益母草碱
| 益母草碱 | |
|---|---|
| |
| 首选IUPAC名 4-(Diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate | |
| 识别 | |
| CAS号 | 24697-74-3 
|
| PubChem | 161464 |
| ChemSpider | 141828 |
| SMILES |
|
| InChI |
|
| InChIKey | WNGSUWLDMZFYNZ-UHFFFAOYAI |
| KEGG | C16985 |
| 性质 | |
| 化学式 | C14H21N3O5 |
| 摩尔质量 | 311.33 g·mol−1 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
益母草碱（英語：Leonurine，研发代号：SCM-198）是一种假生物碱，已从狮耳花、荆芥叶狮耳花、益母草、灰白益母草、细叶益母草以及唇形科的其他植物中分离出来。益母草碱很容易被水提取[1]。
研究
益母草碱可与多种GABA受体位点（包括GABAA受体）较弱地结合[2][3]。然而，它作为5-HT3A受体拮抗剂，表现出更高的亲和力[4]。研究表明，5-HT3A受体拮抗剂有助于预防恶心呕吐以及血清素对胃肠道的不良影响[5][6]。
益母草碱可以调节多种功能，包括氧化应激、炎症、纤维化、细胞凋亡和代谢失调[7][8][9]。
已有研究发现，益母草碱表现出抗抑郁样作用。小鼠慢性轻度应激研究中显示，益母草碱可提高血清素、去甲肾上腺素和多巴胺的水平，并抑制促炎细胞因子的产生[10][11][12]。
益母草碱已被研究作为治疗心血管疾病的潜在药物[13][14][15][16]。它能保护大脑免受缺血性中风引起的氧化损伤，并对大鼠局灶性缺血性脑损伤表现出神经保护作用[17][18][19]。
益母草碱在体外和动物研究中均表现出抗癌活性[21][22][23][24][25]。
参考来源
- ^ The Leonurine and its preparation. An Hui New Star Pharmaceutical Development Co. 2008 [2008-08-28]. （原始内容存档于2008-05-15）.
- ^ Çiçek SS. Structure-Dependent Activity of Natural GABA(A) Receptor Modulators. Molecules. June 2018, 23 (7): 1512. PMC 6100244
. PMID 29932138. doi:10.3390/molecules23071512 .
- ^ Rauwald HW, Savtschenko A, Merten A, Rusch C, Appel K, Kuchta K. GABAA Receptor Binding Assays of Standardized Leonurus cardiaca and Leonurus japonicus Extracts as Well as Their Isolated Constituents. Planta Medica. August 2015, 81 (12–13): 1103–1110. PMID 26218338. doi:10.1055/s-0033-1352395.
- ^ Hoffmann KM, Herbrechter R, Ziemba PM, Lepke P, Beltrán L, Hatt H, et al. Kampo Medicine: Evaluation of the Pharmacological Activity of 121 Herbal Drugs on GABAA and 5-HT3A Receptors. Frontiers in Pharmacology. 2016, 7: 219. PMC 4965468 . PMID 27524967. doi:10.3389/fphar.2016.00219 .
- ^ Theriot J, Wermuth HR, Ashurst JV. Antiemetic Serotonin-5-HT3 Receptor Blockers. StatPearls. StatPearls Publishing. 2022. PMID 30020690.
- ^ List of 5HT3 receptor antagonists (5hydroxytryptamine receptor antagonists).
- ^ Li YY, Lin YK, Liu XH, Wang L, Yu M, Li DJ, et al. Leonurine: From Gynecologic Medicine to Pleiotropic Agent. Chinese Journal of Integrative Medicine. February 2020, 26 (2): 152–160. PMID 31069695. S2CID 148571306. doi:10.1007/s11655-019-3453-0.
- ^ Li N, Xu Q, Liu Q, Pan D, Jiang Y, Liu M, et al. Leonurine attenuates fibroblast-like synoviocyte-mediated synovial inflammation and joint destruction in rheumatoid arthritis. Rheumatology. August 2017, 56 (8): 1417–1427. PMID 28431044. doi:10.1093/rheumatology/kex142 .
- ^ Zheng S, Zhuang T, Tang Y, Wu R, Xu T, Leng T, et al. Leonurine protects against ulcerative colitis by alleviating inflammation and modulating intestinal microflora in mouse models. Experimental and Therapeutic Medicine. November 2021, 22 (5): 1199. PMC 8422400 . PMID 34584544. doi:10.3892/etm.2021.10633.
- ^ Jia M, Li C, Zheng Y, Ding X, Chen M, Ding J, et al. Leonurine Exerts Antidepressant-Like Effects in the Chronic Mild Stress-Induced Depression Model in Mice by Inhibiting Neuroinflammation. The International Journal of Neuropsychopharmacology. November 2017, 20 (11): 886–895. PMC 5737563 . PMID 29016795. doi:10.1093/ijnp/pyx062 .
- ^ Shi XR, Hong ZY, Liu HR, Zhang YC, Zhu YZ. Neuroprotective effects of SCM198 on 6-hydroxydopamine-induced behavioral deficit in rats and cytotoxicity in neuronal SH-SY5Y cells. Neurochemistry International. July 2011, 58 (8): 851–860. PMID 21093517. S2CID 33986318. doi:10.1016/j.neuint.2010.11.007.
- ^ Liao L, Zhou M, Wang J, Xue X, Deng Y, Zhao X, et al. Identification of the Antithrombotic Mechanism of Leonurine in Adrenalin Hydrochloride-Induced Thrombosis in Zebrafish via Regulating Oxidative Stress and Coagulation Cascade. Frontiers in Pharmacology. 4 November 2021, 12. PMC 8600049 . PMID 34803688. doi:10.3389/fphar.2021.742954 .
