69363-14-0
Schisanhenol
CAS: 69363-14-0
Molecular Formula: C23H30O6
69363-14-0 - Names and Identifiers
69363-14-0 - Physico-chemical Properties
| Molecular Formula | C23H30O6 |
| Molar Mass | 402.48 |
| Density | 1.118±0.06 g/cm3 (20 ºC 760 Torr) |
| Melting Point | 130 °C |
| Boling Point | 563.9±50.0 °C(Predicted) |
| Specific Rotation(α) | +60.8 (CHCl3) |
| Solubility | Soluble in ethyl acetate, DMSO and other solvents, insoluble in water. |
| Appearance | White crystal |
| pKa | 8.96±0.60(Predicted) |
| Storage Condition | 2-8℃ |
| MDL | MFCD28411506 |
| Physical and Chemical Properties | Appearance: white granular crystal or white crystalline powder melting point: 132~133 ℃ refractive index: 1.536 flash point: 294.8oC density: 1.118g/cm3 boiling point: 563.9oC at 760 mmHg solubility: soluble in ethanol, ether, ethyl acetate, DMSO and other solvents, almost insoluble in water. storage method: 2-8°C (usually 4°C), refrigerated, sealed and protected from light. main use: used for content determination/identification/pharmacological experiment, etc. UVλmaxC2H5OHnm (LG ε):218(4.75),248 (4.31),282 (3.92). IR λmax μm:3.48 (OCH3),6.23 and 6.28 (aromatic ring). MSm/z:402 (m, 100),235,205,181,167. NMR δ:6.50 and 6.30 (1H each, s, two aromatic rings h),5.78 (1H,br,OH),3.87,3.84 and 3.56 (3H,9H,3H respectively, all s, five methoxy groups),1.06,0.80 (3H each, J = 7Hz, two methyl groups). fig. 1 is the structural formula of schisandrin. |
69363-14-0 - Reference
| Reference Show more | 1. Dai Hui, Suhang, Cai Pengfei, et al. Changes of color and eight lignans of schisandra vinegar before and after steaming [J]. Chinese patent medicine 2019 41(05):1091-1096. 2. Soviet Union Lin, Li Min, Xu Min, etc. Predictive analysis of quality markers of schisandra chinensis before and after processing with vinegar based on multivariate statistical analysis and network pharmacology [J]. Chinese herbal medicine, 50 Vol. 19, 2019 pp. 4643-4653. 3. [IF = 4.759] Huifen Ma et al."The in-capsule -2,2-azinobis-(USB acid)." J Ch 4. [IF = 3.935] Yunlong Guo et al."Rapid characterization of Schisandra species by using direct analysis in real time mass spectrometry."J Pharmaceut Biomed. 2021 Jan;192:113648 5. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 |
69363-14-0 - Reference Information
| plant extract | schisanhenol (schisanhenol), chemical name is ()-golmicin K3, also known as dedesdeoxyschisandrin. It can be extracted from many Schisandraceae plants isolated from a kind of benzene Cyclooctene lignin compounds, literature studies have shown that schisandrin has antioxidant effect, can inhibit a variety of chemical induced cell damage caused by mitochondrial swelling and decreased membrane fluidity has obvious protective effect, at the same time, schisandrin has anticoagulant fibrinolysis, inhibition of platelet aggregation and vasodilation activity, cerebral infarction and in terms of brain function and morphology have therapeutic and protective effects, is a potential drug for the treatment of ischemic stroke. |
| physical and chemical properties | Appearance Properties: white granular crystals or white crystalline powder Melting Point: 132~133 ℃ refractive index: 1.536 flash point: 294.8oC density: 1.118g/cm3 Boiling Point: 563.9oC at 760 mmHg solubility: soluble in ethanol, ethyl ether, ethyl acetate, DMSO and other solvents, almost insoluble in water. storage method: 2-8°C (usually 4°C), refrigerated, sealed and protected from light. main purposes: for content determination/identification/pharmacological experiments. uvmax c2h5ohnm (lg ε):218(4.75),248 (4.31),282 (3.92). IR λmax μm:3.48 (OCH3),6.23 and 6.28 (aromatic rings). Ms M/z:402 (M ,100),235,205,181,167. NMR δ:6.50 and 6.30 (1H,s, two aromatic rings H each),5.78 (1H,br,OH),3.87,3.84 and 3.56 (3H,9H,3H, are s, five Methoxy),1.06,0.80 (each 3h, J = 7Hz, two methyl). FIG. 1 shows the structural formula of schisandrin. |
