Pyrroloquinoline quinone (BioDeep_00000004383)
Secondary id: BioDeep_00001867910
human metabolite PANOMIX_OTCML-2023 Endogenous 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 Homo sapiens(natural_products) 16.6%
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
Enzymes containing PQQ are called quinoproteins. PQQ and quinoproteins play a role in the redox metabolism and structural integrity of cells and tissues [PMID:2558842]. It was reported that aminoadipate semialdehyde dehydrogenase (AASDH) might also use PQQ as a cofactor, suggesting a possibility that PQQ is a vitamin in mammals. [PMID:12712191].
Believed to be a mammalian redox-cofactor vitamin (B group). Widely distributed in various foods such as vegetables and meat. Methoxatin is found in animal foods and green vegetables.
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
27 个代谢物同义名
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid; 4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-F)quinoline-2,7,9-tricarboxylic acid; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylic acid; 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylate; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9- tricarboxylate; 4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-F]quinoline-2,7,9-tricarboxylate; 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid; 2,4,6-Tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone; 2,7,9-Tricarboxy-1H-pyrrolo-(2,3-F)quinoline-4,5-dione; 2,7,9-Tricarboxy-1H-pyrrolo(2,3-F)quinoline-4,5-dione; 2,7,9-Tricarboxypyrroloquinoline quinone; Quinone, pyrrolo-quinoline; Quinone, pyrroloquinoline; Pyrrolo quinoline quinone; Pyrrolo-quinoline quinone; pyrroloquinoline quinone; Pyrroloquinoline-quinone; Coenzyme, PQQ; Cofactor, PQQ; PQQ, Coenzyme; PQQ Coenzyme; Coenzyme PQQ; PQQ Cofactor; methoxatin; PQQ; PQQ
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:18315
- KEGG: C00113
- PubChem: 1024
- HMDB: HMDB0013636
- Metlin: METLIN63125
- DrugBank: DB03205
- ChEMBL: CHEMBL1235421
- Wikipedia: Pyrroloquinoline_quinone
- MeSH: PQQ Cofactor
- KNApSAcK: C00053736
- foodb: FDB012848
- chemspider: 997
- CAS: 72909-34-3
- PMhub: MS000016801
- 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
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(2)
- quinate degradation I:
3-dehydroshikimate ⟶ H2O + protocatechuate
- shikimate degradation I:
3-dehydroshikimate ⟶ H2O + protocatechuate
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
6 个相关的物种来源信息
- 28211 - Alphaproteobacteria: LTS0120678
- 2 - Bacteria: LTS0120678
- 9606 - Homo sapiens: -
- 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
. [PMID: 35325831] - Lena J Daumann, Arjan Pol, Huub J M Op den Camp, N Cecilia Martinez-Gomez. A perspective on the role of lanthanides in biology: Discovery, open questions and possible applications.
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
. [PMID: 33142455] - Chenxi Wang, Boru Zhang, Hongyun Zhang, Wei Yang, Qingwei Meng, Baoming Shi, Anshan Shan. Effect of dietary pyrroloquinoline quinone disodium in sows on intestinal health of the offspring.
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
. [PMID: 32073012] - Junru Wen, Junwei Shen, Yajie Zhou, Xianhui Zhao, Zhensheng Dai, Yueling Jin. Pyrroloquinoline quinone attenuates isoproterenol hydrochloride‑induced cardiac hypertrophy in AC16 cells by inhibiting the NF‑κB signaling pathway.
International journal of molecular medicine.
2020 Mar; 45(3):873-885. doi:
10.3892/ijmm.2020.4463
. [PMID: 31922230] - Man You, Shumei Fang, Jacqueline MacDonald, Jianping Xu, Ze-Chun Yuan. Isolation and characterization of Burkholderia cenocepacia CR318, a phosphate solubilizing bacterium promoting corn growth.
Microbiological research.
