astragalin
Kaempferol-3-glucoside
CAS: 480-10-4
Molecular Formula: C21H20O11
astragalin - Names and Identifiers
| Name | Kaempferol-3-glucoside |
| Synonyms | k5 ASTRAGALIN astragalin astragaline KAEMPFEROL-3-GLUCOSIDE Kaempferol-3-glucoside KAEMPFEROL-3-O-GLUCOSIDE Kaempferol-3-O-glucoside KAEMPFEROL-3-O-BETA-D-GLUCOPYRANOSIDE 4h-1-benzopyran-4-one,3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyp 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside 3-(β-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one |
| CAS | 480-10-4 |
| InChI | InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1 |
| InChIKey | JPUKWEQWGBDDQB-QSOFNFLRSA-N |
astragalin - Physico-chemical Properties
| Molecular Formula | C21H20O11 |
| Molar Mass | 448.38 |
| Density | 1.79±0.1 g/cm3(Predicted) |
| Melting Point | 223-229°C |
| Boling Point | 823.2±65.0 °C(Predicted) |
| Specific Rotation(α) | +16.9 (c, 0.62 in MeOH) |
| Flash Point | 291.5°C |
| Solubility | Soluble in DMSO, a mixed solvent of methanol and chloroform, soluble in hot methanol, insoluble in petroleum ether. |
| Vapor Presure | 1.09E-28mmHg at 25°C |
| Appearance | Yellow needle crystal |
| pKa | 6.20±0.40(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.774 |
| MDL | MFCD00075932 |
| Physical and Chemical Properties | Soluble in DMSO, methanol chloroform mixed solvent, soluble in hot methanol, insoluble in petroleum ether. From Thesium chinense |
astragalin - Risk and Safety
| Safety Description | 22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | DJ3080000 |
| HS Code | 29389090 |
astragalin - Reference Information
| Background and Overview | Thymus chinensis is a dry whole herb of Thymus chinensis (ThesiumChineseTurcz.) or its variety Long-stemmed Thymus chinensis (ThesiumChineseTurcz.Var.longipedunculatum Chu). Its taste is pungent, slightly bitter, and cold in nature. It has the effects of clearing heat, promoting dampness, and detoxification. It is mainly used to treat cold, heat stroke, lymphatic tuberculosis and jaundice. The main active ingredient of Thymus chinensis is flavonoids, among which astragaloside is the representative ingredient in flavonoids. At the same time, astragaloside is also one of the active ingredients in Eucommia ulmoides leaves. Eucommia ulmoides (eucommiaulmoies) is a plant of the genus Eucommia of the Eucommia family. It uses skin as medicine. It is a rare nourishing Chinese medicine commonly used in my country. Shennong's Materia Medica listed Eucommia ulmoides as the top grade, which has the effect of nourishing the middle and strengthening the bones and bones. The resources of Eucommia ulmoides bark are scarce. The research on replacing, the pharmacological effects are also the same. In addition, the active ingredients of lotus leaves also contain astragaloside, etc., which are mainly used for neurasthenia, neurasthenia syndrome, sedation, hypnosis and other diseases. It can resist convulsions, analgesia and lower body temperature, and has an antagonistic effect on arrhythmia. It can reduce blood lipids and regulate lipid proteins to inhibit the formation and development of atherosclerosis. The chemical name of astragaloside is kaempferol -3-glucoside. It is a natural flavonoid compound widely found in medicinal plants. It has significant anti-inflammatory, antioxidant, cardiotonic, Analgesic, antibacterial, anti-allergic, anti-liver toxicity, and can enhance the body's resistance, stimulate the production of interferon, anti-arrhythmia, expand blood vessels, protect myocardium, etc., and also repair damaged DNA, And in vitro TNF-α, the production of IL-1β and IL-6 has inhibitory effect. |
| drug overview | common name: astragaloside English name: Astragalin chemical name: 5, 7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy -6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Alias: astragaloside, astragaloside, camphene non-alcohol-3-O-glucoside, thypetrin Ⅱ Cas No:480-10-4 Molecular weight: 448.38 Molecular formula: C21H20O11 Structural formula: |
