Querciturone (BioDeep_00000229595)
Main id: BioDeep_00000398145
natural product human metabolite PANOMIX_OTCML-2023
代谢物信息卡片
QUERCETIN-3-O-GLUCURONIDE
化学式: C21H18O13 (478.0747378)
中文名称: 槲皮素-3-O-葡萄糖醛酸苷
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
InChI: InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
描述信息
Acquisition and generation of the data is financially supported in part by CREST/JST.
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.
同义名列表
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:66395
- PubChem: 5274585
- HMDB: HMDB29212
- ChEMBL: CHEMBL520546
- CAS: 22688-79-5
- MoNA: PS093301
- MoNA: PS093302
- MoNA: PS093303
- MoNA: PS093304
- MoNA: PS093305
- MoNA: PS093306
- MoNA: PS093307
- MoNA: PS093308
- MoNA: PS093309
- MoNA: PS093310
- MoNA: PS093311
- MoNA: PR101031
- MoNA: PR100978
- medchemexpress: HY-13930
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)
3 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
- Muxin Zheng, Shenghao Chen, Yi Liu, Yang He. α-Glucosidase inhibitory activities of constituents from Psidium guajava leaves.
Natural product research.
2023 Jul; ?(?):1-4. doi:
10.1080/14786419.2023.2238113. [PMID: 37506309] - 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] - Zhenyu Wang, Chaoyi Xue, Xuan Wang, Maomao Zeng, Zhaojun Wang, Qiuming Chen, Jie Chen, Mark Christian, Zhiyong He. Quercetin 3-O-glucuronide-rich lotus leaf extract promotes a Brown-fat-phenotype in C3H10T1/2 mesenchymal stem cells.
Food research international (Ottawa, Ont.).
2023 01; 163(?):112198. doi:
10.1016/j.foodres.2022.112198. [PMID: 36596137] - Daniel Muñoz-Reyes, Alfredo G Casanova, Ana María González-Paramás, Ángel Martín, Celestino Santos-Buelga, Ana I Morales, Francisco J López-Hernández, Marta Prieto. Protective Effect of Quercetin 3-O-Glucuronide against Cisplatin Cytotoxicity in Renal Tubular Cells.
Molecules (Basel, Switzerland).
2022 Feb; 27(4):. doi:
10.3390/molecules27041319. [PMID: 35209106] - Małgorzata Domżalska, Wiesław Wiczkowski, Aleksandra Szczepkowska, Sylwia Chojnowska, Tomasz Misztal, Fruzsina R Walter, Maria A Deli, Hiroshi Ishikawa, Horst Schroten, Christian Schwerk, Janina Skipor. Effect of Lipopolysaccharide-Induced Inflammatory Challenge on β-Glucuronidase Activity and the Concentration of Quercetin and Its Metabolites in the Choroid Plexus, Blood Plasma and Cerebrospinal Fluid.
International journal of molecular sciences.
2021 Jul; 22(13):. doi:
10.3390/ijms22137122. [PMID: 34281178] - Singeun Kim, Ki-Bae Hong, Kyungae Jo, Hyung Joo Suh. Quercetin-3-O-glucuronide in the Ethanol Extract of Lotus Leaf (Nelumbo nucifera) Enhances Sleep Quantity and Quality in a Rodent Model via a GABAergic Mechanism.
Molecules (Basel, Switzerland).
2021 May; 26(10):. doi:
10.3390/molecules26103023. [PMID: 34069439] - Tae Heon Kim, Hyun Young Shin, Soon Yeong Park, Hoon Kim, Dae Kyun Chung. Development and Validation of a Method for Determining the Quercetin-3-O-glucuronide and Ellagic Acid Content of Common Evening Primrose (Oenothera biennis) by HPLC-UVD.
Molecules (Basel, Switzerland).
2021 Jan; 26(2):. doi:
10.3390/molecules26020267. [PMID: 33430409] - Enkhtaivan Gansukh, Arti Nile, Doo Hwan Kim, Jae Wook Oh, Shivraj Hariram Nile. New insights into antiviral and cytotoxic potential of quercetin and its derivatives - A biochemical perspective.
Food chemistry.
2021 Jan; 334(?):127508. doi:
10.1016/j.foodchem.2020.127508. [PMID: 32711265] - Kirsten Berger, Johanna Josefine Ostberg-Potthoff, Tamara Bakuradze, Peter Winterhalter, Elke Richling. Carbohydrate Hydrolase-Inhibitory Activity of Juice-Based Phenolic Extracts in Correlation to Their Anthocyanin/Copigment Profile.
Molecules (Basel, Switzerland).
2020 Nov; 25(22):. doi:
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Scientific reports.