2020 Mar; 233(?):126395. doi:
10.1016/j.micres.2019.126395
. [PMID: 31865096] - Jingjing Hao, Xiushi Ni, Sergio Giunta, Junzhen Wu, Xiaoping Shuang, Kangqiao Xu, Rui Li, Wei Zhang, Shijin Xia. Pyrroloquinoline quinone delays inflammaging induced by TNF-α through the p16/p21 and Jagged1 signalling pathways.
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:
10.1016/j.bbrc.2018.11.140
. [PMID: 30502093] - Haoxin Lv, Akio Tani. Genomic characterization of methylotrophy of Oharaeibacter diazotrophicus strain SM30T.
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
. [PMID: 28826139] - Liliana M Ludueña, Maria S Anzuay, Cynthia Magallanes-Noguera, Maria L Tonelli, Fernando J Ibañez, Jorge G Angelini, Adriana Fabra, Matthew McIntosh, Tania Taurian. Effects of P limitation and molecules from peanut root exudates on pqqE gene expression and pqq promoter activity in the phosphate-solubilizing strain Serratia sp. S119.
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:
10.1007/s00253-017-8207-7
. [PMID: 28283693] - Ruma Raghuvanshi, Archana Chaudhari, G Naresh Kumar. Amelioration of cadmium- and mercury-induced liver and kidney damage in rats by genetically engineered probiotic Escherichia coli Nissle 1917 producing pyrroloquinoline quinone with oral supplementation of citric acid.
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.
2015 May; 70(5):690-7. doi:
10.1007/s00284-014-0763-9
. [PMID: 25586077] - Mounira Ben Farhat, Ines Boukhris, Hichem Chouayekh. Mineral phosphate solubilization by Streptomyces sp. CTM396 involves the excretion of gluconic acid and is stimulated by humic acids.
FEMS microbiology letters.
2015 Mar; 362(5):. doi:
10.1093/femsle/fnv008
. [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:
10.1017/s1751731114002328
. [PMID: 25229409] - J Wang, H J Zhang, K G Samuel, C Long, S G Wu, H Y Yue, L L Sun, G H Qi. Effects of dietary pyrroloquinoline quinone disodium on growth, carcass characteristics, redox status, and mitochondria metabolism in broilers.
Poultry science.
2015 Feb; 94(2):215-25. doi:
10.3382/ps/peu050
. [PMID: 25609689] - Chunlai Liang, Xin Zhang, Wei Wang, Yan Song, Xudong Jia. A subchronic oral toxicity study on pyrroloquinoline quinone (PQQ) disodium salt in rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2015 Jan; 75(?):146-50. doi:
10.1016/j.fct.2014.11.005
. [PMID: 25445509] - Kouta Takeda, Hirotoshi Matsumura, Takuya Ishida, Masahiro Samejima, Hiroyuki Ohno, Makoto Yoshida, Kiyohiko Igarashi, Nobuhumi Nakamura. Characterization of a novel PQQ-dependent quinohemoprotein pyranose dehydrogenase from Coprinopsis cinerea classified into auxiliary activities family 12 in carbohydrate-active enzymes.
PloS one.
2015; 10(2):e0115722. doi:
10.1371/journal.pone.0115722
. [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:
10.1139/cjpp-2014-0270
. [PMID: 25474723] - Lijuan Zhao, Dongying Chen. Characterization of interactions between methoxatin disodium salt and human serum albumin by pressure-assisted capillary electrophoresis/frontal analysis and circular dichroism spectroscopy.
Biomedical chromatography : BMC.
2015 Jan; 29(1):123-8. doi:
10.1002/bmc.3248
. [PMID: 24849131] - Masahiko Nakano, Yuuki Kawasaki, Naoko Suzuki, Tsuyoshi Takara. Effects of Pyrroloquinoline Quinone Disodium Salt Intake on the Serum Cholesterol Levels of Healthy Japanese Adults.
Journal of nutritional science and vitaminology.
2015; 61(3):233-40. doi:
10.3177/jnsv.61.233
. [PMID: 26226960] - Masahiko Nakano, Hisaaki Takahashi, Seiko Koura, Catherine Chung, Shahrzad Tafazoli, Ashley Roberts. Acute and subchronic toxicity studies of pyrroloquinoline quinone (PQQ) disodium salt (BioPQQ™) in rats.