| Uses | Astragaloside is a natural flavonoid compound widely found in medicinal plants. It has anti-inflammatory, antioxidant, cardiotonic, analgesic, antibacterial, Anti-allergic, anti-liver toxicity, and can enhance the body's resistance, stimulate the production of interferon, anti-arrhythmia, dilate blood vessels, protect myocardium, etc. Some of its activities are as follows: 1. antibacterial activity: the growth inhibition effect of purple vine glycoside on the tested bacteria is shown in the following table: from the above table, it can be seen that the antibacterial circle diameters of purple vine glycoside on Escherichia coli, Salmonella, Staphylococcus aureus, Bacillus subtilis, Rhizopus, Aspergillus niger and Saccharomyces cerevisiae are 23.2mm and 19.3mm respectively, 20.4mm,15.3mm,16.2mm,15.1mm and 13.7mm. From this, it can be seen that the lotus leaf amein has a strong inhibitory effect on bacteria, mold and Saccharomyces cerevisiae, and its antibacterial spectrum is wide. 2. Effects on osteoblast proliferation and alkaline phosphatase activity: MC3T3-E1 cells are osteoblast beads isolated and cultured from the skull and parietal bone of newborn C57BL/6 mice. Their proliferation is stable and can be subcultured indefinitely, and they have the biological characteristics of osteoblasts such as ALP activity type I collagen synthesis. This cell line has become an important in vitro cell model for studying the effect of drugs on osteoblasts. 1) the effect of Astragaloside on the proliferation of MC3T3-E1 cells: the concentration of 2.2 × 10-4mol/L, 2.2 × 10-5mol/L, 2.2 × 10-6mol/L can obviously promote the proliferation of MC3T3-E1 cells (P<0.05), of which the concentration of 2.2 × 10-5mol/L has the strongest effect and the difference is highly statistically significant (P<0.01). 2) the effect of purple vetch glycoside on the differentiation of MC3T3-E1 cells: the cells were cultured for 48 hours after administration, and the ALP activity of MC3T3-E1 cells was enhanced in the 2.2 × 10-4mol/L and 2.2 × 10-5mol/L purple vetch glycoside administration groups, with extremely significant difference (P<0.01). the cells were cultured for 72 hours after administration, compared with the blank control group, there was no significant difference in ALP activity among concentration groups (P<0.05). used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: regulate blood sugar in the body, enhance body immunity, promote growth, and improve body antioxidant capacity. |
| pharmacokinetics | plasma drug concentration was processed by DAS(drugandstatistics,version 2.0) software program, and the main pharmacokinetic parameters were estimated by atrioventricular model. rats reached a peak concentration of 231.1±67.3ng/ml at 0.5±0.1h after intragastric administration, with a plasma half-life of 3.9±1.3h,AUC0-∞ is 782.6±152.8(ng • h/ml), and other numerical results are shown in the table: |
| detection | method 1: use RP-HPLC to determine the content of milk vanyside in thecium chinensis 1) chromatographic conditions: Diamonsil C18 column (4.6mm × 250mm, 5 μm); Mobile phase acetonitrile-water (23: 77), pH 3.85 adjusted with glacial acetic acid; Flow rate 1.0 mL/min; Column temperature is normal temperature; the detection wavelength is 346nm; Under the selected chromatographic conditions, the theoretical plate number is not less than 2500 according to the calculation of milk vetch glycoside, the separation degree is more than 1.5, and the tailing factor is 0 .95~1.05, as shown in the following figure: 2) preparation of reference substance solution: precisely weigh 10.30mg of dried milk vetch glycoside reference substance to constant weight, place it in a 10 mL volumetric flask, add ethanol to dissolve to scale, shake well to prepare 1. 030 mg/mL reference substance solution. 3) preparation of the test sample solution: take 1.0g of dried Thymus chinensis fine powder, weigh it accurately, add 100 mL of 50% ethanol, reflux extract twice, 1.0 h for the first time, 0.5 h for the second time, filter, combine the filtrates for the second time, concentrate to dry, fix the volume of residue with 50% ethanol to 10 mL, shake well, and filter through 0.45 μm microporous filter membrane to obtain the result. 4) results: the mass fraction of milk vetch glycoside was 0.120% ~ 0.155% for different batches of thmus chinensis from the same origin. method 2: liquid chromatography-tandem mass spectrometry (LC-MS/MS) was used to determine the concentration of milk vetch in rat plasma. 