2,4-Diacetylphloroglucinol

Last updated
2,4-Diacetylphloroglucinol
2,4-diacetylphloroglucinol.PNG
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.316 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3 Yes check.svgY
    Key: PIFFQYJYNWXNGE-UHFFFAOYSA-N Yes check.svgY
  • CC(=O)C1=C(C(=C(C=C1O)O)C(=O)C)O
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).
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Infobox references

2,4-Diacetylphloroglucinol or Phl [1] [2] is a natural phenol found in several bacteria:

Related Research Articles

Biofilm Aggregation of bacteria or cells on a surface

A biofilm comprises any syntrophic consortium of microorganisms in which cells stick to each other and often also to a surface. These adherent cells become embedded within a slimy extracellular matrix that is composed of extracellular polymeric substances (EPSs). The cells within the biofilm produce the EPS components, which are typically a polymeric conglomeration of extracellular polysaccharides, proteins, lipids and DNA. Because they have three-dimensional structure and represent a community lifestyle for microorganisms, they have been metaphorically described as "cities for microbes".

<i>Pseudomonas</i> Genus of Gram-negative bacteria

Pseudomonas is a genus of Gram-negative, Gammaproteobacteria, belonging to the family Pseudomonadaceae and containing 191 validly described species. The members of the genus demonstrate a great deal of metabolic diversity and consequently are able to colonize a wide range of niches. Their ease of culture in vitro and availability of an increasing number of Pseudomonas strain genome sequences has made the genus an excellent focus for scientific research; the best studied species include P. aeruginosa in its role as an opportunistic human pathogen, the plant pathogen P. syringae, the soil bacterium P. putida, and the plant growth-promoting P. fluorescens, P. lini, P. migulae, and P. graminis.

<i>Pseudomonas fluorescens</i> Species of bacterium

Pseudomonas fluorescens is a common Gram-negative, rod-shaped bacterium. It belongs to the Pseudomonas genus; 16S rRNA analysis as well as phylogenomic analysis has placed P. fluorescens in the P. fluorescens group within the genus, to which it lends its name.

Pseudomonas putida is a Gram-negative, rod-shaped, saprotrophic soil bacterium.

Pseudomonadaceae Family of gram-negative bacteria

The Pseudomonadaceae are a family of bacteria which includes the genera Azomonas, Azorhizophilus, Azotobacter, Mesophilobacter, Pseudomonas, and Rugamonas. The family Azotobacteraceae was recently reclassified into this family.

<i>Pseudomonas aeruginosa</i> Species of bacterium

Pseudomonas aeruginosa is a common encapsulated, Gram-negative, strict aerobic, rod-shaped bacterium that can cause disease in plants and animals, including humans. A species of considerable medical importance, P. aeruginosa is a multidrug resistant pathogen recognized for its ubiquity, its intrinsically advanced antibiotic resistance mechanisms, and its association with serious illnesses – hospital-acquired infections such as ventilator-associated pneumonia and various sepsis syndromes.

Pseudomonas chlororaphis is a bacterium used as a soil inoculant in agriculture and horticulture. It can act as a biocontrol agent against certain fungal plant pathogens via production of phenazine-type antibiotics. Based on 16S rRNA analysis, similar species have been placed in its group.

Pseudomonas tolaasii is a species of Gram-negative soil bacteria that is the causal agent of bacterial blotch on cultivated mushrooms. It is known to produce a toxin, called tolaasin, which is responsible for the brown blotches associated with the disease. It also demonstrates hemolytic activity, causing lysis of erythrocytes. Based on 16S rRNA analysis, P. tolaasii has been placed in the P. fluorescens group.

Pseudomonas citronellolis is a Gram-negative, bacillus bacterium that is used to study the mechanisms of pyruvate carboxylase. It was first isolated from forest soil, under pine trees, in northern Virginia, United States.

Pseudomonas veronii is a Gram-negative, rod-shaped, fluorescent, motile bacterium isolated from natural springs in France. It may be used for bioremediation of contaminated soils, as it has been shown to degrade a variety of simple aromatic organic compounds. Based on 16S rRNA analysis, P. veronii has been placed in the P. fluorescens group.

Pseudomonas aurantiaca is an orange Gram-negative soil bacterium, originally isolated from the rhizosphere soil of potatoes. It produces di-2,4-diacetylfluoroglucylmethan, which is antibiotically active against Gram-positive organisms. It has shown potential for use as a biocontrol agent against plant-pathogenic microbes. Based on 16S rRNA analysis, P. aurantiaca has been placed in the P. chlororaphis group.