Regulatory toxicology and pharmacology : RTP.
2014 Oct; 70(1):107-21. doi:
10.1016/j.yrtph.2014.06.024
. [PMID: 24995591] - Narendra Kumar, Anand Kar, Sunanda Panda. Pyrroloquinoline quinone ameliorates l-thyroxine-induced hyperthyroidism and associated problems in rats.
Cell biochemistry and function.
2014 Aug; 32(6):538-46. doi:
10.1002/cbf.3048
. [PMID: 25048014] - Ashish K Singh, Sumeet K Pandey, Gattupalli Naresh Kumar. Pyrroloquinoline quinone-secreting probiotic Escherichia coli Nissle 1917 ameliorates ethanol-induced oxidative damage and hyperlipidemia in rats.
Alcoholism, clinical and experimental research.
2014 Jul; 38(7):2127-37. doi:
10.1111/acer.12456
. [PMID: 24930470] - Sumeet Pandey, Ashish Singh, Prasant Kumar, Archana Chaudhari, G Nareshkumar. Probiotic Escherichia coli CFR 16 producing pyrroloquinoline quinone (PQQ) ameliorates 1,2-dimethylhydrazine-induced oxidative damage in colon and liver of rats.
Applied biochemistry and biotechnology.
2014 Jun; 173(3):775-86. doi:
10.1007/s12010-014-0897-z
. [PMID: 24718737] - Lei Li, Ziwei Jiao, Lauren Hale, Wenliang Wu, Yanbin Guo. Disruption of gene pqqA or pqqB reduces plant growth promotion activity and biocontrol of crown gall disease by Rahnella aquatilis HX2.
PloS one.
2014; 9(12):e115010. doi:
10.1371/journal.pone.0115010
. [PMID: 25502691] - Calliandra B Harris, Winyoo Chowanadisai, Darya O Mishchuk, Mike A Satre, Carolyn M Slupsky, Robert B Rucker. Dietary pyrroloquinoline quinone (PQQ) alters indicators of inflammation and mitochondrial-related metabolism in human subjects.
The Journal of nutritional biochemistry.
2013 Dec; 24(12):2076-84. doi:
10.1016/j.jnutbio.2013.07.008
. [PMID: 24231099] - Gerasimos F Kremmydas, Anastasia P Tampakaki, Dimitrios G Georgakopoulos. Characterization of the biocontrol activity of pseudomonas fluorescens strain X reveals novel genes regulated by glucose.
PloS one.
2013; 8(4):e61808. doi:
10.1371/journal.pone.0061808
. [PMID: 23596526] - Dezheng Gong, Chengyan Geng, Liping Jiang, Yoshinori Aoki, Masahiko Nakano, Laifu Zhong. Effect of pyrroloquinoline quinone on neuropathic pain following chronic constriction injury of the sciatic nerve in rats.
European journal of pharmacology.
2012 Dec; 697(1-3):53-8. doi:
10.1016/j.ejphar.2012.09.052
. [PMID: 23063836] - Ariel Efrati, Omer Yehezkeli, Ran Tel-Vered, Dorit Michaeli, Rachel Nechushtai, Itamar Willner. Electrochemical switching of photoelectrochemical processes at CdS QDs and photosystem I-modified electrodes.
ACS nano.
2012 Oct; 6(10):9258-66. doi:
10.1021/nn3037286
. [PMID: 23009682] - H S Misra, Y S Rajpurohit, N P Khairnar. Pyrroloquinoline-quinone and its versatile roles in biological processes.
Journal of biosciences.
2012 Jun; 37(2):313-25. doi:
10.1007/s12038-012-9195-5
. [PMID: 22581337] - Akio Tani, Yuichiro Takai, Ikko Suzukawa, Motomu Akita, Haruhiko Murase, Kazuhide Kimbara. Practical application of methanol-mediated mutualistic symbiosis between Methylobacterium species and a roof greening moss, Racomitrium japonicum.
