pyrroloquinoline quinone (BioDeep_00001867910)
Main id: BioDeep_00000004383
PANOMIX_OTCML-2023 natural product
代谢物信息卡片
化学式: C14H6N2O8 (330.0124)
中文名称: 吡咯喹啉醌
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O
InChI: InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)
描述信息
Pyrroloquinoline quinone (PQQ), a redox co-factor, is an anionic, redox-cycling orthoquinone. Pyrroloquinoline quinone is isolated from cultures of methylotropic bacteria and tissues of mammals. Pyrroloquinoline quinone is an essential nutrient for mammals and is important for immune function[1][2].
同义名列表
4 个代谢物同义名
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:18315
- KEGG: C00113
- PubChem: 1024
- DrugBank: DB03205
- ChEMBL: CHEMBL1235421
- MeSH: PQQ Cofactor
- CAS: 72909-34-3
- PubChem: 3413
- PDB-CCD: PQQ
- 3DMET: B00030
- NIKKAJI: J126.218A
- medchemexpress: HY-100196
- KNApSAcK: 18315
- LOTUS: LTS0120678
分类词条
相关代谢途径
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)
5 个相关的物种来源信息
- 28211 - Alphaproteobacteria: LTS0120678
- 2 - Bacteria: LTS0120678
- 45401 - Hyphomicrobiaceae: LTS0120678
- 81 - Hyphomicrobium: 10.1016/0014-5793(88)80178-9
- 81 - Hyphomicrobium: LTS0120678
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
- Kazuto Ikemoto, Nur Syafiqah Mohamad Ishak, Mitsugu Akagawa. The effects of pyrroloquinoline quinone disodium salt on brain function and physiological processes.
The journal of medical investigation : JMI.
2024; 71(1.2):23-28. doi:
10.2152/jmi.71.23
. [PMID: 38735721] - Jinyuan Wang, Shun Zhang, Linlin Hu, Yan Wang, Ke Liu, Jianghua Le, Yongpeng Tan, Tianlong Li, Haoxuan Xue, Yanhong Wei, Ou Zhong, Junhui He, Dan Zi, Xin Lei, Renhe Deng, Yafei Luo, Masong Tang, Mingxuan Su, Yichang Cao, Qingyou Liu, Zhihan Tang, Xiaocan Lei. Pyrroloquinoline quinone inhibits PCSK9-NLRP3 mediated pyroptosis of Leydig cells in obese mice.
Cell death & disease.
2023 11; 14(11):723. doi:
10.1038/s41419-023-06162-8
. [PMID: 37935689] - Shou-Chen Lo, Shang-Yieng Tsai, Wei-Hsiang Chang, I-Chen Wu, Nga-Lai Sou, Shih-Hsun Walter Hung, En-Pei Isabel Chiang, Chieh-Chen Huang. Characterization of the Pyrroloquinoline Quinone Producing Rhodopseudomonas palustris as a Plant Growth-Promoting Bacterium under Photoautotrophic and Photoheterotrophic Culture Conditions.
International journal of molecular sciences.
2023 Sep; 24(18):. doi:
10.3390/ijms241814080
. [PMID: 37762380] - Jan L Krüsemann, Vittorio Rainaldi, Charles Ar Cotton, Nico J Claassens, Steffen N Lindner. The cofactor challenge in synthetic methylotrophy: bioengineering and industrial applications.
Current opinion in biotechnology.
2023 Jun; 82(?):102953. doi:
10.1016/j.copbio.2023.102953
. [PMID: 37320962] - Klaus Hantke, Simon Friz. The TonB-dependent uptake of pyrroloquinoline-quinone (PQQ) and secretion of gluconate by Escherichia coli K-12.
Molecular microbiology.
2022 10; 118(4):417-425. doi:
10.1111/mmi.14975
. [PMID: 36054785] - Xuefeng Qu, Bingzhong Zhai, Yifeng Liu, Yihao Chen, Zemi Xie, Qinxi Wang, Yuejin Wu, Zhen Liu, Jianguo Chen, Song Mei, Jie Wu, Zhenqiang You, Yongjie Yu, Yin Wang. Pyrroloquinoline quinone ameliorates renal fibrosis in diabetic nephropathy by inhibiting the pyroptosis pathway in C57BL/6 mice and human kidney 2 cells.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2022 Jun; 150(?):112998. doi:
10.1016/j.biopha.2022.112998
. [PMID: 35489281] - Prassan Choudhary, Arpan Bhowmik, Hillol Chakdar, Mohammad Aqueel Khan, Chandrabose Selvaraj, Sanjeev Kumar Singh, Kumar Murugan, Sunil Kumar, Anil Kumar Saxena. Understanding the biological role of PqqB in Pseudomonas stutzeri using molecular dynamics simulation approach.
