Galloyl glucose (BioDeep_00000003720)

Main id: BioDeep_00000018815

 

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate

化学式: C13H16O10 (332.0743436)
中文名称: 1-没食子酸酰葡萄糖
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(cc(cc(c1O)O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O
InChI: InChI=1S/C13H16O10/c14-3-7-9(18)10(19)11(20)13(22-7)23-12(21)4-1-5(15)8(17)6(16)2-4/h1-2,7,9-11,13-20H,3H2/t7-,9-,10+,11-,13+/m1/s1

描述信息

Galloyl glucose, also known as 1-galloyl-beta-D-glucose or beta-glucogallin, is a member of the class of compounds known as tannins. Tannins are naturally occurring polyphenols which be categorized into four main classes: hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). Galloyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Galloyl glucose can be found in a number of food items such as pomegranate, strawberry, redcurrant, and rubus (blackberry, raspberry), which makes galloyl glucose a potential biomarker for the consumption of these food products. Galloyl glucose is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and glucogallin. This enzyme can be found in oak leaf preparations .

同义名列表

18 个代谢物同义名

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 3,4,5-trihydroxybenzoate; 1-O-Galloyl-beta-D-glucose; 1-Galloyl-beta-D-glucose; 1-O-Galloyl-β-D-glucose; 1-O-Galloyl-b-D-glucose; 1-Galloyl-beta-glucose; 1-Galloyl-b-D-glucose; 1-Galloyl-β-D-glucose; 1-Galloyl-b-glucose; 1-Galloyl-β-glucose; 1-O-Galloylglucose; beta-Glucogallin; Galloyl glucose; Galloylglucose; b-Glucogallin; Β-glucogallin; Glucogallin; 1-O-Galloyl-beta-D-glucose



数据库引用编号

19 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(3)

