-
International Journal of Molecular... 2011The biocatalytic synthesis of xylooligosaccharides of daidzein was investigated using cultured cells of Catharanthus roseus and Aspergillus sp. β-xylosidase. The...
The biocatalytic synthesis of xylooligosaccharides of daidzein was investigated using cultured cells of Catharanthus roseus and Aspergillus sp. β-xylosidase. The cultured cells of C. roseus converted daidzein into its 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside, which was a new compound. The 7-O-β-primeveroside of daidzein was further xylosylated by Aspergillus sp. β-xylosidase to daidzein trisaccharide, i.e., 7-O-[6-O-(4-O-(β-d-xylopyranosyl))-β-d-xylopyranosyl]-β-d-glucopyranoside, which was a new compound. The 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside of daidzein exerted DPPH free-radical scavenging and superoxide radical scavenging activity. On the other hand, 7-O-β-glucoside and 7-O-β-primeveroside of daidzein showed inhibitory effects on IgE antibody production.
Topics: Anti-Allergic Agents; Antioxidants; Aspergillus; Biosynthetic Pathways; Biphenyl Compounds; Catharanthus; Cell Line; Free Radical Scavengers; Glucuronates; Isoflavones; Molecular Structure; Oligosaccharides; Picrates; Solubility; Superoxides; Water; Xylosidases
PubMed: 22016613
DOI: 10.3390/ijms12095616 -
BioImpacts : BI 2011We have already shown the protective effects of soy protein on rheumatoid arthritis in rats. In this study, the effects of genistein and daidzein, two isoflavones from...
INTRODUCTION
We have already shown the protective effects of soy protein on rheumatoid arthritis in rats. In this study, the effects of genistein and daidzein, two isoflavones from soy on rheumatoid arthritis prognosis and prevention in rats have been investigated.
METHODS
Rheumatoid arthritis was induced in female Sprague-Dawley rats using collagen type II plus adjuvant. Rats were then treated with soy protein (7 g/kg), dexamethasone (1 mg/kg), genistein (20 mg/kg genistein), daidzein (20 mg/kg genistein) and casein (in control groups) by daily gavage feedings for 50 days. Scores of arthritis were recorded every day for each paw of animal. Serum concentrations of TNF-α, IL-6, adiponectin and leptin were characterized. Tibiotarsal tissue was used for histopathologic analyses.
RESULTS
Treatment with genistein and daidzein resulted in not only a reduction in disease symptoms but also a delay in the onset of symptoms. Results from delayed-type hypersensitivity test demonstrated that the ear thickness in treated rats was significantly lower than that in the control group (p<0.05). There was a reduction in TNF-α, IL-6, adiponectin and leptin serum concentrations after treatment with genistein and daidzein. Dexamethasone reduced the serum concentrations of TNF-α, IL-6 and adiponectin but increased leptin serum level. Prevention of the tissue damage and joint inflammation was also observed following treatment with two soy isoflavones.
CONCLUSION
soy isoflavones, daidzein and especially genistein, could significantly improve rheumatoid arthritis symptoms in rats. The structural similarity of isoflavones to estrogen could be the possible underlying mechanism involved in the function.
PubMed: 23678422
DOI: 10.5681/bi.2011.022 -
Biological & Pharmaceutical Bulletin Oct 2002To evaluate the antithrombotic activities of puerarin and daidzin from the rhizome of Pueraria lobata, in vitro and ex vivo inhibitory activities of these compounds and...
To evaluate the antithrombotic activities of puerarin and daidzin from the rhizome of Pueraria lobata, in vitro and ex vivo inhibitory activities of these compounds and their metabolite, daidzein, were measured. These compounds inhibited ADP- and collagen-induced platelet aggregation. Daidzein was the most potent. However, when puerarin and daidzin were intraperitoneally administered, their antiaggregation activities were weaker than when these compounds were administered orally. When in vivo antithrombotic activities of these compounds against collagen and epinephrine were measured, these compounds showed significant protection from death due to pulmonary thrombosis in mice. To evaluate the antiallergic activity of puerarin, daidzin, and daidzein, their inhibitory effects on the release of beta-hexosaminidase from RBL 2H3 cells and on the passive cutaneous anaphylaxis (PCA) reaction in mice were examined. Daidzein exhibited potent inhibitory activity on the beta-hexosaminidase release induced by DNP-BSA and potently inhibited the PCA reaction in rats. Daidzein administered intraperitoneally showed the strongest inhibitory activity and significantly inhibited the PCA reaction at doses of 25 and 50mg/kg with inhibitory activity of 37 and 73%, respectively. The inhibitory activity of intraperitoneally administered daidzein was stronger than those of intraperitoneally and orally administered puerarin and daidzin. Therefore we believe that puerarin and daidzin in the rhizome of Pueraria lobata are prodrugs, which have antiallergic and antithrombotic activities, produced by intestinal microflora.
