Astragaloside IV
Astragaloside IV
CAS: 84687-43-4
Molecular Formula: C41H68O14
Astragaloside IV - Names and Identifiers
| Name | Astragaloside IV |
| Synonyms | astragalosideⅣ Astragaloside IV Astrasieversianin XIV 20,24-epoxy-16,25-dihydroxy-3-(β-D- β-D-Glucopyranoside, (3β,6α,16β,20R,24S)- xylopyranosyloxy)-9,19-cyclolanostan-6-yl beta-D-Glucopyranoside, (3beta,6alpha,16beta,20R,24S)-20,24-epoxy-16,25-dihydroxy-3-(beta-D-xylopyranosyloxy)-9,19-cyclolanostan-6-yl beta-D-Glucopyranoside, (3beta,6alpha,16beta,20R,24S)-20,24-epoxy-16,25-dihydroxy-3-(beta-D-xylopyranosyloxy)-9,19-cyclolanostan-6-yl (5xi,6beta,8xi,9xi,16alpha,20R,24S)-16,25-dihydroxy-3-(beta-D-xylopyranosyloxy)-20,24-epoxy-9,19-cyclolanostan-6-yl beta-D-glucopyranoside |
| CAS | 84687-43-4 |
| EINECS | 1532714-185-1 |
| InChI | InChI=1/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19-,20-,21-,22-,23?,24?,25+,26+,27-,28+,29-,30-,31+,32?,33+,34-,37-,38+,39-,40?,41-/m1/s1 |
| InChIKey | QMNWISYXSJWHRY-BTUAQNSKSA-N |
Astragaloside IV - Physico-chemical Properties
| Molecular Formula | C41H68O14 |
| Molar Mass | 784.97 |
| Density | 1.39 |
| Melting Point | 295-296°C |
| Boling Point | 895.7±65.0 °C(Predicted) |
| Specific Rotation(α) | +24.4°(c=0.23，methanol) |
| Flash Point | 495.5°C |
| Solubility | Soluble in methanol, ethanol, acetone, insoluble in chloroform, ethyl acetate and other weak polar organic solvents. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Colorless needle crystal |
| Color | White to Off-White |
| pKa | 12.91±0.70(Predicted) |
| Storage Condition | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| Refractive Index | 1.62 |
| MDL | MFCD16036240 |
| Physical and Chemical Properties | It is derived from the roots of Astragalus membranaceus in the leguminous family. |
Astragaloside IV - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29389090 |
Astragaloside IV - Reference Information
| overview | astragaloside IV is a cycloaltin triterpene saponin compound, which is one of the main effective components in traditional Chinese medicine astragalus membranaceus. its content is the main criterion for evaluating the quality of astragalus membranaceus. Astragaloside IV has a wide range of pharmacological effects and is very broad in anti-tumor, anti-inflammatory, antioxidant, hypoglycemic, myocardial protection, anti-viral myocarditis, brain tissue protection, anti-hepatitis B virus, etc. |
| astragalus extract | astragalus extract is a product extracted from dried roots of astragalus Astralgus membranceus (Fisch) Bge Var. mongholicus (Bye) Hsiao. [Pharmacological Resources] There are about 1600 species of Astragalus plants in the world, more than 200 species in China, and currently there are about 7 species for medicinal purposes. Astragalus membranaceus is mainly distributed in Heilongjiang, Liaoning, Inner Mongolia, Hebei, Shandong, Shanxi, Shaanxi, Ningxia, Gansu, Qinghai, Xinjiang, Sichuan and Yunnan, as well as in Mongolia, North Korea and Russia. Commercial Astragalus Bukuqi is mainly distributed in Daxinganling, Nenjiang, Aihui, Sunwu and other counties, Molidawa Banner in Inner Mongolia, Ningguqi is mainly distributed in Ning'an, Dongning, Linkou, Muling, Hailin in Heilongjiang Province, Zhengguqi is mainly distributed in Hebei and Zhangjiakou. Mongolian Astragalus is mainly distributed in Jilin, Hebei, Shanxi and Inner Mongolia in China, as well as in Mongolia and Russia. There are few wild resources of Astragalus membranaceus in China, and Astragalus membranaceus and Astragalus mongolicus are listed as national three-level key protected species. At present, the medicinal materials are mainly cultivated varieties, mainly produced in Hunyuan, Fanzhi, Yingxian, Daixian, Guangling in Shanxi, Guyang, Wuchuan, Zhuozi in Inner Mongolia, Heilongjiang and Jilin. [Main ingredients] Astragaloside IV, flavonoids, polysaccharides, amino acids, organic acids, as well as trace elements, riboflavin, folic acid, vitamin P, sitosterol, lupeol, n-hexanol, etc. Fig. 1 shows astragalus membranaceus |
| physical and chemical properties | white to light yellow powder with melting point of 295.0~296.0 ℃. Soluble in methanol, ethanol, acetone, insoluble in chloroform, ethyl acetate and other weak polar organic solvents. |