PloS one.
2012; 7(3):e33800. doi:
10.1371/journal.pone.0033800
. [PMID: 22479445] - Mariana H Massaoka, Alisson L Matsuo, Carlos R Figueiredo, Camyla F Farias, Natália Girola, Denise C Arruda, Jorge A B Scutti, Paulete Romoff, Oriana A Favero, Marcelo J P Ferreira, João H G Lago, Luiz R Travassos. Jacaranone induces apoptosis in melanoma cells via ROS-mediated downregulation of Akt and p38 MAPK activation and displays antitumor activity in vivo.
PloS one.
2012; 7(6):e38698. doi:
10.1371/journal.pone.0038698
. [PMID: 22701695] - Joana Beatrice Meyer, Michele Frapolli, Christoph Keel, Monika Maurhofer. Pyrroloquinoline quinone biosynthesis gene pqqC, a novel molecular marker for studying the phylogeny and diversity of phosphate-solubilizing pseudomonads.
Applied and environmental microbiology.
2011 Oct; 77(20):7345-54. doi:
10.1128/aem.05434-11
. [PMID: 21856827] - Hao-huan Li, Bin He, Hao Peng, Shi-qing Liu. [Effects of pyrroloquinoline quinone on proliferation and expression of c-fos, c-jun, CREB and PCNA in cultured Schwann cells].
Zhonghua zheng xing wai ke za zhi = Zhonghua zhengxing waike zazhi = Chinese journal of plastic surgery.
2011 Jul; 27(4):298-303. doi:
NULL
. [PMID: 22097319] - Boris V Nemzer, Liliana C Rodriguez, Linda Hammond, Robert Disilvestro, John M Hunter, Zbigniew Pietrzkowski. Acute reduction of serum 8-iso-PGF2-alpha and advanced oxidation protein products in vivo by a polyphenol-rich beverage; a pilot clinical study with phytochemical and in vitro antioxidant characterization.
Nutrition journal.
2011 Jun; 10(?):67. doi:
10.1186/1475-2891-10-67
. [PMID: 21676230] - Laura B Zimmerman, Brittany V Worley, Edmund F Palermo, Jeffrey R Brender, Kyung-Dall Lee, Kenichi Kuroda, Ayyalusamy Ramamoorthy, Mark E Meyerhoff. Absorbance-based assay for membrane disruption by antimicrobial peptides and synthetic copolymers using pyrroloquinoline quinone-loaded liposomes.
Analytical biochemistry.
2011 Apr; 411(2):194-9. doi:
10.1016/j.ab.2011.01.009
. [PMID: 21237129] - Kazuo Mukai, Aya Ouchi, Masahiko Nakano. Kinetic study of the quenching reaction of singlet oxygen by Pyrroloquinolinequinol (PQQH(2), a reduced form of Pyrroloquinolinequinone) in micellar solution.
Journal of agricultural and food chemistry.
2011 Mar; 59(5):1705-12. doi:
10.1021/jf104420y
. [PMID: 21309575] - Kathryn Bauerly, Calliandra Harris, Winyoo Chowanadisai, James Graham, Peter J Havel, Eskouhie Tchaparian, Mike Satre, Joel S Karliner, Robert B Rucker. Altering pyrroloquinoline quinone nutritional status modulates mitochondrial, lipid, and energy metabolism in rats.
PloS one.
2011; 6(7):e21779. doi:
10.1371/journal.pone.0021779
. [PMID: 21814553] - Manoj Shrivastava, Yogendra S Rajpurohit, Hari S Misra, S F D'Souza. Survival of phosphate-solubilizing bacteria against DNA damaging agents.
Canadian journal of microbiology.
2010 Oct; 56(10):822-30. doi:
10.1139/w10-067
. [PMID: 20962905] - Malika Ammam, Jan Fransaer. Micro-biofuel cell powered by glucose/O2 based on electro-deposition of enzyme, conducting polymer and redox mediators: preparation, characterization and performance in human serum.
