(-)-Epicatechin 3-O-gallate (BioDeep_00000017213)

 

Secondary id: BioDeep_00000033794, BioDeep_00000267569, BioDeep_00000402890, BioDeep_00000406553, BioDeep_00000407825, BioDeep_00000864020, BioDeep_00000865240

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-cis)-

化学式: C22H18O10 (442.0899928)
中文名称: (-)-表儿茶素没食子酸酯, 表儿茶素没食子酸酯, 表儿茶精没食子酸酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.04%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(c(c(c1)O)O)O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

描述信息

(-)-epicatechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. It has a role as a metabolite, an EC 3.2.1.1 (alpha-amylase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a catechin, a gallate ester and a polyphenol. It is functionally related to a (-)-epicatechin and a gallic acid.
(-)-Epicatechin gallate is a natural product found in Scurrula atropurpurea, Acacia omalophylla, and other organisms with data available.
Isolated from tea and numerous other plant subspecies inc. rhubarb and grapes. Epicatechin 3-gallate is found in many foods, some of which are cucumber, muskmelon, black raspberry, and cashew nut.
A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.
(-)-Epicatechin 3-O-gallate is found in almond. (-)-Epicatechin 3-O-gallate is isolated from tea and numerous other plant species including rhubarb and grapes.
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors
D020011 - Protective Agents > D000975 - Antioxidants
D000970 - Antineoplastic Agents
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

同义名列表

61 个代谢物同义名

Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-cis)-; Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7- dihydroxy-2H-1-benzopyran-3-yl ester, (-)-cis-; Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate; [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate; 3,4,5-Trihydroxy-benzoic acid (2R,3R)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester; 3,4,5-Trihydroxy-benzoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl ester; rel-(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate; [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate; Epicatechin gallate, primary pharmaceutical reference standard; (-)-Epicatechin gallate, >=98\\% (HPLC), from green tea; (-)-cis-3,3,4,5,7-Pentahydroxyflavane 3-gallic acid; (-)-cis-3,3,4,5,7-Pentahydroxyflavane 3-gallate; epicatechin gallate, (2R-cis)-isomer; (-)-Epicatechin 3-O-gallic acid; 3-Gallic acid(-)-epicatechol; (-)-EPI CATECHIN-3-O-GALLATE; Epicatechol, 3-gallate, (-)-; (-)-Epicatechin-3-O-gallate; (-)-Epicatechin 3-O-gallate; epicatechin-3-galloyl ester; (?)-Epicatechin 3-gallate; (-)-Epicatechin-3-gallate; Epicatechin 3-gallic acid; (-)-Epicatechin 3-gallate; epi-Catechin 3-O-gallate; 3-Gallate(-)-Epicatechol; epicatechin monogallate; EPICATECHIN 3-O-GALLATE; epicatechin-gallate-(-); epicatechin-3-O-gallate; (-)-Epicatechin gallate; (-) epicatechin gallate; (-)-epicatechingallate; (-)EPICATECHIN GALLATE; EPICATECHINGALLATE, L-; 3-O-Galloylepicatechin; (-)epicatechingallate; L-Epicatechin gallate; epicatechin-3-gallate; EPICATECHOL 3-GALLATE; Epicatechin 3-gallate; Epicatechol, gallate; epicatechin gallate; Spectrum5_000080; Spectrum3_000246; Spectrum4_001540; Spectrum2_000165; (-)-Epicatechin; MEGxp0_000810; DivK1c_006371; KBio1_001315; KBio2_005930; KBio2_003362; KBio2_000794; KBio3_001132; Teatannin; L-ECG; ECG



