Dicumarol (BioDeep_00000000776)

   

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs Volatile Flavor Compounds natural product


代谢物信息卡片


3,3 inverted exclamation mark -Methylenebis(4-hydroxy-2H-chromen-2-one)

化学式: C19H12O6 (336.06338519999997)
中文名称: 双羟香豆素
谱图信息: 最多检出来源 Homo sapiens(blood) 0.14%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
InChI: InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

描述信息

Dicoumarol is a hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group. Related to warfarin, it has been used as an anticoagulant. It has a role as a vitamin K antagonist, an anticoagulant, an EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor and a Hsp90 inhibitor.
Dicoumarol is an oral anticoagulant agent that works by interfering with the metabolism of vitamin K. In addition to its clinical use, it is also used in biochemical experiments as an inhibitor of reductases.
Dicumarol is a natural product found in Homo sapiens and Viola arvensis with data available.
Dicumarol is a hydroxycoumarin originally isolated from molding sweet-clover hay, with anticoagulant and vitamin K depletion activities. Dicumarol is a competitive inhibitor of vitamin K epoxide reductase; thus, it inhibits vitamin K recycling and causes depletion of active vitamin K in blood. This prevents the formation of the active form of prothrombin and several other coagulant enzymes, and inhibits blood clotting.
Dicumarol is only found in individuals that have used or taken this drug. It is an oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem] Dicumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.
Dicumarol is only found in individuals that have used or taken this drug. It is an oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]Dicumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
B - Blood and blood forming organs > B01 - Antithrombotic agents > B01A - Antithrombotic agents > B01AA - Vitamin k antagonists
A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group.
D006401 - Hematologic Agents > D000925 - Anticoagulants > D015110 - 4-Hydroxycoumarins
C78275 - Agent Affecting Blood or Body Fluid > C263 - Anticoagulant Agent
D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents
Isolated from Melilotus alba (white melilot)