| source plant | It is well known that schisandras is derived from Schisandra chinensis Schisandra (Franch.) rehd. et Wils. The drying of the mature fruit. Therefore, we should first understand the next schisandra (as shown in Figure 2). schisandra chinensis, commonly known as Capsicum annuum, Turcz, fructus schisandrae, caulis faciens, fructus schisandrae, Etc., Tang et al, "the new version of the grass" contains "five kinds of flesh, sweet acid, hard in the nucleus, all have a salty taste", so there is the name of schisandra. The ancient medical book said that it was first listed in Shen Nong's herbal Meridian. The efficacy of traditional Chinese medicine lies in its nourishing and strong power, and its medicinal value is extremely high. It is a perennial deciduous vine, plants for ornamental. It is the mature fruit of Schisandra chinensis(Turcz.)Baill. And Schisandra chinensis Schisandra sphenanthera Rehd.et Wils. Schisandra chinensis is the traditional use of genuine. Mainly produced in the northeast, Inner Mongolia, Hebei, Shanxi and other places. Schisandra sphenanthera, mostly in the south of the Yangtze River basin and the Southwest region. Its dry fruit, slightly spherical or flat spherical, 5~8mm in diameter. The skin is bright red, purple or dark red, oily, with irregular shrinkage. The pulp is soft, containing 1-2 seeds, reniform, brown-yellow, shiny, hard, and the seed kernel is white. Pulp, gas weak and special, sour. When the seeds were broken, they had an aroma and bitter taste. With purple red, large grain, thick meat, oily and gloss is better. FIG. 2 is a picture of schisandra chinensis. |
| efficacy and function | schisandra chinensis has sour astringency, longer than the Qi and Yin of the lung and kidney to stop cough and sweat, astringent essence, antidiarrheal, but also convergence of the heart to calm the mind. Although the gas is warm, but soft texture, warm and not dry, so the lung deficiency of long cough, kidney deficiency of asthmatic cough, yang deficiency of spontaneous sweating, Yin deficiency of night sweats, smooth, diarrhea, thirst due to injury and more than Sleep Initiation and Maintenance Disorders dream are commonly used products. However, because of its convergence too much, the expression of the evil is not resolved, Cough, measles and other new diseases, such as the beginning of the application of the real evil. For those who have always had cold drinks, external feeling of wind-cold, with Cough shortness of breath and clear phlegm, the dosage of this product should be small, and they can be mixed with warm lung and cold dispelling products, it can not only prevent the dissipation of lung gas too much, but also prevent the harmful effects of suppression. Its pharmacology is: direct action of the spinal cord motor cells, enhance the spinal cord reflex, improve the regulation of the cerebral cortex, but also enhance the body's defense against non-specific stimuli. Decoction, can enhance the contractility of the heart, and can regulate the cardiovascular improve blood circulation; Can excite the uterus, so that the uterine contraction to strengthen the rhythm. Its extract has obvious antitussive and expectorant effects. In addition, it can enhance the perception of visual, auditory and skin receptors. Pseudomonas aeruginosa, Shigella, Salmonella typhi and Staphylococcus aureus have antibacterial effect. Schisandra seed kernel ethanol extract not only has a central inhibitory effect, There are anti-convulsant effect, and the characteristics of a tranquilizer. Another anti-virus, anti-aging, reduce transaminase, improve myocardial nutrition and other effects. The above information is compiled with few waves. |
| Chemical constituents | The Main effective components of schisandra chinensis are lignans, more than 150 lignans have been isolated from Schisandraceae plants at home and abroad, and more than 50 species belonging to biphenyl Cyclooctene type have been isolated and their structures have been determined. 1. Schisantherin A: molecular formula C30H32O9, molecular weight 536.56. Rectangular crystal (ethanol), mp.122 ℃ ~ 124 ℃(116~8 ℃),[α]D23-175(C = 0.12, chloroform). Soluble in benzene, chloroform and acetone, soluble in methanol, ethanol, insoluble in petroleum ether, insoluble in water. 2. Schisantherin B: molecular formula C28H34O9, molecular weight 514.55. MP. 97 ° C. To 99 ° C.,[α]D- 50 °(C = 1.12, chloroform). 3. Schisantherin C: molecular formula C28H34O9, molecular weight 514.55. mp.99 °c to 101 °c,[α]D- 151 °(C = 1.04, chloroform). 4. Schisantherin D: molecular formula C29H28O9, molecular weight 520.51. MP. 108 °c to 110 °c (103 °c softening),[α]D-180.1 °(C = 1.07, chloroform). 5. Schisandrin it is prepared from schisandra chinensis by petroleum ether extraction, steam distillation and crystallization. Schisandra seeds can also be used as raw materials for separation and purification of lignan monomer components in schisandra chinensis by Silica Gel chromatography and Countercurrent chromatography, which is referred to as high-speed Countercurrent Chromatography (HSCCC). 6. Other ingredients: schisandrin A (deoxyschisandrin dexyschizandrin, schisandrin A), schisandrin B (r-schisandrin, r-Schisandrin, schisandrin B), schisandrin C (Schisandrin C, Schisandrin C). |
