SCHISANTHERINGOMISIN
Schisantherin A
CAS: 58546-56-8
Molecular Formula: C30H32O9
SCHISANTHERINGOMISIN - Names and Identifiers
| Name | Schisantherin A |
| Synonyms | Schisantherin A SCHISANTHERINGOMISIN Schisantherin A (Gomisin-C Gomisin C(Schisantherin A) Benzo[3,4]cycloocta[1,2-f][1,3]benzodioxole-5,6-diol, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, 5-benzoate, (5S,6S,7S,13aS)- (5S-(5alpha,6beta,7beta))-5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethylbenzo(3,4)cycloocta(1,2-f)(1,3)benzodioxole-5,6-diol 5-benzoate Benzo(3,4)cycloocta(1,2-f)(1,3)benzodioxole-5,6-diol, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, 5-benzoate, (5S-(5alpha,6beta,7beta))- |
| CAS | 58546-56-8 |
| InChI | InChI=1/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28+,30-/m0/s1 |
SCHISANTHERINGOMISIN - Physico-chemical Properties
| Molecular Formula | C30H32O9 |
| Molar Mass | 536.57 |
| Density | 1.33±0.1 g/cm3(Predicted) |
| Melting Point | 110～112℃ |
| Boling Point | 675.6±55.0 °C(Predicted) |
| Specific Rotation(α) | -175°(c=0.12，chloroform) |
| Flash Point | 218.9°C |
| Solubility | Soluble in benzene, chloroform, acetone, soluble in methanol, ethanol, insoluble in petroleum ether, insoluble in water |
| Vapor Presure | 3.54E-19mmHg at 25°C |
| Appearance | Rectangular crystal |
| Color | White to Off-White |
| pKa | 13.70±0.60(Predicted) |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.622 |
| MDL | MFCD09026937 |
| Physical and Chemical Properties | Rectangular crystal (ethanol),mp 122 ℃ ~ 124 ℃,[α]D23 -175 (c = 0.12, chloroform). Soluble in benzene, chloroform, acetone, soluble in methanol, ethanol, insoluble in petroleum ether, insoluble in water. Deoxyschisandrin, schisandrin, schisandrin B, Schisandrin C, Schisandrin B, Schisandrin B, Schisandrin B, Schisandrin B, Schisandrin A and Schisandrin Ester B were separated from the ethanol extract of Schisandra L. 7 biphenylcyclooctene lignans with transaminase lowering activity. All seven ingredients have the effect of reducing SGPT, promoting glycogen generation and prolonging pentobarbital sleep time. Schisandra chinensis ester B has the strongest SGPT-lowering effect, Schisandra chinensis alcohol B has the most significant effect on promoting liver glycogen production, and Schisandra chinensis C has the most prominent effect on prolonging pentobarbital sleep time. |
| In vitro study | The concentrations of TNF-α and IL-6 in the supernatant of cells pretreated with 2.5 or 25 mg/L of Schisantherin A are significantly decreased compared to the LPS control group (p<0.05, p<0.01). The potential cytotoxicity of Schisantherin A is evaluated by the MTT assay after incubating cells for 24 h in the absence or presence of LPS, result shows cell viabilities are not affected by the cytokines at concentrations used (0.5, 2.5, 25 mg/L). RAW 264.7 murine macrophage cells are pre-incubated with Schisantherin A for 1 h and then stimulated with 1 mg/L LPS for 12 h. Both LPS and samples are untreated in control group. After the cell culture media are collected, nitrite and PGE 2 levels are determined, and Schisantherin A is found to reduce NO and PGE 2 production in a dose-dependent manner. |
| In vivo study | Schisantherin A, a dibenzocyclooctadiene lignan isolated from the fruit of Schisandra sphenanthera , has been reported to possess varied beneficial pharmacological effects. Schisantherin A protects lipopolysaccharide-induced acute respiratory distress syndrome in mice through inhibiting NF-κB and MAPKs signaling pathways. Pretreatment with Schisantherin A markedly ameliorates LPS-induced histopathologic changes and decreases the levels of TNF-α, IL-6 and IL-1β in the BALF. In addition, the phosphorylation of NF-κB p65, IκB-α, JNK, ERK and p38 induced by LPS are suppressed by Schisantherin A. The lung wet/dry weight ratio is evaluated at 7 h after the intranasal instillation of LPS. The results show that there are no differences between control group and Schisantherin A (40 mg/kg) group (p>0.05). LPS causes a significant increase in lung wet/dry weight ratio (p<0.01) compared with the control group. Schisantherin A dose-dependently decreases the lung wet/dry weight ratio (p<0.05) compared to those in the LPS group. |
SCHISANTHERINGOMISIN - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| HS Code | 29329990 |