同义名列表

130 个代谢物同义名

3,3 inverted exclamation mark -Methylenebis(4-hydroxy-2H-chromen-2-one); 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one; 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-2H-chromen-2-one; 4-hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)methyl]chromen-2-one; Dicumarol, United States Pharmacopeia (USP) Reference Standard; 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one; 2H-1-Benzopyran-2-one, 3,3-methylenebis[4-hydroxy- (9CI); 2H-1-Benzopyran-2-one), 3,3-methylenebis(4-hydroxy-; 2H-1-Benzopyran-2-one, 3,3-methylenebis(4-hydroxy)-; 2H-1-Benzopyran-2-one, 3,3-methylenebis(4-hydroxy-; 2H-1-Benzopyran-2-one, 3,3-methylenebis[4-hydroxy-; 3,3-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one); 3,3-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]; 2H-1-Benzopyran-2-one],3-methylenebis[4-hydroxy-; 2H-1-Benzopyran-2-one,3-methylenebis[4-hydroxy-; 3,3-methanediylbis(4-hydroxy-2H-chromen-2-one); 3,3-Methylene-bis(4-hydroxycoumarine) [French]; 3,3-Methyleen-bis(4-hydroxy-cumarine) [Dutch]; 3,3-Metilen-bis(4-idrossi-cumarina) [Italian]; 5-19-06-00682 (Beilstein Handbook Reference); 3,3-methylenebis(4-hydroxy-2H-chromen-2-one); 3,3-Methylen-bis(4-hydroxy-cumarin) [German]; Coumarin, 3,3-methylenebis[4-hydroxy- (8CI); 3,3-Methylenebis[4-hydroxy-1,2-benzopyrone]; 3,3-Methylenebis(4-hydroxy-1,2-benzopyrone); 3,3-Methylene-bis(4-hydroxycoumarin), 99\\%; 4,4-Dihydroxy-3,3-methylene bis coumarin; Coumarin, 3,3-methylenebis(4-hydroxy-; 3,3-Methyleen-bis(4-hydroxy-cumarine); 3,3-Methylene-bis(4-hydroxycoumarine); Bis-3,3-(4-oxycoumarinyl)ethylacetate; Bis-3,3-(4-hydroxycoumarinyl)methane; 3,3-Methylene-bis(4-hydroxycoumarin); Di-4-hydroxy-3,3-methylenedicoumarin; 3,3-Methylenebis[4-hydroxycoumarin]; 3,3-Methylen-bis(4-hydroxy-cumarin); 3,3-methylenebis(4-hydroxycoumarin); 3,3-Metilen-bis(4-idrossi-cumarina); 3,3-Methylenebis(4-hydroxycoumarin); 3,3-methylenebis(4-hydroxy-coumarin; 3,3-methylenebis[4-hydroxycoumarin; Bis(4-hydroxycoumarin-3-yl)methane; Coumarin,3-methylenebis[4-hydroxy-; Di-(4-hydroxy-3-coumarinyl)methane; uncoupler of oxidative respiration; ETHYLM-TRIFLUOROMETHYLCARBANILATE; WLN: T66 BOVJ EQ D1- DT66 BOVJ EQ; 3,3-Methylenbis(4-hydroxycumarin); DICOUMAROLUM [WHO-IP LATIN]; Dicoumarol - CAS 66-76-2; Dicoumarolum (INN-Latin); Dicoumarolum [INN-Latin]; Dicumarol (INN-Spanish); Dicumarol [INN-Spanish]; DICUMAROL [ORANGE BOOK]; Dicumarol [USAN:USP]; Dicumarol (USAN:USP); DICOUMAROL [WHO-DD]; Dwukumarol [Polish]; bis-hydroxycoumarin; DICOUMAROL [WHO-IP]; Bishydroxycoumarin; DICOUMAROL (MART.); DICOUMAROL [MART.]; Prestwick0_000785; Prestwick1_000785; Prestwick2_000785; Dicumarolo [DCIT]; DICUMAROL [VANDF]; Prestwick3_000785; Dicoumarol (INN); Spectrum3_000387; Spectrum4_000508; DICUMAROL [HSDB]; 3,2-benzopyrone]; Spectrum2_000144; Spectrum5_000871; Dicumarol (USAN); Dicumarol [USAN]; Dicoumarol [INN]; ChemDiv2_003436; UNII-7QID3E7BG7; Dicumarol (TN); DICUMAROL [MI]; Tox21_110357_1; BPBio1_000980; DivK1c_000896; Oprea1_150990; Antitrombosin; KBio2_003213; KBio2_005781; KBio3_001393; Anathrombase; Prestwick_90; Tox21_110357; KBio1_000896; Dicoumarolum; KBio2_000645; Dicumarolum; IDI1_000896; Dicumarinum; CAS-66-76-2; Baracoumin; Dicumarine; Dicoumerol; Dicoumarol; Dwukumarol; Dicumarolo; 7QID3E7BG7; Dicumaol R; dicoumarin; Apekumarol; Dicumarol; Trombosan; Dikumarol; AI3-14546; melitoxin; Temparin; Dicoumal; Dufalone; Dicumol; Kumoran; B01AA01; Dicuman; Acadyl; Acavyl; Cumid; Cuma; Dicumarol; Dicumarol



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(7)

PlantCyc(4)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 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