| pharmacological action | 1. immunomodulatory effect incubates astragaloside IV, mouse peritoneal macrophages and Mycobacterium tuberculosis together to detect the phagocytic ability of macrophages to Mycobacterium tuberculosis, the contents of γ-interferon (IFN-γ) and interleukin-1β (IL-1β) in the culture medium were detected. The results showed that when the dosage of astragaloside IV was 0.2, 0.6, 1.5 and 4.0g L-1 respectively, the copy number of Mycobacterium tuberculosis DNA(TB-DNA) engulfed by macrophages and the contents of IFN-γ and IL-1β in supernatant were significantly higher than those in control group. Astragaloside IV has the effect of increasing macrophage phagocytosis of Mycobacterium tuberculosis. Astragaloside IV can promote the proliferation and antibody production of mouse T and B lymphocytes in vivo and in vitro, promote B cell proliferation, plasma cell mass formation and antibody synthesis in non-thymus dependent region, but has no obvious effect on T cells in thymus dependent region. 2. Organ protection (1) Brain protection Astragaloside IV has a protective effect on brain damage caused by instantaneous focal ischemia in mice, and its effect is related to antioxidant effect, and it is expected to become a clinical drug for the treatment of stroke. Astragaloside IV has a protective effect on the blood-brain barrier in rats after cerebral ischemia-reperfusion. (2) Renal protection Astragaloside IV has a certain protective effect on kidney injury caused by ischemia-reperfusion. It can effectively protect the kidney and improve the success rate of transplantation during kidney transplantation. Moreover, astragaloside IV can down-regulate the protein content and mRNA overexpression of monocyte chemoattractant protein -1(MCP-1) in kidney tissue. (3) Lung protection Astragaloside IV has a certain protective effect on lung ischemia-reperfusion injury in experimental rats, and can reduce lung blood stasis and focal lung hemorrhage in rats. Astragaloside IV can effectively inhibit ovalbumin-induced chronic asthma. (4) Myocardial protective effect Astragaloside IV can significantly improve cardiac function in rats with myocardial ischemia and myocardial infarction, which is positively correlated with dose and time. After intraperitoneal injection of Coxsackie virus (CVB3) into Balb/C mice to create a viral myocarditis model, intragastric administration of 9% astragaloside for 7 days can improve the survival rate of myocarditis mice, reduce collagen synthesis and myocardial cell apoptosis. (5) Liver protection Astragaloside IV can inhibit collagen synthesis and proliferation of hepatic stellate cells, and has obvious inhibitory effect on liver fibrosis. 3. Hypoglycemic Effect Taking type 2 diabetic rats as the research object, the regulation effect of astragaloside IV on liver glucose enzyme in diabetic rats induced by streptomycin and high-fat diet was studied. The results showed that the dosage of astragaloside IV at 25 mg/kg and 50 mg/kg could significantly reduce the blood glucose, triglyceride (TG) and insulin levels, and inhibit the expression of related mRNA and protein. In addition, astragaloside IV can inhibit the lipolysis of 3T3-L1 lipid cells induced by TNF-α, thereby reducing the level of free fatty acids (FFA), increasing insulin sensitivity, and reducing blood sugar and blood lipids. 4. Anti-apoptosis effect Astragaloside IV can significantly reduce the apoptosis index of myocardial cells in CVB3 viral myocarditis. Astragaloside IV has a certain inhibitory effect on the apoptosis of mouse bone marrow mesenchymal stem cells (BMSCs) induced by adriamycin, but there is no obvious dose-dependent. 5. Anti-inflammatory and antiviral effects Astragaloside IV has obvious inhibitory effect on xylene-induced ear swelling in mice, showing strong anti-inflammatory effect. Astragaloside IV has anti-hepatitis B virus effect. After 10 days of administration, the HBV inhibition rates were 64.0%, 49.6% and 41.7% at 120, 40 and 10 mg/kg doses, respectively. At the same time, a decrease in the level of hepatitis B virus (DHBV)DNA in serum was observed. 6. Anti-aging effect The anti-aging effect of astragaloside IV is related to its ability to scavenge free radicals and anti-lipid peroxidation, promote protein renewal, eliminate nucleic acid metabolism disorders, and promote the proliferation and apoptosis of human skin fibroblasts. At a lower concentration (5~20 mg/L), astragaloside IV can promote the proliferation of wrinkled and wrinkled skin fibroblasts, promote the synthesis of type I collagen in wrinkled, wrinkled and aged skin fibroblasts, and reduce the apoptosis rate of wrinkled and wrinkled skin fibroblasts. 7. Promote cell proliferation. Astragaloside IV with appropriate concentration can promote the rapid proliferation of chondrocytes and maintain the activity of chondrocytes, which provides a new way for cartilage tissue engineering to obtain a large number of seed cells and maintain the activity of chondrocytes in a short period of time. 8. Other effects Astragaloside IV plays a certain anti-cancer activity by inhibiting the expression of Vav3.1 gene. Through NO-cGMP pathway, it inhibits the flow of calcium ions into cells, inhibits the release of intracellular calcium ions, inhibits the activities of phenylephrine and angiotensin II, and has certain relaxation effects on rat aortic ring vessels and isolated mesenteric arteries. |
