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Nanoscale Research Letters Oct 2019In this study, daidzein long-circulating liposomes (DLCL) were prepared using the ultrasonication and lipid film-hydration method. The optimized preparation conditions...
In this study, daidzein long-circulating liposomes (DLCL) were prepared using the ultrasonication and lipid film-hydration method. The optimized preparation conditions by the orthogonal design was as follows: 55 to 40 for the molar ratio of soybean phosphatidylcholine (SPC) to cholesterol, 1 to 10 for the mass ratio of daidzein to total lipid (SPC and cholesterol) (w:w), the indicated concentration of 5% DSPE-mPEG2000 (w:w), 50 °C for the hydration temperature, and 24 min for the ultrasonic time. Under these conditions, the encapsulation efficiency and drug loading of DLCL were 85.3 ± 3.6% and 8.2 ± 1.4%, respectively. The complete release times of DLCL in the medium of pH 1.2 and pH 6.9 increased by four- and twofold of that of free drugs, respectively. After rats were orally administered, a single dose of daidzein (30 mg/kg) and DLCL (containing equal dose of daidzein), respectively, and the MRT (mean residence time, which is the time required for the elimination of 63.2% of drug in the body), t (the elimination half-life, which is the time required to halve the plasma drug concentration of the terminal phase), and AUC (the area under the plasma drug concentration-time curve, which represents the total absorption after a single dose and reflects the drug absorption degree) of daidzein in DLCL group, increased by 1.6-, 1.8- and 2.5-fold as compared with those in the free group daidzein. Our results indicated that DLCL could not only reduce the first-pass effect of daidzein to promote its oral absorption, but also prolong its mean resident time to achieve the slow-release effect.
PubMed: 31617108
DOI: 10.1186/s11671-019-3164-y -
Molecules (Basel, Switzerland) Feb 2023Herbal drugs have been attracting much scientific interest in the last few decades and nowadays, phytoconstituents-based research is in progress to disclose their... (Review)
Review
Herbal drugs have been attracting much scientific interest in the last few decades and nowadays, phytoconstituents-based research is in progress to disclose their unidentified medicinal potential. Daidzein (DAI) is the natural phytoestrogen isoflavone derived primarily from leguminous plants, such as the soybean and mung bean, and its IUPAC name is 4',7-dihydroxyisoflavone. This compound has received great attention as a fascinating pharmacophore with remarkable potential for the therapeutic management of several diseases. Certain pharmacokinetic properties of DAI such as less aqueous solubility, low permeability, and poor bioavailability are major obstacles restricting the therapeutic applications. In this review, distinctive physicochemical characteristics and pharmacokinetics of DAI has been elucidated. The pharmacological applications in treatment of several disorders like oxidative stress, cancer, obesity, cardiovascular, neuroprotective, diabetes, ovariectomy, anxiety, and inflammation with their mechanism of action are explained. Furthermore, this review article comprehensively focuses to provide up-to-date information about nanotechnology-based formulations which have been investigated for DAI in preceding years which includes polymeric nanoparticles, solid lipid nanoparticles, nanostructured lipid carrier, polymer-lipid nanoparticles, nanocomplexes, polymeric micelles, nanoemulsion, nanosuspension, liposomes, and self-microemulsifying drug delivery systems.
Topics: Drug Delivery Systems; Nanotechnology; Nanoparticles; Isoflavones; Micelles; Polymers
PubMed: 36838751
DOI: 10.3390/molecules28041765 -
Food & Function May 2011Polyphenols in dietary and botanical matrices are usually present as simple and complex O-glycosides. In fermented dietary materials, the glycosidic moiety is removed... (Review)
Review
Polyphenols in dietary and botanical matrices are usually present as simple and complex O-glycosides. In fermented dietary materials, the glycosidic moiety is removed and accompanied in some cases by more complex changes to the polyphenol. As for most xenobiotics, polyphenols undergo phase II conjugation in the intestinal wall during their absorption from the gut. In contrast, a few polyphenols, such as puerarin in the kudzu vine, are C-glycosides and are stable in the gut and during absorption, distribution and excretion. Large bowel bacteria reduce polyphenol aglycones, causing opening of the heterocyclic B-ring and ring cleavage. The products are mostly absorbed and enter the bloodstream. Phase I and II metabolism events occur in the intestine and the liver - most polyphenols predominantly circulate as β-glucuronides and sulfate esters with very little as the aglycones, the presumed active forms. In addition, metabolism can occur in non-hepatic tissues and cells including breast tumor cells that have variable amounts of cytochrome P450s, sulfatase and sulfotransferase activities. Inflammatory cells produce chemical oxidants (HOCl, HOBr, ONO(2)(-)) that will react with polyphenols. The isoflavones daidzein and genistein and the flavonol quercetin form mono- and dichlorinated products in reaction with HOCl. Genistein is converted to 3'-nitrogenistein in the lung tissue of lipopolysaccharide-treated rats. Whereas polyphenols that can be converted to quinones or epoxides react with glutathione (GSH) to form adducts, chlorinated isoflavones do not react with GSH; instead, they are converted to β-glucuronides and are excreted in bile. Analysis of polyphenols and their metabolites is routinely carried out with great sensitivity, specificity and quantification by LC-tandem mass spectrometry. Critical questions about the absorption and tissue uptake of complex polyphenols such as the proanthocyanins can be answered by labeling these polyphenols with (14)C-sucrose in plant cell culture and then purifying them for use in animal experiments. The (14)C signature is quantified using accelerator mass spectrometry, a technique capable of detecting one (14)C atom in 10(15) carbon atoms. This permits the study of the penetration of the polyphenols into the interstitial fluid, the fluid that is actually in contact with non-vascular cells.