  • Wenjie Ge, Xian Zhang, Qing Wang, Jianjie Mao, Pengfei Jia, Jianping Cai. Dicoumarol attenuates NLRP3 inflammasome activation to inhibit inflammation and fibrosis in knee osteoarthritis. Molecular medicine reports. 2024 Jun; 29(6):. doi: 10.3892/mmr.2024.13224. [PMID: 38639180]
  • Na Zhu, Xu-Dong Zhu, Yi-Sheng Yang, Fei-Xia Yan, Peng Zhang, Lin-Chun Wan, Yi Wu, Li-Ping Huang. [Different processed products of Polygonati Rhizoma treat Alzheimer's disease in rats: urine metabolomics based on UPLC-Q/TOF-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Dec; 48(24):6663-6675. doi: 10.19540/j.cnki.cjcmm.20231019.301. [PMID: 38212026]
  • Yerlan M Suleimen, Rani A Jose, Raigul N Suleimen, Margarita Y Ishmuratova, Suzanne Toppet, Wim Dehaen, Aisha A Alsfouk, Eslam B Elkaeed, Ibrahim H Eissa, Ahmed M Metwaly. Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from Artemisia glauca. Molecules (Basel, Switzerland). 2022 Mar; 27(7):. doi: 10.3390/molecules27072281. [PMID: 35408682]
  • Lisa Maier, Camille V Goemans, Jakob Wirbel, Michael Kuhn, Claudia Eberl, Mihaela Pruteanu, Patrick Müller, Sarela Garcia-Santamarina, Elisabetta Cacace, Boyao Zhang, Cordula Gekeler, Tisya Banerjee, Exene Erin Anderson, Alessio Milanese, Ulrike Löber, Sofia K Forslund, Kiran Raosaheb Patil, Michael Zimmermann, Bärbel Stecher, Georg Zeller, Peer Bork, Athanasios Typas. Unravelling the collateral damage of antibiotics on gut bacteria. Nature. 2021 11; 599(7883):120-124. doi: 10.1038/s41586-021-03986-2. [PMID: 34646011]
  • Medjda Bellamri, Kyle Brandt, Christina V Brown, Ming-Tsang Wu, Robert J Turesky. Cytotoxicity and genotoxicity of the carcinogen aristolochic acid I (AA-I) in human bladder RT4 cells. Archives of toxicology. 2021 06; 95(6):2189-2199. doi: 10.1007/s00204-021-03059-3. [PMID: 33938965]
  • Lídia Alcoberro Torres, Eduard Claver Garrido, Pedro Moliner Borja. Thrombus in the right atrium after COVID-19 pneumonia. Revista espanola de cardiologia (English ed.). 2020 10; 73(10):845. doi: 10.1016/j.rec.2020.06.023. [PMID: 32773347]
  • Halley Shukla, Gabriella Gaje, Ashkon Koucheki, Ho Young Lee, Xiaolun Sun, Michael A Trush, Hong Zhu, Y Robert Li, Zhenquan Jia. NADPH-quinone oxidoreductase-1 mediates Benzo-[a]-pyrene-1,6-quinone-induced cytotoxicity and reactive oxygen species production in human EA.hy926 endothelial cells. Toxicology and applied pharmacology. 2020 10; 404(?):115180. doi: 10.1016/j.taap.2020.115180. [PMID: 32739527]
  • Meilin Liu, Wei Song, Xi Du, Jingtian Su, Kang Dong, Yong Chen, Zhihong Peng. NQO1-Selective Activated Prodrug of Triptolide: Synthesis and Antihepatocellular Carcinoma Activity Evaluation. ACS medicinal chemistry letters. 2018 Dec; 9(12):1253-1257. doi: 10.1021/acsmedchemlett.8b00404. [PMID: 30613335]
  • Dušica Simijonović, Evangelia-Eirini Vlachou, Zorica D Petrović, Dimitra J Hadjipavlou-Litina, Κonstantinos E Litinas, Nevena Stanković, Nezrina Mihović, Milan P Mladenović. Dicoumarol derivatives: Green synthesis and molecular modelling studies of their anti-LOX activity. Bioorganic chemistry. 2018 10; 80(?):741-752. doi: 10.1016/j.bioorg.2018.07.021. [PMID: 30077781]
  • Katarína Hroboňová, Andrea Machyňáková, Jozef Čižmárik. Determination of dicoumarol in Melilotus officinalis L. by using molecularly imprinted polymer solid-phase extraction coupled with high performance liquid chromatography. Journal of chromatography. A. 2018 Mar; 1539(?):93-102. doi: 10.1016/j.chroma.2018.01.043. [PMID: 29395163]
  • Shih-Yu Chang, Elijah J Weber, Viktoriya S Sidorenko, Alenka Chapron, Catherine K Yeung, Chunying Gao, Qingcheng Mao, Danny Shen, Joanne Wang, Thomas A Rosenquist, Kathleen G Dickman, Thomas Neumann, Arthur P Grollman, Edward J Kelly, Jonathan Himmelfarb, David L Eaton. Human liver-kidney model elucidates the mechanisms of aristolochic acid nephrotoxicity. JCI insight. 2017 11; 2(22):. doi: 10.1172/jci.insight.95978. [PMID: 29202460]