Topics: Animals; Anti-Allergic Agents; Feces; Fibrinolytic Agents; Humans; Intestinal Mucosa; Intestines; Isoflavones; Male; Mice; Mice, Inbred ICR; Rats; Rats, Sprague-Dawley
PubMed: 12392089
DOI: 10.1248/bpb.25.1328 -
Scientific Reports Feb 2021Soybean meal-induced enteropathy (SBMIE) is prevalent in aquaculture. The aim of this study is to evaluate the role of daidzein on SBMIE of juvenile turbot (Scophthalmus...
Soybean meal-induced enteropathy (SBMIE) is prevalent in aquaculture. The aim of this study is to evaluate the role of daidzein on SBMIE of juvenile turbot (Scophthalmus maximus L.) by feeding with fish meal diet (FM), soybean meal diet (SBM, 40% fish meal protein in FM replaced by soybean meal protein) and daidzein diet (DAID, 40 mg/kg daidzein supplemented to SBM) for 12 weeks. We found that daidzein supplementation elevated the gene expression of anti-inflammatory cytokine TGF-β, decreased gene expression of pro-inflammatory cytokines TNF-α and signal molecules p38, JNK and NF-κB. SBM up-regulated the genes expression related to oxidative stress and apoptosis, but dietary daidzein restored it to the similar level with that in FM group. Moreover, dietary daidzein up-regulated gene expression of tight junction protein, and modified the intestinal microbial profiles with boosted relative abundance of phylum Proteobacteria and Deinococcus-Thermus, genera Sphingomonas and Thermus, species Lactococcus lactis, and decreased abundance of some potential pathogenic bacteria. In conclusion, dietary daidzein could ameliorate SBM-induced intestinal inflammatory response, oxidative stress, mucosal barrier injury and microbiota community disorder of turbot. Moreover, p38, JNK and NF-κB signaling might be involved in the anti-inflammatory process of daidzein, and daidzein itself might act as an antioxidant to resist SBM-induced oxidative damage.
Topics: Animal Feed; Animals; Fish Diseases; Fish Proteins; Flatfishes; Gene Expression Regulation; Isoflavones; Signal Transduction; Soybean Proteins
PubMed: 33558631
DOI: 10.1038/s41598-021-82866-1 -
Animal Nutrition (Zhongguo Xu Mu Shou... Dec 2021Certain hormones play important roles in modulating mammalian reproductive behaviour. Daidzein is a well-known isoflavonic phytoestrogen that possesses oestrogenic...
Certain hormones play important roles in modulating mammalian reproductive behaviour. Daidzein is a well-known isoflavonic phytoestrogen that possesses oestrogenic activity. This study was conducted to probe the effects of daidzein supplementation in gestation diets on the reproductive performance in sows. A total of 120 multiparous sows (Landrace × Yorkshire) were randomly assigned to 2 groups ( = 60) and fed either a base diet (control) or one containing 200 mg/kg daidzein during gestation. We discovered that daidzein supplementation significantly increased the total number of piglets born per litter and number of piglets born alive per litter ( < 0.05), decreased the farrowing time ( < 0.05) and increased the serum oestrogen and progesterone concentrations ( < 0.05) at 35 d of gestation. Moreover, serum immunoglobulin G (IgG) concentration and superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activities were higher in the daidzein-treated group than in the control group at 35 d of gestation ( < 0.05). Daidzein increased the serum SOD activity and total anti-oxidative capacity (T-AOC) at 85 d of gestation ( < 0.05). Interestingly, daidzein elevated the expression levels of the sodium-coupled neutral amino acid transporter 1 () and insulin-like growth factor 1 () genes in the placenta ( < 0.05). These results suggest that daidzein ingestion could improve sow reproductive performance by changing serum hormones, elevating anti-oxidative capacity and up-regulating critical functional genes in the placenta.
PubMed: 34738035
DOI: 10.1016/j.aninu.2021.09.002 -
Applied and Environmental Microbiology Jun 2013Gut bacteria play a key role in the metabolism of dietary isoflavones, thereby influencing the availability and bioactivation of these polyphenols in the intestine. The...
