4-hydroxyphenylacetate (BioDeep_00000000855)

 

Secondary id: BioDeep_00000265138, BioDeep_00000419023, BioDeep_00000862189

natural product human metabolite PANOMIX_OTCML-2023 blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-(4-hydroxyphenyl)acetic acid

化学式: C8H8O3 (152.0473418)
中文名称: 4-羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸, 对羟基苯乙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.13%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

4-hydroxyphenylacetate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4-hydroxyphenylacetate (retrieved 2024-11-05) (BioDeep RN: BioDeep_00000000855). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC(=CC=C1CC(=O)O)O
InChI: InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

描述信息

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain.
4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.
4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available.
4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.
Constituent of sweet clover (Melilotus officinalis) and yeast

Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].
4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

同义名列表

61 个代谢物同义名

InChI=1/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11; 4-Hydroxyphenylacetic acid, Vetec(TM) reagent grade, 98\\%; 4-10-00-00543 (Beilstein Handbook Reference); 2-[4-(hydroxy)phenyl)acetic acid; 4-Hydroxyphenylacetic acid, 98\\%; 2-(4-(HYDROXY)PHENYL)ACETIC ACID; Acetic acid, (p-hydroxyphenyl)-; (4-Hydroxy-phenyl)-essigsaeure; (4-hydroxy-phenyl)-acetic acid; (4-hydroxyphenyl)ethanoic acid; 2-(4-hydroxyphenyl)acetic acid; benzeneacetic acid, 4-hydroxy-; 4-Hydroxyphenylacetic Acid,(S); (4-hydroxyphenyl)-acetic acid; Acetic acid, 4-hydroxyphenyl-; Parahydroxy phenylacetic acid; (p-hydroxyphenyl)-Acetic acid; (4-hydroxyphenyl) acetic acid; para-hydroxyphenylacetic acid; p-hydroxy phenyl acetic acid; 4-hydroxy-phenyl acetic acid; (4-Hydroxyphenyl)acetic acid; 4-Hydroxybenzene acetic acid; 4-Hydroxy-Benzeneacetic acid; 4-hydroxyphenylethanoic acid; (p-Hydroxyphenyl)acetic acid; 4-hydroxy phenyl acetic acid; 4- hydroxyphenylacetic acid; 4-Hydroxybenzeneacetic acid; 4-Hydroxyphenyl acetic acid; p-Hydroxyphenyl acetic acid; 4-hydroxyphenyl-acetic acid; 4-hydroxy-phenylacetic acid; (4-hydroxy-phenyl)-acetate; 4-Hydroxyphenylacetic acid; p-hydroxyphenylacetic acid; 4-hyroxyphenylacetic acid; Parahydroxy phenylacetate; (p-hydroxyphenyl)-Acetate; 4-hydroxyphenyacetic acid; 4-hydroxyphenylactic acid; (4-Hydroxyphenyl)acetate; 4-Hydroxy-Benzeneacetate; Parahydroxyphenylacetate; (p-hydroxyphenyl)acetate; 4-hydroxybenzeneacetate; 4-(Carboxymethyl)phenol; p-hydroxyphenylacetate; 4-hydroxyphenylacetate; 4-Carboxymethylphenol; UNII-3J9SHG0RCN; ChemDiv3_005483; IDI1_023393; 3J9SHG0RCN; AI3-17755; 4-HPA; 3pcg; HPAA; 1ai6; 4HP; p-Hydroxyphenylacetic acid



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

29 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(2)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