| determination method | HPLC method for determination of astragaloside iv content chromatographic conditions: column: C18 5u 4.6mm × 250mm; Mobile phase: acetonitrile-water (1:2); Flow rate: 0.8 ml/min; Column temperature: 25 ℃; Detection wavelength: 200nm. Preparation of test solution: precisely weigh 0.1g of extract powder, add appropriate amount of water for ultrasonic dissolution, then shake and extract with 15ml × 4 n-butanol (saturated with water), divide the n-butanol layer, volatilize and dry, dissolve the residue with methanol and fix the volume to 10ml, and then pass through a 0.45 μm microporous filter membrane after mixing. Preparation of standard solution: accurately weigh appropriate amount of astragaloside IV standard, dissolve it with methanol, and prepare a solution with a concentration of 0.1 mg/ml. Determination method: 20 μl of the test solution and the control solution were sucked with a micro injector, injected into a liquid chromatograph, recorded the peak area, and calculated the content according to the peak area external standard method. |
| extraction process | the content of astragaloside iv in astragalus is very low. currently, astragalus iv iv extraction adopts traditional processes such as decoction water extraction and decoction reflux ethanol extraction, which have the disadvantages of high extraction temperature, low extraction rate and time-consuming extraction. The latest extraction technologies include high-speed centrifugation, microwave-assisted extraction, ultrasonic extraction, ultrafiltration, supercritical fluid extraction, ultra-high pressure extraction, and high-speed countercurrent extraction. The new extraction technology plays an important role in improving the extraction rate of astragaloside IV, shortening the extraction time and preventing the destruction of active ingredients. Extraction process of astragaloside IV by CO2 supercritical extraction: weigh 15g of astragalus membranaceus, crush it to 40 mesh, load it into an extraction kettle, and inject a quantitative entrainer (volume fraction 75% ethanol) into it. The extraction kettle was put into supercritical equipment. Adjust the temperature and pressure of the supercritical carbon dioxide fluid, pump the supercritical fluid into the extraction kettle at a certain flow rate, the extract is cyclically separated to collect the extract, and the extract is centrifugally concentrated and evaporated. The optimal process conditions for supercritical carbon dioxide extraction of astragaloside IV are as follows: extraction pressure 40Mpa, temperature 45 ℃, extraction time 2 hours, entrainer 95% ethanol, entrainer dosage 4ml(95% ethanol)/g (dried astragalus powder), CO2 flow rate 10kg/kg h. |
| toxicological analysis | effect of astragaloside IV on embryo and fetal development of SD rats and New Zealand rabbits results show that astragaloside IV shows maternal toxicity when the dosage is greater than 1 mg/kg. When the dose is greater than 0.5 mg/kg, shows toxicity to the fetus. Therefore, it is recommended that pregnant women use astragaloside IV carefully. Further studies have shown that astragaloside IV can significantly delay hair development, eye opening time and Parry reflex in rats. However, astragaloside IV had no significant effect on memory and learning ability. |
| chemical properties | derived from the root of leguminous astragalus. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effect: It has the ability to scavenge superoxide anion free radicals. Promote fibrinolysis and inhibit endotoxin. The deformability of hatched red blood cells is obviously improved, which may be an important mechanism for Astragalus to improve hemorheological indexes. A main active ingredient extracted from Astragalus membranaceus has broad application prospects, especially in modern high-incidence and high-risk diseases such as cardiovascular disease, digestive tract disease, cancer, etc., and can be used as a drug development and utilization. The protective effects of astragaloside IV include cardiovascular system, immune system, digestive system, and nervous system. Its mechanism of action is related to regulating calcium balance, anti-oxidation, anti-apoptosis, and anti-virus. |
Last Update：2024-04-09 21:54:55
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