中文名 | 欧前胡素 |
英文名 | 9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one |
别名 | 白茅苷 前胡素 主人草素 殴前胡素 欧前胡素 欧前胡素(欧芹属素乙 欧前胡素(分析标准品) IMPERATORIN 欧前胡素 标准品 |
英文别名 | imperatorin IMPERATORIN 8-isopentenyloxypsoralene 9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one 2-g)(1)benzopyran-7-one,9-((3-methyl-2-butenyl)oxy)-7h-furo( 9-[(3-methyl-2-butenyl)oxy]-7h-furo[3,2-g][1]benzopyran-7-one 9-((3-methyl-2-butenyl)oxy)-7h-furo(3,2-g)(1)benzopyran-7-one 6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lacto 6-hydroxy-7-(3-methyl-2-butenyloxy)-5-benzofuranacrylicacidomega-lactone 6-hydroxy-7-((3-methyl-2-butenyl)oxy)-5-benzofuranacrylicacidelta-lactone |
CAS | 482-44-0 |
EINECS | 207-581-1 |
化学式 | C16H14O4 |
分子量 | 270.28 |
InChI | InChI=1/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 |
InChIKey | OLOOJGVNMBJLLR-UHFFFAOYSA-N |
密度 | 1.1311 (rough estimate) |
熔点 | 98-100°C |
沸点 | 333.4°C (rough estimate) |
闪点 | 224.9°C |
蒸汽压 | 3.13E-08mmHg at 25°C |
溶解度 | DMSO: ≥ 5 mg/mL |
折射率 | 1.4350 (estimate) |
存储条件 | -20°C |
外观 | 粉末 |
颜色 | off-white to light brown |
最大波长(λmax) | ['301nm(MeOH)(lit.)'] |
Merck | 14,4925 |
物化性质 | 来源于大风子科(Flacourtiaceae) 罗旦梅 Flacourtiajangomas(Lour.)Raeusch茎, |
MDL号 | MFCD00016881 |
体外研究 | Imperatorin is a plant secondary metabolite belonging to the coumarins-specifically the furanocoumarins. Imperatorin enhances the GABA-induced chloride ion current (I GABA ) through the α 1 β 2 γ 2S receptors. Imperatorin potentiates I GABA at 100 μmol by 50.5±16.3 % and at 300 μmol by 109.8±37.7 %, respectively. Imperatorin, together with Phellopterin, found in the roots of A. dahurica, inhibit [ 3 H]diazepam binding to the benzodiazepine site of the rat brain GABA A receptor in vitro with an IC 50 of 12.3 μmol for Imperatorin and 400 nmol for Phellopterin. Imperatorin, in a concentration ranging from 3.5 to 14 mmol, significantly and irreversibly inhibits GABA-T in a time-dependent and concentration-dependent manner, by irreversibly binding with the active site of GABA-T.Imperatorin is a reversible acetylcholinesterase (AChE) inhibitor, and acts in dose-dependent manner. The AChE and BChE inhibitory activities of Imperatorin and a crude extract from the fruits of Angelica archangelica L. is tested by the spectrophotometric method at concentrations of 12.5, 25, 50, and 100 μg/mL. Imperatorin displays low inhibition towards AChE (13.75-46.11 %), whereas it has remarkable inhibitory effect against BChE (37.46-83.98 %). Imperatorin shows selectivity toward BChE rather than AChE, with an IC 50 for BChE of 31.4 μmol. Imperatorin, together with (+)-Byakangelicol, are found to be the most effective BACE-1 inhibitors, with IC 50 s of 91.8 and 104.9 μmol, respectively. Imperatorin (IC 50 =9.2 μmol) is also effective as an inhibitor of NO synthesis. Imperatorin is a weak agonist of TRPV1, a channel implicated in detecting several noxious stimuli, exhibiting EC 50 of 12.6±3.2 μM. |
体内研究 | At doses of 10 and 20 mg/kg and 30 min after injection, Imperatorin shows an anxiolytic effect and improved different stages of memory and learning processes-both acquisition and consolidation. It is also shown that acute administration Imperatorin at doses of 10 and 20 mg/kg reduced the anxiogenic effect of nicotine (0.1 mg/kg, subcutaneous, s.c.). At 30 and 40 mg/kg, i.p. Imperatorin significantly potentiates the anticonvulsant activity of carbamazepine against maximal electroshock-induced seizures expressed by lowering the ED 50 from 10.8 to 6.8 mg/kg (by 34 %) and 6 mg/kg (by 42 %), respectively. Moreover, Imperatorin at 30 mg/kg and carbamazepine at 6.8 mg/kg shows increases the total brain concentration of carbamazepine from 1.260 to 2.328 μg/mL (by 85%), which may be caused by modifying the blood-barrier permeability or acting like an inhibitor of multi-drug resistance proteins. Imperatorin, a naturally occurring furanocoumarin, inactivates gamma-aminobutyric acid transaminase and inhibits acetylcholinesterase activity. Imperatorin administered acutely at the doses of 5 and 10 mg/kg prior to the injection of scopolamine (1 mg/kg) improves memory acquisition and consolidation impaired by scopolamine. Furthermore, repeatable (7 days, twice daily) administration of the highest dose of Imperatorin (10 mg/kg) significantly attenuates the effects of scopolamine on memory acquisition, whereas the doses of 5 and 10 mg/kg of this furanocoumarin are effective when memory consolidation is measured . |
安全术语 | 24/25 - 避免与皮肤和眼睛接触。 |
WGK Germany | 3 |
RTECS | LV1575000 |
海关编号 | 29419090 |
参考资料 展开查看 | 1. 刘小芬 赖冰 宋秀碧 等. HPLC法分析闽产北沙参3种香豆素含量[J]. 中国中医药现代远程教育 2020年18卷10期 107-110页 2020. 2. 马海平 王曼 许尚 等. HPLC法测定鼻炎康胶囊中欧前胡素的含量[J]. 亚太传统医药 2020 v.16;No.223(03):56-61. 3. 柯璐琳 冯先铨 黄品芳 等. LC-MS/MS法同时测定欧前胡素与异欧前胡素血药浓度[J]. 临床检验杂志 2019 037(012):885-888. 4. 杨兰 李欠 冯彦梅 等. 一测多评法测定川白芷药材中5种指标成分的含量[J]. 江苏农业学报 2020(1):199-205. 5. 张薇, 朱智甲, 张晗,等. 液相色谱-串联质谱法测定白芷中3种香豆素[J]. 分析试验室, 2012(05):104-108. 6. 黄家佳, 龙晓燕, 王瑞,等. 白芷中香豆素类成分渗漉提取工艺的优化[J]. 中成药, 2019. 7. 丛建民, 陈凤清, 野俊双,等. 草木犀香豆素的提取工艺及抑菌活性研究[J]. 天然产物研究与开发, 2014, 026(004):588-593,596. 8. 刘灵改 支旭然 郭进 等. HPLC-MS法同时测定防芷鼻咽颗粒中6个成分的含量[J]. 药物分析杂志 2014(5):830-835. 9. 朱春璐, 王静, 乔宇航,等. 酒炖白芷中总香豆素及4种香豆素类成分的含量测定[J]. 中国民族民间医药, 2019(19). 10. 刘灵改, 支旭然, 吴宗耀,等. 高效液相色谱法测定防芷鼻咽颗粒中7种活性成分的含量[J]. 中国药学杂志, 2014, 49(017):1554-1558. 11. 张烨, 孙艳雪, 马宇衡,等. 白芷HPLC指纹图谱的研究[J]. 食品与药品, 2020, 022(002):130-134. 12. 杨爽, 何妍茜, 杨洁,等. 感冒软胶囊质量标准提高的研究[J]. 时珍国医国药, 2013, 24(008):1930-1932. 13. 王雪莲, 李敏敏, 胡军华,等. 18种香豆素类化合物对柑桔炭疽菌的抑制作用[J]. 中国南方果树, 2013, 42(004):73-74. 14. Zheng, Liwei, et al. "Imperatorin is a mechanism-based inactivator of CYP2B6." Drug Metabolism and Disposition 43.1 (2015): 82-88.https://doi.org/10.1124/dmd.114.060558 15. Yang, P, Gao, R, Liu, Z, et al. Analysis of chemical constituents and six compounds in Qu-feng-sheng-shi Granules via HPLC–ESI–Q/TOF–MSn and HPLC–UV technique. Biomedical Chromatography. 2020; 34:e4829. https://doi.org/10.1002/bmc.4829 16. [IF=4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum."Molecules. 2016 Apr;21(4):468 17. [IF=2.044] Tang Cheng et al."Ligand Fishing with Cellular Membrane-Coated Magnetic Beads: A New Method for the Screening of Potentially Active Compounds from Natural Products."Chromatographia. 2017 Oct;80(10):1517-1525 18. [IF=6.576] Li Guijie et al."Effects of Cold-Pressing and Hydrodistillation on the Active Non-volatile Components in Lemon Essential Oil and the Effects of the Resulting Oils on Aging-Related Oxidative Stress in Mice."Front Nutr. 2021 Jun;0:329 19. [IF=5.34] Xiaohui Zhang et al."Discovery of tetrahydropalmatine and protopine regulate the expression of dopamine receptor D2 to alleviate migraine from Yuanhu Zhitong formula."Phytomedicine. 2021 Oct;91:153702 20. [IF=2.193] Yang Lan et al."Simultaneous Determination of Three Coumarins in Angelica dahurica by 1H-qNMR Method: A Fast and Validated Method for Crude Drug Quality Control."J Anal Methods Chem. 2020;2020:8987560 21. [IF=1.902] Pengshuo Yang et al."Analysis of chemical constituents and six compounds in Qu-feng-sheng-shi Granules via HPLC–ESI–Q/TOF–MSn and HPLC–UV technique."Biomed Chromatogr. 2020 Jul;34(7):e4829 22. [IF=3.269] Haosheng Zhang et al."Imperatorin alleviated NLR family pyrin domain-containing 3 inflammasome cascade-induced synovial fibrosis and synovitis in rats with knee osteoarthritis."Bioengineered. 2021;12(2):12954-12964 |
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