Glucopyranoside, rhapontigenin-3, beta-D-
Rhapontin
CAS: 155-58-8
Molecular Formula: C21H24O9
Glucopyranoside, rhapontigenin-3, beta-D- - Names and Identifiers
Glucopyranoside, rhapontigenin-3, beta-D- - Physico-chemical Properties
| Molecular Formula | C21H24O9 |
| Molar Mass | 420.41 |
| Density | 1.2828 (rough estimate) |
| Melting Point | 236-240 °C |
| Boling Point | 457.61°C (rough estimate) |
| Specific Rotation(α) | D32 -59.5° (acetone) |
| Flash Point | 406.9°C |
| Solubility | Soluble in methanol, DMSO |
| Vapor Presure | 1.39E-23mmHg at 25°C |
| Appearance | Pale yellow or yellow powder |
| Color | Brown |
| Merck | 13,8258 |
| pKa | 9.16±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.6230 (estimate) |
| MDL | MFCD00010117 |
| Physical and Chemical Properties | Soluble in methanol, DMSO derived from rhubarb |
Glucopyranoside, rhapontigenin-3, beta-D- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/38 - Irritating to eyes and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29389090 |
Glucopyranoside, rhapontigenin-3, beta-D- - Reference
| Reference Show more | 1. Lin, Longfei, et al. "Characterization of the constituents in rat plasma after oral administration of radix polygoni multiflori extracts by ultra‐performance liquid chromatography/quadrupole time‐of‐flight mass spectrometry." Biomedical Chromatography 29.1 2. Longfei Lin, Hongmei Lin, Miao Zhang, Boran Ni, Xingbin Yin, Changhai Qu, Jian Ni,A novel method to analyze hepatotoxic components in Polygonum multiflorum using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry,Journal 3. [IF=10.588] Longfei Lin et al."A novel method to analyze hepatotoxic components in Polygonum multiflorum using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry."J Hazard Mater. 2015 Dec;299:249 4. [IF=1.902] Longfei Lin et al."Simultaneous determination of 14 constituents of Radix polygoni multiflori from different geographical areas by liquid chromatography–tandem mass spectrometry."Biomed Chromatogr. 2015 Jul;29(7):1048-1055 5. [IF=1.902] Longfei Lin et al."Characterization of the constituents in rat plasma after oral administration of radix polygoni multiflori extracts by ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry."Biomed Chromatogr. 2015 Oct;29(10 6. [IF=4.759] Yueping Jiang et al."Application of multifold characteristic ion filtering combined with statistical analysis for comprehensive profiling of chemical constituents in anti-renal interstitial fibrosis I decoction by ultra-high performance liquid chromatogra 7. [IF=4.36] Li Lin et al."Study on the protection of water extracts of Polygoni Multiflori Radix and Polygoni Multiflori Radix Praeparata against NAFLD and its mechanism."J Ethnopharmacol. 2020 Apr;252:112577 |
Glucopyranoside, rhapontigenin-3, beta-D- - Reference Information
| Overview | Le Pang Ting (rhaponticin, rhaponitin or poniticin), molecular formula is C21 H24 O9, chemical name is 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl) vinyl] phenyl-β-D-glucoside, a derivative of stilbene, belongs to stilbene. Under the rhubarb contained in the first edition of the 2005 edition of the Chinese Pharmacopoeia, it is stipulated that lepon stop cannot be detected. However, recent studies have shown that Le Pang Ting has antibacterial, improving microcirculation, lowering blood lipids, lowering blood sugar, anti-tumor, inhibiting allergic reactions, regulating the body's immune defense system, anti-thrombotic and antioxidant effects. In addition, Legantin and its metabolites have a variety of pharmacological activities. Among them, Legantin may be used as an agonist of PPAR-γ to reduce blood sugar concentration to achieve the effect of treating diabetes and the effect and thiazolidinedione The ketone drug pyrrolidone is quite eye-catching. Legantin is likely to become a diabetic drug with high efficiency and low adverse reactions from natural products. |