Gut bacteria play a key role in the metabolism of dietary isoflavones, thereby influencing the availability and bioactivation of these polyphenols in the intestine. The human intestinal bacterium Slackia isoflavoniconvertens converts the main soybean isoflavones daidzein and genistein to equol and 5-hydroxy-equol, respectively. Cell extracts of S. isoflavoniconvertens catalyzed the conversion of daidzein via dihydrodaidzein to equol and that of genistein to dihydrogenistein. Growth of S. isoflavoniconvertens in the presence of daidzein led to the induction of several proteins as observed by two-dimensional difference gel electrophoresis. Based on determined peptide sequences, we identified a cluster of eight genes encoding the daidzein-induced proteins. Heterologous expression of three of these genes in Escherichia coli and enzyme activity tests with the resulting cell extracts identified the corresponding gene products as a daidzein reductase (DZNR), a dihydrodaidzein reductase (DHDR), and a tetrahydrodaidzein reductase (THDR). The recombinant DZNR also converted genistein to dihydrogenistein at higher rates than were observed for the conversion of daidzein to dihydrodaidzein. Higher rates were also observed with cell extracts of S. isoflavoniconvertens. The recombinant DHDR and THDR catalyzed the reduction of dihydrodaidzein to equol, while the corresponding conversion of dihydrogenistein to 5-hydroxy-equol was not observed. The DZNR, DHDR, and THDR were expressed as Strep-tag fusion proteins and subsequently purified by affinity chromatography. The purified enzymes were further characterized with regard to their activity, stereochemistry, quaternary structure, and content of flavin cofactors.
Topics: Actinobacteria; Base Sequence; Chromatography, Affinity; Chromatography, High Pressure Liquid; Electrophoresis, Gel, Two-Dimensional; Equol; Escherichia coli; Genistein; Humans; Intestines; Isoflavones; Molecular Sequence Data; Oxidoreductases; Polymerase Chain Reaction; Sequence Analysis, DNA; Sequence Homology
PubMed: 23542626
DOI: 10.1128/AEM.03693-12 -
Molecules (Basel, Switzerland) Jul 2010The production of beta-maltooligosaccharides of glycitein and daidzein using Lactobacillus delbrueckii and cyclodextrin glucanotransferase (CGTase) as biocatalysts was...
The production of beta-maltooligosaccharides of glycitein and daidzein using Lactobacillus delbrueckii and cyclodextrin glucanotransferase (CGTase) as biocatalysts was investigated. The cells of L. delbrueckii glucosylated glycitein and daidzein to give their corresponding 4'- and 7-O-beta-glucosides. The beta-glucosides of glycitein and daidzein were converted into the corresponding beta-maltooligosides by CGTase. The 7-O-beta-glucosides of glycitein and daidzein and 7-O-beta-maltoside of glycitein showed inhibitory effects on IgE antibody production. On the other hand, beta-glucosides of glycitein and daidzein exerted 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging activity and supeoxide-radical scavenging activity.
Topics: Animals; Anti-Allergic Agents; Antibody Formation; Antioxidants; Glycosides; Immunoglobulin E; Isoflavones; Oligosaccharides; Rats
PubMed: 20714292
DOI: 10.3390/molecules15085153 -
Molecules (Basel, Switzerland) Jun 2018Entomopathogenic filamentous fungi of the genus are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species...
Entomopathogenic filamentous fungi of the genus are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species and isolated from the environment were used. Their catalytic capacity to carry out biotransformations of flavones-unsubstituted, with hydroxy- and amino-substituents as well as a hydroxylated isoflavone-was investigated. Biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, and daidzein resulted in the formation of -methylglucosides, in the case of flavone and 5-hydroxyflavone with additional hydroxylations. 7-Aminoflavone was transformed into two acetamido derivatives. The following products were obtained: From flavone⁻flavone 2'--β-d-(4''--methyl)-glucopyranoside, flavone 4'--β-d-(4''--methyl)-glucopyranoside and 3'-hydroxyflavone 4'--β-d-(4''--methyl)-glucopyranoside; from 5-hydroxyflavone⁻5-hydroxyflavone 4'--β-d-(4''--methyl)-glucopyranoside; from 6-hydroxyflavone⁻flavone 6--β-d-(4''--methyl)-glucopyranoside; from 7-hydroxyflavone⁻flavone 7--β-d-(4''--methyl)-glucopyranoside; from daidzein⁻daidzein 7--β-d-(4''--methyl)-glucopyranoside; and from 7-aminoflavone⁻7-acetamidoflavone and 7-acetamido-4'-hydroxyflavone. Seven of the products obtained by us have not been previously reported in the literature.
