1,2,3-Trihydroxybenzene (BioDeep_00000000233)

 

Secondary id: BioDeep_00000859385

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


2,3-Dihydroxyphenol; Benzene-1,2,3-triol; NSC 5035

化学式: C6H6O3 (126.0316926)
中文名称: 焦性没食子酸, 邻苯三酚
谱图信息: 最多检出来源 Homo sapiens(blood) 0.08%

分子结构信息

SMILES: C1=CC(=C(C(=C1)O)O)O
InChI: InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H

描述信息

1,2,3-trihydroxybenzene, also known as pyrogallic acid or 1,2,3-benzenetriol, is a member of the class of compounds known as 5-unsubstituted pyrrogallols. 5-unsubstituted pyrrogallols are pyrrogallols that are unsubstituted at th5-position of the benzene ring. 1,2,3-trihydroxybenzene is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,2,3-trihydroxybenzene can be found in arabica coffee, beer, cocoa powder, and coffee, which makes 1,2,3-trihydroxybenzene a potential biomarker for the consumption of these food products. 1,2,3-trihydroxybenzene can be found primarily in blood, feces, and urine. 1,2,3-trihydroxybenzene is an organic compound with the formula C6H3(OH)3. It is a white water-soluble solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomeric benzenetriols .
Pyrogallic acid is an odorless white to gray solid. Sinks and mixes with water. (USCG, 1999)
Pyrogallol is a benzenetriol carrying hydroxy groups at positions 1, 2 and 3. It has a role as a plant metabolite. It is a phenolic donor and a benzenetriol.
Pyrogallol is a natural product found in Gunnera perpensa, Nigella glandulifera, and other organisms with data available.
A trihydroxybenzene or dihydroxy phenol that can be prepared by heating GALLIC ACID.
See also: Stevia rebaudiuna Leaf (part of); Alchemilla monticola whole (part of); Agrimonia eupatoria flowering top (part of).
1,2,3-Trihydroxybenzene, or pyrogallol is a benzenetriol. It is a white crystalline powder and a powerful reducing agent. It was first prepared by Scheele 1786 by heating gallic acid. An alternate preparation is heating para-chlorophenoldisulphonic acid with potassium hydroxide. 1,2,3-Trihydroxybenzene has been found to be a metabolite of Aspergillus (https://www.tandfonline.com/doi/pdf/10.1080/00021369.1982.10865473).
A benzenetriol carrying hydroxy groups at positions 1, 2 and 3.
D020011 - Protective Agents > D000975 - Antioxidants
Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.
Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.

同义名列表

67 个代谢物同义名

2,3-Dihydroxyphenol; Benzene-1,2,3-triol; NSC 5035; InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9; 4-06-00-07327 (Beilstein Handbook Reference); Pyrogallol, JIS special grade, >=99.0\\%; Pyrogallol, SAJ first grade, >=98.0\\%; Pyrogallol, Vetec(TM) reagent grade; Pyrogallol, purum, >=98.0\\% (HPLC); 1,2,3-Benzenetriol (ACD/Name 4.0); Benzene-1,2,3-triol (Pyrogallol); Pyrogallol, analytical standard; Pyrogallol, ACS reagent, >=99\\%; 1,2,3-Trihydroxybenzen [Czech]; 1,2,3-Trihydroxybenzen (CZECH); Pyrogallol, p.a., ACS reagent; 1,2,3-Trihydroxybenzene, XIV; Benzene, 1,2,3-trihydroxy-; Pyrogallol, >=98\\% (HPLC); 1,2,3-TRIHYDROXY-BENZENE; 1,2,3-trihydroxybenzene; Pyrogallol, ACS reagent; Benzene,2,3-trihydroxy-; 1,2,3-Trihydroxybenzen; C.I. Oxidation Base 32; 1,3-Trihydroxybenzene; Pyrogallol ACS grade; 1,3-Trihydroxybenzen; CI Oxidation Base 32; 2,3-Dihydroxyphenol; Pyrogallic Acid,(S); benzene-1,2-3-triol; PYROGALLOL [WHO-DD]; benzene-1,2,3-triol; PYROGALLOL [VANDF]; PYROGALLOL [MART.]; Fouramine Brown AP; 1,2,3-benzenetriol; PYROGALLOL (MART.); fouramine base ap; PYROGALLOL [HSDB]; PYROGALLOL [INCI]; trihydroxybenzene; acid, Pyrogallic; Pyrogallol, 98\\%; 1,3-Benzenetriol; Pyrogallol [NF]; UNII-01Y4A2QXY0; PYROGALLOL [MI]; PYROGALLOL, ACS; pyrogallic acid; WLN: QR BQ CQ; Benzenetriol; Tox21_202373; Tox21_111143; fourrine PG; Pyrogallate; CAS-87-66-1; fourrine 85; Pyrogallol;; 01Y4A2QXY0; Pyrogallol; AI3-00709; Phenol; PYROP; Piral; Pyro; PYG; GMN



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(0)