51 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

  • Shaoshuai Xin, Mengqi Zhang, Peihai Li, Lizhen Wang, Xuanming Zhang, Shanshan Zhang, Zhenqiang Mu, Houwen Lin, Xiaobin Li, Kechun Liu. Marine-Fungus-Derived Natural Compound 4-Hydroxyphenylacetic Acid Induces Autophagy to Exert Antithrombotic Effects in Zebrafish. Marine drugs. 2024 Mar; 22(4):. doi: 10.3390/md22040148. [PMID: 38667765]
  • Sheng An, Yi Yao, Junjie Wu, Hongbin Hu, Jie Wu, Maomao Sun, Jiaxin Li, Yaoyuan Zhang, Lulan Li, Weihuang Qiu, Yuying Li, Zhiya Deng, Haihong Fang, Shenhai Gong, Qiaobing Huang, Zhongqing Chen, Zhenhua Zeng. Gut-derived 4-hydroxyphenylacetic acid attenuates sepsis-induced acute kidney injury by upregulating ARC to inhibit necroptosis. Biochimica et biophysica acta. Molecular basis of disease. 2023 Sep; 1870(1):166876. doi: 10.1016/j.bbadis.2023.166876. [PMID: 37714058]
  • Yu-Ping Shen, Yuyang Pan, Fu-Xing Niu, Yu-Ling Liao, Mingtao Huang, Jian-Zhong Liu. Biosensor-assisted evolution for high-level production of 4-hydroxyphenylacetic acid in Escherichia coli. Metabolic engineering. 2022 03; 70(?):1-11. doi: 10.1016/j.ymben.2021.12.008. [PMID: 34965469]
  • Danny Orabi, Lucas J Osborn, Kevin Fung, William Massey, Anthony J Horak, Federico Aucejo, Ibrahim Choucair, Beckey DeLucia, Zeneng Wang, Jan Claesen, J Mark Brown. A surgical method for continuous intraportal infusion of gut microbial metabolites in mice. JCI insight. 2021 05; 6(9):. doi: 10.1172/jci.insight.145607. [PMID: 33986195]
  • Kiana Ashley West, Chidimma Kanu, Tanya Maric, Julie Anne Kathryn McDonald, Jeremy K Nicholson, Jia V Li, Mark R Johnson, Elaine Holmes, Makrina D Savvidou. Longitudinal metabolic and gut bacterial profiling of pregnant women with previous bariatric surgery. Gut. 2020 08; 69(8):1452-1459. doi: 10.1136/gutjnl-2019-319620. [PMID: 31964751]
  • Xianyu Liang, Fan Liu, Yiqun Wan, Xiaoying Yin, Weiting Liu. Facile synthesis of molecularly imprinted polymers for selective extraction of tyrosine metabolites in human urine. Journal of chromatography. A. 2019 Feb; 1587(?):34-41. doi: 10.1016/j.chroma.2018.12.014. [PMID: 30551942]
  • Jing Zhu, Mu Zhang, Tingli Han, Hua Wu, Zhibo Xiao, Shihui Lin, Chuanjiang Wang, Fang Xu. Exploring the Biomarkers of Sepsis-Associated Encephalopathy (SAE): Metabolomics Evidence from Gas Chromatography-Mass Spectrometry. BioMed research international. 2019; 2019(?):2612849. doi: 10.1155/2019/2612849. [PMID: 31781604]
  • Bo Chen, Jie Zhou, Qilu Meng, Yang Zhang, Shihua Zhang, Liang Zhang. Comparative analysis of fecal phenolic content between normal and obese rats after oral administration of tea polyphenols. Food & function. 2018 Sep; 9(9):4858-4864. doi: 10.1039/c8fo00609a. [PMID: 30156246]
  • Yanzhen Lu, Nan Wu, Yingtong Fang, Nusrat Shaheen, Yun Wei. An automatic on-line 2,2-diphenyl-1-picrylhydrazyl-high performance liquid chromatography method for high-throughput screening of antioxidants from natural products. Journal of chromatography. A. 2017 Oct; 1521(?):100-109. doi: 10.1016/j.chroma.2017.09.030. [PMID: 28939230]
  • Ana Sousa, Fábio Santos, Maria Manuela Gaspar, Susana Calado, João D Pereira, Eduarda Mendes, Ana Paula Francisco, Maria Jesus Perry. The selective cytotoxicity of new triazene compounds to human melanoma cells. Bioorganic & medicinal chemistry. 2017 08; 25(15):3900-3910. doi: 10.1016/j.bmc.2017.04.049. [PMID: 28602669]
  • Weiqun Lin, Wenting Wang, Hai Yang, Dongliang Wang, Wenhua Ling. Influence of Intestinal Microbiota on the Catabolism of Flavonoids in Mice. Journal of food science. 2016 Dec; 81(12):H3026-H3034. doi: 10.1111/1750-3841.13544. [PMID: 27792839]
  • Volha Zabela, Chethan Sampath, Mouhssin Oufir, Fahimeh Moradi-Afrapoli, Veronika Butterweck, Matthias Hamburger. Pharmacokinetics of dietary kaempferol and its metabolite 4-hydroxyphenylacetic acid in rats. Fitoterapia. 2016 Dec; 115(?):189-197. doi: 10.1016/j.fitote.2016.10.008. [PMID: 27810397]
  • Ali R Mani, José C Moreno, Theo J Visser, Kevin P Moore. The metabolism and de-bromination of bromotyrosine in vivo. Free radical biology & medicine. 2016 Jan; 90(?):243-51. doi: 10.1016/j.freeradbiomed.2015.11.030. [PMID: 26638695]