Journal of biomolecular structure & dynamics.
2022 06; 40(9):4237-4249. doi:
10.1080/07391102.2020.1854860
. [PMID: 33287678] - Ashok Mandala, Evgenia Dobrinskikh, Rachel C Janssen, Oliver Fiehn, Angelo D'Alessandro, Jacob E Friedman, Karen R Jonscher. Maternal Pyrroloquinoline Quinone Supplementation Improves Offspring Liver Bioactive Lipid Profiles throughout the Lifespan and Protects against the Development of Adult NAFLD.
International journal of molecular sciences.
2022 May; 23(11):. doi:
10.3390/ijms23116043
. [PMID: 35682720] - Cheng Long, Ziteng Wang, Yong Guo, Xihui Sheng, Kai Xing, Heming Ni, Xiangguo Wang, Longfei Xiao, Xiaolong Qi. Research Note: Dietary supplementation with pyrroloquinoline quinone disodium (PQQ.Na2) improves oxidative status and semen quality in aging layer breeder roosters.
Poultry science.
2022 May; 101(5):101812. doi:
10.1016/j.psj.2022.101812
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Advances in microbial physiology.
2022; 81(?):1-24. doi:
10.1016/bs.ampbs.2022.06.001
. [PMID: 36167440] - Kai Qiu, Qin Zhao, Jing Wang, Guang-Hai Qi, Shu-Geng Wu, Hai-Jun Zhang. Effects of Pyrroloquinoline Quinone on Lipid Metabolism and Anti-Oxidative Capacity in a High-Fat-Diet Metabolic Dysfunction-Associated Fatty Liver Disease Chick Model.
International journal of molecular sciences.
2021 Feb; 22(3):. doi:
10.3390/ijms22031458
. [PMID: 33535680] - Elżbieta Supruniuk, Agnieszka Mikłosz, Adrian Chabowski. Pyrroloquinoline Quinone Modifies Lipid Profile, but Not Insulin Sensitivity, of Palmitic Acid-Treated L6 Myotubes.
International journal of molecular sciences.
2020 Nov; 21(21):. doi:
10.3390/ijms21218382
. [PMID: 33171690] - Y W Zheng, J Y Zhang, H B Zhou, Y P Guo, Q G Ma, C Ji, L H Zhao. Effects of dietary pyrroloquinoline quinone disodium supplementation on inflammatory responses, oxidative stress, and intestinal morphology in broiler chickens challenged with lipopolysaccharide.
Poultry science.
2020 Nov; 99(11):5389-5398. doi:
10.1016/j.psj.2020.08.007
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Food & function.
2020 Sep; 11(9):7804-7816. doi:
10.1039/d0fo01403f
. [PMID: 32808626] - Xinhui Lin, Fei Yang, Ju Huang, Su Jiang, Yunping Tang, Jianrong Li. Ameliorate effect of pyrroloquinoline quinone against cyclophosphamide-induced nephrotoxicity by activating the Nrf2 pathway and inhibiting the NLRP3 pathway.
Life sciences.
2020 Sep; 256(?):117901. doi:
10.1016/j.lfs.2020.117901
. [PMID: 32504759] - Karan Devasani, Rachna Kaul, Anuradha Majumdar. Supplementation of pyrroloquinoline quinone with atorvastatin augments mitochondrial biogenesis and attenuates low grade inflammation in obese rats.
European journal of pharmacology.
2020 Aug; 881(?):173273. doi:
10.1016/j.ejphar.2020.173273
. [PMID: 32535101] - Min Zhang, Jiangzhao Zhang, Yan Xiong, Jiaqing Peng, Xiaoyan Wu. Pyrroloquinoline Quinone Inhibits Oxidative Stress in Rats with Diabetic Nephropathy.
Medical science monitor : international medical journal of experimental and clinical research.