2020 08; 10(1):14241. doi:
10.1038/s41598-020-70706-7. [PMID: 32859977] - Jeffrey P Davis, Mihoko Koyanagi, Robert R Maronpot, Leslie Recio, Shim-Mo Hayashi. Identification of compound causing yellow bone discoloration following alpha-glycosyl isoquercitrin exposure in Sprague-Dawley rats.
Archives of toxicology.
2020 07; 94(7):2413-2421. doi:
10.1007/s00204-020-02760-z. [PMID: 32388820] - Diahann J Perdicaro, Cecilia Rodriguez Lanzi, Julián Gambarte Tudela, Roberto M Miatello, Patricia I Oteiza, Marcela A Vazquez Prieto. Quercetin attenuates adipose hypertrophy, in part through activation of adipogenesis in rats fed a high-fat diet.
The Journal of nutritional biochemistry.
2020 05; 79(?):108352. doi:
10.1016/j.jnutbio.2020.108352. [PMID: 32145471] - Yumi Kitahiro, Hiroshi Ikeda, Hyoung-Tak Im, Eiichi Kodaira, Makio Shibano. Phytochemical characterization of Rosa multiflora Thunb. (Rosaceae) in Japan and South Korea, with a focus on the bioactive flavonol glycoside 'multiflorin A'.
Journal of natural medicines.
2019 Jun; 73(3):555-565. doi:
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Plant physiology and biochemistry : PPB.
2019 Apr; 137(?):169-178. doi:
10.1016/j.plaphy.2019.02.012. [PMID: 30797184] - Itziar Eseberri, Jonatan Miranda, Arrate Lasa, Andrea Mosqueda-Solís, Susana González-Manzano, Celestino Santos-Buelga, Maria P Portillo. Effects of Quercetin Metabolites on Triglyceride Metabolism of 3T3-L1 Preadipocytes and Mature Adipocytes.
International journal of molecular sciences.
2019 Jan; 20(2):. doi:
10.3390/ijms20020264. [PMID: 30641871] - Manuela Mandrone, Aline Coqueiro, Ferruccio Poli, Fabiana Antognoni, Young Hae Choi. Identification of a Collagenase-Inhibiting Flavonoid from Alchemilla vulgaris Using NMR-Based Metabolomics.
Planta medica.
2018 Aug; 84(12-13):941-946. doi:
10.1055/a-0630-2079. [PMID: 29797306] - Yang Liu, Yanni Cao, Shengzuo Fang, Tongli Wang, Zhiqi Yin, Xulan Shang, Wanxia Yang, Xiangxiang Fu. Antidiabetic Effect of Cyclocarya paliurus Leaves Depends on the Contents of Antihyperglycemic Flavonoids and Antihyperlipidemic Triterpenoids.
Molecules (Basel, Switzerland).
2018 Apr; 23(5):. doi:
10.3390/molecules23051042. [PMID: 29710841] - A Garbetta, L Nicassio, I D'Antuono, A Cardinali, V Linsalata, G Attolico, F Minervini. Influence of in vitro digestion process on polyphenolic profile of skin grape (cv. Italia) and on antioxidant activity in basal or stressed conditions of human intestinal cell line (HT-29).
Food research international (Ottawa, Ont.).
2018 04; 106(?):878-884. doi:
10.1016/j.foodres.2018.01.072. [PMID: 29579999] - Roger Remy Dresch, Maria Terezinha Kreinecker Dresch, Renata Biegelmeyer, Débora Fretes Argenta, Ricardo Fagundes da Rocha, Helder Ferreira Teixeira, José Cláudio Fonseca Moreira, Amélia Teresinha Henriques. Potential use of secondary products of the agri-food industry for topical formulations and comparative analysis of antioxidant activity of grape leaf polyphenols.
Natural product research.
2018 Feb; 32(4):486-492. doi:
10.1080/14786419.2017.1315573. [PMID: 28403634] - Cristina Sgherri, Usue Pérez-López, Francesco Micaelli, Jon Miranda-Apodaca, Amaia Mena-Petite, Alberto Muñoz-Rueda, Mike Frank Quartacci. Elevated CO2 and salinity are responsible for phenolics-enrichment in two differently pigmented lettuces.
Plant physiology and biochemistry : PPB.
2017 Jun; 115(?):269-278. doi:
10.1016/j.plaphy.2017.04.006. [PMID: 28411511] - Hyun Soo Jang, Seung In Um, Sung Hee Lee, Wan Kyunn Whang, Young Sil Min, Sun Young Park, Uy Dong Sohn. The protective mechanism of QGC in feline esophageal epithelial cells by interleukin-1β treatment.
Archives of pharmacal research.