| source | rhubarb plants: polygonaceae (Polygonaceae) rhubarb (Rheum L.) plants, about 50 species in the world, distributed in temperate and subtropical regions of Asia, there are more than 30 species in China, from the southwest to the northeast, of which rhubarb R.officinale Baill. is one of the famous Chinese medicines. Previous studies on rhubarb mainly focused on anthraquinone compounds with laxative effects, including rhein, emodin, chrysophanol, physcion and aloe emodin. mulberry: Morus alba L. is distributed below 600 m above sea level in the country and is rich in resources. Morus albaL mulberry leaves(Morus albaL.) is one of the traditional Chinese medicines in China. It contains a variety of functional components, such as minerals, vitamins, dietary fiber, amino acids, flavonoids, polysaccharides, etc., and has various physiological functions such as lowering blood sugar, lowering blood pressure, lowering cholesterol, anti-aging, preventing cancer, and improving immunity. DAD/UV HPLC was used to detect that the leaves and fruits of mulberry trees contain lepangatin, 389.26±5.22 mg per 100 g of mulberry leaves and 99.17±2.79 mg per 100 g of mulberry fruits (accounting for 52.5% of the total stilbene chemical components) eucalyptus: eucalyptus is a common name for eucalyptus plants of Myrtle family, native to Australia, Indonesia and the Philippines, China (South) introduced planting, has a history of more than 100 years. Eucalyptus leaves have anti-fungal and anti-infection effects, and are often used to treat intestinal mycosis, various dermatitis, herpes eczema, cervical erosion, etc. Etoh et al. [10] isolated Lepangtin from Eucalyptus rubida and confirmed that its repellent effect on blue mussel is equivalent to that of copper sulfate Picture: Mulberry |
| extraction and separation | currently lepon stop is mainly obtained by alcohol extraction column chromatography from rhubarb plants, and no other simple methods or chemical synthesis methods have been reported. The chromatography column used is divided into two types, one is alumina column chromatography, which uses this method to separate Lepon from Rhubarb and the stop yield is 4.44%; the other is silica gel column chromatography, with ethyl acetate-methanol (8:2) elution, ether purification, using this method to separate Lepon from Rhubarb North China and the stop yield is 0.022%. |
| pharmacological activity | hypoglycemic effect: rhubarb extract is often used to weaken metabolic abnormalities such as diabetes, high blood cholesterol, platelet aggregation, etc. Experiments show that [14]: 70% ethanol extract of rhubarb can significantly reduce blood glucose concentration in streptozotocin-induced diabetic mice. The extract was separated by XAD-4 column chromatography, and its 60%, 80% and 100% methanol elution partially enhanced insulin sensitivity and inhibited α-glucose activity. Further separated the active substances Lepangting, rhein, etc. Among them, Legantin enhances the insulin-induced glucose absorption and triglyceride accumulation in 3T3-L1 adipocytes. The effect is equivalent to that of the thiazolidinedione drug pyrrolidone, suggesting that Legantin may be PPAR-γ agonists, thereby reducing blood sugar concentration to achieve the effect of treating diabetes. antioxidant effect: 10 stilbene compounds including legantin isolated from rhubarb have antioxidant activity. kinetic studies show that these compounds compete with linoleic acid to inhibit the active site of lipoxygenase, and their IC50 value is 6.7~74.1 μL, and they also have significant scavenging effect on ABTS + free radicals (TEAC = 1.16~4.64). There are also studies that have shown that Legantin has a scavenging effect on intracellular ROS, DPPH free radicals and H2O2. Further research on its mechanism has found that Legantin can increase the antioxidant activity of cells and adjust the cell signal transduction pathway (enhance extracellular ERK Phosphorylation and inhibit AP-1 activity) so that lung fibroblasts are V94-7 not oxidized. antithrombotic and platelet aggregation: in vivo and in vitro experiments on ADP and collagen-induced platelet aggregation mice have confirmed that lepon and its 8-O-β-D-glucose derivatives have antiplatelet aggregation effects, IC50 values are 4 mg • L-1 and 70 mg • L-1, respectively, which are