producing phenotypes and oppositely regulated expression for equol producers (down) and nonproducers (up) after HG supplementation (n = 31). Expression of inflammation-related genes was upregulated in equol producers but downregulated in nonproducers, independent of supplement type. Only 4.4-7.0% of the genes with significantly changed expression were estrogen responsive. Body weight, adipocyte size, and plasma lipid profile were not affected by isoflavone supplementation.. Effects of isoflavones on adipose tissue gene expression were influenced by supplement composition and equol-producing phenotype, whereas estrogen-responsive effects were lacking. LG isoflavone supplementation resulted in a caloric restriction-like gene expression profile for both producer phenotypes and pointed toward a potential beneficial effect, whereas both supplements induced anti-inflammatory gene expression in equol producers. The study was registered at clinicaltrials.gov as NCT01556737.

Topics: Adipose Tissue; Adiposity; Aged; Cross-Over Studies; Dietary Supplements; Double-Blind Method; Equol; Female; Gene Expression; Genistein; Humans; Isoflavones; Middle Aged; Netherlands; Nutritional Status; Postmenopause; Surveys and Questionnaires

Soy isoflavones are popular ingredients with anti-adipogenic and anti-lipogenic properties. The anti-adipogenic and anti-lipogenic properties of genistein are well-known, but those of genistin and glycitein remain unknown, and those of daidzein are characterized by contrasting data. Therefore, the purpose of our study was to investigate the effects of daidzein, glycitein, genistein, and genistin on adipogenesis and lipogenesis in 3T3-L1 cells. Proliferation of 3T3-L1 preadipocytes was unaffected by genistin and glycitein, but it was affected by 50 and 100 µM genistein and 100 µM daidzein for 48 h. Among the four isoflavones, only 50 and 100 µM genistin and genistein markedly suppressed lipid accumulation during adipogenesis in 3T3-L1 cells through a similar signaling pathway in a dose-dependent manner. Genistin and genistein suppress adipocyte-specific proteins and genes, such as peroxisome proliferator-activated receptor γ (PPARγ), CCAAT-enhancer-binding protein α (C/EBPα), and adipocyte binding protein 2 (aP2)/fatty acid-binding protein 4 (FABP4), and lipogenic enzymes such as ATP citrate lyase (ACL), acetyl-CoA carboxylase 1 (ACC1), and fatty acid synthase (FAS). Both isoflavones also activate AMP-activated protein kinase α (AMPKα), an essential factor in adipocyte differentiation, and inhibited sterol regulatory element-binding transcription factor 1c (SREBP-1c). These results indicate that genistin is a potent anti-adipogenic and anti-lipogenic agent.

Topics: 3T3-L1 Cells; Acetyl-CoA Carboxylase; Adipocytes; Adipogenesis; AMP-Activated Protein Kinases; Animals; Anti-Obesity Agents; ATP Citrate (pro-S)-Lyase; CCAAT-Enhancer-Binding Protein-alpha; Cell Survival; Fatty Acid Synthases; Fatty Acid-Binding Proteins; Gene Expression Regulation; Glycine max; Isoflavones; Lipogenesis; Mice; PPAR gamma; Sterol Regulatory Element Binding Protein 1

Soybean (Glycine max L.) is a good source of natural antioxidants and commonly consumed as fermented products such as cheonggukjang, miso, tempeh, and sufu in Asian countries. The aim of the current study was to examine the influence of novel endophytic bacterial strain,

Topics: Amino Acids; Antioxidants; Bacillus amyloliquefaciens; Fermentation; Food Hypersensitivity; Genistein; Glycine max; Isoflavones; Nutritive Value; Phenols

Topics: Anticarcinogenic Agents; Apoptosis; Breast Neoplasms; Cell Cycle; Cell Line, Tumor; Cell Proliferation; Female; Glycine max; Humans; Isoflavones; MCF-7 Cells

Daidzin, genistin, and glycitein are major isoflavone compounds in soybean that are indispensable nutrients in traditional Chinese foods. Generally, strategies for detecting and separating soy isoflavones have been based on HPLC and chromatographic techniques, which are tedious and time-consuming procedures. In the present study, we developed an ELISA-based approach for daidzin detection using a broad-specificity monoclonal antibody (clone number: AA9) with an effective detection range of 10-10 000 ng/mL. Subsequently, we prepared an immunoaffinity column by coupling the monoclonal antibody AA9 to CNBr-activated Sepharose 4B. Our results demonstrate that the immunoaffinity column can efficiently and specifically extract daidzin, glycitein, and genistin from numerous structurally similar soy isoflavones in leguminous plants, thereby providing a new method for the extraction of target components from similar compounds in natural products.

