| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
Natural isoflavone; flavonoids
Glycitin targets bitter taste receptors (TAS2Rs) as an agonist. It also modulates differentiation of mesenchymal stem cells (MSC) through TGF-β or AKT signaling pathways. The compound inhibits matrix metalloproteinases (MMP-1, MMP-3, MMP-9) through down-regulation of ERK/JNK/p38 mitogen-activated protein kinases. It may regulate osteoblast differentiation and bone formation via TGF-β or AKT signaling. |
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| ln Vitro |
Daidzin (0.01-10 µM; 7 days) has the ability to stimulate cell division and BMSC osteoblast formation [1]. In BMSCs, daizenein (0, 0.5, 1 and 5 µM) stimulates the expression of the Col I and ALP genes.
In vitro, glycitin exhibits good inhibitory effect on α-glucosidase with an IC₅₀ of 0.5646 mg/mL, better than the positive control acarbose. It inhibits the expression of matrix metalloproteinases 3 and 9 and suppresses the invasive activity of glioma cells. Glycitin increases proliferation of mouse bone marrow stromal cells and osteoblasts. It inhibits adipocytic transdifferentiation of osteoblasts, promoting osteogenic differentiation. |
| ln Vivo |
Daidzin (5–20 mg/kg; intraperitoneal injection; three times; once every eight hours)) inhibits TLR4-mediated NF-κB and MAPK activation, which helps safeguard the LPS-sensing pathway at the base of lung tissue [2].
In vivo, glycitin has been shown to prevent bone loss and reverse unfavorable changes in lipid metabolism. A mixture of daidzin and glycitin has anti-obese and anti-diabetic effects on C57BL/6J mice fed with a high-fat diet through regulation of oxidative stress. The compound may modulate differentiation of MSC to cause a lineage shift toward osteoblasts and away from adipocytes, helping to prevent osteonecrosis development. |
| Enzyme Assay |
The aim of the present study was to examine the effect of glycitin on the regulation of osteoblasts from bone marrow stem cells (BMSCs) through transforming growth factor (TGF)-β or protein kinase B (AKT) signaling pathways. BMSCs were extracted from New Zealand white rabbits and used to analyze the effect of glycitin on BMSCs. BMSCs were cleared using xylene and observed via light microscopy. BMSCs were subsequently induced with glycitin (0.01, 0.5, 1, 5 and 10 µM) for 7 days, and stained with Oil Red O. The mechanism of action of glycitin on BMSCs was investigated, in which contact with collagen type I (Col I), alkaline phosphatase (ALP), TGF-β and AKT was studied. Firstly, BMSCs appeared homogeneously mazarine blue, and which showed that BMSCs were successful extracted. Administration of glycitin increased cell proliferation and promoted osteoblast formation from BMSCs. Furthermore, glycitin activated the gene expression of Col I and ALP in BMSCs. Notably, glycitin suppressed protein expression of TGF-β and AKT in BMSCs. These results indicated that glycitin may regulate osteoblasts through TGF-β or AKT signaling pathways in BMSCs[1].