Biosensors & bioelectronics.
2010 Feb; 25(6):1474-80. doi:
10.1016/j.bios.2009.11.001
. [PMID: 20005695] - Burla Sashidhar, Krishna Kishore Inampudi, Lalitha Guruprasad, Anil Kondreddy, Kodetham Gopinath, Appa Rao Podile. Highly conserved Asp-204 and Gly-776 are important for activity of the quinoprotein glucose dehydrogenase of Escherichia coli and for mineral phosphate solubilization.
Journal of molecular microbiology and biotechnology.
2010; 18(2):109-19. doi:
10.1159/000293819
. [PMID: 20215780] - Yan Bin Guo, Jinyun Li, Lei Li, Fan Chen, Wenliang Wu, Jianhui Wang, Huimin Wang. Mutations that disrupt either the pqq or the gdh gene of Rahnella aquatilis abolish the production of an antibacterial substance and result in reduced biological control of grapevine crown gall.
Applied and environmental microbiology.
2009 Nov; 75(21):6792-803. doi:
10.1128/aem.00902-09
. [PMID: 19734331] - Robert Rucker, Winyoo Chowanadisai, Masahiko Nakano. Potential physiological importance of pyrroloquinoline quinone.
Alternative medicine review : a journal of clinical therapeutic.
2009 Sep; 14(3):268-77. doi:
. [PMID: 19803551]
- Katelijne M J Floré, Joris R Delanghe. Analytical interferences in point-of-care testing glucometers by icodextrin and its metabolites: an overview.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis.
2009 Jul; 29(4):377-83. doi:
. [PMID: 19602602]
- Peng Zhang, Yongping Xu, Jingxian Sun, Xiaoyu Li, Linhui Wang, Liji Jin. Protection of pyrroloquinoline quinone against methylmercury-induced neurotoxicity via reducing oxidative stress.
Free radical research.
2009 Mar; 43(3):224-33. doi:
10.1080/10715760802677348
. [PMID: 19191107] - Song Hee Han, Chul Hong Kim, Jang Hoon Lee, Ju Yeon Park, Song Mi Cho, Seur Kee Park, Kil Yong Kim, Hari B Krishnan, Young Cheol Kim. Inactivation of pqq genes of Enterobacter intermedium 60-2G reduces antifungal activity and induction of systemic resistance.
FEMS microbiology letters.
2008 May; 282(1):140-6. doi:
10.1111/j.1574-6968.2008.01120.x
. [PMID: 18355275] - Okhee Choi, Jinwoo Kim, Jung-Gun Kim, Yeonhwa Jeong, Jae Sun Moon, Chang Seuk Park, Ingyu Hwang. Pyrroloquinoline quinone is a plant growth promotion factor produced by Pseudomonas fluorescens B16.
Plant physiology.
2008 Feb; 146(2):657-68. doi:
10.1104/pp.107.112748
. [PMID: 18055583] - Ruyi Xue, Si Zhang, Chunhui Deng, Ling Dong, Taotao Liu, Jiyao Wang, Hongyi Wu, Jianxin Gu, Xizhong Shen. Simultaneous determination of blood glucose and isoleucine levels in rats after chronic alcohol exposure by microwave-assisted derivatization and isotope dilution gas chromatography/mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2008; 22(2):245-52. doi:
10.1002/rcm.3350
. [PMID: 18085507] - Valérie de Crécy-Lagard, Basma El Yacoubi, Rocío Díaz de la Garza, Alexandre Noiriel, Andrew D Hanson. Comparative genomics of bacterial and plant folate synthesis and salvage: predictions and validations.
BMC genomics.
2007 Jul; 8(?):245. doi:
10.1186/1471-2164-8-245
. [PMID: 17645794] - Janja Trcek, Katarina Jernejc, Kazunobu Matsushita. The highly tolerant acetic acid bacterium Gluconacetobacter europaeus adapts to the presence of acetic acid by changes in lipid composition, morphological properties and PQQ-dependent ADH expression.
Extremophiles : life under extreme conditions.