代谢反应

7 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

44 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

  • Mohamed Hamed, Hamdy A M Soliman, Rashad E M Said, Christopher J Martyniuk, Alaa G M Osman, Alaa El-Din H Sayed. Oxidative stress, antioxidant defense responses, and histopathology: Biomarkers for monitoring exposure to pyrogallol in Clarias gariepinus. Journal of environmental management. 2024 Feb; 351(?):119845. doi: 10.1016/j.jenvman.2023.119845. [PMID: 38109825]
  • Ly Thi Huong Nguyen, Nhi Phuc Khanh Nguyen, Khoa Nguyen Tran, Heung-Mook Shin, In-Jun Yang. Intranasal administration of the essential oil from Perillae Folium ameliorates social defeat stress-induced behavioral impairments in mice. Journal of ethnopharmacology. 2024 Jan; 324(?):117775. doi: 10.1016/j.jep.2024.117775. [PMID: 38224793]
  • Beixian Zhou, Linxin Wang, Zhixian Ren, Yueyun Liang, Sushan Yang, Yuehan Zhang, Siyao Che, Weiyi Fang. Pyrogallol promotes growth arrest by activating the p53-mediated up-regulation of p21 and p62/SQSTM1-dependent degradation of β-catenin in nonsmall cell lung cancer cells. Environmental toxicology. 2023 Dec; ?(?):. doi: 10.1002/tox.24099. [PMID: 38108618]
  • Karyn Bischoff. Pyrogallol Toxicosis in Horses. The Veterinary clinics of North America. Equine practice. 2023 Nov; ?(?):. doi: 10.1016/j.cveq.2023.10.001. [PMID: 37923643]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Yuehan Zhang, Sushan Yang, Zhenhua Qiu, Li Huang, Linyan Huang, Yueyun Liang, Xuanyu Liu, Maosheng Wang, Beixian Zhou. Pyrogallol enhances therapeutic effect of human umbilical cord mesenchymal stem cells against LPS-mediated inflammation and lung injury via activation of Nrf2/HO-1 signaling. Free radical biology & medicine. 2022 10; 191(?):66-81. doi: 10.1016/j.freeradbiomed.2022.08.030. [PMID: 36028178]
  • M D Milan Gowda, K Jayachandra, Vikram Joshi, Vaddarahally N Manjuprasanna, Gotravalli V Rudresha, Devadasan Velmurugan, Raman Pachaiappan, Noor Mohamed Jameel, Bannikuppe S Vishwanath. Syringol isolated from Eleusine coracana (L.) Gaertn bran suppresses inflammatory response through the down-regulation of cPLA2, COX-2, IκBα, p38 and MPO signaling in sPLA2 induced mice paw oedema. Inflammopharmacology. 2022 Oct; 30(5):1853-1870. doi: 10.1007/s10787-022-00983-3. [PMID: 35639234]
  • Adriel Ekozin, Chiagoziem A Otuechere, Adewale Adewuyi. Apocynin loaded silver nanoparticles displays potent in vitro biological activities and mitigates pyrogallol-induced hepatotoxicity. Chemico-biological interactions. 2022 Sep; 365(?):110069. doi: 10.1016/j.cbi.2022.110069. [PMID: 35944648]
  • Lele Tang, Yuan Dang, Yu Wang, Yunlong Zhang, Tianshuo Hu, Cuicui Ding, Hui Wu, Yonghao Ni, Lihui Chen, Liulian Huang, Min Zhang. Rapid fabrication of bionic pyrogallol-based self-adhesive hydrogel with mechanically tunable, self-healing, antibacterial, wound healing, and hemostatic properties. Biomaterials advances. 2022 May; 136(?):212765. doi: 10.1016/j.bioadv.2022.212765. [PMID: 35929329]
  • Francesca Torrini, Lapo Renai, Simona Scarano, Massimo Del Bubba, Pasquale Palladino, Maria Minunni. Colorimetric selective quantification of anthocyanins with catechol/pyrogallol moiety in edible plants upon zinc complexation. Talanta. 2022 Apr; 240(?):123156. doi: 10.1016/j.talanta.2021.123156. [PMID: 34942476]
  • Xinwen Zhang, Delphis F Levia, Elvis Osamudiamhen Ebikade, Jeffrey Chang, Dionisios G Vlachos, Changqing Wu. The impact of differential lignin S/G ratios on mutagenicity and chicken embryonic toxicity. Journal of applied toxicology : JAT. 2022 03; 42(3):423-435. doi: 10.1002/jat.4229. [PMID: 34448506]
  • Min Zhang, Qili Yang, Tianshuo Hu, Lele Tang, Yonghao Ni, Lihui Chen, Hui Wu, Liulian Huang, Cuicui Ding. Adhesive, Antibacterial, Conductive, Anti-UV, Self-Healing, and Tough Collagen-Based Hydrogels from a Pyrogallol-Ag Self-Catalysis System. ACS applied materials & interfaces. 2022 Feb; 14(7):8728-8742. doi: 10.1021/acsami.1c21200. [PMID: 35143167]
  • Yi Zhang, Mufan Ji, Zhenyang Gu, Wenlong Pei, Jun Zhu, Qian Wu, Lei Li, Zhan Zhang. Elemicin exposure induced aberrant lipid metabolism via modulation of gut microbiota in mice. Toxicology. 2022 02; 467(?):153088. doi: 10.1016/j.tox.2021.153088. [PMID: 34979169]
  • Hossein Tavallali, Gohar Deilamy-Rad, Abolftah Parhami, Reza Zebarjadi, Arshida Najafi-Nejad, Narges Mosallanejad. A novel design of multiple ligands for ultrasensitive colorimetric chemosensor of glutathione in plasma sample. Analytical biochemistry. 2022 01; 637(?):114475. doi: 10.1016/j.ab.2021.114475. [PMID: 34813770]