  • Manuel Anguita-Sánchez, Pascual Marco-Vera, Francisco J Alonso-Moreno, Fernando Arribas-Ynsaurriaga, Jaime Gállego-Culleré, Jesús Honorato-Pérez, Carmen Suárez-Fernández. [Perception of physicians on factors that influence the choice of a dicoumarin or a new oral anticoagulant in patients with non-valvular atrial fibrillation]. Atencion primaria. 2016 Oct; 48(8):527-534. doi: 10.1016/j.aprim.2015.11.004. [PMID: 26971361]
  • Duru Aras, Ozgur Cinar, Zeynep Cakar, Sinan Ozkavukcu, Alp Can. Can dicoumarol be used as a gonad-safe anticancer agent: an in vitro and in vivo experimental study. Molecular human reproduction. 2016 Jan; 22(1):57-67. doi: 10.1093/molehr/gav065. [PMID: 26612783]
  • Marie Stiborová, Kateřina Levová, František Bárta, Miroslav Šulc, Eva Frei, Volker M Arlt, Heinz H Schmeiser. The influence of dicoumarol on the bioactivation of the carcinogen aristolochic acid I in rats. Mutagenesis. 2014 May; 29(3):189-200. doi: 10.1093/mutage/geu004. [PMID: 24598128]
  • Eun Jung Park, Kyoung-Jin Min, Kyeong Sook Choi, Taeg Kyu Kwon. Dicoumarol sensitizes renal cell carcinoma Caki cells to TRAIL-induced apoptosis through down-regulation of Bcl-2, Mcl-1 and c-FLIP in a NQO1-independent manner. Experimental cell research. 2014 Apr; 323(1):144-154. doi: 10.1016/j.yexcr.2014.01.009. [PMID: 24462458]
  • Mei-Chi Chang, Yi-Jane Chen, Hsiao-Hua Chang, Chiu-Po Chan, Chien-Yang Yeh, Yin-Lin Wang, Ru-Hsiu Cheng, Liang-Jiunn Hahn, Jiiang-Huei Jeng. Areca nut components affect COX-2, cyclin B1/cdc25C and keratin expression, PGE2 production in keratinocyte is related to reactive oxygen species, CYP1A1, Src, EGFR and Ras signaling. PloS one. 2014; 9(7):e101959. doi: 10.1371/journal.pone.0101959. [PMID: 25051199]
  • Marie Stiborova, Katerina Levova, Frantisek Barta, Helena Dracinska, Miroslav Sulc, Petr Hodek, Eva Frei, Volker M Arlt, Heinz H Schmeiser. Dicoumarol inhibits rat NAD(P)H:quinone oxidoreductase in vitro and induces its expression in vivo. Neuro endocrinology letters. 2014; 35 Suppl 2(?):123-32. doi: . [PMID: 25638376]
  • Yicun Wu, Jin Dai, Weilin Zhang, Rong Yan, Yiwen Zhang, Changgeng Ruan, Kesheng Dai. Arsenic trioxide induces apoptosis in human platelets via C-Jun NH2-terminal kinase activation. PloS one. 2014; 9(1):e86445. doi: 10.1371/journal.pone.0086445. [PMID: 24466103]
  • Jing Han, Lidan Sun, Yingying Chu, Zheng Li, Dandan Huang, Xiaoyun Zhu, Hai Qian, Wenlong Huang. Design, synthesis, and biological activity of novel dicoumarol glucagon-like peptide 1 conjugates. Journal of medicinal chemistry. 2013 Dec; 56(24):9955-68. doi: 10.1021/jm4017448. [PMID: 24308627]
  • Jonas Šarlauskas, Aušra Nemeikaitė-Čėnienė, Lina Misevičienė, Kastis Krikštopaitis, Žilvinas Anusevičius, Narimantas Čėnas. Redox properties and prooxidant cytotoxicity of a neuroleptic agent 6,7-dinitrodihydroquinoxaline-2,3-dione (DNQX). Acta biochimica Polonica. 2013; 60(2):227-31. doi: . [PMID: 23757451]
  • Andrzej Woznica, Agnieszka Nowak, Przemyslaw Ziemski, Mirosław Kwasniewski, Tytus Bernas. Stimulatory effect of xenobiotics on oxidative electron transport of chemolithotrophic nitrifying bacteria used as biosensing element. PloS one. 2013; 8(1):e53484. doi: 10.1371/journal.pone.0053484. [PMID: 23326438]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Raquel Urtasun, Francisco Javier Cubero, Natalia Nieto. Oxidative stress modulates KLF6Full and its splice variants. Alcoholism, clinical and experimental research. 2012 Nov; 36(11):1851-62. doi: 10.1111/j.1530-0277.2012.01798.x. [PMID: 22486562]