α-Glucosidase inhibition assays: glycitin at various concentrations is incubated with α-glucosidase enzyme and substrate (e.g., p-nitrophenyl-α-D-glucopyranoside) in assay buffer at 37°C. After incubation, the reaction is stopped by adding sodium carbonate, and absorbance is measured at 405 nm. IC₅₀ values are calculated from dose-response curves. Receptor binding studies for TAS2Rs are performed using calcium mobilization assays in cells expressing recombinant bitter taste receptors. |
| Cell Assay |
Cell viability assay [1]
Cell Types: bone marrow stem cells (BMSC) Tested Concentrations: 0.01, 0.5, 1, 5 and 10 µM Incubation Duration: 7 days The results can inhibit the protein expression of TGF-β and AKT in BMSC [1]. Experimental Results: Increase cell proliferation and promote BMSC osteoblast formation. Osteoblast cells or bone marrow stromal cells are cultured in differentiation medium containing glycitin at various concentrations (typically 1-100 μM). Cell proliferation is assessed using MTT or CCK-8 assays. Osteogenic differentiation is evaluated by alkaline phosphatase (ALP) activity staining and Alizarin Red S staining for mineralization. Adipocytic differentiation is assessed by Oil Red O staining. MMP expression is measured by qRT-PCR or Western blot. |
| Animal Protocol |
Animal/Disease Models: BALB/c male mice (6-8 weeks old, weight 18-22 grams) treated with LPS [2]
Doses: 5 mg/kg, 10 mg/kg and 20 mg/kg Route of Administration: intraperitoneal (ip) injection ; 3 times (once every 8 hrs (hrs (hours))) Experimental Results:Dramatically diminished lung damage caused by LPS. Animal studies are conducted using C57BL/6J mice fed with a high-fat diet. Glycitin or a mixture containing glycitin is administered orally at specified doses. Body weight, food intake, and blood glucose levels are monitored. Oxidative stress markers and lipid profiles are measured in serum. Bone density and bone loss are assessed by micro-CT or dual-energy X-ray absorptiometry (DEXA). Glycitin exhibits anticancer chemotherapeutic activity in xenograft models. |
| ADME/Pharmacokinetics |
Glycitin has a molecular weight of 446.41 and is soluble in DMSO (55.00 mg/mL, 123.21 mM). It is a glycosyloxyisoflavone with a methoxy group at position 6, a hydroxy group at position 4', and a β-D-glucopyranosyloxy group at position 7. The compound has antibacterial, antiviral, anti-obese, anti-diabetic, and estrogenic activities. It may exert preventative effects on alcoholism, osteonecrosis, cardiovascular and cerebrovascular diseases, and some types of cancer.
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| References |
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| Additional Infomation |
Glycitin is a glycosyl isoflavone with a structure in which the isoflavone is substituted with a methoxy group at the 6' position, a hydroxy group at the 4' position, and a β-D-glucopyranoside at the 7' position. It is a plant metabolite. Glycitin is a methoxy isoflavone, a hydroxy isoflavone, a monosaccharide derivative, and a 7-hydroxy isoflavone 7-O-β-D-glucoside. It has been reported to be found in Salvia hispanica, soybean (Glycine max), and several other organisms with relevant data.
Glycitin is a natural isoflavone found in soy that activates bitter taste receptors (TAS2Rs). It has been investigated for protective effects on skin aging through inhibition of MMP-1 and increasing collagen via ERK/JNK/p38 down-regulation. The compound may modulate MSC differentiation toward osteoblasts and away from adipocytes, making it a potential agent for treating osteoporosis and preventing osteonecrosis. It also exhibits anticancer chemotherapeutic properties. |
| Molecular Formula |
C22H22O10
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|---|---|
| Molecular Weight |
446.4
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| Exact Mass |
446.121
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| Elemental Analysis |
C, 59.19; H, 4.97; O, 35.84
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| CAS # |
40246-10-4
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| PubChem CID |
187808
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
751.1±60.0 °C at 760 mmHg
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| Melting Point |
210ºC
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| Flash Point |
264.1±26.4 °C
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| Vapour Pressure |
0.0±2.6 mmHg at 25°C
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| Index of Refraction |
1.675
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| LogP |
0.16
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
32
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| Complexity |
690
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C([H])=C2C(C(C(C3C([H])=C([H])C(=C([H])C=3[H])O[H])=C([H])O2)=O)=C([H])C=1OC([H])([H])[H]
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| InChi Key |
OZBAVEKZGSOMOJ-MIUGBVLSSA-N
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| InChi Code |
InChI=1S/C22H22O10/c1-29-15-6-12-14(30-9-13(18(12)25)10-2-4-11(24)5-3-10)7-16(15)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
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| Chemical Name |
3-(4-hydroxyphenyl)-6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
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| Synonyms |
Glycitein-7-beta-O-glucoside; Glycitin; ZX-AFC000687; ZXAFC000687; ZX AFC000687; HY-N0012; HYN0012; HY N0012
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : 89 ~100 mg/mL (199.37 ~224.01 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.60 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 (5.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.60 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2401 mL | 11.2007 mL | 22.4014 mL | |
| 5 mM | 0.4480 mL | 2.2401 mL | 4.4803 mL | |
| 10 mM | 0.2240 mL | 1.1201 mL | 2.2401 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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