2007 Jul; 11(4):627-35. doi:
10.1007/s00792-007-0077-y
. [PMID: 17487444] - Takeshi Kumazawa, Takaki Hiwasa, Masaki Takiguchi, Osamu Suzuki, Keizo Sato. Activation of Ras signaling pathways by pyrroloquinoline quinone in NIH3T3 mouse fibroblasts.
International journal of molecular medicine.
2007 May; 19(5):765-70. doi:
10.3892/ijmm.19.5.765
. [PMID: 17390081] - K A Bauerly, D H Storms, C B Harris, S Hajizadeh, M Y Sun, C P Cheung, M A Satre, A J Fascetti, E Tchaparian, R B Rucker. Pyrroloquinoline quinone nutritional status alters lysine metabolism and modulates mitochondrial DNA content in the mouse and rat.
Biochimica et biophysica acta.
2006 Nov; 1760(11):1741-8. doi:
10.1016/j.bbagen.2006.07.009
. [PMID: 17029795] - Ramesh Saxena, Cheryl West. Peritoneal dialysis: a primary care perspective.
Journal of the American Board of Family Medicine : JABFM.
2006 Jul; 19(4):380-9. doi:
10.3122/jabfm.19.4.380
. [PMID: 16809653] - Bo-qing Zhu, Ursula Simonis, Gary Cecchini, Hui-zhong Zhou, Luyi Li, John R Teerlink, Joel S Karliner. Comparison of pyrroloquinoline quinone and/or metoprolol on myocardial infarct size and mitochondrial damage in a rat model of ischemia/reperfusion injury.
Journal of cardiovascular pharmacology and therapeutics.
2006 Jun; 11(2):119-28. doi:
10.1177/1074248406288757
. [PMID: 16891289] - Tracy Stites, David Storms, Kathryn Bauerly, James Mah, Calliandra Harris, Andrea Fascetti, Quinton Rogers, Eskouhie Tchaparian, Michael Satre, Robert B Rucker. Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice.
The Journal of nutrition.
2006 Feb; 136(2):390-6. doi:
10.1093/jn/136.2.390
. [PMID: 16424117] - Robert Rucker, David Storms, Annemarie Sheets, Eskouhie Tchaparian, Andrea Fascetti. Biochemistry: is pyrroloquinoline quinone a vitamin?.
Nature.
2005 Feb; 433(7025):E10-1; discussion E11. doi:
10.1038/nature03323
. [PMID: 15689994] - Bo-Qing Zhu, Hui-Zhong Zhou, John R Teerlink, Joel S Karliner. Pyrroloquinoline quinone (PQQ) decreases myocardial infarct size and improves cardiac function in rat models of ischemia and ischemia/reperfusion.
Cardiovascular drugs and therapy.
2004 Nov; 18(6):421-31. doi:
10.1007/s10557-004-6219-x
. [PMID: 15770429] - Hiroshi Tsuneki, Mitsuyo Ishizuka, Miki Terasawa, Jin-Bin Wu, Toshiyasu Sasaoka, Ikuko Kimura. Effect of green tea on blood glucose levels and serum proteomic patterns in diabetic (db/db) mice and on glucose metabolism in healthy humans.
BMC pharmacology.
2004 Aug; 4(?):18. doi:
10.1186/1471-2210-4-18
. [PMID: 15331020] - Chul Hong Kim, Song Hee Han, Kil Yong Kim, Baik Ho Cho, Yong Hwan Kim, Bon Sung Koo, Young Cheol Kim. Cloning and expression of pyrroloquinoline quinone (PQQ) genes from a phosphate-solubilizing bacterium Enterobacter intermedium.
Current microbiology.
2003 Dec; 47(6):457-61. doi:
10.1007/s00284-003-4068-7
. [PMID: 14756528] - Kai He, Hitoshi Nukada, Teiji Urakami, Michael P Murphy. Antioxidant and pro-oxidant properties of pyrroloquinoline quinone (PQQ): implications for its function in biological systems.
Biochemical pharmacology.