  • Tao-yang Huang, Long-hao Chen, Yang Huang, Hui Wang, Yan-jun Weng, He Huang, Xin-min Xie. [Simultaneous Determination of Three Components in Ficus microcarpa Leaves by HPLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Feb; 38(2):327-9. doi: . [PMID: 26415411]
  • Chaofu Ke, Yan Hou, Haiyu Zhang, Kai Yang, Jingtao Wang, Bing Guo, Fan Zhang, Hailong Li, Xiaohua Zhou, Ying Li, Kang Li. Plasma Metabolic Profiles in Women are Menopause Dependent. PloS one. 2015; 10(11):e0141743. doi: 10.1371/journal.pone.0141743. [PMID: 26580805]
  • M Bijak, R Ziewiecki, J Saluk, M Ponczek, I Pawlaczyk, H Krotkiewski, B Wachowicz, P Nowak. Thrombin inhibitory activity of some polyphenolic compounds. Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents. 2014; 23(?):2324-2337. doi: 10.1007/s00044-013-0829-4. [PMID: 24610996]
  • Susanne M Henning, Piwen Wang, Narine Abgaryan, Roberto Vicinanza, Daniela Moura de Oliveira, Yanjun Zhang, Ru-Po Lee, Catherine L Carpenter, William J Aronson, David Heber. Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer. Molecular nutrition & food research. 2013 Mar; 57(3):483-93. doi: 10.1002/mnfr.201200646. [PMID: 23319439]
  • Wendy R Russell, Sylvia H Duncan, Lorraine Scobbie, Gary Duncan, Louise Cantlay, A Graham Calder, Susan E Anderson, Harry J Flint. Major phenylpropanoid-derived metabolites in the human gut can arise from microbial fermentation of protein. Molecular nutrition & food research. 2013 Mar; 57(3):523-35. doi: 10.1002/mnfr.201200594. [PMID: 23349065]
  • A A Roĭ, L A Pasichnik, L S Tserkovniak, S F Khodos, I K Kurdish. [Influence of bacteria of Bacillus genus on the causative agent of bacterial cancer of tomatoes]. Mikrobiolohichnyi zhurnal (Kiev, Ukraine : 1993). 2012 Sep; 74(5):74-80. doi: ". [PMID: 23120989]
  • Bo Wei, Fang Li, Huicui Yang, Lei Yu, Kaihong Zhao, Rui Zhou, Yonggang Hu. Magnetic beads-based enzymatic spectrofluorometric assay for rapid and sensitive detection of antibody against ApxIVA of Actinobacillus pleuropneumoniae. Biosensors & bioelectronics. 2012 May; 35(1):390-393. doi: 10.1016/j.bios.2012.03.027. [PMID: 22503209]
  • Mohamed A Farag, Andrea Porzel, Ludger A Wessjohann. Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques. Phytochemistry. 2012 Apr; 76(?):60-72. doi: 10.1016/j.phytochem.2011.12.010. [PMID: 22336263]
  • Jaime Becerra-Jiménez, Adolfo Andrade-Cetto. Effect of Opuntia streptacantha Lem. on alpha-glucosidase activity. Journal of ethnopharmacology. 2012 Jan; 139(2):493-6. doi: 10.1016/j.jep.2011.11.039. [PMID: 22155472]
  • Guangyan Yan, Yina Huang, Qian Bu, Lei Lv, Pengchi Deng, Jiaqing Zhou, Yanli Wang, Yanzhu Yang, Qiangqiang Liu, Xiaobo Cen, Yinglan Zhao. Zinc oxide nanoparticles cause nephrotoxicity and kidney metabolism alterations in rats. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. 2012; 47(4):577-88. doi: 10.1080/10934529.2012.650576. [PMID: 22375541]
  • Ying Qi, Pin Li, Yongyu Zhang, Lulu Cui, Zi Guo, Guoxiang Xie, Mingming Su, Xin Li, Xiaojiao Zheng, Yunping Qiu, Yumin Liu, Aihua Zhao, Weiping Jia, Wei Jia. Urinary metabolite markers of precocious puberty. Molecular & cellular proteomics : MCP. 2012 Jan; 11(1):M111.011072. doi: 10.1074/mcp.m111.011072. [PMID: 22027199]
  • Christiaan J Malherbe, Dalene De Beer, Elizabeth Joubert. Development of on-line high performance liquid chromatography (HPLC)-biochemical detection methods as tools in the identification of bioactives. International journal of molecular sciences. 2012; 13(3):3101-3133. doi: 10.3390/ijms13033101. [PMID: 22489144]
  • Mary Iruthayanathan, Brianne O'Leary, Gautam Paul, Joseph S Dillon. Hydrogen peroxide signaling mediates DHEA-induced vascular endothelial cell proliferation. Steroids. 2011 Dec; 76(13):1483-90. doi: 10.1016/j.steroids.2011.08.002. [PMID: 21864554]
  • Soumen K Manna, Andrew D Patterson, Qian Yang, Kristopher W Krausz, Jeffrey R Idle, Albert J Fornace, Frank J Gonzalez. UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. Journal of proteome research. 2011 Sep; 10(9):4120-33. doi: 10.1021/pr200310s. [PMID: 21749142]
