Daidzein is a naturally occuring isoflavone phytoestrogen isolated from Leguminosae, used as a component of foods and dietary supplements. In a dose-dependent manner, daizéin inhibits the production of NO as well as the expression of the iNOS protein and mRNA. Another crucial transcription factor for iNOS, signal transducer and activator of transcription 1 (STAT-1), is likewise inhibited by daizenein. Protein content, alkaline phosphatase activity, and DNA content are all significantly elevated in cells when daizeben (1 μM and 10 μM) is added; these increases are approximately 1.4-, 1.5-, and 2.0-fold, respectively.
Physicochemical Properties
| Molecular Formula | C15H10O4 | |
| Molecular Weight | 254.24 | |
| Exact Mass | 254.057 | |
| Elemental Analysis | C, 70.86; H, 3.96; O, 25.17 | |
| CAS # | 486-66-8 | |
| Related CAS # | Daidzein (Standard);486-66-8;Daidzein-d4;1219803-57-2;Daidzein-d6;291759-05-2 | |
| PubChem CID | 5281708 | |
| Appearance | White to off-white solid powder | |
| Density | 1.4±0.1 g/cm3 | |
| Boiling Point | 512.8±50.0 °C at 760 mmHg | |
| Melting Point | 315-323°C (dec.) | |
| Flash Point | 201.2±23.6 °C | |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C | |
| Index of Refraction | 1.699 | |
| LogP | 2.78 | |
| Hydrogen Bond Donor Count | 2 | |
| Hydrogen Bond Acceptor Count | 4 | |
| Rotatable Bond Count | 1 | |
| Heavy Atom Count | 19 | |
| Complexity | 382 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | OC1C=CC(C2C(=O)C3C(=CC(=CC=3)O)OC=2)=CC=1 |
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| InChi Key | ZQSIJRDFPHDXIC-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H | |
| Chemical Name | 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one | |
| Synonyms |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | PPAR-γ/α |
| ln Vitro | Daidzein inhibits the expression of the iNOS protein and mRNA as well as the generation of NO in a dose-dependent manner. Additionally, daizenein prevents the activation of another crucial transcription factor for iNOS, signal transducer and activator of transcription 1 (STAT-1). (Source: ) Daidzein (1 μM and 10 μM) significantly increases the amount of DNA, protein, and alkaline phosphatase activity in cells; these increases are approximately 1.4-, 1.5-, and 2.0-fold, respectively.[2] Daidzein (2-50 mM) increases the viability of osteoblasts by about 1.4-fold. The alkaline phosphatase activity and osteocalcin synthesis of osteoblasts are increased by approximately 1.4 and 2.0 times, respectively, by daifzein (2-100 mM). Osteoblast differentiation is stimulated by daizenein at different stages (from osteoprogenitors to terminally differentiated osteoblasts).[3] Calcium contents, deoxyribonucleic acid (DNA), and alkaline phosphatase activity are all markedly increased in bone tissues by daidzein (1 μM and 10 μM). Cycloheximide (1 μM) totally inhibits the rise in calcium content and alkaline phosphatase activity in bone tissues caused by dainzocine.[4] |
| ln Vivo | Daidzein causes body weight to decrease, a phenomenon that could be explained by female rats consuming less feed. In female rats, daidzein causes modest but non-significant reductions in the size of the mammary glands, uterine and ovarian weights.[5] |
| Enzyme Assay | Daidzein, a natural isoflavonoid found in Leguminosae, has received increasing attention because of its possible role in the prevention of osteoporosis. In the present investigation, primary osteoblastic cells isolated from newborn Wistar rats were used to investigate the effect of this isoflavonoid on osteoblasts. Daidzein (2-50 microM) increased the viability (P<0.05) of osteoblasts by about 1.4-fold. In addition, daidzein (2-100 microM) increased the alkaline phosphatase activity and osteocalcin synthesis (P<0.05) of osteoblasts by about 1.4- and 2.0-fold, respectively. Alkaline phosphatase and osteocalcin are phenotypic markers for early-stage differentiated osteoblasts and terminally differentiated osteoblasts, respectively. Our results indicated that daidzein stimulated osteoblast