  • Islam M Mostafa, Muhammad Rehan Hasan Shah Gilani, Yequan Chen, Baohua Lou, Jianping Li, Guobao Xu. Lucigenin-pyrogallol chemiluminescence for the multiple detection of pyrogallol, cobalt ion, and tyrosinase. Journal of food and drug analysis. 2021 09; 29(3):510-520. doi: 10.38212/2224-6614.3361. [PMID: 35696239]
  • Iftikhar Ali, Yan Mu, Muhammad Atif, Hidayat Hussain, Jinping Li, Dandan Li, Muhammad Shabbir, Jean Jules Kezetas Bankeu, Li Cui, Shahida Sajjad, Daijie Wang, Xiao Wang. Separation and anti-inflammatory evaluation of phytochemical constituents from Pleurospermum candollei (Apiaceae) by high-speed countercurrent chromatography with continuous sample load. Journal of separation science. 2021 Jul; 44(13):2663-2673. doi: 10.1002/jssc.202100155. [PMID: 33914393]
  • Sascha K Manier, Lea Wagmann, Armin A Weber, Markus R Meyer. Abuse of nutmeg seeds: Detectable by means of liquid chromatography-mass spectrometry techniques?. Drug testing and analysis. 2021 Jul; 13(7):1440-1444. doi: 10.1002/dta.3027. [PMID: 33720530]
  • Dongting Yao, Guanyi Zhang, Weiqin Chen, Jia Chen, Zhen Li, Xin Zheng, Hongmei Yin, Xiaobo Hu. Pyrogallol and Fluconazole Interact Synergistically In Vitro against Candida glabrata through an Efflux-Associated Mechanism. Antimicrobial agents and chemotherapy. 2021 06; 65(7):e0010021. doi: 10.1128/aac.00100-21. [PMID: 33875436]
  • Haixia Su, Sheng Yao, Wenfeng Zhao, Yumin Zhang, Jia Liu, Qiang Shao, Qingxing Wang, Minjun Li, Hang Xie, Weijuan Shang, Changqiang Ke, Lu Feng, Xiangrui Jiang, Jingshan Shen, Gengfu Xiao, Hualiang Jiang, Leike Zhang, Yang Ye, Yechun Xu. Identification of pyrogallol as a warhead in design of covalent inhibitors for the SARS-CoV-2 3CL protease. Nature communications. 2021 06; 12(1):3623. doi: 10.1038/s41467-021-23751-3. [PMID: 34131140]
  • Janaina E Rocha, Tássia T A M Guedes, Camila F Bezerra, Maria do S Costa, Fabia F Campina, Thiago S de Freitas, Amanda K Sousa, Celestina E Sobral Souza, Maria K N Silva, Yedda M Lobo, Francisco N Pereira-Junior, João H da Silva, Irwin R A Menezes, Raimundo N P Teixeira, Aracélio V Colares, Henrique D M Coutinho. FTIR analysis of pyrogallol and phytotoxicity-reductive effect against mercury chloride. Environmental geochemistry and health. 2021 Jun; 43(6):2433-2442. doi: 10.1007/s10653-020-00607-1. [PMID: 32488795]
  • Chao Ma, Huiwen Pang, Hongguang Liu, Qian Yan, Jianzhang Li, Shifeng Zhang. A tough, adhesive, self-healable, and antibacterial plant-inspired hydrogel based on pyrogallol-borax dynamic cross-linking. Journal of materials chemistry. B. 2021 05; 9(20):4230-4240. doi: 10.1039/d1tb00763g. [PMID: 33998631]
  • Yuanyong Yao, Shixue Chen, Hu Li. An Improved System to Evaluate Superoxide-Scavenging Effects of Bioflavonoids. ChemistryOpen. 2021 04; 10(4):503-514. doi: 10.1002/open.202100013. [PMID: 33908702]
  • Dedieu Luc, Brunel Jean Michel, Lorenzi Vanina, Muselli Alain, Berti Liliane, Bolla Jean Michel. Antibacterial Mode of Action of the Daucus carota Essential Oil Active Compounds against Campylobacter jejuni and Efflux-Mediated Drug Resistance in Gram-Negative Bacteria. Molecules (Basel, Switzerland). 2020 Nov; 25(22):. doi: 10.3390/molecules25225448. [PMID: 33233754]
  • Hai Liu, Xingyu Zhang, Zhipeng Xu, Yimin Wang, Yihu Ke, Zhibo Jiang, Zhen Yuan, Heng Li. Role of polyphenols in plant-mediated synthesis of gold nanoparticles: identification of active components and their functional mechanism. Nanotechnology. 2020 Oct; 31(41):415601. doi: 10.1088/1361-6528/ab9e25. [PMID: 32554878]
  • Hafiz Saqib Ali, Richard H Henchman, Sam P de Visser. Lignin Biodegradation by a Cytochrome P450 Enzyme: A Computational Study into Syringol Activation by GcoA. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Oct; 26(57):13093-13102. doi: 10.1002/chem.202002203. [PMID: 32613677]
  • Joris R Delanghe, Marc L De Buyzere, Matthijs Oyaert, Sigurd E Delanghe, Marijn M Speeckaert. Urine test strips vs. pyrogallol red-molybdate assays for proteinuria: a critical approach. Clinical and experimental nephrology. 2020 05; 24(5):489-490. doi: 10.1007/s10157-020-01863-2. [PMID: 32103387]
  • Yunni Gao, Jing Lu, Philip T Orr, Ann Chuang, Hannah M Franklin, Michele A Burford. Enhanced resistance of co-existing toxigenic and non-toxigenic Microcystis aeruginosa to pyrogallol compared with monostrains. Toxicon : official journal of the International Society on Toxinology. 2020 Mar; 176(?):47-54. doi: 10.1016/j.toxicon.2020.01.013. [PMID: 32103795]