Topics: Animals; Biological Availability; Food; Genistein; Glucuronides; Glycosides; Humans; Intestinal Mucosa; Isoflavones; Liver; Mass Spectrometry; Polyphenols
PubMed: 21779561
DOI: 10.1039/c1fo10025d -
Journal of Microbiology and... May 2017Lactic acid bacteria (LAB) are used as fermentation starters in vegetable and dairy products and influence the pH and flavors of foods. For many centuries, LAB have been... (Review)
Review
Lactic acid bacteria (LAB) are used as fermentation starters in vegetable and dairy products and influence the pH and flavors of foods. For many centuries, LAB have been used to manufacture fermented foods; therefore, they are generally regarded as safe. LAB produce various substances, such as lactic acid, β-glucosidase, and β-galactosidase, making them useful as fermentation starters. Existing functional substances have been assessed as fermentation substrates for better component bioavailability or other functions. Representative materials that were bioconverted using LAB have been reported and include minor ginsenosides, γ-aminobutyric acid, equol, aglycones, bioactive isoflavones, genistein, and daidzein, among others. Fermentation mainly involves polyphenol and polysaccharide substrates and is conducted using bacterial strains such as and sp. In this review, we summarize recent studies of bioconversion using LAB and discuss future directions for this field.
Topics: Bacteria; Bifidobacterium; Cultured Milk Products; Equol; Fermentation; Food Microbiology; Genistein; Ginsenosides; Isoflavones; Lactic Acid; Lactobacillus; Lactobacillus plantarum; Phenols; Streptococcus thermophilus; beta-Galactosidase; beta-Glucosidase; gamma-Aminobutyric Acid
PubMed: 28297748
DOI: 10.4014/jmb.1612.12005 -
Molecules (Basel, Switzerland) Mar 2016The structure of the inclusion complexes of β-cyclodextrin (β-CD) with daidzein and daidzin in D2O were investigated using NMR spectroscopy. For the β-CD and daidzein...
The structure of the inclusion complexes of β-cyclodextrin (β-CD) with daidzein and daidzin in D2O were investigated using NMR spectroscopy. For the β-CD and daidzein system, two types of 1:1 complexes were formed with the daidzein deeply inserted into the CD cavity with different orientations. For the β-CD/daidzin system, a 1:1 complex was formed with the flavonoid part of daidzin entering the CD cavity from the wide rim. The inclusion complexes determined by NMR were constructed using molecular docking. Furthermore, the mixture of puerarin, daidzein and daidzin, which are the major isoflavonoid components present in Radix puerariae, was analyzed by diffusion-ordered spectroscopy (DOSY) alone and upon addition of β-CD in order to mimic chromatographic conditions and compare their binding affinities.
Topics: Isoflavones; Magnetic Resonance Spectroscopy; Molecular Docking Simulation; Molecular Structure; beta-Cyclodextrins
PubMed: 27043500
DOI: 10.3390/molecules21040372 -
Poultry Science Jun 2023This study aims to compare the effect of quercetin and daidzein on production performance, anti-oxidation, hormones, and cecal microflora in laying hens during the late...