Topics: Chromatography, Affinity; Enzyme-Linked Immunosorbent Assay; Glycine max; Isoflavones; Time Factors

Isoflavone profile is greatly affected by heating process. However, kinetic analyses of isoflavone conversion and degradation using a continuous industry processing method have never been characterized. In this study, Proto soybean was soaked and blanched at 80 °C for 2 min and then processed into soymilk, which underwent UHT (ultra-high temperature) at 135 to 150 °C for 10 to 50 s with a pilot plant-scale Microthermics processor. The isoflavone profile was determined at different time/temperature combinations. The results showed that all isoflavone forms exhibited distinct changing patterns over time. In the soymilk under UHT conditions, the degradation (disappearance) of malonyldaizin and malonylgenistin exhibited first-order kinetics with activation energies of 59 and 84 kj/mole, respectively. At all UHT temperatures, malonylgenistin showed higher rate constants than malonyldaidzin. However, malonylglycitin changed irregularly under these UHT temperatures. The increase of genistin, daidzin, glycitein and acetlydaidzin during heating demonstrated zero-order kinetics and the rate constants increased with temperature except for the conditions of 145 to 150 °C for 50 s. Overall, genistein series exhibited higher stability than daidzein series. Under all UHT conditions, total isoflavone decreased from 12% to 24%.

Topics: Food Handling; Glucosides; Glycine max; Hot Temperature; Humans; Isoflavones; Kinetics; Soy Milk

Several dietary intervention studies examining the health effect of soy isoflavones allude to the importance of equol in establishing the cardiovascular response to soy protein. Although, the specific mechanism by which this action occurs has not been established. The aim of this study was to investigate the inhibitory effect of soy-isoflavones and the metabolite of daidzein, equol, on agonist-induced platelet responses dependent on thromboxane A(2) (TxA(2)) receptor.. Competitive radioligand binding assay was used to screen for affinity of these compounds to the TxA(2) receptor. The effect of equol on platelet activation, evaluate through of release of the ATP, by analogs of TxA(2) was analyzed. The effect of equol on platelet aggregation was investigated with ADP, U46619 (a TxA(2) mimic) and the calcium ionophore A23187.. The data showed that aglycone isoflavones and equol bind to TxA(2) receptor in the micromol/L range, whereas their glucoside derivates had very low binding activity for this receptor. Under equilibrium conditions, the following order of the relative affinity in inhibiting [(3)H]-SQ29585 binding was: equol>genistein>daidzein>glycitein>>genistin, daidzin, glycitin. Equol interaction was reversible and competitive for labeled-SQ29548 with not apparent decrease in the number of TxA(2) binding sites. In addition, from platelet activation studies, equol effectively inhibited ATP secretion elicited by the TxA(2) analog U46619. On the other hand, equol inhibited the platelet aggregation induced by U46619 and A23187, while it failed to inhibit that induced by ADP.. The aglycone isoflavones from soy, and particularly equol, have been found to have biological effects attributable to thromboxane A(2) receptor antagonism. These findings may help elucidate how dietary isoflavone modulate platelet function and explain why soy-rich foods are claimed to have beneficial effects in the prevention of thrombotic events.

Topics: Binding, Competitive; Bridged Bicyclo Compounds, Heterocyclic; Calcium; Equol; Fatty Acids, Unsaturated; Genistein; Humans; Hydrazines; Isoflavones; Platelet Activation; Platelet Aggregation; Platelet Aggregation Inhibitors; Receptors, Thromboxane A2, Prostaglandin H2