  • Sumayya Saied, Shazia Shah, Zulfiqar Ali, Ajmal Khan, Bishnu P Marasini, Muhammad Iqbal Choudhary. Chemical constituents of Cichorium intybus and their inhibitory effects against urease and alpha-chymotrypsin enzymes. Natural product communications. 2011 Aug; 6(8):1117-20. doi: . [PMID: 21922913]
  • Sophie Liabeuf, Tilman B Drüeke, Ziad A Massy. Protein-bound uremic toxins: new insight from clinical studies. Toxins. 2011 07; 3(7):911-9. doi: 10.3390/toxins3070911. [PMID: 22069747]
  • Dongli Zhang, Wenli Li, Junbo Zhang, Wanrong Tang, Chenxu Qian, Minghao Feng, Qingcui Chu, Jiannong Ye. Study on urinary metabolic profile of phenylketonuria by micellar electrokinetic capillary chromatography with dual electrochemical detection--potential clinical application in fast diagnosis of phenylketonuria. Analytica chimica acta. 2011 May; 694(1-2):61-6. doi: 10.1016/j.aca.2011.03.044. [PMID: 21565303]
  • Lian Zhou, Peggy Liu-Kreyche, Ramaswamy A Iyer. Metabolism of [2-14C]p-hydroxyphenyl acetic acid in rat, monkey and human hepatocytes and in bile-duct cannulated rats. Xenobiotica; the fate of foreign compounds in biological systems. 2011 Apr; 41(4):312-9. doi: 10.3109/00498254.2010.540681. [PMID: 21143006]
  • Maja Jakesevic, Kjersti Aaby, Grethe-Iren A Borge, Bengt Jeppsson, Siv Ahrné, Göran Molin. Antioxidative protection of dietary bilberry, chokeberry and Lactobacillus plantarum HEAL19 in mice subjected to intestinal oxidative stress by ischemia-reperfusion. BMC complementary and alternative medicine. 2011 Jan; 11(?):8. doi: 10.1186/1472-6882-11-8. [PMID: 21272305]
  • Adolfo Andrade-Cetto, Helmut Wiedenfeld. Anti-hyperglycemic effect of Opuntia streptacantha Lem. Journal of ethnopharmacology. 2011 Jan; 133(2):940-3. doi: 10.1016/j.jep.2010.11.022. [PMID: 21111796]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jürg Utzinger, Elaine Holmes, Oliver Balmer. Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections. The American journal of tropical medicine and hygiene. 2011 Jan; 84(1):91-8. doi: 10.4269/ajtmh.2011.10-0402. [PMID: 21212208]
  • S J Chatterjee, P Ovadje, M Mousa, C Hamm, S Pandey. The efficacy of dandelion root extract in inducing apoptosis in drug-resistant human melanoma cells. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):129045. doi: 10.1155/2011/129045. [PMID: 21234313]
  • Chris I R Gill, Gordon J McDougall, Sheila Glidewell, Derek Stewart, Qing Shen, Kieran Tuohy, Aine Dobbin, Adele Boyd, Emma Brown, Sumanto Haldar, Ian R Rowland. Profiling of phenols in human fecal water after raspberry supplementation. Journal of agricultural and food chemistry. 2010 Oct; 58(19):10389-95. doi: 10.1021/jf1017143. [PMID: 20809621]
  • James Cartwright, Richard M Green. Tyrosine-derived 4-hydroxyphenylpyruvate reacts with ketone test fields of 3 commercially available urine dipsticks. Veterinary clinical pathology. 2010 Sep; 39(3):354-7. doi: 10.1111/j.1939-165x.2010.00231.x. [PMID: 20487432]
  • Soumen K Manna, Andrew D Patterson, Qian Yang, Kristopher W Krausz, Henghong Li, Jeffrey R Idle, Albert J Fornace, Frank J Gonzalez. Identification of noninvasive biomarkers for alcohol-induced liver disease using urinary metabolomics and the Ppara-null mouse. Journal of proteome research. 2010 Aug; 9(8):4176-88. doi: 10.1021/pr100452b. [PMID: 20540569]
  • Daniele Del Rio, Angelique Stalmach, Luca Calani, Alan Crozier. Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols. Nutrients. 2010 08; 2(8):820-33. doi: 10.3390/nu2080820. [PMID: 22254058]
  • Federico E Rey, Jeremiah J Faith, James Bain, Michael J Muehlbauer, Robert D Stevens, Christopher B Newgard, Jeffrey I Gordon. Dissecting the in vivo metabolic potential of two human gut acetogens. The Journal of biological chemistry. 2010 Jul; 285(29):22082-90. doi: 10.1074/jbc.m110.117713. [PMID: 20444704]