  • Merja A Neukamm, Hannes M Schwelm, Simon Vieser, Nadine Schiesel, Volker Auwärter. Detection of Nutmeg Abuse by Gas Chromatography-Mass Spectrometric Screening of Urine. Journal of analytical toxicology. 2020 Jan; 44(1):103-108. doi: 10.1093/jat/bkz054. [PMID: 31504590]
  • Sayuki Oka, Ryo Kuniba, Nozomi Tsuboi, Sayaka Tsuchida, Kazunari Ushida, Shusuke Tomoshige, Kouji Kuramochi. Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum. Bioscience, biotechnology, and biochemistry. 2020 Jan; 84(1):31-36. doi: 10.1080/09168451.2019.1662279. [PMID: 31794330]
  • Roland Wedekind, Pekka Keski-Rahkonen, Nivonirina Robinot, Vivian Viallon, Pietro Ferrari, Erwan Engel, Marie-Christine Boutron-Ruault, Yahya Mahamat-Saleh, Francesca Romana Mancini, Tilman Kühn, Theron Johnson, Heiner Boeing, Manuela Bergmann, Anna Karakatsani, Antonia Trichopoulou, Heleni Peppa, Claudia Agnoli, Maria Santucci de Magistris, Domenico Palli, Carlotta Sacerdote, Rosario Tumino, Marc J Gunter, Inge Huybrechts, Augustin Scalbert. Syringol metabolites as new biomarkers for smoked meat intake. The American journal of clinical nutrition. 2019 12; 110(6):1424-1433. doi: 10.1093/ajcn/nqz222. [PMID: 31559413]
  • Hongyu Rao, Peibo Li, Hao Wu, Chong Liu, Wei Peng, Weiwei Su. Simultaneous Determination of Six Compounds in Destructive Distillation Extracts of Hawthorn Seed by GC-MS and Evaluation of Their Antimicrobial Activity. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234328. [PMID: 31783502]
  • Myeongjoo Son, Seyeon Oh, Hye Sun Lee, Dong-Min Chung, Ji Tae Jang, You-Jin Jeon, Chang Hu Choi, Kook Yang Park, Kuk Hui Son, Kyunghee Byun. Ecklonia Cava Extract Attenuates Endothelial Cell Dysfunction by Modulation of Inflammation and Brown Adipocyte Function in Perivascular Fat Tissue. Nutrients. 2019 Nov; 11(11):. doi: 10.3390/nu11112795. [PMID: 31731817]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Junwon Choi, Seyeon Oh, Myeongjoo Son, Kyunghee Byun. Pyrogallol-Phloroglucinol-6,6-Bieckol Alleviates Obesity and Systemic Inflammation in a Mouse Model by Reducing Expression of RAGE and RAGE Ligands. Marine drugs. 2019 Oct; 17(11):. doi: 10.3390/md17110612. [PMID: 31661887]
  • Myeongjoo Son, Seyeon Oh, Chang Hu Choi, Kook Yang Park, Kuk Hui Son, Kyunghee Byun. Pyrogallol-Phloroglucinol-6,6-Bieckol from Ecklonia cava Attenuates Tubular Epithelial Cell (TCMK-1) Death in Hypoxia/Reoxygenation Injury. Marine drugs. 2019 Oct; 17(11):. doi: 10.3390/md17110602. [PMID: 31652920]
  • Xiao-Nan Yang, Yi-Kun Wang, Xu Zhu, Xue-Rong Xiao, Man-Yun Dai, Ting Zhang, Yan Qu, Xiu-Wei Yang, Hong-Bo Qin, Frank J Gonzalez, Fei Li. Metabolic Activation of Elemicin Leads to the Inhibition of Stearoyl-CoA Desaturase 1. Chemical research in toxicology. 2019 10; 32(10):1965-1976. doi: 10.1021/acs.chemrestox.9b00112. [PMID: 31468958]
  • Chuan-Qin Wu, Guan-Hua Chen. Detection of synergistic effect of superoxide dismutase and jujubosides on scavenging superoxide anion radical by capillary electrophoresis. Biomedical chromatography : BMC. 2019 Oct; 33(10):e4630. doi: 10.1002/bmc.4630. [PMID: 31243785]
  • Seemaisamy Revathi, Faruck Lukmanul Hakkim, Neelamegam Ramesh Kumar, Hamid A Bakshi, Alagar Yadav Sangilimuthu, Murtaza M Tambuwala, Mohammad Changez, Mohamed M Nasef, Muthukalingan Krishnan, Nagarajan Kayalvizhi. In Vivo Anti Cancer Potential of Pyrogallol in Murine Model of Colon Cancer. Asian Pacific journal of cancer prevention : APJCP. 2019 09; 20(9):2645-2651. doi: 10.31557/apjcp.2019.20.9.2645. [PMID: 31554359]
  • Lenka Applová, Jana Karlíčková, Paul Warncke, Kateřina Macáková, Marcel Hrubša, Miloslav Macháček, Václav Tvrdý, Dagmar Fischer, Přemysl Mladěnka. 4-Methylcatechol, a Flavonoid Metabolite with Potent Antiplatelet Effects. Molecular nutrition & food research. 2019 08; 63(20):e1900261. doi: 10.1002/mnfr.201900261. [PMID: 31343835]
  • Yi-Kun Wang, Xiao-Nan Yang, Xu Zhu, Xue-Rong Xiao, Xiu-Wei Yang, Hong-Bo Qin, Frank J Gonzalez, Fei Li. Role of Metabolic Activation in Elemicin-Induced Cellular Toxicity. Journal of agricultural and food chemistry. 2019 Jul; 67(29):8243-8252. doi: 10.1021/acs.jafc.9b02137. [PMID: 31271289]
  • Melodie M Machovina, Sam J B Mallinson, Brandon C Knott, Alexander W Meyers, Marc Garcia-Borràs, Lintao Bu, Japheth E Gado, April Oliver, Graham P Schmidt, Daniel J Hinchen, Michael F Crowley, Christopher W Johnson, Ellen L Neidle, Christina M Payne, Kendall N Houk, Gregg T Beckham, John E McGeehan, Jennifer L DuBois. Enabling microbial syringol conversion through structure-guided protein engineering. Proceedings of the National Academy of Sciences of the United States of America. 2019 07; 116(28):13970-13976. doi: 10.1073/pnas.1820001116. [PMID: 31235604]