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

113 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Ziqiong Zhou, Yan Li, Fangyuan Wang, Guanghao Zhu, Shenglan Qi, Haonan Wang, Yuhe Ma, Rong Zhu, Yuejuan Zheng, Guangbo Ge, Ping Wang. Bioactive components and mechanisms of Pu-erh tea in improving levodopa metabolism in rats through COMT inhibition. Food & function. 2024 May; 15(10):5287-5299. doi: 10.1039/d4fo00538d. [PMID: 38639730]
  • Huimin Yong, Zeyu Wang, Jinbao Huang, Jun Liu. Preparation, characterization and application of antioxidant packaging films based on chitosan-epicatechin gallate conjugates with different substitution degrees. International journal of biological macromolecules. 2024 Mar; 260(Pt 2):129568. doi: 10.1016/j.ijbiomac.2024.129568. [PMID: 38246436]
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  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Maniraj Rathinam, Shaily Tyagi, Narasimham Dokka, Sathish Kumar Marimuthu, Hemant Kumar, Doddachowdappa Sagar, Prasanta K Dash, Ajit Kumar Shasany, Rohini Sreevathsa. The plant specialized metabolite epicatechin- 3-gallate (EC3G) perturbs lipid metabolism and attenuates fat accumulation in pigeonpea pod borer, Helicoverpa armigera. International journal of biological macromolecules. 2023 Mar; 231(?):123325. doi: 10.1016/j.ijbiomac.2023.123325. [PMID: 36681223]
  • Luyao Chen, Yaping Guo, Zixuan Wu, Shuwu Zhao, Zhaiyi Zhang, Fang Zheng, Likang Sun, Zheng Hao, Chen Xu, Tao Wang, Yanfei Peng. Epicatechin gallate prevents the de novo synthesis of fatty acid and the migration of prostate cancer cells. Acta biochimica et biophysica Sinica. 2021 Dec; 53(12):1662-1669. doi: 10.1093/abbs/gmab144. [PMID: 34718375]
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  • Yuyang Zhang, Zhenglei Yang, Gege Liu, Yanwen Wu, Jie Ouyang. Inhibitory effect of chestnut (Castanea mollissima Blume) inner skin extract on the activity of α-amylase, α-glucosidase, dipeptidyl peptidase IV and in vitro digestibility of starches. Food chemistry. 2020 Sep; 324(?):126847. doi: 10.1016/j.foodchem.2020.126847. [PMID: 32344340]
  • Sara Crotti, Sara D'Aronco, Laura Moracci, Francesco Tisato, Marina Porchia, Luisa Mattoli, Michela Burico, Stella Bedont, Pietro Traldi, Marco Agostini. Evidence of noncovalent complexes in some natural extracts: Ceylon tea and mate extracts. Journal of mass spectrometry : JMS. 2020 Jul; 55(7):e4459. doi: 10.1002/jms.4459. [PMID: 31663260]
  • Qian Wu, Shimiao Tang, Liang Zhang, Jinsong Xiao, Qing Luo, Yuanyuan Chen, Mengzhou Zhou, Nianjie Feng, Chao Wang. The inhibitory effect of the catechin structure on advanced glycation end product formation in alcoholic media. Food & function. 2020 Jun; 11(6):5396-5408. doi: 10.1039/c9fo02887k. [PMID: 32469349]
  • Md Akil Hossain, Hae-Chul Park, Kwang-Jick Lee, Sung-Won Park, Seung-Chun Park, JeongWoo Kang. In vitro synergistic potentials of novel antibacterial combination therapies against Salmonella enterica serovar Typhimurium. BMC microbiology. 2020 05; 20(1):118. doi: 10.1186/s12866-020-01810-x. [PMID: 32410630]
  • Wei Zhu, Mei C Li, Feng R Wang, Gerardo G Mackenzie, Patricia I Oteiza. The inhibitory effect of ECG and EGCG dimeric procyanidins on colorectal cancer cells growth is associated with their actions at lipid rafts and the inhibition of the epidermal growth factor receptor signaling. Biochemical pharmacology. 2020 05; 175(?):113923. doi: 10.1016/j.bcp.2020.113923. [PMID: 32217102]
  • Priscila Mayara de Lima Oliveira, Aline Macedo Dantas, Alany Raquel Dos Santos Morais, Luciana Gibbert, Claudia Carneiro Hecke Krüger, Marcos Dos Santos Lima, Marciane Magnani, Graciele da Silva Campelo Borges. Juá fruit (Ziziphus joazeiro) from Caatinga: A source of dietary fiber and bioaccessible flavanols. Food research international (Ottawa, Ont.). 2020 03; 129(?):108745. doi: 10.1016/j.foodres.2019.108745. [PMID: 32036923]
  • Jin Li, Jian Zeng, Jinming Peng, Yangyang Jia, Chun-Mei Li. Simultaneous determination of the pharmacokinetics of A-type EGCG and ECG dimers in mice plasma and its metabolites by UPLC-QTOF-MS. International journal of food sciences and nutrition. 2020 Mar; 71(2):211-220. doi: 10.1080/09637486.2019.1635089. [PMID: 31266395]
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  • Gulsim Zhumashova, Wirginia Kukula-Koch, Wojciech Koch, Tomasz Baj, Galiya Sayakova, Alma Shukirbekova, Kazimierz Głowniak, Zuriyadda Sakipova. Phytochemical and Antioxidant Studies on a Rare Rheum cordatum Losinsk. Species from Kazakhstan. Oxidative medicine and cellular longevity. 2019; 2019(?):5465463. doi: 10.1155/2019/5465463. [PMID: 31827680]
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