Chemistry:2,4-Diacetylphloroglucinol
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| Preferred IUPAC name
1,1′-(2,4,6-Trihydroxy-1,3-phenylene)di(ethan-1-one) | |
| Other names
1-(3-Acetyl-2,4,6-trihydroxyphenyl)ethanone
2,4-DAPG | |
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3D model (JSmol)
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| Properties | |
| C10H10O5 | |
| Molar mass | 210.18 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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Tracking categories (test):
2,4-Diacetylphloroglucinol or Phl[1][2] is a natural phenol found in several bacteria:
- Specific strains of the Gram-negative bacterium Pseudomonas fluorescens.[3] This compound is found to be responsible for the antiphytopathogenic[4] and biocontrol[5] properties in these strains.
- It is also found in Pseudomonas protegens, where it has the same activity against various plant pathogens.[6][7]
- Lysobacter gummosus, a bacterium which lives on the skin of red-backed salamanders.[8]
- Isolates of Pseudomonas aurantiaca found in Ukraine , living in root symbiosis produce it to control Fusarium oxysporum.[9][10][1]
References
- ↑ 1.0 1.1 Cook, RJ; Thomashow, LS; Weller, DM; Fujimoto, D; Mazzola, M; Bangera, G; Kim, DS (May 1995). "Molecular mechanisms of defense by rhizobacteria against root disease". Proceedings of the National Academy of Sciences of the United States of America 92 (10): 4197–4201. doi:10.1073/pnas.92.10.4197. PMID 11607544. Bibcode: 1995PNAS...92.4197C.
- ↑ Duffy, BK; Défago, G (June 1999). "Environmental factors modulating antibiotic and siderophore biosynthesis by Pseudomonas fluorescens biocontrol strains". Applied and Environmental Microbiology 65 (6): 2429–2438. doi:10.1128/aem.65.6.2429-2438.1999. PMID 10347023. Bibcode: 1999ApEnM..65.2429D.
- ↑ Achkar, J; Xian, M; Zhao, H; Frost, JW (April 2005). "Biosynthesis of phloroglucinol". Journal of the American Chemical Society 127 (15): 5332–5333. doi:10.1021/ja042340g. PMID 15826166.
- ↑ Bangera, MG; Thomashow, LS (May 1999). "Identification and characterization of a gene cluster for synthesis of the polyketide antibiotic 2,4-diacetylphloroglucinol from Pseudomonas fluorescens Q2-87". Journal of Bacteriology 181 (10): 3155–3163. doi:10.1128/JB.181.10.3155-3163.1999. PMID 10322017.
- ↑ Cronin, D; Moenne-Loccoz, Y; Fenton, A; Dunne, C; Dowling, DN; O'gara, F (April 1997). "Role of 2,4-Diacetylphloroglucinol in the Interactions of the Biocontrol Pseudomonad Strain F113 with the Potato Cyst Nematode Globodera rostochiensis". Applied and Environmental Microbiology 63 (4): 1357–1361. doi:10.1128/AEM.63.4.1357-1361.1997. PMID 16535571. Bibcode: 1997ApEnM..63.1357C.
- ↑ Ramette, A; Frapolli, M; Fischer-Le Saux, M; Gruffaz, C; Meyer, JM; Défago, G et al. (May 2011). "Pseudomonas protegens sp. nov., widespread plant-protecting bacteria producing the biocontrol compounds 2,4-diacetylphloroglucinol and pyoluteorin". Systematic and Applied Microbiology 34 (3): 180–188. doi:10.1016/j.syapm.2010.10.005. PMID 21392918.
- ↑ Haas, D; Défago, G (April 2005). "Biological control of soil-borne pathogens by fluorescent pseudomonads". Nature Reviews. Microbiology 3 (4): 307–319. doi:10.1038/nrmicro1129. PMID 15759041.
- ↑ Brucker, RM; Baylor, CM; Walters, RL; Lauer, A; Harris, RN; Minbiole, KP (January 2008). "The identification of 2,4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus". Journal of Chemical Ecology 34 (1): 39–43. doi:10.1007/s10886-007-9352-8. PMID 18058176.
- ↑ Garagulia, AD; Kiprianova, EA; Boĭko, OI (1974). "[Antibiotic action of bacteria of the genus Pseudomonas on phytopathogenic fungi]" (in Ukrainian). Mikrobiolohichnyi Zhurnal 36 (2): 197–202. OCLC 1063241398. PMID 4465652.
- ↑ Pidoplichko, VN; Garagulya, AD (1974). "[Effect of antagonistic bacteria on development of wheat root rot]" (in Ukrainian). Zhurnal Mikrobiologii (Kyiv) 36: 599–602. ISSN 1028-0987. OCLC 1063241398.
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