Complete separation of aglycones and glucosides of selected isoflavones (genistin, genistein, daidzin, daidzein, glycitin, glycitein, ononin, sissotrin, formononetin, and biochanin A) was possible in 1.5 min using an ultrahigh-pressure liquid chromatography (U-HPLC) on a different particular chemically modified stationary phases with a particle size under 2 microm. In addition, selected separation conditions for simultaneous determination of isoflavones together with a group of phenolic acids (gallic, protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, and sinapic acid) allowed separation of all 19 compounds in 1.9 min. Separations were conducted on a non-polar reversed phase (C(18)) and also on more polar phases with cyanopropyl or phenyl groups using a gradient elution with a mobile phase consisting of 0.3% aqueous acetic acid and methanol. Chromatographic peaks were characterised using parameters such as resolution, symmetry, selectivity, etc. Individual substances were identified and quantified using UV-vis diode array detector at wavelength 270 nm. Limits of detection (3S/N) were in the range 200-400 pg ml(-1). Proposed U-HPLC technique was used for separation of isoflavones and phenolic acids in samples of plant materials (Trifolium pratense, Glycine max, Pisum sativum and Ononis spinosa) after acid hydrolysis of the samples and modified Soxhlet extraction.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Gallic Acid; Genistein; Glycine max; Hydroxybenzoates; Isoflavones; Molecular Structure; Pisum sativum; Plant Extracts; Propionates; Trifolium; Vanillic Acid

A method for simultaneous detection and quantification is presented to determine the presence of isoflavones and bisphenol A in a biological sample. A coulometric array detector was used with reversed-phase high-performance liquid chromatography (HPLC). Daidzein (1), glycitein (2), genistein (3) and their glucoside conjugates, daidzin (4), glycitin (5) and genistin (6), were measured as phytochemicals. Also assayed here was equol (7), a metabolite from compound 1, and bisphenol A (8), an industrial chemical that acts as an endocrine disrupter. All chemicals were simultaneously detected by using a 600-mV single detection voltage with high efficacy. A mixture of 1, 3 and 8 was orally administered to rats, and the levels of these three chemicals in the serum were clearly increased after a 4 kU beta-glucuronidase treatment. The levels of compounds 1 and 3 in the serum were detected at 1665 and 2040 ng/ml, while 8 was at a low level of 417 ng/ml. Compound 7 in the serum was not detected until after enzymatic hydrolysis (72 ng/ml). These results suggest that this analytical method would be useful for metabolic and pharmacokinetic studies on isoflavones and bisphenol A.

Topics: Administration, Oral; Animals; Benzhydryl Compounds; Calibration; Chromatography, High Pressure Liquid; Colorimetry; Genistein; Glucuronidase; Isoflavones; Male; Phenols; Rats; Rats, Sprague-Dawley; Sensitivity and Specificity

The estrogenic isoflavones of soybeans and their glycosides are products of the shikimate pathway, the target pathway of glyphosate. This study tested the hypothesis that nonphytotoxic levels of glyphosate and other herbicides known to affect phenolic compound biosynthesis might influence levels of these nutraceutical compounds in glyphosate-resistant soybeans. The effects of glyphosate and other herbicides were determined on estrogenic isoflavones and shikimate in glyphosate-resistant soybeans from identical experiments conducted on different cultivars in Mississippi and Missouri. Four commonly used herbicide treatments were compared to a hand-weeded control. The herbicide treatments were (1) glyphosate at 1260 g/ha at 3 weeks after planting (WAP), followed by glyphosate at 840 g/ha at 6 WAP; (2) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied preemergence (PRE), followed by glyphosate at 1260 g/ha at 6 WAP; (3) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied PRE, followed by glyphosate at 1260 g/ha at full bloom; and (4) sulfentrazone at 168 g/ha plus chlorimuron at 34 g/ha applied PRE, followed by acifluorfen at 280 g/ha plus bentazon at 560 g/ha plus clethodim at 140 g/ha at 6 WAP. Soybeans were harvested at maturity, and seeds were analyzed for daidzein, daidzin, genistein, genistin, glycitin, glycitein, shikimate, glyphosate, and the glyphosate degradation product, aminomethylphosphonic acid (AMPA). There were no remarkable effects of any treatment on the contents of any of the biosynthetic compounds in soybean seed from either test site, indicating that early and later season applications of glyphosate have no effects on phytoestrogen levels in glyphosate-resistant soybeans. Glyphosate and AMPA residues were higher in seeds from treatment 3 than from the other two treatments in which glyphosate was used earlier. Intermediate levels were found in treatments 1 and 2. Low levels of glyphosate and AMPA were found in treatment 4 and a hand-weeded control, apparently due to herbicide drift.