differentiation at various stages (from osteoprogenitors to terminally differentiated osteoblasts). We also investigated the effect of daidzein on bone morphogenetic protein (BMP) production in osteoblasts that display the mature osteoblast phenotype. The results indicated that BMP2 synthesis was elevated significantly in response to daidzein (the mRNA increased 5.0-fold, and the protein increased 7.0-fold), suggesting that some of the effects of daidzein on the cell may be mediated by the increased production of BMPs by the osteoblasts. In conclusion, daidzein has a direct stimulatory effect on bone formation in cultured osteoblastic cells in vitro, which may be mediated by increased production of BMPs in osteoblasts [1]. |
| Cell Assay | Placing HEK293T cells on 24-well plates, they are grown to 70–80% confluence at a cell density of roughly 2.5×104 cells/well. The cells are then transfected using an X-treme GENE HP DNA Transfection Reagent with a plasmid expressing PPAR-α or PPAR-γ expression, and a plasmid containing the luciferase gene under the control of three tandem PPAR response elements (PPRE × 3 TK-luciferase) cyclically. The transfection efficiency is monitored by co-transfecting Renilla luciferase control vectors. Cells are incubated in DMSO-containing medium or different concentrations (6.25, 12.5, 25 μM) of Daidzein for an additional 24 hours following transfection. The luciferase activity of lysed cells is quantified and expressed as fold induction, which is standardized to the activity of the plasmid that controls renilla luciferase[1]. |
| Animal Protocol | Mice: Male C57 (C57 bl/6) and Apoe KO (C57 background) mice aged 10 to 11 weeks are used for the experiments. Mice are given Moxifloxacin (100 mg/kg) for 3 days in order to aid in long-term stroke recovery. In an animal model of stroke, prophylactic antibiotic treatment has been demonstrated to effectively reduce mortality by attenuating peripheral infection. To further prevent dehydration, hydrogel (Clear H2O) is given and saline is injected subcutaneously every day. Mice that receive poststroke care (medication, hydration, and hydrogels with soft diet) during the acute phase (less than one week) begin to regain body weight by day five and continue to heal from stroke. For vehicle or Daidzein treatment, animals are chosen at random. After confirming the reperfusion of blood flow, vehicle or Daidzein (10 mg/kg) is administered subcutaneously within 30 minutes. This is done daily for 7 days, and then every other day for up to 1 month. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites Daidzein has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid and Dihydrodazein. Daidzein is a known human metabolite of formononetin. |
| Toxicity/Toxicokinetics | mouse LD50 intraperitoneal >2 gm/kg Pharmaceutical Chemistry Journal, 13(51), 1979 |
| References |
[1]. Biochem Pharmacol . 2003 Mar 1;65(5):709-15. [2]. Mol Cell Biochem . 1999 Apr;194(1-2):93-7. [3]. Toxicol Sci . 2002 Feb;65(2):228-38. [4]. Mediators Inflamm . 2007:2007:45673. [5]. Biochem Pharmacol . 2000 Mar 1;59(5):471-5. |
| Additional Infomation |
Daidzein is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'. It has a role as an antineoplastic agent, a phytoestrogen, a plant metabolite, an EC 3.2.1.20 (alpha-glucosidase) inhibitor and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is a conjugate acid of a daidzein(1-). Daidzein has been reported in Streptomyces padanus, Glycine soja, and other organisms with data available. Daidzein is an isoflavone extract from soy, which is an inactive analog of the tyrosine kinase inhibitor genistein. It has antioxidant and phytoestrogenic properties. (NCI) Daidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (A3191, A3189). See also: Trifolium pratense flower (part of). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: 20 mg/mL (78.67 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9333 mL | 19.6665 mL | 39.3329 mL | |
| 5 mM | 0.7867 mL | 3.9333 mL | 7.8666 mL | |
| 10 mM | 0.3933 mL | 1.9666 mL | 3.9333 mL |