  • Jasmina Saric, Jia V Li, Jonathan R Swann, Jürg Utzinger, Gail Calvert, Jeremy K Nicholson, Stephan Dirnhofer, Maggie J Dallman, Magda Bictash, Elaine Holmes. Integrated cytokine and metabolic analysis of pathological responses to parasite exposure in rodents. Journal of proteome research. 2010 May; 9(5):2255-64. doi: 10.1021/pr901019z. [PMID: 20092362]
  • I Jerković, Z Marijanović, C I G Tuberoso, D Bubalo, N Kezić. Molecular diversity of volatile compounds in rare willow (Salix spp.) honeydew honey: identification of chemical biomarkers. Molecular diversity. 2010 May; 14(2):237-48. doi: 10.1007/s11030-009-9164-6. [PMID: 19517263]
  • Ronald L Prior, Theodore R Rogers, Ramesh C Khanal, Samuel E Wilkes, Xianli Wu, Luke R Howard. Urinary excretion of phenolic acids in rats fed cranberry. Journal of agricultural and food chemistry. 2010 Apr; 58(7):3940-9. doi: 10.1021/jf9028392. [PMID: 20052972]
  • Lan Luan, Gang-li Wang, Rui-chao Lin. [Studies on the chemical constituents of extract with water from Forsythia suspensa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Feb; 33(2):220-1. doi: . [PMID: 20575415]
  • Klaudia Michalska, Marek Zylewski, Jolanta Marciniuk, Wanda Kisiel. Structural analysis of 1L-chiro-inositol diester from Taraxacum udum. Carbohydrate research. 2010 Jan; 345(1):172-4. doi: 10.1016/j.carres.2009.10.019. [PMID: 19926080]
  • Hyun-Sun Ko, Rong-De Jin, Hari B Krishnan, Sang-Bog Lee, Kil-Yong Kim. Biocontrol ability of Lysobacter antibioticus HS124 against Phytophthora blight is mediated by the production of 4-hydroxyphenylacetic acid and several lytic enzymes. Current microbiology. 2009 Dec; 59(6):608-15. doi: 10.1007/s00284-009-9481-0. [PMID: 19727949]
  • Hojung Nam, Bong Chul Chung, Younghoon Kim, KiYoung Lee, Doheon Lee. Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification. Bioinformatics (Oxford, England). 2009 Dec; 25(23):3151-7. doi: 10.1093/bioinformatics/btp558. [PMID: 19783829]
  • Maaike M Appeldoorn, Jean-Paul Vincken, Anna-Marja Aura, Peter C H Hollman, Harry Gruppen. Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-gamma-valerolactone as the major metabolites. Journal of agricultural and food chemistry. 2009 Feb; 57(3):1084-92. doi: 10.1021/jf803059z. [PMID: 19191673]
  • Yoji Kato, Natsuko Dozaki, Toshiyuki Nakamura, Noritoshi Kitamoto, Akihiro Yoshida, Michitaka Naito, Masayasu Kitamura, Toshihiko Osawa. Quantification of Modified Tyrosines in Healthy and Diabetic Human Urine using Liquid Chromatography/Tandem Mass Spectrometry. Journal of clinical biochemistry and nutrition. 2009 Jan; 44(1):67-78. doi: 10.3164/jcbn.08-185. [PMID: 19177191]
  • Brian Crow, Michael Bishop, Ekaterina Paliakov, Dean Norton, Joe George, J Alexander Bralley. Analysis of urinary aromatic acids by liquid chromatography tandem mass spectrometry. Biomedical chromatography : BMC. 2008 Dec; 22(12):1346-53. doi: 10.1002/bmc.1064. [PMID: 18655225]
  • Hong-Yan Ma, Li Yang, Mian Zhang, Chang-Hong Wang, Zheng-Tao Wang. A new compound from Senecio cannabifolius var integrilifolius. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Jun; 43(6):626-9. doi: . [PMID: 18822966]
  • Michael J Epton, Robin D Dawson, Wendy M Brooks, Simon Kingham, Teresa Aberkane, Jo-Anne E Cavanagh, Christopher M Frampton, Tracey Hewitt, Julie M Cook, Susan McLeod, Fiona McCartin, Katherine Trought, Leslie Brown. The effect of ambient air pollution on respiratory health of school children: a panel study. Environmental health : a global access science source. 2008 May; 7(?):16. doi: 10.1186/1476-069x-7-16. [PMID: 18479529]
  • Gino Boily, Erin L Seifert, Lisa Bevilacqua, Xiao Hong He, Guillaume Sabourin, Carmen Estey, Cynthia Moffat, Sean Crawford, Sarah Saliba, Karen Jardine, Jian Xuan, Meredith Evans, Mary-Ellen Harper, Michael W McBurney. SirT1 regulates energy metabolism and response to caloric restriction in mice. PloS one. 2008 Mar; 3(3):e1759. doi: 10.1371/journal.pone.0001759. [PMID: 18335035]
  • Thomas Hoehn, Sylvia Janssen, Ali R Mani, Gernot Brauers, Kevin P Moore, Peter Schadewaldt, Ertan Mayatepek. Urinary excretion of the nitrotyrosine metabolite 3-nitro-4-hydroxyphenylacetic acid in preterm and term infants. Neonatology. 2008; 93(2):73-6. doi: 10.1159/000106783. [PMID: 17684421]