Topics: Drug Resistance; Genistein; Glycine; Glycine max; Glyphosate; Herbicides; Isoflavones; Isoxazoles; Organophosphonates; Seeds; Shikimic Acid; Tetrazoles

The soy isoflavones daidzin, glycitin, and genistin were purified from defatted soy flour using preparative-scale reverse-phase HPLC. The stabilities of the three isoflavones at different heating temperatures were investigated. Daidzin, glycitin, and genistin were lost at a rate of 26, 27, and 27% of their original concentration, respectively, after 3 min at 185 degrees C. At 215 degrees C, decreases of daidzin, glycitin, and genistin were 65, 98, and 74% after 3 min and 91, 99, and 94% after 15 min, respectively. The order of the thermal stabilities, from lowest to highest, was glycitin, genistin, and daidzin. Acetyl daidzin and acetyl genistin, daidzein, glycitein, and genistein were produced during heating at temperatures above 135 degrees C. The rate of binding of an acetyl group to form acetyl daidzin and acetyl genistin from daidzin and genistin was higher than the rate of loss of a glucoside group to form daidzein and genistein. However, acetyl daidzin and acetyl genistin decreased sharply at temperatures above 200 degrees C, while daidzein, glycitein, and genistein were relatively stable over 30 min. The stability of daidzein was higher than that of glycitein or genistein.

Topics: Acetylation; Chromatography, High Pressure Liquid; Genistein; Glycine max; Hot Temperature; Isoflavones; Kinetics

Daily intake of isoflavones (daidzin, glycitin, genistin, daidzein, glycitein, and genistein) was determined quantitatively, based on the market basket method. Acid hydrolysis during extraction of foods was chosen to convert phytoestrogenes into the respective aglycons, facilitating HPLC analysis and allowing quantitation of total isoflavones as aglycones including both originally present glycosides and "free" aglycones. The isoflavones were extracted from samples with methanol and determined by reversed-phase HPLC analysis using a linear gradient of methanol-water as the eluent. From the results of hydrolysis, the daily intake of total isoflavon was 38.1 mg/adult Japanese. The values obtained by the market basket method and the National Nutrition Survey method were similar.

Topics: Adult; Aged; Child; Chromatography, High Pressure Liquid; Diet; Eating; Edible Grain; Glycine max; Humans; Isoflavones; Vegetables

An in vitro model, designated the Simulator of the Human Intestinal Microbial Ecosystem (SHIME), was used to study the effect of a soygerm powder rich in beta-glycosidic phytoestrogenic isoflavones on the fermentation pattern of the colon microbiota and to determine to what extent the latter metabolize the conjugated phytoestrogens. Initially, an inoculum prepared from human feces was introduced into the reactor vessels and stabilized over 3 wk using a culture medium. This stabilization period was followed by a 2-wk control period during which the microbiota were monitored. The microbiota were then subjected to a 2-wk treatment period by adding 2.5 g/d soygerm powder to the culture medium. The addition resulted into an overall increase of bacterial marker populations (Enterobacteriaceae:, coliforms, Lactobacillus: sp., Staphylococcus: sp. and Clostridium: sp.), with a significant increase of the Lactobacillus: sp. population. The short-chain fatty acid (SCFA) concentration increased approximately 30% during the supplementation period; this was due mainly to a significant increase of acetic and propionic acids. Gas analysis revealed that the methane concentration increased significantly. Ammonium and sulfide concentrations were not influenced by soygerm supplementation. Use of an electronic nose apparatus indicated that odor concentrations decreased significantly during the treatment period. The beta-glycosidic bonds of the phytoestrogenic isoflavones were cleaved under the conditions prevailing in the large intestine. The increased bacterial fermentation after addition of the soygerm powder was paralleled by substantial metabolism of the free isoflavones (genistein, daidzein and glycitein), resulting in recovery of only 12-17% of the supplemented isoflavones.

Topics: Bioreactors; Clostridium; Colon; Ecosystem; Electric Impedance; Enterobacteriaceae; Escherichia coli; Estrogens, Non-Steroidal; Feces; Fermentation; Glycine max; Humans; Intestines; Isoflavones; Lactobacillus; Models, Biological; Phytoestrogens; Plant Preparations; Staphylococcus