2,4-Diacetylphloroglucinol (BioDeep_00000015247)

   

natural product Volatile Flavor Compounds


代谢物信息卡片


2,4-Diacetylphloroglucinol

化学式: C10H10O5 (210.052821)
中文名称: 2,4-二乙酰基间苯三酚, 2,4-二乙酰间苯三酚
谱图信息: 最多检出来源 Viridiplantae(plant) 5.02%

分子结构信息

SMILES: CC(=O)C1=C(C(=C(C=C1O)O)C(=O)C)O
InChI: InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3

描述信息

A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D013501 - Surface-Active Agents > D003902 - Detergents

同义名列表

2 个代谢物同义名

2,4-Diacetylphloroglucinol; 2,4-Diacetylphloroglucinol



数据库引用编号

17 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

14 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

  • Artyom A Stepanov, Anastasia V Vasilchenko, Alexey S Vasilchenko. Subinhibitory effects of 2,4-diacetylphloroglucinol on filamentous fungus Aspergillus fumigatus. Journal of applied microbiology. 2023 Dec; 134(12):. doi: 10.1093/jambio/lxad294. [PMID: 38086610]
  • Bingxin Wang, Zeyu Zhang, Fugui Xu, Zixiang Yang, Zihan Li, Danyu Shen, Limin Wang, Huijun Wu, Tao Li, Qing Yan, Qi Wei, Xiaolong Shao, Guoliang Qian. Soil bacterium manipulates antifungal weapons by sensing intracellular type IVA secretion system effectors of a competitor. The ISME journal. 2023 Dec; 17(12):2232-2246. doi: 10.1038/s41396-023-01533-7. [PMID: 37838821]
  • Tristan Lurthy, Ségolène Perot, Florence Gerin-Eveillard, Marjolaine Rey, Florence Wisniewski-Dyé, Jordan Vacheron, Claire Prigent-Combaret. Inhibition of broomrape germination by 2,4-diacetylphloroglucinol produced by environmental Pseudomonas. Microbial biotechnology. 2023 Oct; ?(?):. doi: 10.1111/1751-7915.14336. [PMID: 37897154]
  • Qingqing Yang, Qing Yan, Bo Zhang, Li-Qun Zhang, Xiaogang Wu. Citrate Synthase GltA Modulates the 2,4-Diacetylphloroglucinol Biosynthesis of Pseudomonas fluorescens 2P24 and is Essential for the Biocontrol Capacity. Journal of agricultural and food chemistry. 2023 Aug; 71(31):11892-11901. doi: 10.1021/acs.jafc.3c03051. [PMID: 37523467]
  • Mingming Yang, Linda S Thomashow, David M Weller. Evaluation of the Phytotoxicity of 2,4-Diacetylphloroglucinol and Pseudomonas brassicacearum Q8r1-96 on Different Wheat Cultivars. Phytopathology. 2021 Nov; 111(11):1935-1941. doi: 10.1094/phyto-07-20-0315-r. [PMID: 33876647]
  • Morten Lindqvist Hansen, Zhiming He, Mario Wibowo, Lars Jelsbak. A Whole-Cell Biosensor for Detection of 2,4-Diacetylphloroglucinol (DAPG)-Producing Bacteria from Grassland Soil. Applied and environmental microbiology. 2021 01; 87(3):. doi: 10.1128/aem.01400-20. [PMID: 33218996]
  • William T Julian, Anastasia V Vasilchenko, Daniil D Shpindyuk, Darya V Poshvina, Alexey S Vasilchenko. Bacterial-Derived Plant Protection Metabolite 2,4-Diacetylphloroglucinol: Effects on Bacterial Cells at Inhibitory and Subinhibitory Concentrations. Biomolecules. 2020 12; 11(1):. doi: 10.3390/biom11010013. [PMID: 33375656]