2017 Feb; 40(2):204-213. doi:
10.1007/s12272-016-0858-x. [PMID: 28012047] - Fei Li, Xiao-Yue Sun, Xiao-Wei Li, Tong Yang, Lian-Wen Qi. Enrichment and separation of quercetin-3-O-β-d-glucuronide from lotus leaves (nelumbo nucifera gaertn.) and evaluation of its anti-inflammatory effect.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jan; 1040(?):186-191. doi:
10.1016/j.jchromb.2016.12.017. [PMID: 27987489] - Le-Le Yang, Na Xiao, Xiao-Wei Li, Yong Fan, Raphael N Alolga, Xiao-Yue Sun, Shi-Lei Wang, Ping Li, Lian-Wen Qi. Pharmacokinetic comparison between quercetin and quercetin 3-O-β-glucuronide in rats by UHPLC-MS/MS.
Scientific reports.
2016 10; 6(?):35460. doi:
10.1038/srep35460. [PMID: 27775094] - Cheng-Hung Chuang, Chiao-Lin Yeh, Shu-Lan Yeh, En-Shyh Lin, Li-Yu Wang, Ying-Hsuna Wang. Quercetin metabolites inhibit MMP-2 expression in A549 lung cancer cells by PPAR-γ associated mechanisms.
The Journal of nutritional biochemistry.
2016 07; 33(?):45-53. doi:
10.1016/j.jnutbio.2016.03.011. [PMID: 27260467] - Chiemi Kamada, Rie Mukai, Akari Kondo, Shinya Sato, Junji Terao. Effect of quercetin and its metabolite on caveolin-1 expression induced by oxidized LDL and lysophosphatidylcholine in endothelial cells.
Journal of clinical biochemistry and nutrition.
2016 May; 58(3):193-201. doi:
10.3164/jcbn.16-2. [PMID: 27257344] - Shu-Lan Yeh, Yi-Chin Lin, Yi-Ling Lin, Chien-Chun Li, Cheng-Hung Chuang. Comparing the metabolism of quercetin in rats, mice and gerbils.
European journal of nutrition.
2016 Feb; 55(1):413-22. doi:
10.1007/s00394-015-0862-9. [PMID: 25691233] - Lu Lu Wang, Zhi Chao Zhang, Waseem Hassan, Yu Li, Jun Liu, Jing Shang. Amelioration of free fatty acid-induced fatty liver by quercetin-3-O-β-D-glucuronide through modulation of peroxisome proliferator-activated receptor-alpha/sterol regulatory element-binding protein-1c signaling.
Hepatology research : the official journal of the Japan Society of Hepatology.
2016 Feb; 46(2):225-38. doi:
10.1111/hepr.12557. [PMID: 26190035] - Alessandro Venditti, Laura Guarcini, Armandodoriano Bianco, Sergio Rosselli, Maurizio Bruno, Felice Senatore. Phytochemical analysis of Achillea ligustica All. from Lipari Island (Aeolian Islands).
Natural product research.
2016; 30(8):912-9. doi:
10.1080/14786419.2015.1079188. [PMID: 26327332] - Rungnapa Boonpawa, Nooshin Moradi, Albertus Spenkelink, Ivonne M C M Rietjens, Ans Punt. Use of physiologically based kinetic (PBK) modeling to study interindividual human variation and species differences in plasma concentrations of quercetin and its metabolites.
Biochemical pharmacology.
2015 Dec; 98(4):690-702. doi:
10.1016/j.bcp.2015.09.022. [PMID: 26441251] - Jonathan G Messer, Robin G Hopkins, Deborah E Kipp. Quercetin Metabolites Up-Regulate the Antioxidant Response in Osteoblasts Isolated From Fetal Rat Calvaria.
Journal of cellular biochemistry.
2015 Sep; 116(9):1857-66. doi:
10.1002/jcb.25141. [PMID: 25716194] - Karsten Beekmann, Laura Rubió, Laura H J de Haan, Lucas Actis-Goretta, Bart van der Burg, Peter J van Bladeren, Ivonne M C M Rietjens. The effect of quercetin and kaempferol aglycones and glucuronides on peroxisome proliferator-activated receptor-gamma (PPAR-γ).
Food & function.
2015 Apr; 6(4):1098-107. doi:
10.1039/c5fo00076a. [PMID: 25765892] - R Jimenez, R Lopez-Sepulveda, M Romero, M Toral, A Cogolludo, F Perez-Vizcaino, J Duarte. Quercetin and its metabolites inhibit the membrane NADPH oxidase activity in vascular smooth muscle cells from normotensive and spontaneously hypertensive rats.
Food & function.
2015 Feb; 6(2):409-14. doi:
10.1039/c4fo00818a. [PMID: 25562607] - James Daubney, Philip L Bonner, Alan J Hargreaves, John M Dickenson. Cardioprotective and cardiotoxic effects of quercetin and two of its in vivo metabolites on differentiated h9c2 cardiomyocytes.