  • Hery Sutanto, Bambang Heru Susanto, Mohammad Nasikin. Solubility and Antioxidant Potential of a Pyrogallol Derivative for Biodiesel Additive. Molecules (Basel, Switzerland). 2019 Jul; 24(13):. doi: 10.3390/molecules24132439. [PMID: 31269770]
  • Carla Guijarro-Real, Adrián Rodríguez-Burruezo, Jaime Prohens, María D Raigón, Ana Fita. HS-SPME analysis of the volatiles profile of water celery (Apium nodiflorum), a wild vegetable with increasing culinary interest. Food research international (Ottawa, Ont.). 2019 07; 121(?):765-775. doi: 10.1016/j.foodres.2018.12.054. [PMID: 31108807]
  • Leila Roufegarinejad, Ryszard Amarowicz, Ali Jahanban-Esfahlan. Characterizing the interaction between pyrogallol and human serum albumin by spectroscopic and molecular docking methods. Journal of biomolecular structure & dynamics. 2019 Jul; 37(11):2766-2775. doi: 10.1080/07391102.2018.1496854. [PMID: 30052121]
  • Myeongjoo Son, Seyeon Oh, Hye Sun Lee, BoMi Ryu, Yunfei Jiang, Ji Tae Jang, You-Jin Jeon, Kyunghee Byun. Pyrogallol-Phloroglucinol-6,6'-Bieckol from Ecklonia cava Improved Blood Circulation in Diet-Induced Obese and Diet-Induced Hypertension Mouse Models. Marine drugs. 2019 May; 17(5):. doi: 10.3390/md17050272. [PMID: 31071969]
  • Natalia Mikołajczak, Małgorzata Tańska, Iwona Konopka. Impact of the addition of 4-vinyl-derivatives of ferulic and sinapic acids on retention of fatty acids and terpenoids in cold-pressed rapeseed and flaxseed oils during the induction period of oxidation. Food chemistry. 2019 Apr; 278(?):119-126. doi: 10.1016/j.foodchem.2018.11.001. [PMID: 30583352]
  • Xu Zhu, Yi-Kun Wang, Xiao-Nan Yang, Xue-Rong Xiao, Ting Zhang, Xiu-Wei Yang, Hong-Bo Qin, Fei Li. Metabolic Activation of Myristicin and Its Role in Cellular Toxicity. Journal of agricultural and food chemistry. 2019 Apr; 67(15):4328-4336. doi: 10.1021/acs.jafc.9b00893. [PMID: 30912427]
  • Daniela Dias-Pedroso, Joel Guerra, Andreia Gomes, Carole Oudot, Catherine Brenner, Cláudia N Santos, Helena L A Vieira. Phenolic Metabolites Modulate Cardiomyocyte Beating in Response to Isoproterenol. Cardiovascular toxicology. 2019 04; 19(2):156-167. doi: 10.1007/s12012-018-9485-8. [PMID: 30302669]
  • Negin Seifzadeh, Mohammad Ali Sahari, Mohsen Barzegar, Hassan Ahmadi Gavlighi, Luca Calani, Daniele Del Rio, Gianni Galaverna. Evaluation of polyphenolic compounds in membrane concentrated pistachio hull extract. Food chemistry. 2019 Mar; 277(?):398-406. doi: 10.1016/j.foodchem.2018.10.001. [PMID: 30502163]
  • W P D Wass Thilakarathna, H P Vasantha Rupasinghe. Microbial metabolites of proanthocyanidins reduce chemical carcinogen-induced DNA damage in human lung epithelial and fetal hepatic cells in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Mar; 125(?):479-493. doi: 10.1016/j.fct.2019.02.010. [PMID: 30735747]
  • Houwen Matthew Pan, Shengyang Chen, Tae-Sik Jang, Win Tun Han, Hyun-do Jung, Yaning Li, Juha Song. Plant seed-inspired cell protection, dormancy, and growth for large-scale biofabrication. Biofabrication. 2019 02; 11(2):025008. doi: 10.1088/1758-5090/ab03ed. [PMID: 30708358]
  • Hadjer Fodil, Madani Sarri, Noui Hendel, Filippo Maggi, Djamel Sarri. Essential oil composition of aerial parts from Algerian Anacyclus monanthos subsp. cyrtolepidioides (Pomel) Humphries. Natural product research. 2019 Jan; 33(2):292-295. doi: 10.1080/14786419.2018.1443094. [PMID: 29495887]
  • Shang-Ling Xiong, Gyu Tae Lim, Shang-Jun Yin, Jinhyuk Lee, Yue-Xiu Si, Jun-Mo Yang, Yong-Doo Park, Guo-Ying Qian. The inhibitory effect of pyrogallol on tyrosinase activity and structure: Integration study of inhibition kinetics with molecular dynamics simulation. International journal of biological macromolecules. 2019 Jan; 121(?):463-471. doi: 10.1016/j.ijbiomac.2018.10.046. [PMID: 30326223]
  • Anne Hay-Lombardie, Nicolas Pallet, Edith Bigot-Corbel. Quantitative measurement of urinary proteins in 2018: advantages, disadvantages, limits. Annales de biologie clinique. 2018 Dec; 76(6):627-631. doi: 10.1684/abc.2018.1389. [PMID: 30543186]
  • Seyeon Oh, Myeongjoo Son, Hye Sun Lee, Hyun-Soo Kim, You-Jin Jeon, Kyunghee Byun. Protective Effect of Pyrogallol-Phloroglucinol-6,6-Bieckol from Ecklonia cava on Monocyte-Associated Vascular Dysfunction. Marine drugs. 2018 Nov; 16(11):. doi: 10.3390/md16110441. [PMID: 30423960]