  • Hiromi Yuji, Jochen Weiss, Pierre Villeneuve, Luis J López Giraldo, Maria-Cruz Figueroa-Espinoza, Eric A Decker. Ability of surface-active antioxidants to inhibit lipid oxidation in oil-in-water emulsion. Journal of agricultural and food chemistry. 2007 Dec; 55(26):11052-6. doi: 10.1021/jf072586f. [PMID: 18038996]
  • J F Hawumba, V S Brözel, J Theron. Cloning and characterization of a 4-hydroxyphenylacetate 3-hydroxylase from the thermophile Geobacillus sp. PA-9. Current microbiology. 2007 Dec; 55(6):480-4. doi: 10.1007/s00284-007-9016-5. [PMID: 17805928]
  • Ali R Mani, Silvia Ippolito, José C Moreno, Theo J Visser, Kevin P Moore. The metabolism and dechlorination of chlorotyrosine in vivo. The Journal of biological chemistry. 2007 Oct; 282(40):29114-21. doi: 10.1074/jbc.m704270200. [PMID: 17686770]
  • Liwei Gu, Suzanne E House, Lloyd Rooney, Ronald L Prior. Sorghum bran in the diet dose dependently increased the excretion of catechins and microbial-derived phenolic acids in female rats. Journal of agricultural and food chemistry. 2007 Jun; 55(13):5326-34. doi: 10.1021/jf070100p. [PMID: 17536823]
  • Jeroen Kool, Sebastiaan M Van Liempd, Stefan Harmsen, Tim Schenk, Hubertus Irth, Jan N M Commandeur, Nico P E Vermeulen. An on-line post-column detection system for the detection of reactive-oxygen-species-producing compounds and antioxidants in mixtures. Analytical and bioanalytical chemistry. 2007 Jun; 388(4):871-9. doi: 10.1007/s00216-007-1296-x. [PMID: 17468853]
  • Sopheareth Mao, Seung-Je Lee, Hoon Hwangbo, Yong-Woong Kim, Keun-Hyung Park, Gyu-Suk Cha, Ro-Dong Park, Kil-Yong Kim. Isolation and characterization of antifungal substances from Burkholderia sp. culture broth. Current microbiology. 2006 Nov; 53(5):358-64. doi: 10.1007/s00284-005-0333-2. [PMID: 17066340]
  • Guo-Hong Ruan, Qiang-En Wu, Ping Gu, Li-Xing Zheng, Xi-An Gu, Zhi-Jun Zhou. [Effect of dimethoate on serum monoamines neurotransmitters in rats]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2006 Nov; 24(11):645-8. doi: NULL. [PMID: 17181939]
  • Cinzia Stella, Bridgette Beckwith-Hall, Olivier Cloarec, Elaine Holmes, John C Lindon, Jonathan Powell, Frans van der Ouderaa, Sheila Bingham, Amanda J Cross, Jeremy K Nicholson. Susceptibility of human metabolic phenotypes to dietary modulation. Journal of proteome research. 2006 Oct; 5(10):2780-8. doi: 10.1021/pr060265y. [PMID: 17022649]
  • Ananth S Pannala, Ali R Mani, Catherine A Rice-Evans, Kevin P Moore. pH-dependent nitration of para-hydroxyphenylacetic acid in the stomach. Free radical biology & medicine. 2006 Sep; 41(6):896-901. doi: 10.1016/j.freeradbiomed.2006.05.010. [PMID: 16934672]
  • Eric Stern, Steven Jay, James Bertram, Benjamin Boese, Ilona Kretzschmar, Daniel Turner-Evans, Carl Dietz, David A LaVan, Tadeusz Malinski, Tarek Fahmy, Mark A Reed. Electropolymerization on microelectrodes: functionalization technique for selective protein and DNA conjugation. Analytical chemistry. 2006 Sep; 78(18):6340-6. doi: 10.1021/ac060410r. [PMID: 16970307]
  • Albert van der Vliet. Tyrosine nitration: who did it, and how do we prove it? A commentary on 'pH dependent nitration of para-hydroxyphenylacetic acid in the stomach'. Free radical biology & medicine. 2006 Sep; 41(6):869-71. doi: 10.1016/j.freeradbiomed.2006.05.015. [PMID: 16934668]
  • Mirella Nardini, Fausta Natella, Cristina Scaccini, Andrea Ghiselli. Phenolic acids from beer are absorbed and extensively metabolized in humans. The Journal of nutritional biochemistry. 2006 Jan; 17(1):14-22. doi: 10.1016/j.jnutbio.2005.03.026. [PMID: 16242314]
  • Luis B Rojas, Stéphane Quideau, Patrick Pardon, Zoubida Charrouf. Colorimetric evaluation of phenolic content and GC-MS characterization of phenolic composition of alimentary and cosmetic argan oil and press cake. Journal of agricultural and food chemistry. 2005 Nov; 53(23):9122-7. doi: 10.1021/jf051082j. [PMID: 16277411]