SCHISANTHERINGOMISIN - Reference
| Reference Show more | 1. Wang Zhenheng, Jin Ling, Ma Yi, etc. Analysis of commercial specification grade of schisandra sphenanthera based on content of schisandra chinensis [J]. Chinese Journal of Traditional Chinese Medicine, 2017(19):3728-3732. 2. Ma, Hui, Yu, liantin, Yang, Li, Heng, et al. Purification and antioxidant activity of lignans from schisandra chinensis [J]. Chinese Journal of Traditional Chinese Medicine 2019(12). 3. Wang Guoli wishes Hong, Yan, Lin, Hai, et al. Simultaneous determination of six lignans in schisandra chinensis by Reversed-phase high performance liquid chromatography [J]. Journal of Food Safety and quality testing 2014 000(008):2470-2475. 4. Ma, Hui, Feng, Bo, Zhu, Heyun, et al. Antioxidant and anti-inflammatory activities of total lignans from schisandra chinensis [J]. Food Research and development 2019(11). 5. Wei Yajie, Zhang Zekun, Guan Yanling, etc. Hugan Pian HPLC fingerprint and multi-component quantitative analysis [J]. Central South Pharmaceutical Journal, 2018, 016(001):31-34. 6. Bai Yidan, Qiao Zhou, Xue Jingwei et al. Simultaneous determination of multi-components in shensong Yangxin capsules and its methodological validation [J]. Journal of Pharmaceutical Analysis, 2018 v.38(08):80-90. 7. Zhou Haixu, Xie Meiyu, Gao Yan, Li Bo, Su Tongchao, Li Zhonghai. Optimization of ultrasonic-assisted simultaneous extraction of lignans and polyphenols from Cinnamomum camphora leaves [J]. Food and machinery, 2020,36(10):143-148. 8. Jin Miao, Liu Jinna, Liu Hui, Black Yu Rong, Liu Yulan. Effects of different processing methods on lignans of introduced schisandra chinensis in Shaanxi [J]. Shaanxi Agricultural Sciences, 2020,66(11):17-20. 9. Jiao Meiyu, Yu-yue, Wu Haoxian, Kang Tingguo, Zhang Hui. Study on the mechanism and qualitative recognition model of "color discrimination and qualitative analysis" of schisandra chinensis [J]. China Pharmacy, 2020,31(24):3007-3012. 10. Zhang, Qi, et al. "Development of a matrix solid-phase dispersion extraction combined with high-performance liquid chromatography for determination of five lignans from the Schisandra chinensis." Journal of Chromatography B 1011 (2016): 151-157.https://doi 11. [IF=6.079] Hongyan Zhu et al."Sedative and hypnotic effects of supercritical carbon dioxide fluid extraction from Schisandra chinensis in mice."J Food Drug Anal. 2016 Oct;24:831 12. [IF=4.759] Huifen Ma et al."The in-capillary- 2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)-sweeping micellar electrokinetic chromatography - Diode array detector method for screening and quantifying trace natural antioxidants from Schisandra chinensis."J Ch 13. [IF=4.545] Huimin Wu et al."Study on the potential effective ingredients of Xiaosheng prescription for dry eye disease."Biomed Pharmacother. 2020 Jul;127:110051 14. [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 15. [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 16. [IF=4.36] Zhenghua Wu et al."Schisandrol A, the main active ingredient of Schisandrae Chinensis Fructus, inhibits pulmonary fibrosis through suppression of the TGF-β signaling pathway as revealed by UPLC-Q-TOF/MS, network pharmacology and experimental verification. |
SCHISANTHERINGOMISIN - Reference Information
| chemical properties | rectangular crystal (ethanol),mp 122 ℃ ~ 124 ℃,[α]D23 -175 (c = 0.12, chloroform). Soluble in benzene, chloroform, acetone, soluble in methanol, ethanol, insoluble in petroleum ether, insoluble in water. Deoxyschisandrin, schisandrin, schisandrin B, Schisandrin C, Schisandrin B, Schisandrin B, Schisandrin B, Schisandrin B, Schisandrin A and Schisandrin Ester B were separated from the ethanol extract of Schisandra L. 7 biphenylcyclooctene lignans with transaminase lowering activity. All seven ingredients have the effect of reducing SGPT, promoting glycogen generation and prolonging pentobarbital sleep time. Schisandra chinensis ester B has the strongest SGPT-lowering effect, Schisandra chinensis alcohol B has the most significant effect on promoting liver glycogen production, and Schisandra chinensis C has the most prominent effect on prolonging pentobarbital sleep time. |