  • Xiao-Quan Yu, Xu Yan, Meng-Yuan Zhang, Li-Qun Zhang, Yong-Xing He. Flavonoids repress the production of antifungal 2,4-DAPG but potentially facilitate root colonization of the rhizobacterium Pseudomonas fluorescens. Environmental microbiology. 2020 12; 22(12):5073-5089. doi: 10.1111/1462-2920.15052. [PMID: 32363709]
  • Dae-Han Chae, Da-Ran Kim, Gyeongjun Cho, Suhyeon Moon, Youn-Sig Kwak. Genome-Wide Investigation of 2,4-Diacetylphloroglucinol Protection Genes in Arabidopsis thaliana. Molecular plant-microbe interactions : MPMI. 2020 Aug; 33(8):1072-1079. doi: 10.1094/mpmi-04-20-0084-r. [PMID: 32370644]
  • Yang Zhang, Bo Zhang, Haiyan Wu, Xiaogang Wu, Qing Yan, Li-Qun Zhang. Pleiotropic effects of RsmA and RsmE proteins in Pseudomonas fluorescens 2P24. BMC microbiology. 2020 07; 20(1):191. doi: 10.1186/s12866-020-01880-x. [PMID: 32615927]
  • Ming-Min Zhao, Ning Lyu, Dong Wang, Xiao-Gang Wu, Yuan-Zheng Zhao, Li-Qun Zhang, Hong-You Zhou. PhlG mediates the conversion of DAPG to MAPG in Pseudomonas fluorescens 2P24. Scientific reports. 2020 03; 10(1):4296. doi: 10.1038/s41598-020-60555-9. [PMID: 32152338]
  • Yang Zhang, Bo Zhang, Xiaogang Wu, Li-Qun Zhang. Characterization the role of GacA-dependent small RNAs and RsmA family proteins on 2,4-diacetylphloroglucinol production in Pseudomonas fluorescens 2P24. Microbiological research. 2020 Mar; 233(?):126391. doi: 10.1016/j.micres.2019.126391. [PMID: 31865097]
  • Bo Zhang, Hui Zhao, Xiaogang Wu, Li-Qun Zhang. The Oxidoreductase DsbA1 negatively influences 2,4-diacetylphloroglucinol biosynthesis by interfering the function of Gcd in Pseudomonas fluorescens 2P24. BMC microbiology. 2020 02; 20(1):39. doi: 10.1186/s12866-020-1714-1. [PMID: 32093646]
  • Johanna Nelkner, Gonzalo Torres Tejerizo, Julia Hassa, Timo Wentong Lin, Julian Witte, Bart Verwaaijen, Anika Winkler, Boyke Bunk, Cathrin Spröer, Jörg Overmann, Rita Grosch, Alfred Pühler, And Andreas Schlüter. Genetic Potential of the Biocontrol Agent Pseudomonas brassicacearum (Formerly P. trivialis) 3Re2-7 Unraveled by Genome Sequencing and Mining, Comparative Genomics and Transcriptomics. Genes. 2019 08; 10(8):. doi: 10.3390/genes10080601. [PMID: 31405015]
  • Marco Andreolli, Giacomo Zapparoli, Elisa Angelini, Gianluca Lucchetta, Silvia Lampis, Giovanni Vallini. Pseudomonas protegens MP12: A plant growth-promoting endophytic bacterium with broad-spectrum antifungal activity against grapevine phytopathogens. Microbiological research. 2019 Feb; 219(?):123-131. doi: 10.1016/j.micres.2018.11.003. [PMID: 30642463]
  • Fangnan Yu, Xiaoshu Jing, Xiaochen Li, Hailong Wang, Hanna Chen, Lin Zhong, Jia Yin, Deng Pan, Yulong Yin, Jun Fu, Liqiu Xia, Xiaoying Bian, Qiang Tu, Youming Zhang. Recombineering Pseudomonas protegens CHA0: An innovative approach that improves nitrogen fixation with impressive bactericidal potency. Microbiological research. 2019 Jan; 218(?):58-65. doi: 10.1016/j.micres.2018.09.009. [PMID: 30454659]
  • Mingming Yang, Dmitri V Mavrodi, Linda S Thomashow, David M Weller. Differential Response of Wheat Cultivars to Pseudomonas brassicacearum and Take-All Decline Soil. Phytopathology. 2018 Dec; 108(12):1363-1372. doi: 10.1094/phyto-01-18-0024-r. [PMID: 29905506]