Topics: Biocatalysis; Biotransformation; Carbon-13 Magnetic Resonance Spectroscopy; Flavones; Hypocreales; Isoflavones; Proton Magnetic Resonance Spectroscopy
PubMed: 29874813
DOI: 10.3390/molecules23061356 -
Journal of Physiology and Pharmacology... Jun 2009The aims of the study were to compare the in vitro effects of daidzein or 17beta-estradiol (E(2)) on: 1) progesterone (P(4)) secretion by luteinized granulosa cells... (Comparative Study)
Comparative Study
The aims of the study were to compare the in vitro effects of daidzein or 17beta-estradiol (E(2)) on: 1) progesterone (P(4)) secretion by luteinized granulosa cells harvested from large porcine follicles, as well as 2) estrogen receptor alpha and beta (ERalpha and ERbeta) mRNA and protein expression in the cells. In addition, the effect of daidzein on E(2) secretion and viability of the granulosa cells was examined. We found that basal and gonadotropin-stimulated P(4) secretion were inhibited in granulosa cells cultured in the presence of daidzein either for 24 or 48 hours. In contrast to daidzein, E(2) reduced P(4) secretion only during 24-hour cell cultures increasing it during longer cultures. Daidzein did not affect E(2) secretion by granulosa cells. The expression of ERalpha and ERbeta mRNA, as well as ERbeta protein, was up-regulated by daidzein but unaffected by E(2). To conclude, the soy estrogen daidzein acts directly on the porcine ovary to decrease progesterone production and to increase expression of ERbeta mRNA and protein. Daidzein actions in porcine luteinized granulosa cells differ from those of estradiol and it may suggest disadvantageous effects of the phytoestrogen on reproductive processes in females.
Topics: Animals; Cell Survival; Cells, Cultured; Dose-Response Relationship, Drug; Estradiol; Estrogen Receptor alpha; Estrogen Receptor beta; Female; Gene Expression; In Vitro Techniques; Isoflavones; Luteal Cells; Ovarian Follicle; Phytoestrogens; Progesterone; RNA, Messenger; Receptors, Estrogen; Swine
PubMed: 19617652
DOI: No ID Found -
PloS One 2016Vegetarian and vegan diets have become more popular among adolescents and young adults. However, few studies have investigated the nutritional status of vegans, who may... (Comparative Study)
Comparative Study
BACKGROUND
Vegetarian and vegan diets have become more popular among adolescents and young adults. However, few studies have investigated the nutritional status of vegans, who may be at risk of nutritional deficiencies.
OBJECTIVE
To compare dietary intake and nutritional status of Finnish long-term vegans and non-vegetarians.
METHODS
Dietary intake and supplement use were estimated using three-day dietary records. Nutritional status was assessed by measuring biomarkers in plasma, serum, and urine samples. Vegans' (n = 22) data was compared with those of sex- and age-matched non-vegetarians (n = 19).
RESULTS
All vegans adhered strictly to their diet; however, individual variability was marked in food consumption and supplementation habits. Dietary intakes of key nutrients, vitamins B12 and D, were lower (P < 0.001) in vegans than in non-vegetarians. Nutritional biomarker measurements showed lower concentrations of serum 25-hydroxyvitamin D3 (25(OH)D3), iodine and selenium (corrected for multiple comparisons, P < 0.001), Vegans showed more favorable fatty acid profiles (P < 0.001) as well as much higher concentrations of polyphenols such as genistein and daidzein (P < 0.001). Eicosapentaenoic acid proportions in vegans were higher than expected. The median concentration of iodine in urine was below the recommended levels in both groups.
CONCLUSIONS
Long-term consumption of a vegan diet was associated with some favorable laboratory measures but also with lowered concentrations of key nutrients compared to reference values. This study highlights the need for nutritional guidance to vegans.
Topics: Adult; Cholecalciferol; Diet, Vegan; Diet, Vegetarian; Dietary Supplements; Eating; Eicosapentaenoic Acid; Energy Intake; Fatty Acids; Feeding Behavior; Female; Finland; Food; Genistein; Humans; Iodine; Isoflavones; Male; Middle Aged; Nutritional Requirements; Nutritional Status; Polyphenols; Selenium; Vegans; Vegetarians; Vitamin B 12; Young Adult
PubMed: 26840251
DOI: 10.1371/journal.pone.0148235