1) chromatographic conditions: the chromatographic column is Agilent ZORBAX SB-C18 analytical column (150mm × 4.6mm,5 μm), the mobile phase is methanol -10mmol/L ammonium acetate aqueous solution-formic acid (80: 20: 0.15,v/v/v/v), the flow rate is 0.6 ml/min, the column temperature is 30 ℃, and the injection volume is 20 μl. 2) ionization mode of mass spectrometry condition: electrospray; Scanning mode: multi-reaction monitoring; Ion polarity: milk vetch glycoside selects positive ion, internal standard quercetin is negative ion monitoring; Residence time: 200ms; Capillary voltage: 4.0kV; Atomizing gas temperature: 300 ℃; Flow rate of atomizing gas: 10L/min; Atomizing gas pressure: 30psi. Detection objects: milk vetch glycoside,[M + H]+,m/z449.1 → m/z287.1, cracking voltage 110V, collision energy 8eV; Quercetin,[M-H]-,m/z301.1 → m/z151.1, cracking voltage 135V, collision energy 25eV 3) solution preparation reference substance solution: accurately weigh 10.1mg of milk vetch reference substance in a 10ml volumetric flask, dissolve with methanol to a constant volume of 10ml to obtain a stock solution of milk vetch glycoside reference substance with a concentration of 1.00 mg/ml. Then dilute with acetonitrile in turn to a standard curve solution of milk vetch glycoside with concentrations of 1.00, 3.00, 10.0, 30.0, 100, 300 and 1000ng/ml respectively. internal standard solution: accurately weigh 10.1mg of quercetin reference substance in a 10ml volumetric flask, dissolve with methanol and fix the volume to 10ml to obtain quercetin internal standard reserve solution with a concentration of 1.00 mg/ml; Dilute with acetonitrile to form quercetin internal standard working solution with a concentration of 1000ng/ml. 4) the linear relationship of milk vetch glycoside is good in the concentration range of 1.00~1000ng/ml (r2 = 0.9929); The lower limit of quantification is 1.00ng/ml; The extraction recovery rates of low, medium and high concentrations are all greater than 93%. |
| extraction | ultrasonic extraction of purple vetch glycoside from lotus leaf was studied with lotus leaf as raw material: the experimental results showed that the extraction effect of low frequency ultrasonic wave (25.5 kHz) was better. through L9(34) orthogonal test, the best extraction process of ultrasonic-assisted extraction of purple vetch glycoside from lotus leaf was obtained: ultrasonic frequency was low frequency (25.5 kHz), the extraction time was 20 min, the extraction temperature was 55 ℃, and the extraction solvent was 70% ethanol by volume fraction. Under the test conditions, the extraction rate of milk vetch glycoside from lotus leaf was 1.67%. |
| stability | several standard plasma samples of metaxin at low concentration (3.00ng/ml) and high concentration (900ng/ml) were prepared to investigate the stability under different conditions. The results showed that the plasma sample was stable at room temperature for 2h (RE was between 5.0% and 6.3%). The plasma sample was stable at room temperature for 8h (RE was between-2.4% and 3.5%) after being treated with precipitated protein. The plasma sample was stable after 3 freezing-thawing cycles (RE was between-0.7% and 6.4%); The plasma sample was stable at -20 ℃ for 23 days (RE was between-1.1% and 6.8%). |
| synthesis | a method for enzymatic synthesis of metaxin, the steps are as follows: 1) cloning, expression and purification of key enzymes required in the synthesis of metaxin: includes glycogen phosphorylase GP, glucose pyrophosphorylase GalU, flavanone-3-hydroxylase F3H, flavanone synthase FLS1 and flavonoid 3-O-glucosyltransferase UGT78K2; 2) synthesis of glucose -1-phosphate G-1-P by muscle glycogen Gn under the action of GP; 3) synthesis of uridine diphosphate glucose UDPG by G-1-P under the action of GalU; 4) naringenin NRN was used to synthesize dihydrokaempferol DHK under the action of F3H; 5)DHK was used to synthesize kaempferol KMF under the action of FLS1; 6)KMF and UDPG were used to synthesize UGT78K2. The present invention has few steps, mild operating conditions, few by-products, high yield, no pollution, and significantly reduced production costs. |
| main reference | [1] liuhongju et al. determination of the concentration and pharmacokinetics of purple viper in rat plasma by liquid chromatography-tandem mass spectrometry mechanical study. JSouthMedUniv,2013,33(7):1049-1052. [2] Yang Haowei et al. Effects of Astragaloside on Proliferation and Differentiation of Mouse Osteoblast MC3T3-E1. Journal of Traditional Chinese Medicine. 2013,41(4):17-19. [3] Ji Xiaohua. Ultrasonic-assisted Extraction of Astragaloside from Lotus Leaf and Study on Its Antibacterial Activity. Food Industry. 2014,35(10):112-114. [4] Liu Yang et al. RP- HPLC Determination of Astragaloside in Thymus chinensis. Chinese Journal of Traditional Chinese Medicine. 2006,31(21):1766-1767. [5] Zhang Xinyue et al. An Enzymatic Synthesis Method of Astragaloside. Application No. CN201610029307.3. Application Date 2016-01-15. |
Last Update：2024-04-09 15:16:50
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