代谢反应

8 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

166 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

  • Qinsong Yang, Jinjin Li, Yan Wang, Zefu Wang, Ziqi Pei, Nathaniel R Street, Rishikesh P Bhalerao, Zhaowei Yu, Yuhao Gao, Junbei Ni, Yang Jiao, Minghui Sun, Xiong Yang, Yixin Chen, Puyuan Liu, Jiaxi Wang, Yong Liu, Guolei Li. Genomic basis of the distinct biosynthesis of β-glucogallin, a biochemical marker for hydrolyzable tannin production, in three oak species. The New phytologist. 2024 Jun; 242(6):2702-2718. doi: 10.1111/nph.19711. [PMID: 38515244]
  • Manni Rohilla, Rishabh, Seema Bansal, Anjali Garg, Sachin Dhiman, Sanchit Dhankhar, Monika Saini, Samrat Chauhan, Nawal Alsubaie, Gaber El-Saber Batiha, Nisreen Khalid Aref Albezrah, Thakur Gurjeet Singh. Discussing pathologic mechanisms of Diabetic retinopathy & therapeutic potentials of curcumin and β-glucogallin in the management of Diabetic retinopathy. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Dec; 169(?):115881. doi: 10.1016/j.biopha.2023.115881. [PMID: 37989030]
  • Rong-Qing Zhu, Chun-Fang Tian, Xiao-Yan Lan, Zi-Han Wang, Xiang Li, Li Zhou, Mei-Lan Chen, Li-Ping Kang. [Chemical and nutrient differences between medicinal material, residues, and residue compost of Moutan Cortex]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Dec; 48(23):6361-6370. doi: 10.19540/j.cnki.cjcmm.20231017.102. [PMID: 38211992]
  • Chihiro Oda-Yamamizo, Nobutaka Mitsuda, Carsten Milkowski, Hideyuki Ito, Kentaro Ezura, Ko Tahara. Heterologous gene expression system for the production of hydrolyzable tannin intermediates in herbaceous model plants. Journal of plant research. 2023 Aug; ?(?):. doi: 10.1007/s10265-023-01484-2. [PMID: 37526750]
  • Liesl Maria Fernandes E Mendonça, Arun Bhimrao Joshi, Anant Bhandarkar, Himanshu Joshi, Shrinivas Joshi. Phytoconstituents from Piliostigma foveolatum (Dalzell) Thoth. leaves induce antiproliferative effect, apoptosis, and cell cycle arrest in Hop-62 cells. Natural product research. 2023 Apr; ?(?):1-5. doi: 10.1080/14786419.2023.2197228. [PMID: 37013695]
  • Arnold Alexeevich Shamilov, Daniil Nikolaevich Olennikov, Dmitryi Igorevich Pozdnyakov, Valentina Nikolaevna Bubenchikova, Ekaterina Robertovna Garsiya. Investigation of phenolic compounds at the leaves and shoots Arctostaphylos spp. and their antioxidant and antityrosinase activities. Natural product research. 2022 Dec; 36(24):6312-6317. doi: 10.1080/14786419.2021.2025370. [PMID: 35019793]
  • Rajveer Singh, Shivani Chandel, Arijit Ghosh, Tushar Matta, Anupam Gautam, Arka Bhattacharya, Srivalliputturu Sarath Babu, Soumi Sukla, Debasish Nag, Velayutham Ravichandiran, Syamal Roy, Dipanjan Ghosh. Glucogallin Attenuates the LPS-Induced Signaling in Macrophages and Protects Mice against Sepsis. International journal of molecular sciences. 2022 Sep; 23(19):. doi: 10.3390/ijms231911254. [PMID: 36232563]
  • Muhammed Majeed, Lakshmi Mundkur, Shaji Paulose, Kalyanam Nagabhushanam. Novel Emblica officinalis extract containing β-glucogallin vs. metformin: a randomized, open-label, comparative efficacy study in newly diagnosed type 2 diabetes mellitus patients with dyslipidemia. Food & function. 2022 Sep; 13(18):9523-9531. doi: 10.1039/d2fo01862d. [PMID: 35996967]
  • Nelson E Masota, Knut Ohlsen, Curd Schollmayer, Lorenz Meinel, Ulrike Holzgrabe. Isolation and Characterization of Galloylglucoses Effective against Multidrug-Resistant Strains of Escherichia coli and Klebsiella pneumoniae. Molecules (Basel, Switzerland). 2022 Aug; 27(15):. doi: 10.3390/molecules27155045. [PMID: 35956993]
  • Anam Najib Khan, Rajveer Singh, Arka Bhattacharya, Rudra Chakravarti, Syamal Roy, Velayutham Ravichandiran, Dipanjan Ghosh. A Short Review on Glucogallin and its Pharmacological Activities. Mini reviews in medicinal chemistry. 2022; 22(22):2820-2830. doi: 10.2174/1389557522666220513150907. [PMID: 35570562]
  • Eun-Tak Jeong, Seul-Ki Park, Du-Min Jo, Fazlurrahman Khan, Tae Ho Choi, Tae-Mi Yoon, Young-Mog Kim. Synergistic Antibacterial Activity of an Active Compound Derived from Sedum takesimense against Methicillin-Resistant Staphylococcus aureus and Its Clinical Isolates. Journal of microbiology and biotechnology. 2021 Sep; 31(9):1288-1294. doi: 10.4014/jmb.2105.05015. [PMID: 34319257]
  • Yuji Iwaoka, Shoichi Suzuki, Nana Kato, Chisa Hayakawa, Satoko Kawabe, Natsuki Ganeko, Tomohiro Uemura, Hideyuki Ito. Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract. Molecules (Basel, Switzerland). 2021 Sep; 26(19):. doi: 10.3390/molecules26195802. [PMID: 34641346]
  • Qinghua Ye, Shiyan Zhang, Nana Qiu, Linmin Liu, Wei Wang, Qian Xie, Qiang Chang, Qingxi Chen. Identification and Characterization of Glucosyltransferase That Forms 1-Galloyl-β-d-Glucogallin in Canarium album L., a Functional Fruit Rich in Hydrolysable Tannins. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154650. [PMID: 34361803]