  • Young Sang Kwon, Chang-Wook Jeon, Dong-Won Bae, Jong-Su Seo, Linda S Thomashow, David M Weller, Youn-Sig Kwak. Construction of a proteome reference map and response of Gaeumannomyces graminis var. tritici to 2,4-diacetylphloroglucinol. Fungal biology. 2018 11; 122(11):1098-1108. doi: 10.1016/j.funbio.2018.09.001. [PMID: 30342625]
  • Kai Nesemann, Susanna A Braus-Stromeyer, Rebekka Harting, Annalena Höfer, Harald Kusch, Alinne Batista Ambrosio, Christian Timpner, Gerhard H Braus. Fluorescent pseudomonads pursue media-dependent strategies to inhibit growth of pathogenic Verticillium fungi. Applied microbiology and biotechnology. 2018 Jan; 102(2):817-831. doi: 10.1007/s00253-017-8618-5. [PMID: 29151161]
  • Xu Li, Gao-Qi Gu, Wei Chen, Li-Juan Gao, Xue-Hong Wu, Li-Qun Zhang. The outer membrane protein OprF and the sigma factor SigX regulate antibiotic production in Pseudomonas fluorescens 2P24. Microbiological research. 2018 Jan; 206(?):159-167. doi: 10.1016/j.micres.2017.10.006. [PMID: 29146252]
  • Xu Yan, Rui Yang, Rui-Xue Zhao, Jian-Ting Han, Wen-Juan Jia, Di-Yin Li, Yong Wang, Nannan Zhang, Yi Wu, Li-Qun Zhang, Yong-Xing He. Transcriptional Regulator PhlH Modulates 2,4-Diacetylphloroglucinol Biosynthesis in Response to the Biosynthetic Intermediate and End Product. Applied and environmental microbiology. 2017 11; 83(21):. doi: 10.1128/aem.01419-17. [PMID: 28821548]
  • Pragna Lakshmi T, Moumita Mondal, Krishna Ramadas, Sakthivel Natarajan. Molecular interaction of 2,4-diacetylphloroglucinol (DAPG) with human serum albumin (HSA): The spectroscopic, calorimetric and computational investigation. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2017 Aug; 183(?):90-102. doi: 10.1016/j.saa.2017.04.012. [PMID: 28441541]
  • Karina Gutiérrez-García, Adriana Neira-González, Rosa Martha Pérez-Gutiérrez, Giovana Granados-Ramírez, Ramon Zarraga, Kazimierz Wrobel, Francisco Barona-Gómez, Luis B Flores-Cotera. Phylogenomics of 2,4-Diacetylphloroglucinol-Producing Pseudomonas and Novel Antiglycation Endophytes from Piper auritum. Journal of natural products. 2017 07; 80(7):1955-1963. doi: 10.1021/acs.jnatprod.6b00823. [PMID: 28704049]
  • Mélanie M Paulin, Amy Novinscak, Carine Lanteigne, Vijay J Gadkar, Martin Filion. Interaction between 2,4-Diacetylphloroglucinol- and Hydrogen Cyanide-Producing Pseudomonas brassicacearum LBUM300 and Clavibacter michiganensis subsp. michiganensis in the Tomato Rhizosphere. Applied and environmental microbiology. 2017 07; 83(13):. doi: 10.1128/aem.00073-17. [PMID: 28432096]
  • Qing Yan, Benjamin Philmus, Jeff H Chang, Joyce E Loper. Novel mechanism of metabolic co-regulation coordinates the biosynthesis of secondary metabolites in Pseudomonas protegens. eLife. 2017 03; 6(?):. doi: 10.7554/elife.22835. [PMID: 28262092]