- ^ Huang L, Xu DQ, Chen YY, Yue SJ, Tang YP. Leonurine, a potential drug for the treatment of cardiovascular system and central nervous system diseases. Brain and Behavior. February 2021, 11 (2): e01995. PMC 7882174 . PMID 33300684. doi:10.1002/brb3.1995.
- ^ Wang R, Peng L, Lv D, Shang F, Yan J, Li G, et al. Leonurine Attenuates Myocardial Fibrosis Through Upregulation of miR-29a-3p in Mice Post-myocardial Infarction. Journal of Cardiovascular Pharmacology. February 2021, 77 (2): 189–199. PMID 33235025. S2CID 227168673. doi:10.1097/FJC.0000000000000957.
- ^ Zhu Q, Cai W, Sha X, Ma G, Zheng Y, Shi X, Zhu Y. Quantification of leonurine, a novel potential cardiovascular agent, in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic study in rats. Biomedical Chromatography. April 2012, 26 (4): 518–523. PMID 21882210. doi:10.1002/bmc.1699.
- ^ Liu XH, Pan LL, Deng HY, Xiong QH, Wu D, Huang GY, et al. Leonurine (SCM-198) attenuates myocardial fibrotic response via inhibition of NADPH oxidase 4. Free Radical Biology & Medicine. January 2013, 54: 93–104. PMID 23127783. doi:10.1016/j.freeradbiomed.2012.10.555.
- ^ Xie YZ, Zhang XJ, Zhang C, Yang Y, He JN, Chen YX. Protective effects of leonurine against ischemic stroke in mice by activating nuclear factor erythroid 2-related factor 2 pathway. CNS Neuroscience & Therapeutics. September 2019, 25 (9): 1006–1017. PMC 6698971 . PMID 31087454. doi:10.1111/cns.13146.
- ^ Li F, Zhu S, Jiang Q, Hou C, Pang T, Zhang L, Li W. Novel Stachydrine-Leonurine Conjugate SL06 as a Potent Neuroprotective Agent for Cerebral Ischemic Stroke. ACS Chemical Neuroscience. July 2021, 12 (13): 2478–2490. PMID 34180238. S2CID 235660771. doi:10.1021/acschemneuro.1c00200.
- ^ Liu H, Zhang X, Du Y, Ji H, Li S, Li L, et al. Leonurine protects brain injury by increased activities of UCP4, SOD, CAT and Bcl-2, decreased levels of MDA and Bax, and ameliorated ultrastructure of mitochondria in experimental stroke. Brain Research. September 2012, 1474: 73–81. PMID 22842526. S2CID 24119195. doi:10.1016/j.brainres.2012.07.028.
- ^ Qiu LN, Tan YR, Luo YJ, Chen XJ. Leonurine protects against influenza A virus infection-induced pneumonia in mice. Pathogens and Disease. September 2021, 79 (7). PMID 34543397. doi:10.1093/femspd/ftab045.
- ^ Zhuang Q, Ruan L, Jin T, Zheng X, Jin Z. Anti-leukaemia effects of leonurine in vitro and in vivo. General Physiology and Biophysics. September 2021, 40 (5): 397–407. PMID 34602453. doi:10.4149/gpb_2021018 .
- ^ Liu HM, Guo CL, Zhang YF, Chen JF, Liang ZP, Yang LH, Ma YP. Leonurine-Repressed miR-18a-5p/SOCS5/JAK2/STAT3 Axis Activity Disrupts CML malignancy. Frontiers in Pharmacology. 2021, 12. PMC 8087248 . PMID 33935775. doi:10.3389/fphar.2021.657724 .
- ^ Mao F, Zhang L, Cai MH, Guo H, Yuan HH. Leonurine hydrochloride induces apoptosis of H292 lung cancer cell by a mitochondria-dependent pathway. Pharmaceutical Biology. 2 November 2015, 53 (11): 1684–1690. PMID 25856714. S2CID 207526411. doi:10.3109/13880209.2014.1001406 .
- ^ Lin M, Pan C, Xu W, Li J, Zhu X. Leonurine Promotes Cisplatin Sensitivity in Human Cervical Cancer Cells Through Increasing Apoptosis and Inhibiting Drug-Resistant Proteins. Drug Design, Development and Therapy. 15 May 2020, 14: 1885–1895. PMC 7237110 . PMID 32523334. doi:10.2147/DDDT.S252112 .
- ^ Li X, Xie Y, Qu W, Ou X, Ou X, Wang C, et al. Breast Cancer Resistance Protein and Multidrug Resistance Protein 2 Mediate the Disposition of Leonurine-10-O-β-glucuronide. Current Drug Metabolism. November 2020, 21 (13): 1060–1067. PMID 33198612. S2CID 226985047. doi:10.2174/1389200221999201116142742.
延伸阅读
- Cheng KF, Yip CS, Yeung HW, Kong YC. Leonurine, an improved synthesis. Experientia. 1979-05, 35 (5): 571–572. PMID 446644. S2CID 22601565. doi:10.1007/BF01960323.
- Huang L, Xu DQ, Chen YY, Yue SJ, Tang YP. Leonurine, a potential drug for the treatment of cardiovascular system and central nervous system diseases. Brain and Behavior. 2021-02, 11 (2): e01995. PMC 7882174 . PMID 33300684. doi:10.1002/brb3.1995.