3,4,5-Trimethoxycinnamic acid (BioDeep_00000397998)

 

Secondary id: BioDeep_00000017702

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3,4,5-Trimethoxy_ cinnamic acid

化学式: C12H14O5 (238.08411940000002)
中文名称: 3,4,5-三甲氧基肉桂酸, (E)-3,4,5-三甲氧基肉桂酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.18%

分子结构信息

SMILES: COC1=C(OC)C(OC)=CC(/C=C/C(O)=O)=C1
InChI: InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+

描述信息

IPB_RECORD: 2381; CONFIDENCE confident structure
(E)-3,4,5-Trimethoxycinnamic acid (TMCA) is a cinnamic acid substituted by multi-methoxy groups. (E)-3,4,5-Trimethoxycinnamic acid is an orally active and potent GABAA/BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT2C and 5-HT1A receptor, with IC50 values of 2.5 and 7.6 μM, respectively. (E)-3,4,5-Trimethoxycinnamic acid shows anticonvulsant and sedative activity. (E)-3,4,5-Trimethoxycinnamic acid can be used for the research of insomnia, headache and epilepsy[1][2][3].
(E)-3,4,5-Trimethoxycinnamic acid (TMCA) is a cinnamic acid substituted by multi-methoxy groups. (E)-3,4,5-Trimethoxycinnamic acid is an orally active and potent GABAA/BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT2C and 5-HT1A receptor, with IC50 values of 2.5 and 7.6 μM, respectively. (E)-3,4,5-Trimethoxycinnamic acid shows anticonvulsant and sedative activity. (E)-3,4,5-Trimethoxycinnamic acid can be used for the research of insomnia, headache and epilepsy[1][2][3].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].

同义名列表

4 个代谢物同义名

3,4,5-Trimethoxycinnamic acid; 3,4,5-Trimethoxy_ cinnamic acid; TMCA; (E)-3,4,5-Trimethoxycinnamic acid



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文献列表

  • Xin Zhao, Baoxin Xu, Peng Wu, Pan Zhao, Changchuan Guo, Yueli Cui, Yanxue Zhang, Xuelan Zhang, Huifen Li. UHPLC-MS/MS method for pharmacokinetic and bioavailability determination of five bioactive components in raw and various processed products of Polygala tenuifolia in rat plasma. Pharmaceutical biology. 2020 Dec; 58(1):969-978. doi: 10.1080/13880209.2020.1818790. [PMID: 32956609]
  • Yajun Bai, Xirui He, Yujun Bai, Ying Sun, Zefeng Zhao, Xufei Chen, Bin Li, Jing Xie, Yang Li, Pu Jia, Xue Meng, Ye Zhao, Yanrui Ding, Chaoni Xiao, Shixiang Wang, Jie Yu, Sha Liao, Yajun Zhang, Zhiling Zhu, Qiang Zhang, Yuhui Zhao, Fanggang Qin, Yi Zhang, Xiaoyang Wei, Min Zeng, Jing Liang, Ye Cuan, Guangzhi Shan, Tai-Ping Fan, Biao Wu, Xiaohui Zheng. Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study. European journal of medicinal chemistry. 2019 Dec; 183(?):111650. doi: 10.1016/j.ejmech.2019.111650. [PMID: 31539780]
  • Muhammad T Islam, Abul B R Khalipha, Rajat Bagchi, Milon Mondal, Shanita Z Smrity, Shaikh J Uddin, Jamil A Shilpi, Razina Rouf. Anticancer activity of thymol: A literature-based review and docking study with Emphasis on its anticancer mechanisms. IUBMB life. 2019 01; 71(1):9-19. doi: 10.1002/iub.1935. [PMID: 30308112]
  • Baoxin Xu, Congcong Qu, Wenhua Zheng, Yaya Xi, Xin Zhao, Huifen Li, Jiangting Liu, Xuelan Zhang. UHPLC-MS/MS method for simultaneous determination of Radix Polygalae glycolipids and organic acids in rat plasma and application in a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Nov; 1100-1101(?):165-173. doi: 10.1016/j.jchromb.2018.09.037. [PMID: 30340065]
  • Chang-Yuan Chen, Xu-Dong Wei, Chang-Rui Chen. 3,4,5-Trimethoxycinnamic acid, one of the constituents of Polygalae Radix exerts anti-seizure effects by modulating GABAAergic systems in mice. Journal of pharmacological sciences. 2016 May; 131(1):1-5. doi: 10.1016/j.jphs.2015.07.021. [PMID: 26260747]
  • Qian Wang, Bing-Xin Xiao, Rui-Le Pan, Xin-Min Liu, Yong-Hong Liao, Li Feng, Fang-Rui Cao, Qi Chang. An LC-MS/MS method for simultaneous determination of three Polygala saponin hydrolysates in rat plasma and its application to a pharmacokinetic study. Journal of ethnopharmacology. 2015 Jul; 169(?):401-6. doi: 10.1016/j.jep.2015.04.033. [PMID: 25922266]
  • Xiao-Bo Yu, Guang-Lu Liu, Bin Zhu, Kai Hao, Fei Ling, Gao-Xue Wang. In vitro immunocompetence of two compounds isolated from Polygala tenuifolia and development of resistance against grass carp reovirus (GCRV) and Dactylogyrus intermedius in respective host. Fish & shellfish immunology. 2014 Dec; 41(2):541-8. doi: 10.1016/j.fsi.2014.10.004. [PMID: 25450998]
  • Zhenghang Zhao, Minfeng Fang, Dandan Xiao, Mei Liu, Nadezhda Fefelova, Chen Huang, Wei-Jin Zang, Lai-Hua Xie. Potential antiarrhythmic effect of methyl 3,4,5-trimethoxycinnamate, a bioactive substance from roots of polygalae radix: suppression of triggered activities in rabbit myocytes. Biological & pharmaceutical bulletin. 2013; 36(2):238-44. doi: 10.1248/bpb.b12-00654. [PMID: 23196428]
  • Keiko Kawashima, Daishi Miyako, Yasuyuki Ishino, Toshiaki Makino, Ken-Ichi Saito, Yoshihiro Kano. Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji). Biological & pharmaceutical bulletin. 2004 Aug; 27(8):1317-9. doi: 10.1248/bpb.27.1317. [PMID: 15305046]
  • R Viswanathan, S Subramanian, T G Radha. Effect of hypoxia on regional lung perfusion, by scanning. Respiration; international review of thoracic diseases. 1979; 37(3):142-7. doi: 10.1159/000194023. [PMID: 441541]
  • P Szylman, O S Better, C Chaimowitz, A Rosler. Role of hyperkalemia in the metabolic acidosis of isolated hypoaldosteronism. The New England journal of medicine. 1976 Feb; 294(7):361-5. doi: 10.1056/nejm197602122940703. [PMID: 1674]