  • Stephane L Ngahang Kamte, Farahnaz Ranjbarian, Kevin Cianfaglione, Stefania Sut, Stefano Dall'Acqua, Maurizio Bruno, Fariba Heshmati Afshar, Romilde Iannarelli, Giovanni Benelli, Loredana Cappellacci, Anders Hofer, Filippo Maggi, Riccardo Petrelli. Identification of highly effective antitrypanosomal compounds in essential oils from the Apiaceae family. Ecotoxicology and environmental safety. 2018 Jul; 156(?):154-165. doi: 10.1016/j.ecoenv.2018.03.032. [PMID: 29549739]
  • Nazar Abdulameer Hamzah, Eman Salman Raheif. Purification and properties of Manganese Superoxide Dismutase (MnSOD) from Tamarix aphylla L. Cellular and molecular biology (Noisy-le-Grand, France). 2018 May; 64(7):19-23. doi: . [PMID: 29974841]
  • Małgorzata Tańska, Natalia Mikołajczak, Iwona Konopka. Comparison of the effect of sinapic and ferulic acids derivatives (4-vinylsyringol vs. 4-vinylguaiacol) as antioxidants of rapeseed, flaxseed, and extra virgin olive oils. Food chemistry. 2018 Feb; 240(?):679-685. doi: 10.1016/j.foodchem.2017.08.007. [PMID: 28946329]
  • G Bruges, W Venturini, G Crespo, M López Zambrano. Pyrogallol Induces Apoptosis in Human Platelets. Folia biologica. 2018; 64(1):23-30. doi: . [PMID: 29871735]
  • Arshia Hematpoor, Sook Yee Liew, Mohd Sofian Azirun, Khalijah Awang. Insecticidal activity and the mechanism of action of three phenylpropanoids isolated from the roots of Piper sarmentosum Roxb. Scientific reports. 2017 10; 7(1):12576. doi: 10.1038/s41598-017-12898-z. [PMID: 28974710]
  • Ana Elena Quirós-Sauceda, C-Y Oliver Chen, Jeffrey B Blumberg, Humberto Astiazaran-Garcia, Abraham Wall-Medrano, Gustavo A González-Aguilar. Processing 'Ataulfo' Mango into Juice Preserves the Bioavailability and Antioxidant Capacity of Its Phenolic Compounds. Nutrients. 2017 Sep; 9(10):. doi: 10.3390/nu9101082. [PMID: 28961171]
  • R Sánchez-Gómez, A Zalacain, F Pardo, G L Alonso, M R Salinas. Moscatel vine-shoot extracts as a grapevine biostimulant to enhance wine quality. Food research international (Ottawa, Ont.). 2017 08; 98(?):40-49. doi: 10.1016/j.foodres.2017.01.004. [PMID: 28610731]
  • Emmanuelle Dorla, Anne Gauvin-Bialecki, Zoé Deuscher, Agathe Allibert, Isabelle Grondin, Jean-Philippe Deguine, Philippe Laurent. Insecticidal Activity of the Leaf Essential Oil of Peperomia borbonensis Miq. (Piperaceae) and Its Major Components against the Melon Fly Bactrocera cucurbitae (Diptera: Tephritidae). Chemistry & biodiversity. 2017 Jun; 14(6):. doi: 10.1002/cbdv.201600493. [PMID: 28273402]
  • Matthew J Nemec, Hyemee Kim, Alexandria B Marciante, Ryan C Barnes, Erik D Hendrick, William H Bisson, Stephen T Talcott, Susanne U Mertens-Talcott. Polyphenolics from mango (Mangifera indica L.) suppress breast cancer ductal carcinoma in situ proliferation through activation of AMPK pathway and suppression of mTOR in athymic nude mice. The Journal of nutritional biochemistry. 2017 03; 41(?):12-19. doi: 10.1016/j.jnutbio.2016.11.005. [PMID: 27951515]
  • Magdalena Szejk, Tomasz Poplawski, Joanna Sarnik, Izabela Pawlaczyk-Graja, Franciszek Czechowski, Alicja Klaudia Olejnik, Roman Gancarz, Halina Malgorzata Zbikowska. Polyphenolic glycoconjugates from medical plants of Rosaceae/Asteraceae family protect human lymphocytes against γ-radiation-induced damage. International journal of biological macromolecules. 2017 Jan; 94(Pt A):585-593. doi: 10.1016/j.ijbiomac.2016.10.053. [PMID: 27769934]
  • Yu-Dong Ma, Varadharajan Thiyagarajan, May-Jywan Tsai, Sheng-I Lue, Yi-Chen Chia, Song-Kun Shyue, Ching-Feng Weng. Pyrogallol abates VSMC migration via modulation of Caveolin-1, matrix metalloproteinase and intima hyperplasia in carotid ligation mouse. Environmental toxicology and pharmacology. 2016 Dec; 48(?):63-75. doi: 10.1016/j.etap.2016.10.005. [PMID: 27768988]
  • Ji Yup Kim, Hojae Lee, Taegyun Park, Joonhong Park, Mi-Hee Kim, Hyeoncheol Cho, Wongu Youn, Sung Min Kang, Insung S Choi. Artificial Spores: Cytocompatible Coating of Living Cells with Plant-Derived Pyrogallol. Chemistry, an Asian journal. 2016 Nov; 11(22):3183-3187. doi: 10.1002/asia.201601237. [PMID: 27706902]
  • S L Mathews, C E Smithson, A M Grunden. Purification and characterization of a recombinant laccase-like multi-copper oxidase from Paenibacillus glucanolyticus SLM1. Journal of applied microbiology. 2016 Nov; 121(5):1335-1345. doi: 10.1111/jam.13241. [PMID: 27451019]
  • Aisha Ashraf, Raja Adil Sarfraz, Muhammad Abid Rashid, Adeel Mahmood, Muhammad Shahid, Nadia Noor. Chemical composition, antioxidant, antitumor, anticancer and cytotoxic effects of Psidium guajava leaf extracts. Pharmaceutical biology. 2016 Oct; 54(10):1971-81. doi: 10.3109/13880209.2015.1137604. [PMID: 26841303]