better than aspirin, and the latter significantly reduces the death of mice caused by pulmonary thrombosis. Congestion is a series of symptoms caused by blood stagnation or inflammation. Rhubarb is commonly used in traditional Chinese medicine to treat congestion. Japanese scholars have shown that the mechanism of action is the inhibition of NO production in LPS-active macrophages and the protective effect of D-galactosamine/LPS-induced liver damage. Anti-allergic effect: Lepon is transformed into 8-O-β-D-glucose derivative under the action of human intestinal flora. Research table: This derivative is a histamine-hyaluronidase released by mast cells and allergic reactions (PCA reaction) It has an inhibitory effect, and its effect is better than that of non-glucocorticoid anti-inflammatory agent-sodium cromoglycate. Therefore, Le Pang Ting can be developed as a prodrug of anti-allergic drugs. Other studies have shown that Lepangtin 8-O-β -D-glucose derivatives have better inhibitory effects on allergies at 25 mg • L-1 and 50mg • mL-1, with inhibition rates of 48% and 85% respectively. The anti-inflammatory effect of oral administration is better than that of intravenous injection. anti-tumor effect: Ryu et al. [19] research shows that several stilbene compounds including legantin have anti-cancer activity in vitro and have inhibitory effects on five human cancer cell lines-A-549, SK-OV-3, SK-MEL-2, XF-498 and HCT15. vasodilator effect: Yoo et al. [20] studies have shown that methanol extract of rhubarb can stretch 0.3 µmol • L-1 rat thoracic arteries contracted by epinephrine, with an EC50 value of 5.8 µg • mL-1. The extract was further isolated to obtain 7 functional compounds, including Legamantin, and its mechanism of action may be related to the NO signal transduction pathway. Inhibition of cell apoptosis: The accumulation of β-amyloid protein 1-42 is an important cause of the formation of Alzheimer's disease. Studies have shown that: Legantin has a resistance to β-amyloid protein in the IMR-32 system of human neuroblastoma cells. Protein 1-42 has a resistance effect to maintain cell viability and has a protective effect on mitochondria. The mechanism of action is related to the expression of bcl-2 gene family. β amyloid 1-42 induces bax up-regulation and bcl-2 down-regulation, thus triggering neurotoxicity. The bax is down-regulated and bcl-2 up-regulated, thereby inhibiting the formation of Alzheimer's disease. whitening: research shows that: lepon has strong absorption ability and can inhibit melanin production and has whitening function, and its whitening ability is dose-effective related to lepon stop content (0.000 1% ~ 10%). Anti-hangover effect: Studies have shown that: Le Pang Ting reduces the metabolism of ethanol into aldehyde by inhibiting the effect of alcohol dehydrogenase, thereby reducing cytotoxins and hangover symptoms to achieve anti-hangover effect. Estrogen-like effect: Diethyldiethylstilbestrol is the prototype of synthetic hormones. Among the natural stilbene compounds, only Le Pang Ting has an estrogen effect and can be used in the development of contraceptives. picture: hangover effect |
| references | [1] Xu Ying, Guo Zengjun, Tan Lin. Research Progress of Le Pang Stop [J]. Modern Applied Pharmacy in China, 2009 (7):549-552. [2] Shen Yulan, Yang Minzhi, Luan Jie, etc. Improvement of detection method for rhubarb Zhonglepangding [J]. Chinese Pharmaceutical Affairs, 2010, 24(5):493-495. [3] Guo Ming, Xu Xingtao, Wu Zhiwu. Study on the binding reaction mechanism of traditional Chinese medicine active ingredient lepangding and human serum albumin [J]. Chinese Journal of Pharmacy, 2011(9):1084-1092. |
| use | for content determination/identification/pharmacological experiments, etc. |
Last Update：2024-04-09 19:05:10
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Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Rhaponiticin Visit Supplier Webpage Request for quotationCAS: 155-58-8
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Email: 3008007409@qq.com
Mobile: 18021002903
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