2020 Jun; 26(?):e924372. doi:
10.12659/msm.924372
. [PMID: 32592386] - Hongyun Zhang, Jinze Li, Chunyu Cao, Boru Zhang, Wei Yang, Baoming Shi, Anshan Shan. Pyrroloquinoline quinone inhibits the production of inflammatory cytokines via the SIRT1/NF-κB signal pathway in weaned piglet jejunum.
Food & function.
2020 Mar; 11(3):2137-2153. doi:
10.1039/c9fo02609f
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International journal of molecular medicine.
2020 Mar; 45(3):873-885. doi:
10.3892/ijmm.2020.4463
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Microbiological research.
2020 Mar; 233(?):126395. doi:
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Clinical and experimental pharmacology & physiology.
2020 01; 47(1):102-110. doi:
10.1111/1440-1681.13176
. [PMID: 31520547] - Elżbieta Supruniuk, Agnieszka Mikłosz, Adrian Chabowski, Bartłomiej Łukaszuk. Dose- and time-dependent alterations in lipid metabolism after pharmacological PGC-1α activation in L6 myotubes.
Journal of cellular physiology.
2019 07; 234(7):11923-11941. doi:
10.1002/jcp.27872
. [PMID: 30523639] - Ziqiang Wang, Ying Li, Ying Wang, Kunxiao Zhao, Yanqing Chi, Baoxing Wang. Pyrroloquinoline quinine protects HK-2 cells against high glucose-induced oxidative stress and apoptosis through Sirt3 and PI3K/Akt/FoxO3a signaling pathway.
Biochemical and biophysical research communications.
2019 01; 508(2):398-404. doi:
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Journal of bioscience and bioengineering.
2018 Dec; 126(6):667-675. doi:
10.1016/j.jbiosc.2018.05.023
. [PMID: 29914801] - Anikó Várnai, Kiwamu Umezawa, Makoto Yoshida, Vincent G H Eijsink. The Pyrroloquinoline-Quinone-Dependent Pyranose Dehydrogenase from Coprinopsis cinerea Drives Lytic Polysaccharide Monooxygenase Action.
Applied and environmental microbiology.
2018 06; 84(11):. doi:
10.1128/aem.00156-18
. [PMID: 29602785] - Hongyue Li, Weizhu Zeng, Jingwen Zhou. [High-throughput screening of Methylobacterium extorquens for high production of pyrroloquinoline quinone].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2018 May; 34(5):794-802. doi:
10.13345/j.cjb.170440
. [PMID: 29893087] - Mizuho Fukuda, Mahmoud H El-Maghrabey, Naoya Kishikawa, Kazuto Ikemoto, Naotaka Kuroda. Ultrasensitive determination of pyrroloquinoline quinone in human plasma by HPLC with chemiluminescence detection using the redox cycle of quinone.
Journal of pharmaceutical and biomedical analysis.
2017 Oct; 145(?):814-820. doi:
10.1016/j.jpba.2017.08.008
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Research in microbiology.
2017 Oct; 168(8):710-721. doi:
10.1016/j.resmic.2017.07.001
. [PMID: 28709697] - Hiroyuki Sasakura, Hiroki Moribe, Masahiko Nakano, Kazuto Ikemoto, Kosei Takeuchi, Ikue Mori. Lifespan extension by peroxidase and dual oxidase-mediated ROS signaling through pyrroloquinoline quinone in C. elegans.
Journal of cell science.
2017 Aug; 130(15):2631-2643. doi:
10.1242/jcs.202119
. [PMID: 28676501] - Archana Somabhai Chaudhari, Ruma Raghuvanshi, G Naresh Kumar. Genetically engineered Escherichia coli Nissle 1917 synbiotic counters fructose-induced metabolic syndrome and iron deficiency.
Applied microbiology and biotechnology.
2017 Jun; 101(11):4713-4723. doi:
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Nutrition (Burbank, Los Angeles County, Calif.).
2016 Nov; 32(11-12):1285-94. doi:
10.1016/j.nut.2016.03.009
. [PMID: 27209211] - Huizhi Li, Zhen Kang, Jianghua Li, Jingwen Zhou, Guocheng Du. [Mutagenesis of Methylobacterium extorquens AM1 for increasing pyrroloquinoline quinone production by atmospheric and room temperature plasma].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2016 Aug; 32(8):1145-1149. doi:
10.13345/j.cjb.150522
. [PMID: 29022315] - Ran An, Luke A Moe. Regulation of Pyrroloquinoline Quinone-Dependent Glucose Dehydrogenase Activity in the Model Rhizosphere-Dwelling Bacterium Pseudomonas putida KT2440.