  • Wei-Sheng Feng, Chun-Ge Li, Xiao-Ke Zheng, Ling-Ling Li, Wen-Jing Chen, Yan-Li Zhang, Yan-Gang Cao, Jian-Hong Gong, Hai-Xue Kuang. Three new sulphur glycosides from the seeds of Descurainia sophia. Natural product research. 2016 Aug; 30(15):1675-81. doi: 10.1080/14786419.2015.1135141. [PMID: 26795632]
  • Dan Zhu, Antoni Sánchez-Ferrer, Laura Nyström. Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources. Journal of natural products. 2016 Feb; 79(2):308-16. doi: 10.1021/acs.jnatprod.5b00880. [PMID: 26790041]
  • Klara Kraljić, Dubravka Škevin, Lidija Barišić, Monika Kovačević, Marko Obranović, Ivana Jurčević. Changes in 4-vinylsyringol and other phenolics during rapeseed oil refining. Food chemistry. 2015 Nov; 187(?):236-42. doi: 10.1016/j.foodchem.2015.04.039. [PMID: 25977022]
  • R Ravikanth Reddy, Bandaru V N Phani Kumar, Ganesh Shanmugam, Balaraman Madhan, Asit B Mandal. Molecular Level Insights on Collagen-Polyphenols Interaction Using Spin-Relaxation and Saturation Transfer Difference NMR. The journal of physical chemistry. B. 2015 Nov; 119(44):14076-85. doi: 10.1021/acs.jpcb.5b07911. [PMID: 26447653]
  • Ai-Hong Yang, Xin He, Jun-Xiu Chen, Li-Na He, Chun-Huan Jin, Li-Li Wang, Fang-Liang Zhang, Li-Jun An. Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2. Chemico-biological interactions. 2015 Jul; 237(?):133-40. doi: 10.1016/j.cbi.2015.06.018. [PMID: 26091900]
  • Ana Carolina B C Rodrigues, Larissa M Bomfim, Sara P Neves, Leociley R A Menezes, Rosane B Dias, Milena B P Soares, Ana Paula N Prata, Clarissa A Gurgel Rocha, Emmanoel V Costa, Daniel P Bezerra. Antitumor Properties of the Essential Oil From the Leaves of Duguetia gardneriana. Planta medica. 2015 Jul; 81(10):798-803. doi: 10.1055/s-0035-1546130. [PMID: 26125546]
  • Jee Hwan Yi, Haribalan Perumalsamy, Karuppasamy Sankarapandian, Byeoung-Ryeol Choi, Young-Joon Ahn. Fumigant Toxicity of Phenylpropanoids Identified in Asarum sieboldii Aerial Parts to Lycoriella ingenua (Diptera: Sciaridae) and Coboldia fuscipes (Diptera: Scatopsidae). Journal of economic entomology. 2015 Jun; 108(3):1208-14. doi: 10.1093/jee/tov064. [PMID: 26470247]
  • Víctor López, Javier Gerique, Elisa Langa, César Berzosa, Marta Sofía Valero, Carlota Gómez-Rincón. Antihelmintic effects of nutmeg (Myristica fragans) on Anisakis simplex L3 larvae obtained from Micromesistius potassou. Research in veterinary science. 2015 Jun; 100(?):148-52. doi: 10.1016/j.rvsc.2015.03.033. [PMID: 25890576]
  • Dnyanesh Balkrishna Amle, Bidhan C Koner. Use of red vacutainer for collection of CSF causes falsely high estimation of proteins by pyrogallol red method. Clinica chimica acta; international journal of clinical chemistry. 2015 Apr; 444(?):62-5. doi: 10.1016/j.cca.2015.02.001. [PMID: 25668232]
  • Detlef Ulrich, Thomas Nothnagel, Hartwig Schulz. Influence of cultivar and harvest year on the volatile profiles of leaves and roots of carrots (Daucus carota spp. sativus Hoffm.). Journal of agricultural and food chemistry. 2015 Apr; 63(13):3348-56. doi: 10.1021/acs.jafc.5b00704. [PMID: 25797828]
  • Xin Chao Liu, Zhi Long Liu. Analysis of the essential oil of Illicium henryi Diels root bark and its insecticidal activity against Liposcelis bostrychophila Badonnel. Journal of food protection. 2015 Apr; 78(4):772-7. doi: 10.4315/0362-028x.jfp-14-407. [PMID: 25836404]
  • Muhammad Shahzad, Emma Millhouse, Shauna Culshaw, Christine A Edwards, Gordon Ramage, Emilie Combet. Selected dietary (poly)phenols inhibit periodontal pathogen growth and biofilm formation. Food & function. 2015 Mar; 6(3):719-29. doi: 10.1039/c4fo01087f. [PMID: 25585200]
  • Rui C Pimpão, M Rita Ventura, Ricardo B Ferreira, Gary Williamson, Claudia N Santos. Phenolic sulfates as new and highly abundant metabolites in human plasma after ingestion of a mixed berry fruit purée. The British journal of nutrition. 2015 Feb; 113(3):454-63. doi: 10.1017/s0007114514003511. [PMID: 25571923]
  • Veda P Pandey, Upendra N Dwivedi. A ripening associated peroxidase from papaya having a role in defense and lignification: heterologous expression and in-silico and in-vitro experimental validation. Gene. 2015 Jan; 555(2):438-47. doi: 10.1016/j.gene.2014.11.013. [PMID: 25447898]
  • S Beyza Ozturk Sarikaya. Acethylcholinesterase inhibitory potential and antioxidant properties of pyrogallol. Journal of enzyme inhibition and medicinal chemistry. 2015; 30(5):761-6. doi: 10.3109/14756366.2014.965700. [PMID: 25297710]
  • Hamit Yasar Ellidag, Gulten Curek, Esin Eren, Ozgur Aydin, Necat Yilmaz. The Cutoff Level for Urine Protein in Urine Immunofixation Electrophoresis. Clinical laboratory. 2015; 61(10):1525-30. doi: 10.7754/clin.lab.2015.150230. [PMID: 26642715]
