(-)-Epigallocatechin 3-(3-methyl-gallate) (BioDeep_00000017549)

 

Secondary id: BioDeep_00000270209

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


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

化学式: C23H20O11 (472.100557)
中文名称: 表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯, 表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 37.5%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(c(c(c1)OC)O)O)c1cc(c(c(c1)O)O)O)O)O
InChI: InChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1

描述信息

(-)-Epigallocatechin 3-(3-methyl-gallate) is found in tea. (-)-Epigallocatechin 3-(3-methyl-gallate) is isolated from green tea (Thea sinensis) and oolong tea (Camellia sinensis).
(-)-Epigallocatechin 3-(3-methyl-gallate) is a catechin.
Epigallocatechin 3-O-(3-O-methyl)gallate is a natural product found in Limonium sinense with data available.
Isolated from green tea (Thea sinensis) and oolong tea (Camellia sinensis). Epigallocatechin 3-(3-methylgallate) is found in tea.
(-)-Epigallocatechin-3-(3''-O-methyl) gallate is a natural product isolated from the tea leaf, with strong antioxidative activity. (-)-Epigallocatechin-3-(3''-O-methyl) gallate has a strong cytotoxic activity for rat cancer cells[1].
(-)-Epigallocatechin-3-(3''-O-methyl) gallate is a natural product isolated from the tea leaf, with strong antioxidative activity. (-)-Epigallocatechin-3-(3''-O-methyl) gallate has a strong cytotoxic activity for rat cancer cells[1].

同义名列表

27 个代谢物同义名

Benzoic acid, 3,4-dihydroxy-5-methoxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2R-cis)-; Benzoic acid, 3,4-dihydroxy-5-methoxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate; [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4-dihydroxy-5-methoxybenzoate; (2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4-dihydroxy-5-methoxybenzoate; (-)-Epigallocatechin-3-O-(3-O-methyl)-gallate; (-)-Epigallocatechin 3-(3-methyl-gallic acid); (-)-Epigallocatechin 3-O-(3-O-methylgallate); Epigallocatechin 3-O-(3-O-methylgallic acid); (-)-Epigallocatechin-3-(3-O-methyl) gallate; (-)-epigallocatechin-3-(3-O-methyl)gallate; epigallocatechin-3-O-(3-O-methyl)-gallate; Epigallocatechin 3-O-(3-O-Methyl)-Gallate; (-)-Epigallocatechin 3-(3-methyl-gallate); Epigallocatechin 3-O-(3-O-methyl)gallate; Epigallocatechin 3-O-(3-O-methylgallate); Epigallocatechin 3-(3-methylgallic acid); Epigallocatechin 3-(3-O-methyl-gallate); 3-O-(3-O-Methylgalloyl)epigallocatechin; Epigallocatechin 3-(3-methyl-gallate); Epigallocatechin 3-(3-methylgallate); (-)-EGCG-3-O-Me; UNII-O97U9TPY8V; O97U9TPY8V; Egcg3me; (-)-EGCG-3''-O-ME; (-)-Epigallocatechin-3-(3''-O-methyl) gallate



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 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