  • Jihad T Al-Ratrout, Mohammed Al-Muzian, Mona Al-Nazer, Naseem A Ansari. Plantar keratoderma: a manifestation of tyrosinemia type II (Richner-Hanhart syndrome). Annals of Saudi medicine. 2005 Sep; 25(5):422-4. doi: 10.5144/0256-4947.2005.422. [PMID: 16270769]
  • Andrew M Jenner, Joseph Rafter, Barry Halliwell. Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free radical biology & medicine. 2005 Mar; 38(6):763-72. doi: 10.1016/j.freeradbiomed.2004.11.020. [PMID: 15721987]
  • Ali R Mani, Kevin P Moore. Dynamic assessment of nitration reactions in vivo. Methods in enzymology. 2005; 396(?):151-9. doi: 10.1016/s0076-6879(05)96015-1. [PMID: 16291230]
  • Alexa N Seal, James E Pratley, Terry Haig, Min An. Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. Journal of chemical ecology. 2004 Aug; 30(8):1647-62. doi: 10.1023/b:joec.0000042074.96036.14. [PMID: 15537165]
  • Marina DellaGreca, Lucio Previtera, Fabio Temussi, Armando Zarrelli. Low-molecular-weight components of olive oil mill waste-waters. Phytochemical analysis : PCA. 2004 May; 15(3):184-8. doi: 10.1002/pca.766. [PMID: 15202603]
  • Ali R Mani, Ananth S Pannala, Nelson N Orie, Richard Ollosson, David Harry, Catherine A Rice-Evans, Kevin P Moore. Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. The Biochemical journal. 2003 Sep; 374(Pt 2):521-7. doi: 10.1042/bj20030670. [PMID: 12797864]
  • Weibin Ruan, Mohan Liu, Bin Huang, Fei Yan, Jingguo Wang, Yubao Gao. [Allelopathic effect of p- and m-hydroxy-phenylacetic acid on soybean (Glycine max L.) germination]. Ying yong sheng tai xue bao = The journal of applied ecology. 2003 May; 14(5):785-8. doi: ". [PMID: 12924141]
  • Xiaosuo Wang, George A Smythe. Assessment of hydroxyl radical generation and radical scavenging activity of Chinese medicinal herbs using GC-MS. Redox report : communications in free radical research. 2003; 8(4):223-8. doi: 10.1179/135100003225002727. [PMID: 14599346]
  • Young-Sik Jung, Tae-Souk Kang, Joong-Ho Yoon, Bo-Young Joe, Hee-Jong Lim, Churl-Min Seong, Woo-Kyu Park, Jae-Yang Kong, Jungsook Cho, No-Sang Park. Synthesis and evaluation of 4-hydroxyphenylacetic acid amides and 4-hydroxycinnamamides as antioxidants. Bioorganic & medicinal chemistry letters. 2002 Sep; 12(18):2599-602. doi: 10.1016/s0960-894x(02)00479-1. [PMID: 12182869]
  • Tsuneo Deguchi, Sumio Ohtsuki, Masaki Otagiri, Hitomi Takanaga, Hiroshi Asaba, Shinobu Mori, Tetsuya Terasaki. Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. Kidney international. 2002 May; 61(5):1760-8. doi: 10.1046/j.1523-1755.2002.00318.x. [PMID: 11967025]
  • Zhi-xin Liao, Ming-kui Wang, Shu-lin Peng, Yao-zu Chen, Li-sheng Ding. [Chemical constituents of Notoseris rhombiformis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2002 Jan; 37(1):37-40. doi: ". [PMID: 12579897]
  • D Di Gioia, L Bertin, F Fava, L Marchetti. Biodegradation of hydroxylated and methoxylated benzoic, phenylacetic and phenylpropenoic acids present in olive mill wastewaters by two bacterial strains. Research in microbiology. 2001 Jan; 152(1):83-93. doi: 10.1016/s0923-2508(00)01171-2. [PMID: 11281329]
  • L L Acero, F J Benítez, F J Real, A I Leal. Degradation of p-hydroxyphenylacetic acid by photoassisted Fenton reaction. Water science and technology : a journal of the International Association on Water Pollution Research. 2001; 44(5):31-8. doi: 10.2166/wst.2001.0245. [PMID: 11695475]
  • J P Eiserich, C E Cross, A D Jones, B Halliwell, A van der Vliet. Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxide-mediated protein modification. The Journal of biological chemistry. 1996 Aug; 271(32):19199-208. doi: 10.1074/jbc.271.32.19199. [PMID: 8702599]
  • S P Heywood, N M Hooper. Development and application of a fluorometric assay for mammalian membrane dipeptidase. Analytical biochemistry. 1995 Mar; 226(1):10-4. doi: 10.1006/abio.1995.1184. [PMID: 7785760]
  • M D Luque de Castro, R Quiles, J M Fernández-Romero, E Fernández. Continuous-flow assay with immobilized enzymes for determining of inorganic phosphate in serum. Clinical chemistry. 1995 Jan; 41(1):99-102. doi: 10.1093/clinchem/41.1.99. [PMID: 7813089]