  • Ashutosh Gupta, Ramesh Kumar, Piyali Bhattacharyya, Anupam Bishayee, Abhay K Pandey. Terminalia bellirica (Gaertn.) roxb. (Bahera) in health and disease: A systematic and comprehensive review. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Oct; 77(?):153278. doi: 10.1016/j.phymed.2020.153278. [PMID: 32781393]
  • Ying Ma, Fei Liu, Yanli Xu. Protective Effect of β-Glucogallin on Damaged Cataract Against Methylglyoxal Induced Oxidative Stress in Cultured Lens Epithelial Cells. Medical science monitor : international medical journal of experimental and clinical research. 2019 Dec; 25(?):9310-9318. doi: 10.12659/msm.917869. [PMID: 31811113]
  • Honghui Luo, Wenjun Li, Xin Zhang, Shuangfan Deng, Qiuchan Xu, Ting Hou, Xuequn Pang, Zhaoqi Zhang, Xuelian Zhang. In planta high levels of hydrolysable tannins inhibit peroxidase mediated anthocyanin degradation and maintain abaxially red leaves of Excoecaria Cochinchinensis. BMC plant biology. 2019 Jul; 19(1):315. doi: 10.1186/s12870-019-1903-y. [PMID: 31307378]
  • Hongmei Zhao, Lijun Chen, Yiyu Yang, Yan Zhang, Yegao Chen. A new galloyl glycoside from Lotus corniculatus. Natural product research. 2019 Apr; 33(8):1158-1161. doi: 10.1080/14786419.2018.1460839. [PMID: 29656654]
  • Aruanã Joaquim Matheus Costa Rodrigues Pinheiro, Aleff Ricardo Santos Mendes, Milena Dara Farias de Jesus Neves, Carla Máximo Prado, Márcia Isabel Bittencourt-Mernak, Fernanda Paula Roncon Santana, João Henrique G Lago, Joicy Cortez de Sá, Claudia Quintino da Rocha, Eduardo Martins de Sousa, Valéria Costa Fontes, Marco Augusto Gregolin Grisoto, Angela Falcai, Lidio Gonçalves Lima-Neto. Galloyl-Hexahydroxydiphenoyl (HHDP)-Glucose Isolated From Punica granatum L. Leaves Protects Against Lipopolysaccharide (LPS)-Induced Acute Lung Injury in BALB/c Mice. Frontiers in immunology. 2019; 10(?):1978. doi: 10.3389/fimmu.2019.01978. [PMID: 31481965]
  • Ko Tahara, Mitsuru Nishiguchi, Andrej Frolov, Juliane Mittasch, Carsten Milkowski. Identification of UDP glucosyltransferases from the aluminum-resistant tree Eucalyptus camaldulensis forming β-glucogallin, the precursor of hydrolyzable tannins. Phytochemistry. 2018 Aug; 152(?):154-161. doi: 10.1016/j.phytochem.2018.05.005. [PMID: 29775866]
  • Alexander E Wilson, Xiaoxue Feng, Nadia N Ono, Doron Holland, Rachel Amir, Li Tian. Characterization of a UGT84 Family Glycosyltransferase Provides New Insights into Substrate Binding and Reactivity of Galloylglucose Ester-Forming UGTs. Biochemistry. 2017 Dec; 56(48):6389-6400. doi: 10.1021/acs.biochem.7b00946. [PMID: 29140084]
  • Katja Schulenburg, Antje Feller, Thomas Hoffmann, Johannes H Schecker, Stefan Martens, Wilfried Schwab. Formation of β-glucogallin, the precursor of ellagic acid in strawberry and raspberry. Journal of experimental botany. 2016 Apr; 67(8):2299-308. doi: 10.1093/jxb/erw036. [PMID: 26884604]
  • Nadia N Ono, Xiaoqiong Qin, Alexander E Wilson, Gang Li, Li Tian. Two UGT84 Family Glycosyltransferases Catalyze a Critical Reaction of Hydrolyzable Tannin Biosynthesis in Pomegranate (Punica granatum). PloS one. 2016; 11(5):e0156319. doi: 10.1371/journal.pone.0156319. [PMID: 27227328]
  • Wael M Abdel-Mageed, Soad A H Bayoumi, Caixia Chen, Christopher J Vavricka, Li Li, Ajamaluddin Malik, Huanqin Dai, Fuhang Song, Luoqiang Wang, Jingyu Zhang, George F Gao, Yali Lv, Lihong Liu, Xueting Liu, Hanaa M Sayed, Lixin Zhang. Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorganic & medicinal chemistry. 2014 Apr; 22(7):2236-43. doi: 10.1016/j.bmc.2014.02.014. [PMID: 24613627]
  • Linfeng Li, Kun-Che Chang, Yaming Zhou, Biehuoy Shieh, Jessica Ponder, Adedoyin D Abraham, Hadi Ali, Anson Snow, J Mark Petrash, Daniel V LaBarbera. Design of an amide N-glycoside derivative of β-glucogallin: a stable, potent, and specific inhibitor of aldose reductase. Journal of medicinal chemistry. 2014 Jan; 57(1):71-7. doi: 10.1021/jm401311d. [PMID: 24341381]
  • Juha-Pekka Salminen, Alexander N Shikov, Maarit Karonen, Olga N Pozharitskaya, Jorma Kim, Valery G Makarov, Raimo Hiltunen, Bertalan Galambosi. Rapid profiling of phenolic compounds of green and fermented Bergenia crassifolia L. leaves by UPLC-DAD-QqQ-MS and HPLC-DAD-ESI-QTOF-MS. Natural product research. 2014; 28(19):1530-3. doi: 10.1080/14786419.2014.923999. [PMID: 24896228]
  • Pradeep Pratap Singh, S M S Chauhan. Activity-guided isolation of antioxidants from the leaves of Terminalia arjuna. Natural product research. 2014; 28(10):760-3. doi: 10.1080/14786419.2013.879304. [PMID: 24484080]
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  • Muthenna Puppala, Jessica Ponder, Palla Suryanarayana, Geereddy Bhanuprakash Reddy, J Mark Petrash, Daniel V LaBarbera. The isolation and characterization of β-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis. PloS one. 2012; 7(4):e31399. doi: 10.1371/journal.pone.0031399. [PMID: 22485126]
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