| extraction and separation | The main chemical components of schisandra chinensis Extract extraction and separation flow chart is as follows: (1) schisandrin A, B, C, D and E were extracted and separated from the fruit of schisandra sphenanthera. (2) extraction of schisandrin from schisandra chinensis. FIG. 3 is a process flow chart of extraction of schisandrin from schisandra chinensis. (3) extraction of schisandra chinensis schisandrin. |
| pharmacological effects | schisandrin in schisandra chinensis Extract can directly antagonize the heart mitochondria toxicity induced by adriamycin, inhibition of vitamin C- NADPH induced rat brain, liver, kidney microsomal and mitochondrial lipid peroxidation, its effect is stronger than vitamin E. It can also significantly increase the content of cAMP in myocardial cells of aged rats, increase the ratio of cAMP/cGMP, and enhance the activity of the heart. 1. Effect on liver The extract of schisandra chinensis and its preparations can promote hepatic gluconeogenesis, promote the decomposition of hepatic glycogen, and strengthen the glucose phosphorylation process of fructose in brain, liver and muscle; the ethanol extract can significantly reduce serum alanine aminotransferase, and has a protective effect on liver injury caused by carbon tetrachloride. Rat liver microsomal cytochrome P-450, NADPH-cytochrome C reductase, aminopyrine demethylase activity, liver weight and liver microsomal protein content were significantly increased after gavage of schisandrin (Ⅰ), the activity of benzo-specific hydroxylase was increased, and the smooth endoplasmic reticulum of rat liver cells was found to proliferate obviously under electron microscope, which indicated that liver microsomal monooxygenase could be induced. In addition, it can reduce SGPT in ccl4-poisoned mice, inhibit ccl4-induced liver microsomal lipid peroxidation, and convert CCl4 metabolism to CO. These effects are similar to those of other components of schisandra chinensis such as B. 2. Effect on central nervous system The crude extract of schisandra chinensis can increase the excitability of central nervous system, improve the intelligence activity and work efficiency. Schisandra chinensis can significantly prolong the sleep time of pentobarbital sodium in mice, and the two have synergistic effect. Oral administration of pentanol in mice can significantly reduce brain activity. Its alcohol extract has the effect of anti-electric shock and central stimulant induced convulsion. 3. Effect on peptic ulcer The extract of schisandra chinensis has a good inhibitory effect on gastric ulcer disease, and also has a preventive effect on gastric mucosal injury caused by anhydrous alcohol. 4. Effect on cardiovascular system schisandra chinensis and its extract have vasodilation effect, and have significant pressor effect when the circulation is exhausted. In addition, it also has a certain cardiotonic effect. Schisandra chinensis has a beta-blocker effect on isolated and in vivo frog hearts. 5. Effect on immune system inhibition of 25mg/kg/day of schisandra chinensis Extract on spleen antibody secreting cells and specific Rose forming cells in mice same inhibitory effect, the combination of the two has obvious synergistic effect. 6. Anti-aging effect schisandra chinensis Extract can enhance cellular immunity, enhance RNA and PAS synthesis of testis and ovary, promote the proliferation of germ cells, and has obvious anti-free radical effect, it can also play an anti-aging role by changing MAO and its isoenzyme activity. Schisandrin has an antioxidant effect and protects the heart from damage by lipid peroxidation. |
| adverse reactions | the adverse reactions are usually allergy, Palpitations shortness of breath, chest tightness, General itching, whole body urticaria, tachycardia, premature beat. According to its serious conditions are divided into: (1) side effects: hiccups, acid reflux, heartburn, intestinal, drowsiness, occasional allergic reactions. (2) the toxic reactions were as follows: Fever, Head Pain, Fatigue, dry mouth, sense of smell, Nausea, Vomit, urticaria, etc. |
| Use | for content determination/identification/pharmacological experiments. |
Last Update：2024-04-09 20:45:29
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