  • N D Huebert, B D Dulery, J Schoun, V Schwach, C Hinze, K D Haegele. Kinetics and metabolism of p-tyramine during monoamine oxidase inhibition by mofegiline. Clinical pharmacology and therapeutics. 1994 Nov; 56(5):537-42. doi: 10.1038/clpt.1994.175. [PMID: 7955818]
  • M Tuchman, M T McCann, M M Thompson, M Y Tsai, R Giguere, B Lemieux. Screening urine of 3-week-old newborns: transient methylmalonic and hydroxyphenyllactic aciduria. Biochemical medicine and metabolic biology. 1992 Aug; 48(1):64-8. doi: 10.1016/0885-4505(92)90049-5. [PMID: 1524871]
  • R Schulz, K H Antonin, E Hoffmann, M Jedrychowski, E Nilsson, C Schick, P R Bieck. Tyramine kinetics and pressor sensitivity during monoamine oxidase inhibition by selegiline. Clinical pharmacology and therapeutics. 1989 Nov; 46(5):528-36. doi: 10.1038/clpt.1989.181. [PMID: 2510962]
  • V Walker, G A Mills. Urinary organic acid excretion by babies born before 33 weeks of gestation. Clinical chemistry. 1989 Jul; 35(7):1460-6. doi: . [PMID: 2758593]
  • NULL. Gut bacterial metabolism. Lancet (London, England). 1988 Jul; 2(8604):225-6. doi: 10.1016/s0140-6736(88)92338-0. [PMID: 2899706]
  • M Yamaguchi, R Matsunaga, K Fukuda, M Nakamura. Determination of free and total phenylacetic and p- and m-hydroxyphenylacetic acids in human urine by liquid chromatography with fluorimetric detection. Journal of chromatography. 1987 Mar; 414(2):275-84. doi: 10.1016/0378-4347(87)80053-1. [PMID: 3571397]
  • L A Ward, K A Johnson, I M Robinson, M T Yokoyama. Isolation from swine feces of a bacterium which decarboxylates p-hydroxyphenylacetic acid to 4-methylphenol (p-cresol). Applied and environmental microbiology. 1987 Jan; 53(1):189-92. doi: 10.1128/aem.53.1.189-192.1987. [PMID: 3827247]
  • D S Robinson, T B Cooper, S P Jindal, J Corcella, T Lutz. Metabolism and pharmacokinetics of phenelzine: lack of evidence for acetylation pathway in humans. Journal of clinical psychopharmacology. 1985 Dec; 5(6):333-7. doi: 10.1097/00004714-198512000-00005. [PMID: 4066998]
  • E Haan, G Brown, A Bankier, D Mitchell, S Hunt, J Blakey, G Barnes. Severe illness caused by the products of bacterial metabolism in a child with a short gut. European journal of pediatrics. 1985 May; 144(1):63-5. doi: 10.1007/bf00491929. [PMID: 4018104]
  • P N Levett, K D Phillips. Gas chromatographic identification of Clostridium difficile and detection of cytotoxin from a modified selective medium. Journal of clinical pathology. 1985 Jan; 38(1):82-5. doi: 10.1136/jcp.38.1.82. [PMID: 3968212]
  • P F Gulyassy, A T Bottini, E A Jarrard, L A Stanfel. Isolation of inhibitors of ligand: albumin-binding from uremic body fluids and normal urine. Kidney international. Supplement. 1983 Dec; 16(?):S238-42. doi: NULL. [PMID: 6588258]
  • H Machino, Y Miki, T Kawatsu, K Kida, H Matsuda. Successful dietary control of tyrosinemia II. Journal of the American Academy of Dermatology. 1983 Oct; 9(4):533-9. doi: 10.1016/s0190-9622(83)70165-9. [PMID: 6195199]
  • C F Burrows, P F Jezyk. Nitrosonapthol test for screening of small intestinal diarrheal disease in the dog. Journal of the American Veterinary Medical Association. 1983 Aug; 183(3):318-22. doi: NULL. [PMID: 6885605]
  • P H Yu, R C Bowen, B A Davis, A A Boulton. Platelet monoamine oxidase activity and trace acid levels in plasma of agoraphobic patients. Acta psychiatrica Scandinavica. 1983 Mar; 67(3):188-94. doi: 10.1111/j.1600-0447.1983.tb00340.x. [PMID: 6858713]
  • F Endo, A Kitano, I Uehara, N Nagata, I Matsuda, T Shinka, T Kuhara, I Matsumoto. Four-hydroxyphenylpyruvic acid oxidase deficiency with normal fumarylacetoacetase: a new variant form of hereditary hypertyrosinemia. Pediatric research. 1983 Feb; 17(2):92-6. doi: 10.1203/00006450-198302000-00002. [PMID: 6828337]
  • P H Yu, R C Bowen, B A Davis, A A Boulton. A study of the catabolism of trace amines in mentally disordered individuals with particular reference to agoraphobic patients with panic attacks. Progress in neuro-psychopharmacology & biological psychiatry. 1983; 7(4-6):611-5. doi: 10.1016/0278-5846(83)90033-7. [PMID: 6686698]