Basic & clinical pharmacology & toxicology.
2015 Feb; 116(2):96-109. doi:
10.1111/bcpt.12319. [PMID: 25203460] - Almudena Perez, Susana Gonzalez-Manzano, Rosario Jimenez, Rocío Perez-Abud, Jose M Haro, Antonio Osuna, Celestino Santos-Buelga, Juan Duarte, Francisco Perez-Vizcaino. The flavonoid quercetin induces acute vasodilator effects in healthy volunteers: correlation with beta-glucuronidase activity.
Pharmacological research.
2014 Nov; 89(?):11-8. doi:
10.1016/j.phrs.2014.07.005. [PMID: 25076013] - Shu-Ting Chan, Yi-Chin Lin, Cheng-Hung Chuang, Rong-Jen Shiau, Jiunn-Wang Liao, Shu-Lan Yeh. Oral and intraperitoneal administration of quercetin decreased lymphocyte DNA damage and plasma lipid peroxidation induced by TSA in vivo.
BioMed research international.
2014; 2014(?):580626. doi:
10.1155/2014/580626. [PMID: 24868531] - Hideto Kimura, Tomoe Ishihara, Mahoko Michida, Satoshi Ogawa, Takashi Akihiro, Kazushige Yokota. Identification and quantitative analysis of polyphenolic compounds from the indigo plant (Polygonum tinctorium Lour).
Natural product research.
2014; 28(7):492-5. doi:
10.1080/14786419.2013.871719. [PMID: 24437998] - Hyo Hyun Yang, Kyoung Hwangbo, Ming Shan Zheng, Jung Hee Cho, Jong-Keun Son, Hwa Young Kim, Suk Hwan Baek, Hyung Chul Choi, So Young Park, Jae-Ryong Kim. Quercetin-3-O-β-D-glucuronide isolated from Polygonum aviculare inhibits cellular senescence in human primary cells.
Archives of pharmacal research.
2014; 37(9):1219-33. doi:
10.1007/s12272-014-0344-2. [PMID: 24638927] - Magdalena Stolarczyk, Jakub P Piwowarski, Sebastian Granica, Joanna Stefańska, Marek Naruszewicz, Anna K Kiss. Extracts from Epilobium sp. herbs, their components and gut microbiota metabolites of Epilobium ellagitannins, urolithins, inhibit hormone-dependent prostate cancer cells-(LNCaP) proliferation and PSA secretion.
Phytotherapy research : PTR.
2013 Dec; 27(12):1842-8. doi:
10.1002/ptr.4941. [PMID: 23436427] - Kazuaki Ohara, Hideyuki Wakabayashi, Yoshimasa Taniguchi, Kazutoshi Shindo, Hiroaki Yajima, Aruto Yoshida. Quercetin-3-O-glucuronide induces ABCA1 expression by LXRα activation in murine macrophages.
Biochemical and biophysical research communications.
2013 Nov; 441(4):929-34. doi:
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Experimental parasitology.
2013 Jul; 134(3):299-303. doi:
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Journal of natural products.
2013 Feb; 76(2):186-93. doi:
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2013; 27(6):568-73. doi:
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2013 Jan; 36(1):57-60. doi:
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Planta medica.
2012 Nov; 78(16):1796-9. doi:
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Biochemical pharmacology.
2012 Aug; 84(4):564-70. doi:
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Free radical research.
2012 Aug; 46(8):1019-28. doi:
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Biochimica et biophysica acta.
2012 Jul; 1820(7):1027-34. doi:
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Pharmacology.
2012; 90(5-6):288-97. doi:
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Analytical and bioanalytical chemistry.
2012 Jan; 402(3):1389-92. doi:
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Molecular nutrition & food research.
2011 Dec; 55(12):1780-90. doi:
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Archives of pharmacal research.
2011 Sep; 34(9):1527-34. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2011 May; 18(7):557-60. doi:
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Biochemical pharmacology.
2011 Apr; 81(7):942-9. doi:
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Journal of pharmacological sciences.
2011; 115(4):466-70. doi:
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Fitoterapia.
2010 Mar; 81(2):85-92. doi:
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Natural product communications.
2009 Oct; 4(10):1357-62. doi:
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Wei sheng yan jiu = Journal of hygiene research.
2009 Jul; 38(4):417-9. doi:
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Atherosclerosis.
2009 May; 204(1):34-9. doi:
10.1016/j.atherosclerosis.2008.08.007. [PMID: 18801486] - Mark S Winterbone, Sandra Tribolo, Paul W Needs, Paul A Kroon, David A Hughes. Physiologically relevant metabolites of quercetin have no effect on adhesion molecule or chemokine expression in human vascular smooth muscle cells.
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