1-oxide,(1-beta)-matridin-15-on
Oxymatrine
CAS: 16837-52-8
Molecular Formula: C15H24N2O2
1-oxide,(1-beta)-matridin-15-on - Names and Identifiers
| Name | Oxymatrine |
| Synonyms | Oxymatrine OXYMATRINE Ammothamnine Matrine oxide matrine,1-oxide Matrine N-oxide Matrine, 1-oxide Matrine 1beta-oxide Oxymatrine 16837-52-8 Ammothamnine Oxymatrine 1-oxide,(1-beta)-matridin-15-on Matridin-15-one, 1-oxide, (1-beta)- (2alpha,5beta,7beta,10beta,13alpha)-4,10-bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate |
| CAS | 16837-52-8 |
| EINECS | 605-514-4 |
| InChI | InChI=1/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1 |
| InChIKey | XVPBINOPNYFXID-LHDUFFHYSA-N |
1-oxide,(1-beta)-matridin-15-on - Physico-chemical Properties
| Molecular Formula | C15H24N2O2 |
| Molar Mass | 264.36 |
| Density | 1.399g/cm3 |
| Melting Point | 208℃ |
| Boling Point | 957.115°C at 760 mmHg |
| Specific Rotation(α) | +47 (EtOH) |
| Flash Point | 532.644°C |
| Solubility | Soluble in water, chloroform, ethanol, insoluble in ether, methyl ether, petroleum ether. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White crystal or powder |
| Color | white to off-white |
| pKa | 4.87±0.20(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.637 |
| MDL | MFCD00210339 |
| Physical and Chemical Properties | Colorless block Crystal, soluble in chloroform, methanol, difficult to dissolve in petroleum ether, acetone, derived from radix sophorae tonkinensis, Sophora flavescens. |
| In vitro study | Oxymatrine is a quinazoline alkaloid extracted from the root of Sophora, used to treat viral hepatitis, cancer, viral myocarditis, gastrointestinal bleeding and skin diseases (such as vaginitis, psoriasis and eczema). Oxymatrine protects mice against GalN/LPS-induced fulminant hepatitis, and block hepatocyte apoptosis and subsequent necrosis by down-regulating serum tumor necrosis factor alpha production and expression of Fas and Fas ligand in the liver.) Oxymatrine also showed anti-hepatitis B virus effect in vitro by reducing the content of HBsAg and HBcAg in the liver of transgenic mice. |
| In vivo study | LD50: Mouse 521 mg/kg (I. p.) |
1-oxide,(1-beta)-matridin-15-on - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R20/22 - Harmful by inhalation and if swallowed. |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | OQ1770000 |
| HS Code | 29399990 |
1-oxide,(1-beta)-matridin-15-on - Reference
| Reference Show more | 1. Xia Yimao, Finland, Xiang Su et al.. HPLC Determination of Three Alkaloids in Kushen Sophora flavescens [J]. Chinese Pharmacist 2018(1):146-148. 2. Chen Xinmei, Zhao Yuan, Guo Hui. Study on Intestinal Absorption Characteristics of Oxymatrine Phospholipid Complex by Everted Intestinal Capsule Method [J]. Chinese Modern Applied Pharmacy, 2019, v.36(08):50-54. 3. Hou Shanqun, Lu Ping, Zhong Xiaojian, et al. Effects of oxymatrine on IL-10 and IL-17 expression in airway of asthmatic rats [J]. Journal of Xiangnan University (Medical Edition), 2017, 02(v.23;No.463):17-20. 4. Long Xingyun, Zhang Ping, Liu Yanfeng, et al.. Effect of oxymatrine on IL-10 expression in lung tissue of asthmatic rats [J]. Advances in Modern Biomedicine, 2016, 16(016):3036-3039. 5. Long Xingyun, Zhang Ping, Olive. Effect of oxymatrine on IL-17 expression in lung tissue of asthmatic rats [J]. Journal of Xiangnan University (Medical Edition), 2019. 6. Hao Caiqin, Li Jing, Li Xingyu, etc. Two-way regulatory effect of oxymatrine on the growth of bone marrow-derived cells [J]. Advances in Modern Biomedicine, 2013, 13(021):4016-4022. 7. Guo Hui, Chen Xinmei, Duan Zhanghao. Pharmacokinetics and relative bioavailability of oxymatrine phospholipid complex enteric-coated sustained-release capsules in mice [J]. Journal of Shandong University of Traditional Chinese Medicine, 2017, 041(005):482-485. 8. Duan Zhanghao, Chen Xinmei, Guo Hui. Study on Quality Standard of Oxidative Matrine Phospholipid Complex Enteric-coated Sustained Release Capsules [J]. Journal of Shandong University of Traditional Chinese Medicine, 2018, 042(002):179-181. 9. Angel, Tang Xueyang, Lu Guangying, et al. Quality Characterization and Correlation Analysis of Perilla Prescription Drug Preparation [J]. Journal of Beijing University of Traditional Chinese Medicine, 2014. 10. Sun Mudi, Zhang Qingchen, Hu Lijie, et al. Fluorescence quantitative PCR detection of key enzyme genes in host alkaloid synthesis promoted by endophytic fungal elicitors of Sophora alopecuroides [J]. Chinese herbal medicine 2018, vol. 49, No. 19, 4621-4627, ISTIC PKU CSCD CA, 2018. 11. Sun Mudi, Hu Lijie, Li Wenxue, Yan Siyuan, Zhang Zhong, Gu Peiwen. Physiological Defense Response of Endophytic Fungal Inducer of Sophora alopecia sophora to Promote Synthesis and Accumulation of Host Alkaloids [J]. Agricultural Research in Arid Areas, 2019,37(03):60-65 71. 