  • Jennifer C Clifford, Alex Buchanan, Oliver Vining, Teresa A Kidarsa, Jeff H Chang, Kerry L McPhail, Joyce E Loper. Phloroglucinol functions as an intracellular and intercellular chemical messenger influencing gene expression in Pseudomonas protegens. Environmental microbiology. 2016 10; 18(10):3296-3308. doi: 10.1111/1462-2920.13043. [PMID: 26337778]
  • Qingxia Zhang, Yanyan Ji, Qi Xiao, Soonie Chng, Yunhui Tong, Xijun Chen, Fengquan Liu. Role of Vfr in the regulation of antifungal compound production by Pseudomonas fluorescens FD6. Microbiological research. 2016 Jul; 188-189(?):106-112. doi: 10.1016/j.micres.2016.04.013. [PMID: 27296968]
  • Anna Kisiel, Ewa Kępczyńska. Medicago truncatula Gaertn. as a model for understanding the mechanism of growth promotion by bacteria from rhizosphere and nodules of alfalfa. Planta. 2016 May; 243(5):1169-89. doi: 10.1007/s00425-016-2469-7. [PMID: 26861677]
  • Vijay Kumar Veena, Kamaraj Kennedy, Pragna Lakshmi, R Krishna, N Sakthivel. Anti-leukemic, anti-lung, and anti-breast cancer potential of the microbial polyketide 2, 4-diacetylphloroglucinol (DAPG) and its interaction with the metastatic proteins than the antiapoptotic Bcl-2 proteins. Molecular and cellular biochemistry. 2016 Mar; 414(1-2):47-56. doi: 10.1007/s11010-016-2657-6. [PMID: 26833196]
  • Qingxia Zhang, Qi Xiao, Jingyou Xu, Yunhui Tong, Jia Wen, Xijun Chen, Lihui Wei. Effect of retS gene on antibiotics production in Pseudomonas fluorescens FD6. Microbiological research. 2015 Nov; 180(?):23-9. doi: 10.1016/j.micres.2015.07.005. [PMID: 26505308]
  • Kasumi Takeuchi, Naomi Noda, Yuichi Katayose, Yoshiyuki Mukai, Hisataka Numa, Kosumi Yamada, Nobutaka Someya. Rhizoxin analogs contribute to the biocontrol activity of a newly isolated pseudomonas strain. Molecular plant-microbe interactions : MPMI. 2015 Mar; 28(3):333-42. doi: 10.1094/mpmi-09-14-0294-fi. [PMID: 25496595]
  • Brynne C Stanton, Velia Siciliano, Amar Ghodasara, Liliana Wroblewska, Kevin Clancy, Axel C Trefzer, Jonathan D Chesnut, Ron Weiss, Christopher A Voigt. Systematic transfer of prokaryotic sensors and circuits to mammalian cells. ACS synthetic biology. 2014 Dec; 3(12):880-91. doi: 10.1021/sb5002856. [PMID: 25360681]
  • Wei Zhang, Zhao Zhao, Bo Zhang, Xiao-Gang Wu, Zheng-Guang Ren, Li-Qun Zhang. Posttranscriptional regulation of 2,4-diacetylphloroglucinol production by GidA and TrmE in Pseudomonas fluorescens 2P24. Applied and environmental microbiology. 2014 Jul; 80(13):3972-81. doi: 10.1128/aem.00455-14. [PMID: 24747907]
  • Jegan Sekar, Vaiyapuri Ramalingam Prabavathy. Novel Phl-producing genotypes of finger millet rhizosphere associated pseudomonads and assessment of their functional and genetic diversity. FEMS microbiology ecology. 2014 Jul; 89(1):32-46. doi: 10.1111/1574-6941.12354. [PMID: 24819774]
  • Juliana Almario, Claire Prigent-Combaret, Daniel Muller, Yvan Moënne-Loccoz. Effect of clay mineralogy on iron bioavailability and rhizosphere transcription of 2,4-diacetylphloroglucinol biosynthetic genes in biocontrol Pseudomonas protegens. Molecular plant-microbe interactions : MPMI. 2013 May; 26(5):566-74. doi: 10.1094/mpmi-11-12-0274-r. [PMID: 23405868]