This study aims to compare the effect of quercetin and daidzein on production performance, anti-oxidation, hormones, and cecal microflora in laying hens during the late laying period. A total of 360 53-week-old healthy Hyline brown laying hens were randomly divided into 3 groups (control, 0.05% quercetin, and 0.003% daidzein). Diets were fed for 10 wk, afterwards 1 bird per replicate (6 replicates) were euthanized for sampling blood, liver and cecal digesta. Compared with the control, quercetin significantly increased laying rate and decreased feed-to-egg weight ratio from wk 1 to 4, wk 5 to 10, and wk 1 to 10 (P < 0.05). Quercetin significantly increased the activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) and decreased catalase (CAT) activity and malondialdehyde (MDA) content in serum and liver (P < 0.05) and increased content of total antioxidant capacity (T-AOC) in liver (P < 0.05). Quercetin increased content of estradiol (E), luteinizing hormone (LH), follicle-stimulating hormone (FSH), growth hormone (GH), insulin-like growth factor 1 (IGF-1), triiodothyronine (T) and thyroxine (T) in serum (P < 0.05). Quercetin significantly decreased the relative abundance of Bacteroidaceae and Bacteroides (P < 0.01) and significantly increased the relative abundance of Lactobacillaceae and Lactobacillus (P < 0.05) at family and genus levels in cecum. Daidzein did not significantly influence production performance from wk 1 to 10. Daidzein significantly increased SOD activity and decreased CAT activity and MDA content in serum and liver (P < 0.05), and increased T-AOC content in liver (P < 0.05). Daidzein increased content of FSH, IGF-1, T in serum (P < 0.05). Daidzein increased the relative abundance of Rikenellaceae RC9 gut group at genus level in cecum (P < 0.05). Quercetin increased economic efficiency by 137.59% and 8.77%, respectively, compared with daidzein and control. In conclusion, quercetin improved production performance through enhancing antioxidant state, hormone levels, and regulating cecal microflora in laying hens during the late laying period. Quercetin was more effective than daidzein in improving economic efficiency.
Topics: Female; Animals; Quercetin; Antioxidants; Insulin-Like Growth Factor I; Chickens; Gastrointestinal Microbiome; Diet; Luteinizing Hormone; Follicle Stimulating Hormone; Superoxide Dismutase; Cecum; Animal Feed; Dietary Supplements
PubMed: 37104906
DOI: 10.1016/j.psj.2023.102674 -
Molecules (Basel, Switzerland) Dec 2017The inclusion complexes between daidzein and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) and...
The inclusion complexes between daidzein and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) and (2-hydroxy)propyl-β-cyclodextrin (HP-β-CD, DS = 4.2) were prepared. The effects of the inclusion behavior of daidzein with three kinds of cyclodextrins were investigated in both solution and solid state by methods of phase-solubility, XRD, DSC, SEM, ¹H-NMR and 2D ROESY methods. Furthermore, the antioxidant activities of daidzein and daidzein-CDs inclusion complexes were determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method. The results showed that daidzein formed a 1:1 stoichiometric inclusion complex with β-CD, Me-β-CD and HP-β-CD. The results also showed that the solubility of daidzein was improved after encapsulating by CDs. ¹H-NMR and 2D ROESY analyses show that the B ring of daidzein was the part of the molecule that was most likely inserted into the cavity of CDs, thus forming an inclusion complex. Antioxidant activity studies showed that the antioxidant performance of the inclusion complexes was enhanced in comparison to the native daidzein. It could be a potentially promising way to develop a new formulation of daidzein for herbal medicine or healthcare products.
Topics: Antioxidants; Chemistry, Pharmaceutical; Drug Carriers; Drug Liberation; Herbal Medicine; Humans; Isoflavones; Molecular Structure; Phase Transition; Solubility; Water; beta-Cyclodextrins
PubMed: 29292784
DOI: 10.3390/molecules22122183 -
Molecules (Basel, Switzerland) Apr 2024It is well known that daidzein has various significant medicinal values and health benefits, such as anti-oxidant, anti-inflammatory, anti-cancer, anti-diabetic,...
It is well known that daidzein has various significant medicinal values and health benefits, such as anti-oxidant, anti-inflammatory, anti-cancer, anti-diabetic, cholesterol lowering, neuroprotective, cardioprotective and so on. To our disappointment, poor solubility, low permeability and inferior bioavailability seriously limit its clinical application and market development. To optimize the solubility, permeability and bioavailability of daidzein, the cocrystal of daidzein and piperazine was prepared through a scientific and reasonable design, which was thoroughly characterized by single-crystal X-ray diffraction, powder X-ray diffraction, Fourier transform infrared spectroscopy, differential scanning calorimetry and thermogravimetric analysis. Combining single-crystal X-ray diffraction analysis with theoretical calculation, detailed structural information on the cocrystal was clarified and validated. In addition, a series of evaluations on the pharmacogenetic properties of the cocrystal were investigated. The results indicated that the cocrystal of daidzein and piperazine possessed the favorable stability, increased solubility, improved permeability and optimized bioavailability of daidzein. Compared with the parent drug, the formation of cocrystal, respectively, resulted in 3.9-, 3.1-, 4.9- and 60.8-fold enhancement in the solubility in four different media, 4.8-fold elevation in the permeability and 3.2-fold in the bioavailability of daidzein. Targeting the pharmaceutical defects of daidzein, the surprising elevation in the solubility, permeability and bioavailability of daidzein was realized by a clever cocrystal strategy, which not only devoted assistance to the market development and clinical application of daidzein but also paved a new path to address the drug-forming defects of insoluble drugs.