  • Sindhu Mathew, Zainul Akmar Zakaria. Pyroligneous acid-the smoky acidic liquid from plant biomass. Applied microbiology and biotechnology. 2015 Jan; 99(2):611-22. doi: 10.1007/s00253-014-6242-1. [PMID: 25467926]
  • Saher F Ali, Owen L Woodman. Tocotrienol Rich Palm Oil Extract Is More Effective Than Pure Tocotrienols at Improving Endothelium-Dependent Relaxation in the Presence of Oxidative Stress. Oxidative medicine and cellular longevity. 2015; 2015(?):150829. doi: 10.1155/2015/150829. [PMID: 26075031]
  • Kai Yang, Chun-Xue You, Cheng-Fang Wang, Ning Lei, Shan-Shan Guo, Zhu-Feng Geng, Shu-Shan Du, Ping Ma, Zhi-Wei Deng. Chemical Composition and Bioactivity of Essential Oil of Atalantia guillauminii against Three Species Stored Product Insects. Journal of oleo science. 2015; 64(10):1101-9. doi: 10.5650/jos.ess15135. [PMID: 26369599]
  • Gisela Palma-Orozco, Norma A Marrufo-Hernández, José G Sampedro, Hugo Nájera. Purification and partial biochemical characterization of polyphenol oxidase from mango (Mangifera indica cv. Manila). Journal of agricultural and food chemistry. 2014 Oct; 62(40):9832-40. doi: 10.1021/jf5029784. [PMID: 25211397]
  • Hoskote Anand Kiran Kumar, Badal Kumar Mandal, Kesarla Mohan Kumar, Sireesh babu Maddinedi, Tammina Sai Kumar, Pavithra Madhiyazhagan, Asit Ranjan Ghosh. Antimicrobial and antioxidant activities of Mimusops elengi seed extract mediated isotropic silver nanoparticles. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2014 Sep; 130(?):13-8. doi: 10.1016/j.saa.2014.03.024. [PMID: 24759779]
  • Zhibin Wang, Qiuhong Wang, Bingyou Yang, Jing Li, Chunjuan Yang, Yonghai Meng, Haixue Kuang. GC-MS method for determination and pharmacokinetic study of four phenylpropanoids in rat plasma after oral administration of the essential oil of Acorus tatarinowii Schott rhizomes. Journal of ethnopharmacology. 2014 Sep; 155(2):1134-40. doi: 10.1016/j.jep.2014.06.035. [PMID: 25046827]
  • M Zulfiquer Hossain, Kalpesh Patel, Scott E Kern. Salivary α-amylase, serum albumin, and myoglobin protect against DNA-damaging activities of ingested dietary agents in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Aug; 70(?):114-9. doi: 10.1016/j.fct.2014.05.002. [PMID: 24842839]
  • Hatice Sürer, Tuba Özgün, Fatma Meriç Yilmaz, Gülsen Yilmaz. The effect of centrifugation on three urine protein assays: benzethonium chloride, benzalkonium chloride and pyrogallol red. Clinical chemistry and laboratory medicine. 2014 Apr; 52(4):e71-3. doi: 10.1515/cclm-2013-0868. [PMID: 24280287]
  • Jun Shigeto, Mariko Nagano, Koki Fujita, Yuji Tsutsumi. Catalytic profile of Arabidopsis peroxidases, AtPrx-2, 25 and 71, contributing to stem lignification. PloS one. 2014; 9(8):e105332. doi: 10.1371/journal.pone.0105332. [PMID: 25137070]
  • Guido Flamini, Tahar Smaili, Amar Zellagui, Noureddine Gherraf, Pier Luigi Cioni. Effect of growth stage on essential-oil yield and composition of Daucus sahariensis. Chemistry & biodiversity. 2013 Nov; 10(11):2014-20. doi: 10.1002/cbdv.201300052. [PMID: 24243610]
  • David G Reid, Susan L Bonnet, Gabre Kemp, Jan H van der Westhuizen. Analysis of commercial proanthocyanidins. Part 4: solid state (13)C NMR as a tool for in situ analysis of proanthocyanidin tannins, in heartwood and bark of quebracho and acacia, and related species. Phytochemistry. 2013 Oct; 94(?):243-8. doi: 10.1016/j.phytochem.2013.06.007. [PMID: 23838626]
  • Chen Xu, Shu Liu, Zhiqiang Liu, Fengrui Song, Shuying Liu. Superoxide generated by pyrogallol reduces highly water-soluble tetrazolium salt to produce a soluble formazan: a simple assay for measuring superoxide anion radical scavenging activities of biological and abiological samples. Analytica chimica acta. 2013 Sep; 793(?):53-60. doi: 10.1016/j.aca.2013.07.027. [PMID: 23953206]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Malai Taweechotipatr, Sumalee Kamchonwongpaisan. GC/GC-MS analysis, isolation and identification of bioactive essential oil components from the Bhutanese medicinal plant, Pleurospermum amabile. Natural product communications. 2013 Sep; 8(9):1305-8. doi: . [PMID: 24273872]
  • Sanja Matić, Snežana Stanić, Desanka Bogojević, Melita Vidaković, Nevena Grdović, Svetlana Dinić, Slavica Solujić, Milan Mladenović, Nevena Stanković, Mirjana Mihailović. Methanol extract from the stem of Cotinus coggygria Scop., and its major bioactive phytochemical constituent myricetin modulate pyrogallol-induced DNA damage and liver injury. Mutation research. 2013 Aug; 755(2):81-9. doi: 10.1016/j.mrgentox.2013.03.011. [PMID: 23830930]