2003 Jan; 65(1):67-74. doi:
10.1016/s0006-2952(02)01453-3
. [PMID: 12473380] - Yumin Zhang, Paul A Rosenberg. The essential nutrient pyrroloquinoline quinone may act as a neuroprotectant by suppressing peroxynitrite formation.
The European journal of neuroscience.
2002 Sep; 16(6):1015-24. doi:
10.1046/j.1460-9568.2002.02169.x
. [PMID: 12383230] - Takayo Inoue, Jon R Kirchhoff. Determination of thiols by capillary electrophoresis with amperometric detection at a coenzyme pyrroloquinoline quinone modified electrode.
Analytical chemistry.
2002 Mar; 74(6):1349-54. doi:
10.1021/ac0108515
. [PMID: 11922303] - C E Bernardelli, M F Luna, M L Galar, J L Boiardi. Periplasmic PQQ-dependent glucose oxidation in free-living and symbiotic rhizobia.
Current microbiology.
2001 May; 42(5):310-5. doi:
10.1007/s002840010222
. [PMID: 11400050] - Alisa S Vangnai, Daniel J Arp. An inducible 1-butanol dehydrogenase, a quinohaemoprotein, is involved in the oxidation of butane by 'Pseudomonas butanovora'.
Microbiology (Reading, England).
2001 Mar; 147(Pt 3):745-756. doi:
10.1099/00221287-147-3-745
. [PMID: 11238982] - K Miyauchi, T Urakami, H Abeta, H Shi, N Noguchi, E Niki. Action of pyrroloquinolinequinol as an antioxidant against lipid peroxidation in solution.
Antioxidants & redox signaling.
1999; 1(4):547-54. doi:
10.1089/ars.1999.1.4-547
. [PMID: 11233151] - K Y Kim, D Jordan, H B Krishnan. Expression of genes from Rahnella aquatilis that are necessary for mineral phosphate solubilization in Escherichia coli.
FEMS microbiology letters.
1998 Feb; 159(1):121-7. doi:
10.1111/j.1574-6968.1998.tb12850.x
. [PMID: 9485602] - T Urakami, A Tanaka, T Tanimoto, E Niki. Synthesis and aldose reductase-inhibitory activity of imidazopyrroloquinoline esters.
Chemical & pharmaceutical bulletin.
1996 Aug; 44(8):1493-7. doi:
10.1248/cpb.44.1493
. [PMID: 8795268] - E A Decker. The role of phenolics, conjugated linoleic acid, carnosine, and pyrroloquinoline quinone as nonessential dietary antioxidants.
Nutrition reviews.
1995 Mar; 53(3):49-58. doi:
10.1111/j.1753-4887.1995.tb01502.x
. [PMID: 7770184] - Y Esaka, Y Yamaguchi, K Kano, M Goto. Separation of amino acid-oxazole derivatives of the redox coenzyme pyrroloquinoline quinone by capillary zone electrophoresis.
Journal of chromatography. A.
1993 Oct; 652(1):225-32. doi:
10.1016/0021-9673(93)80663-s
. [PMID: 8281258] - S Marini, B Giardina, G F Fasciglione, A Finazzi-Agrò. Monoclonal antibody recognizes different quinone moieties in enzymes.
The Journal of biological chemistry.
1993 Jun; 268(18):13352-5. doi:
10.1016/s0021-9258(19)38658-2
. [PMID: 8390461] - P M Gallop, M A Paz, R Flückiger, E Henson. Is the antioxidant, anti-inflammatory putative new vitamin, PQQ, involved with nitric oxide in bone metabolism?.
Connective tissue research.
1993; 29(2):153-61. doi:
10.3109/03008209309014242
. [PMID: 8403896] - Y Naito, T Kumazawa, I Kino, O Suzuki. Effects of pyrroloquinoline quinone (PQQ) and PQQ-oxazole on DNA synthesis of cultured human fibroblasts.
Life sciences.
1993; 52(24):1909-15. doi:
10.1016/0024-3205(93)90631-c
. [PMID: 8389410]