Topics: Solubility; Biological Availability; Isoflavones; Piperazine; Permeability; Crystallization; X-Ray Diffraction; Spectroscopy, Fourier Transform Infrared; Animals; Crystallography, X-Ray; Calorimetry, Differential Scanning; Humans
PubMed: 38675529
DOI: 10.3390/molecules29081710 -
Indian Journal of Pharmacology 2017The objective of the study was to investigate the effect of daidzein flavonoid on cisplatin (CP)-induced hematotoxicity and hepatotoxicity in experimental rats.
OBJECTIVE
The objective of the study was to investigate the effect of daidzein flavonoid on cisplatin (CP)-induced hematotoxicity and hepatotoxicity in experimental rats.
MATERIALS AND METHODS
The Wistar rats were randomly divided into four equal groups: Normal (saline 1 ml p.o.), CP (7.5 mg/kg once intraperioteneally on 16 day), test group of low dose (combination of CP and daidzein 20 mg/kg p.o. for 21 days), and test group of high dose (combination of CP and daidzein 40 mg/kg p.o. for 21 days). Blood samples were collected on 22 day from each rat and subjected for evaluation of hematological parameters such as red blood corpuscles (RBC), white blood corpuscles, hemoglobin (Hb) and platelets, and serum biomarkers such as alanine aminotransferase (ALT), aspartate aminotransferase (AST), and alkaline phosphatase (ALP). Liver of each rat was excised and subjected for antioxidants evaluation such as malonyl dialdehyde (MDA), glutathione (GSH), superoxide dismutase (SOD), catalase, and histopathological study.
RESULTS
Daidzein had a significant ( < 0.001) beneficial role in CP-induced hemotoxicity by increasing RBC, Hb, packed cell volume, and platelets. Daidzein also exhibited a significant ( < 0.001) protection against CP-induced hepatotoxicity by decreasing ALT, AST, ALP, and MDA level and by elevating the GSH, SOD, and catalase.
CONCLUSIONS
Daidzein attenuates CP-induced oxidative stress on blood cells and antioxidants in rats.
Topics: Alanine Transaminase; Animals; Antineoplastic Agents; Antioxidants; Aspartate Aminotransferases; Chemical and Drug Induced Liver Injury; Cisplatin; Dose-Response Relationship, Drug; Female; Glutathione; Isoflavones; Male; Oxidative Stress; Rats; Rats, Wistar; Superoxide Dismutase
PubMed: 28458422
DOI: 10.4103/0253-7613.201022 -
Nutrients Feb 2024Menopause marks a critical life stage characterized by hormonal changes that significantly impact bone health, leading to a heightened susceptibility to bone fractures....
Menopause marks a critical life stage characterized by hormonal changes that significantly impact bone health, leading to a heightened susceptibility to bone fractures. This research seeks to elucidate the impact of daidzein and tempeh on calcium status, calcium transporters, and bone metabolism in an ovariectomized rat model. Forty female Wistar rats, aged 3 months, participated in a two-phase experiment. The initial phase involved inducing a calcium deficit, while the second phase comprised dietary interventions across five groups: Sham (S) and Ovariectomy (O) with a standard diet, O with bisphosphonate (OB), O with pure daidzein (OD), and O with tempeh (OT). Multiple parameters, encompassing calcium levels, calcium transporters, bone histopathology, and serum bone metabolism markers, were evaluated. The findings revealed that the OT group showcased heightened levels of bone turnover markers, such as pyridinoline, C-telopeptide of type I collagen, bone alkaline phosphatase, and procollagen type I N-terminal propeptide, in contrast to S and O groups, with statistical significance ( < 0.05). Histopathologically, both the OD and OT groups exhibited effects akin to the OB group, indicating a decrease in the surface area occupied by adipocytes in the femoral bone structure, although statistically non-equivalent, supporting the directionally similar trends. Although TRPV5 and TRPV6 mRNA expression levels in the jejunum and duodenum did not display statistically significant differences ( > 0.05), the OD and OT groups exhibited increased expression compared to the O group. We hypothesized that obtained results may be related to the effect of isoflavones on estrogen pathways because of their structurally similar to endogenous estrogen and weak estrogenic properties. In conclusion, the daily consumption of pure daidzein and tempeh could potentially improve and reinstate calcium status, calcium transport, and bone metabolism in ovariectomized rats. Additionally, isoflavone products demonstrate effects similar to bisphosphonate drugs on these parameters in ovariectomized rats.
Topics: Rats; Female; Animals; Humans; Calcium; Osteoporosis; Rats, Wistar; Soy Foods; Calcium, Dietary; Isoflavones; Estrogens; Biomarkers; Diphosphonates; Ovariectomy; Bone Density
PubMed: 38474779
DOI: 10.3390/nu16050651