Applied and environmental microbiology.
2016 08; 82(16):4955-64. doi:
10.1128/aem.00813-16
. [PMID: 27287323] - J Wang, H J Zhang, L Xu, C Long, K G Samuel, H Y Yue, L L Sun, S G Wu, G H Qi. Dietary supplementation of pyrroloquinoline quinone disodium protects against oxidative stress and liver damage in laying hens fed an oxidized sunflower oil-added diet.
Animal : an international journal of animal bioscience.
2016 Jul; 10(7):1129-36. doi:
10.1017/s175173111600001x
. [PMID: 26837542] - J Z Wu, J H Huang, R Khanabdali, B Kalionis, S J Xia, W J Cai. Pyrroloquinoline quinone enhances the resistance to oxidative stress and extends lifespan upon DAF-16 and SKN-1 activities in C. elegans.
Experimental gerontology.
2016 07; 80(?):43-50. doi:
10.1016/j.exger.2016.04.008
. [PMID: 27090484] - Narendra Kumar, Anand Kar. Pyrroloquinoline quinone (PQQ) has potential to ameliorate streptozotocin-induced diabetes mellitus and oxidative stress in mice: A histopathological and biochemical study.
Chemico-biological interactions.
2015 Oct; 240(?):278-90. doi:
10.1016/j.cbi.2015.08.027
. [PMID: 26343954] - Muhammad Naveed, Younas Sohail, Nauman Khalid, Iftikhar Ahmed, Abdul Samad Mumtaz. Evaluation of Glucose Dehydrogenase and Pyrroloquinoline Quinine (pqq) Mutagenesis that Renders Functional Inadequacies in Host Plants.
Journal of microbiology and biotechnology.
2015 Aug; 25(8):1349-60. doi:
10.4014/jmb.1501.01075
. [PMID: 25839331] - Ashish Kumar Singh, Sumeet Kumar Pandey, Gourav Saha, Naresh Kumar Gattupalli. Pyrroloquinoline quinone (PQQ) producing Escherichia coli Nissle 1917 (EcN) alleviates age associated oxidative stress and hyperlipidemia, and improves mitochondrial function in ageing rats.
Experimental gerontology.
2015 Jun; 66(?):1-9. doi:
10.1016/j.exger.2015.04.001
. [PMID: 25843018] - Sumeet Pandey, Ashish Singh, Nirja Chaudhari, Laxmipriya P Nampoothiri, G Naresh Kumar. Protection against 1,2-di-methylhydrazine-induced systemic oxidative stress and altered brain neurotransmitter status by probiotic Escherichia coli CFR 16 secreting pyrroloquinoline quinone.
Current microbiology.
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FEMS microbiology letters.
2015 Mar; 362(5):. doi:
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. [PMID: 25743071] - K G Samuel, H J Zhang, J Wang, S G Wu, H Y Yue, L L Sun, G H Qi. Effects of dietary pyrroloquinoline quinone disodium on growth performance, carcass yield and antioxidant status of broiler chicks.
Animal : an international journal of animal bioscience.
2015 Mar; 9(3):409-16. doi:
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Poultry science.
2015 Feb; 94(2):215-25. doi:
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
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PloS one.
2015; 10(2):e0115722. doi:
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. [PMID: 25679509] - Narendra Kumar, Anand Kar. Pyrroloquinoline quinone ameliorates oxidative stress and lipid peroxidation in the brain of streptozotocin-induced diabetic mice.
Canadian journal of physiology and pharmacology.
2015 Jan; 93(1):71-9. doi:
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Journal of nutritional science and vitaminology.
2015; 61(3):233-40. doi:
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Regulatory toxicology and pharmacology : RTP.
2014 Oct; 70(1):107-21. doi:
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Cell biochemistry and function.
2014 Aug; 32(6):538-46. doi:
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Alcoholism, clinical and experimental research.
2014 Jul; 38(7):2127-37. doi:
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Applied biochemistry and biotechnology.
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PloS one.
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The Journal of nutritional biochemistry.
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PloS one.
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European journal of pharmacology.
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ACS nano.
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PloS one.
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PloS one.
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Applied and environmental microbiology.
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Zhonghua zheng xing wai ke za zhi = Zhonghua zhengxing waike zazhi = Chinese journal of plastic surgery.
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