| determination of total lignans content of schisandra chinensis | schisandra chinensis is the dry mature fruit of Schisandra chinensis (Turcz.) Baill. It mainly contains lignans, volatile oils, polysaccharides and other components. The lignans in Schisandra chinensis mainly include schisandra ester A, B, C, D, E and deoxyschisandrin. Mainly schisandra ester A, the content is higher. In addition to schisandra, lignans have methylenedioxy groups on the B ring in the structural formula, which can react with chromotrypsin. So using Schisandra ester A as the control, the measured results basically reflect the total lignans content in Schisandra. (1) preparation of reference substance solution: take appropriate amount of schisandra chinensis ester a reference substance, weigh it accurately, and prepare a solution of 5 mg/ml with methanol. (2) preparation of sample solution: take about 1g of fruit powder of schisandra chinensis (schisandra chinensis) and weigh it accurately. Place in a stopper bottle, add 20ml of methanol precisely, treat with ultrasound for 20min, cool to room temperature, shake well, filter, discard the initial filtrate, and take the continuous filtrate to obtain. (3) determination: 20 μl of reference substance solution, 20 μl of test substance solution and 20 μl of methanol are respectively absorbed into plug test tubes, methanol is removed from water bath, 0.5ml of clarified aqueous solution of 10% chromotropic acid, 3.0ml of concentrated sulfuric acid and 1.5ml of distilled water are respectively accurately added into the three residues, shaken well, heated in boiling water bath for 30min, cooled quickly, and the above methanol tube is blank, according to the spectrophotometric method, the absorbance is measured at the wavelength of 570nm, and the calculation is obtained. (4) determination results: for southern schisandra chinensis from different producing areas, the results were measured according to the proposed method. |
| biological activity | Schisantherin A (Gomisin C, Schisanwilsonin H, Arisanschinin K) is a schisandrin with antitussive, sedative, anti-inflammatory, anti-osteoporosis, neuroprotective, cognitive and cardioprotective activities. Schisantherin A can also inhibit p65-NF-κB translocation into the nucleus by IκBα degradation. |
| target | TargetValue NF-κB () |
| Target | Value |
| in vitro study | The concentrations of TNF-α and IL-6 in the supernatant of cells pretreated with 2.5 or 25 mg/L of Schisantherin A are significantly decreased compared to the LPS control group (p<0.05, P <0.01). The potential cytotoxicity of Schisantherin A is evaluated by the MTT say after incubating cells for 24 h in the absence or presence of LPS, result shows cell viabilities are not affected by the cytokines at concentrations used (0.5, 2.5, 25 mg/L). RAW 264.7 murine macrophage cells are pre-incubated with Schisantherin A for 1 h and then stimulated with 1 mg/L LPS for 12 h. Both LPS and samples are untreated in control group. After the cell culture media are collected, nitrite and PGE 2 levels are determined, and Schisantherin A is found to reduce NO and PGE 2 production in a dose-dependent manner. |
| in vivo study | Schisantherin a, a dibenzocyclooctadiene lignan isolated from the fruit of Schisandra sphenanthera , has been reported to possess varied beneficial pharmacological effects. Schisantherin A protects lipopolysaccharide-induced acute respiratory distress syndrome in mice through inhibiting NF-κB and MAPKs signaling pathways. Pretreatment with Schisantherin A markedly ameliorates LPS-induced histopathologic changes and decreases the levels of TNF-α, IL-6 and IL-1β in the BALF. In addition, the phosphorylation of NF-κB p65, IκB-α, JNK, ERK and p38 induced by LPS are suppressed by Schisantherin A. The lung wet/dry weight ratio is evaluated at 7 h after the intranasal instillation of LPS. The results show that there are no differences between control group and Schisantherin A (40 mg/kg) group (p>0.05). LPS a significant increase in lung wet/dry weight ratio (p<0.01) compared with the control group. Schisantherin a dose-dependently decreases the lung wet/dry weight ratio (p<0.05) compared to those in the LPS group. |
Last Update：2024-04-09 21:04:16
Supplier List
Spot supply
Product Name: Schisantherin A Visit Supplier Webpage Request for quotationCAS: 58546-56-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Schisantherin A Visit Supplier Webpage Request for quotationCAS: 58546-56-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History