  • Maren Stella Müller, Stefan Scheu, Alexandre Jousset. Protozoa Drive the Dynamics of Culturable Biocontrol Bacterial Communities. PloS one. 2013; 8(6):e66200. doi: 10.1371/journal.pone.0066200. [PMID: 23840423]
  • Carine Lanteigne, Vijay J Gadkar, Thérèse Wallon, Amy Novinscak, Martin Filion. Production of DAPG and HCN by Pseudomonas sp. LBUM300 contributes to the biological control of bacterial canker of tomato. Phytopathology. 2012 Oct; 102(10):967-73. doi: 10.1094/phyto-11-11-0312. [PMID: 22713078]
  • Tiantian Zhou, Da Chen, Chunyu Li, Qian Sun, Lingzhi Li, Fang Liu, Qirong Shen, Biao Shen. Isolation and characterization of Pseudomonas brassicacearum J12 as an antagonist against Ralstonia solanacearum and identification of its antimicrobial components. Microbiological research. 2012 Jul; 167(7):388-94. doi: 10.1016/j.micres.2012.01.003. [PMID: 22361469]
  • Xiaogang Wu, Yarui Wei, Jiucheng Liu, Liqun Zhang. [MvaT and MvaV transcriptionally regulate PcoI/PcoR quorum-sensing system in Pseudomonas fluorescens 2P24]. Wei sheng wu xue bao = Acta microbiologica Sinica. 2012 Jun; 52(6):710-7. doi: ". [PMID: 22934351]
  • Michele Frapolli, Joël F Pothier, Geneviève Défago, Yvan Moënne-Loccoz. Evolutionary history of synthesis pathway genes for phloroglucinol and cyanide antimicrobials in plant-associated fluorescent pseudomonads. Molecular phylogenetics and evolution. 2012 Jun; 63(3):877-90. doi: 10.1016/j.ympev.2012.02.030. [PMID: 22426436]
  • Sang-Dal Kim, Leonardo De La Fuente, David M Weller, Linda S Thomashow. Colonizing ability of Pseudomonas fluorescens 2112, among collections of 2,4-diacetylphloroglucinol-producing Pseudomonas fluorescens spp. in pea rhizosphere. Journal of microbiology and biotechnology. 2012 Jun; 22(6):763-70. doi: 10.4014/jmb.1112.12039. [PMID: 22573152]
  • Olga V Mavrodi, Dmitri V Mavrodi, James A Parejko, Linda S Thomashow, David M Weller. Irrigation differentially impacts populations of indigenous antibiotic-producing pseudomonas spp. in the rhizosphere of wheat. Applied and environmental microbiology. 2012 May; 78(9):3214-20. doi: 10.1128/aem.07968-11. [PMID: 22389379]
  • David M Weller, Dmitri V Mavrodi, Johan A van Pelt, Corné M J Pieterse, Leendert C van Loon, Peter A H M Bakker. Induced systemic resistance in Arabidopsis thaliana against Pseudomonas syringae pv. tomato by 2,4-diacetylphloroglucinol-producing Pseudomonas fluorescens. Phytopathology. 2012 Apr; 102(4):403-12. doi: 10.1094/phyto-08-11-0222. [PMID: 22409433]
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  • Ming-Ming Yang, Dmitri V Mavrodi, Olga V Mavrodi, Robert F Bonsall, James A Parejko, Timothy C Paulitz, Linda S Thomashow, He-Tong Yang, David M Weller, Jian-Hua Guo. Biological control of take-all by fluorescent Pseudomonas spp. from Chinese wheat fields. Phytopathology. 2011 Dec; 101(12):1481-91. doi: 10.1094/phyto-04-11-0096. [PMID: 22070279]
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