12. Ran Xin, Lu Shunzhong, Teng Liang, et al. Qualitative Identification and Content Determination of Mongolian Medicine Zhuang Glenn -5 Bulk [J]. Northwest Journal of Pharmacy, 2019, 034(006):731-735. 13. Wang Ling, Zhang Ting, Qian Dawei, et al. Effects of Volatile Oils of Three Spicy Traditional Chinese Medicines on Transdermal Absorption of Sophora flavescens Alkaloids [J]. Chinese Journal of Traditional Chinese Medicine 2019 v.44(02):110-115. 14. Zhang Wei, Ma Guizhi, Wang Chunfang, et al. Determination of Four Alkaloids in Silver Chips Formula Granules by One Test and Multiple Evaluation Method [J]. Northwest Journal of Pharmacy 2018(5):595-600. 15. Valkó, Klára. "Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution." Journal of chromatography A 1037.1-2 (2004): 299-310.https://doi.org/10.1016/j.chroma. 2003.10.084 16. Valkó, Klára. "Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution." Journal of chromatography A 1037.1-2 (2004): 299-310.https://doi.org/10.1016/j.chroma. 2003.10.084 17. [IF=4.411] Jifeng Gu et al."Application of High-Performance Liquid Chromatography Coupled with Linear Ion Trap Quadrupole Orbitrap Mass Spectrometry for Qualitative and Quantitative Assessment of Shejin-Liyan Granule Supplements."Molecules. 2018 Apr;23(4):884 18. [IF=4.087] Lan-Lan Lou et al."( )‐Isobicyclogermacrenal and spathulenol from Aristolochia yunnanensis alleviate cardiac fibrosis by inhibiting transforming growth factor β/small mother against decapentaplegic signaling pathway."Phytother Res. 2019 Jan;33(1):214-223 19. [IF=3.212] Gao Chun-Jie et al."Oxymatrine Sensitizes the HaCaT Cells to the IFN-γ Pathway and Downregulates MDC, ICAM-1, and SOCS1 by Activating p38, JNK, and Akt."Inflammation. 2018 Mar;41(2):606-613 20. [IF=11.622] Zheng Chunli et al."Systems pharmacology: a combination strategy for improving efficacy of PD-1/PD-L1 blockade."Brief Bioinform. 2021 Sep;22(5): 21. [IF=9.229] Linlin Deng et al."Highly Crystalline Covalent Organic Frameworks Act as a Dual-Functional Fluorescent-Sensing Platform for Myricetin and Water, and Adsorbents for Myricetin."Acs Appl Mater Inter. 2021;13(28):33449-33463 22. [IF=4.268] Qing Zhao et al."The water extract of Sophorae tonkinensis Radix et Rhizoma alleviates non-alcoholic fatty liver disease and its mechanism."Phytomedicine. 2020 Oct;77:153270 23. [IF=3.996] Wang Wen-Jun et al."Oxymatrine Alleviates Hyperglycemic Cerebral Ischemia/Reperfusion Injury via Protecting Microvessel."Neurochem Res. 2022 Jan;:1-14 24. [IF=1.978] Chen Ming-jun et al."Composite Sophora Colon-Soluble Capsule Ameliorates DSS-Induced Ulcerative Colitis in Mice via Gut Microbiota-Derived Butyric Acid and NCR ILC3."Chin J Integr Med. 2022 Apr;:1-10 |
1-oxide,(1-beta)-matridin-15-on - Reference Information
| Plant source: | Sophora flavescens |
| properties | white crystalline powder; The gas is slight and the taste is bitter. |
| application | oxymatrine is applied to medicine, pesticides, veterinary drugs, etc. Oxymatrine has the effects of anti-tumor, antibacterial, anti-parasitic, anti-inflammatory, detumescence and diuresis and reducing leukopenia caused by cyclophosphamide. In terms of anti-tumor, oxymatrine has the effect of lowering valley-pyruvic transaminase. In the treatment of CHB combined with thymosin has the effect of regulating the body's immune status and improving liver function, and has a significant effect on liver function recovery, increasing albumin, reducing globulin, and increasing white blood cells. It has a protective effect on liver failure, and has no obvious adverse reactions and toxic side effects on the kidney. |
| biological activity | Oxymatrine (Matrine N-oxide) is a quinazoline alkaloid isolated from the root of Sophora flavescens. it has anti-inflammatory, anti-fibrosis and anti-tumor activities, inhibits iNOS expression and TGF-β/Smad pathway. It is used to treat viral hepatitis, cancer, viral myocarditis, gastrointestinal bleeding and skin diseases. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has diuretic, anti-pathogen, and immune effects. Studies have found that oxymatrine has an inhibitory effect on the proliferation of vascular endothelial cells induced by lung cancer and gastric cancer cells Alkaloids isolated from Sophora flavescens. Anti-fibrosis. Protect the nerves. It is a traditional Chinese medicine and is used in the treatment of anti-hepatitis B virus. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | abdominal cavity-mouse LD50: 521 mg/kg; Intravenous-mouse LD50: 150 mg/kg |
| flammability hazard characteristics | flammability; fire scene decomposition toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse low temperature, ventilation, drying |
| fire extinguishing agent | water, carbon dioxide, dry powder, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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