  • Alexandra Reichstein, Silke Vortherms, Sven Bannwitz, Jan Tentrop, Helge Prinz, Klaus Müller. Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide. Journal of medicinal chemistry. 2012 Aug; 55(16):7273-84. doi: 10.1021/jm3009597. [PMID: 22845014]
  • Min Chen, Likun Gong, Xinming Qi, Guozhen Xing, Yang Luan, Yuanfeng Wu, Ying Xiao, Jun Yao, Yan Li, Xiang Xue, Guoyu Pan, Jin Ren. Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Aug; 122(2):288-96. doi: 10.1093/toxsci/kfr138. [PMID: 21613233]
  • Xiao Wu, Sébastien Monchy, Safiyh Taghavi, Wei Zhu, Juan Ramos, Daniel van der Lelie. Comparative genomics and functional analysis of niche-specific adaptation in Pseudomonas putida. FEMS microbiology reviews. 2011 Mar; 35(2):299-323. doi: 10.1111/j.1574-6976.2010.00249.x. [PMID: 20796030]
  • Carlos Enrique Guerrero-Beltrán, Mariel Calderón-Oliver, Eduardo Martínez-Abundis, Edilia Tapia, Guillermo Zarco-Márquez, Cecilia Zazueta, José Pedraza-Chaverri. Protective effect of sulforaphane against cisplatin-induced mitochondrial alterations and impairment in the activity of NAD(P)H: quinone oxidoreductase 1 and γ glutamyl cysteine ligase: studies in mitochondria isolated from rat kidney and in LLC-PK1 cells. Toxicology letters. 2010 Nov; 199(1):80-92. doi: 10.1016/j.toxlet.2010.08.009. [PMID: 20732396]
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  • Ataru Higa, Yuko Mori, Yoshie Kitamura. Iron deficiency induces changes in riboflavin secretion and the mitochondrial electron transport chain in hairy roots of Hyoscyamus albus. Journal of plant physiology. 2010 Jul; 167(11):870-8. doi: 10.1016/j.jplph.2010.01.011. [PMID: 20181408]
  • An S Tan, Michael V Berridge. Evidence for NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone-dependent redox cycling via plasma membrane electron transport: A sensitive cellular assay for NQO1. Free radical biology & medicine. 2010 Feb; 48(3):421-9. doi: 10.1016/j.freeradbiomed.2009.11.016. [PMID: 19932748]
  • Hai Yan Zhou, Jun Li Hong, Pan Shu, Yue Juan Ni, Min Jian Qin. A new dicoumarin and anticoagulant activity from Viola yedoensis Makino. Fitoterapia. 2009 Jul; 80(5):283-5. doi: 10.1016/j.fitote.2009.03.005. [PMID: 19306914]
  • Li Sheng, Jin-ping Hu, Hui Chen, Yan Li. [Metabolism of nicousamide in rat and human liver in vitro]. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Sep; 43(9):912-6. doi: NULL. [PMID: 19048781]
  • Sonja Sollner, Ruth Nebauer, Heidemarie Ehammer, Anna Prem, Sigrid Deller, Bruce A Palfey, Günther Daum, Peter Macheroux. Lot6p from Saccharomyces cerevisiae is a FMN-dependent reductase with a potential role in quinone detoxification. The FEBS journal. 2007 Mar; 274(5):1328-39. doi: 10.1111/j.1742-4658.2007.05682.x. [PMID: 17298444]
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  • Shuhei Ishikura, Kengo Matsumoto, Masaharu Sanai, Kenji Horie, Toshiyuki Matsunaga, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme. Journal of biochemistry. 2006 Jun; 139(6):1053-63. doi: 10.1093/jb/mvj109. [PMID: 16788056]
  • Birgit M Dietz, Young-Hwa Kang, Guowen Liu, Aimee L Eggler, Ping Yao, Lucas R Chadwick, Guido F Pauli, Norman R Farnsworth, Andrew D Mesecar, Richard B van Breemen, Judy L Bolton. Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase. Chemical research in toxicology. 2005 Aug; 18(8):1296-305. doi: 10.1021/tx050058x. [PMID: 16097803]
  • Rosario I Bello, Consuelo Gómez-Díaz, Guillermo López-Lluch, Nathalie Forthoffer, María C Córdoba-Pedregosa, Plácido Navas, José M Villalba. Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism. Biochemical pharmacology. 2005 Jun; 69(11):1613-25. doi: 10.1016/j.bcp.2005.03.012. [PMID: 15896341]
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