  • Ji-Qiang Jin, Fu-Rong Qu, Huisi Huang, Qing-Shuai Liu, Meng-Yuan Wei, Yuee Zhou, Ke-Lin Huang, Zhibo Cui, Jie-Dan Chen, Wei-Dong Dai, Li Zhu, Ming-Zhe Yao, Zhi-Min Zhang, Liang Chen. Characterization of two O-methyltransferases involved in the biosynthesis of O-methylated catechins in tea plant. Nature communications. 2023 08; 14(1):5075. doi: 10.1038/s41467-023-40868-9. [PMID: 37604798]
  • Yuhai Lin, Xin Zhang, Lu Cheng, Hua Yang. The regulation effect of EGCG3''Me phospholipid complex on gut flora of a high-fat diet-induced obesity mouse model. Journal of food biochemistry. 2019 07; 43(7):e12880. doi: 10.1111/jfbc.12880. [PMID: 31353696]
  • Yong Luo, Shuang-Shuang Yu, Juan Li, Qin Li, Kun-Bo Wang, Jian-An Huang, Zhong-Hua Liu. Characterization of the transcriptional regulator CsbHLH62 that negatively regulates EGCG3'Me biosynthesis in Camellia sinensis. Gene. 2019 May; 699(?):8-15. doi: 10.1016/j.gene.2019.03.002. [PMID: 30851424]
  • Man Zhang, Xin Zhang, Chi-Tang Ho, Qingrong Huang. Chemistry and Health Effect of Tea Polyphenol (-)-Epigallocatechin 3- O-(3- O-Methyl)gallate. Journal of agricultural and food chemistry. 2019 May; 67(19):5374-5378. doi: 10.1021/acs.jafc.8b04837. [PMID: 30346164]
  • Yong Luo, Shuangshuang Yu, Juan Li, Qin Li, Kunbo Wang, Jianan Huang, Zhonghua Liu. Molecular Characterization of WRKY Transcription Factors That Act as Negative Regulators of O-Methylated Catechin Biosynthesis in Tea Plants ( Camellia sinensis L.). Journal of agricultural and food chemistry. 2018 Oct; 66(43):11234-11243. doi: 10.1021/acs.jafc.8b02175. [PMID: 30350966]
  • Takahito Hirai, Yuki Nishimura, Norimitsu Kurata, Hokuto Namba, Mariko Iwase, Yurika Gomi, Hiromichi Tsuchiya, Tomoyuki Yamakawa, Yuji Kiuchi. Effect of Benifuuki Tea on Cytochrome P450-mediated Metabolic Activity in Rats. In vivo (Athens, Greece). 2018 Jan; 32(1):33-40. doi: 10.21873/invivo.11201. [PMID: 29275296]
  • Zhihong Gong, Si Chen, Jiangtao Gao, Meihong Li, Xiaxia Wang, Jun Lin, Xiaomin Yu. [Isolation and purification of seven catechin compounds from fresh tea leaves by semi-preparative liquid chromatography]. Se pu = Chinese journal of chromatography. 2017 Nov; 35(11):1192-1197. doi: 10.3724/sp.j.1123.2017.08002. [PMID: 29372766]
  • Mei Cheng, Xin Zhang, Yingjie Miao, Jinxuan Cao, Zufang Wu, Peifang Weng. The modulatory effect of (-)-epigallocatechin 3-O-(3-O-methyl) gallate (EGCG3″Me) on intestinal microbiota of high fat diet-induced obesity mice model. Food research international (Ottawa, Ont.). 2017 02; 92(?):9-16. doi: 10.1016/j.foodres.2016.12.008. [PMID: 28290302]
  • Yang Yang, Longliang Qiao, Xin Zhang, Zufang Wu, Peifang Weng. Effect of methylated tea catechins from Chinese oolong tea on the proliferation and differentiation of 3T3-L1 preadipocyte. Fitoterapia. 2015 Jul; 104(?):45-9. doi: 10.1016/j.fitote.2015.05.007. [PMID: 26002426]
  • Yue Zhang, Hai-peng Lv, Cheng-ying Ma, Li Guo, Jun-feng Tan, Qun-hua Peng, Zhi Lin. Cloning of a caffeoyl-coenzyme A O-methyltransferase from Camellia sinensis and analysis of its catalytic activity. Journal of Zhejiang University. Science. B. 2015 Feb; 16(2):103-12. doi: 10.1631/jzus.b1400193. [PMID: 25644465]
  • Xin Zhang, Zufang Wu, Peifang Weng. Antioxidant and hepatoprotective effect of (-)-epigallocatechin 3-O-(3-O-methyl) gallate (EGCG3″Me) from Chinese oolong tea. Journal of agricultural and food chemistry. 2014 Oct; 62(41):10046-54. doi: 10.1021/jf5016335. [PMID: 25259858]
  • Qunqin Fei, Yuan Gao, Xin Zhang, Yi Sun, Bing Hu, Li Zhou, Saqib Jabbar, Xiaoxiong Zeng. Effects of Oolong tea polyphenols, EGCG, and EGCG3″Me on pancreatic α-amylase activity in vitro. Journal of agricultural and food chemistry. 2014 Oct; 62(39):9507-14. doi: 10.1021/jf5032907. [PMID: 25222598]
  • Hyoung-June Kim, Huikyoung Chang, Seung Hun Han, Min Seuk Lee, Ji-Yong Jung, SoonAe An, Seok-Yun Baek, Jin Ho Lee, John Hwan Lee, Tae Ryong Lee, Dong Wook Shin, Hongtae Kim. Epigallocatechin-3-O-(3-O-methyl)-gallate-induced differentiation of human keratinocytes involves klotho-mediated regulation of protein kinase-cAMP responsive element-binding protein signaling. International journal of molecular sciences. 2014 Apr; 15(4):5749-61. doi: 10.3390/ijms15045749. [PMID: 24714085]
  • Shuxian Cai, Yuan Zhong, Yinhua Li, Jianan Huang, Jing Zhang, Guoan Luo, Zhonghua Liu. Blockade of the formation of insoluble ubiquitinated protein aggregates by EGCG3'Me in the alloxan-induced diabetic kidney. PloS one. 2013; 8(9):e75687. doi: 10.1371/journal.pone.0075687. [PMID: 24098713]
  • Yukihiro Oritani, Yuko Setoguchi, Ryouichi Ito, Hiroko Maruki-Uchida, Takashi Ichiyanagi, Tatsuhiko Ito. Comparison of (-)-epigallocatechin-3-O-gallate (EGCG) and O-methyl EGCG bioavailability in rats. Biological & pharmaceutical bulletin. 2013; 36(10):1577-82. doi: 10.1248/bpb.b13-00349. [PMID: 24088254]
  • S Y Wu, J I Silverberg, R Joks, H G Durkin, T A Smith-Norowitz. Green tea (Camelia sinensis) mediated suppression of IgE production by peripheral blood mononuclear cells of allergic asthmatic humans. Scandinavian journal of immunology. 2012 Sep; 76(3):306-10. doi: 10.1111/j.1365-3083.2012.02729.x. [PMID: 22670643]
  • Mari Maeda-Yamamoto, Kaori Ema, Mamami Monobe, Yoshiko Tokuda, Hirofumi Tachibana. Epicatechin-3-O-(3″-O-methyl)-gallate content in various tea cultivars (Camellia sinensis L.) and its in vitro inhibitory effect on histamine release. Journal of agricultural and food chemistry. 2012 Mar; 60(9):2165-70. doi: 10.1021/jf204497b. [PMID: 22339247]
  • Takeshi Ishii, Taiki Mori, Tatsuya Ichikawa, Maiko Kaku, Koji Kusaka, Yoshinori Uekusa, Mitsugu Akagawa, Yoshiyuki Aihara, Takumi Furuta, Toshiyuki Wakimoto, Toshiyuki Kan, Tsutomu Nakayama. Structural characteristics of green tea catechins for formation of protein carbonyl in human serum albumin. Bioorganic & medicinal chemistry. 2010 Jul; 18(14):4892-6. doi: 10.1016/j.bmc.2010.06.021. [PMID: 20598557]