<i>Pseudomonas stutzeri</i> Species of bacterium

Pseudomonas stutzeri is a Gram-negative soil bacterium that is motile, has a single polar flagellum, and is classified as bacillus, or rod-shaped. While this bacterium was first isolated from human spinal fluid, it has since been found in many different environments due to its various characteristics and metabolic capabilities. P. stutzeri is an opportunistic pathogen in clinical settings, although infections are rare. Based on 16S rRNA analysis, this bacterium has been placed in the P. stutzeri group, to which it lends its name.

<i>Pantoea agglomerans</i>

Pantoea agglomerans is a Gram-negative bacterium that belongs to the family Erwiniaceae.

Rhizobacteria

Rhizobacteria are root-associated bacteria that form symbiotic relationships with many plants. The name comes from the Greek rhiza, meaning root. Though parasitic varieties of rhizobacteria exist, the term usually refers to bacteria that form a relationship beneficial for both parties (mutualism). They are an important group of microorganisms used in biofertilizer. Biofertilization accounts for about 65% of the nitrogen supply to crops worldwide. Rhizobacteria are often referred to as plant growth-promoting rhizobacteria, or PGPRs. The term PGPRs was first used by Joseph W. Kloepper in the late 1970s and has become commonly used in scientific literature. PGPRs have different relationships with different species of host plants. The two major classes of relationships are rhizospheric and endophytic. Rhizospheric relationships consist of the PGPRs that colonize the surface of the root, or superficial intercellular spaces of the host plant, often forming root nodules. The dominant species found in the rhizosphere is a microbe from the genus Azospirillum. Endophytic relationships involve the PGPRs residing and growing within the host plant in the apoplastic space.

Aryldialkylphosphatase

Aryldialkylphosphatase is a metalloenzyme that hydrolyzes the triester linkage found in organophosphate insecticides.

RsmX

The rsmX gene is part of the Rsm/Csr family of non-coding RNAs (ncRNAs). Members of the Rsm/Csr family are present in a diverse range of bacteria, including Escherichia coli, Erwinia, Salmonella, Vibrio and Pseudomonas. These ncRNAs act by sequestering translational repressor proteins, called RsmA, activating expression of downstream genes that would normally be blocked by the repressors. Sequestering of target proteins is dependent upon exposed GGA motifs in the stem loops of the ncRNAs. Typically, the activated genes are involved in secondary metabolism, biofilm formation and motility.

Pyoverdine Chemical compound

Pyoverdines are fluorescent siderophores produced by certain pseudomonads. Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient, regulation of other virulence factors, supporting the formation of biofilms, and are increasingly recognized for having toxicity themselves.

Pseudomonas protegens are widespread Gram-negative, plant-protecting bacteria. Some of the strains of this novel bacterial species previously belonged to P. fluorescens. They were reclassified since they seem to cluster separately from other fluorescent Pseudomonas species. P. protegens is phylogenetically related to the Pseudomonas species complexes P. fluorescens, P. chlororaphis, and P. syringae. The bacterial species characteristically produces the antimicrobial compounds pyoluteorin and 2,4-diacetylphloroglucinol (DAPG) which are active against various plant pathogens.

Mycorrhiza helper bacteria Group of organisms

Mycorrhiza helper bacteria (MHB) are a group of organisms that form symbiotic associations with both ectomycorrhiza and arbuscular mycorrhiza. MHBs are diverse and belong to a wide variety of bacterial phyla including both Gram-negative and Gram-positive bacteria. Some of the most common MHBs observed in studies belong to the phylas Pseudomonas and Streptomyces. MHBs have been seen to have extremely specific interactions with their fungal hosts at times, but this specificity is lost with plants. MHBs enhance mycorrhizal function, growth, nutrient uptake to the fungus and plant, improve soil conductance, aid against certain pathogens, and help promote defense mechanisms. These bacteria are naturally present in the soil, and form these complex interactions with fungi as plant root development starts to take shape. The mechanisms through which these interactions take shape are not well-understood and needs further study.

Pho regulon

The Phosphate (Pho) regulon is a bacterial regulatory mechanism used for the conservation and management of inorganic phosphate within the cell. It was first discovered in Escherichia coli as an operating system for the bacterial strain, and was later identified in other species. The Pho system is composed of various components including extracellular enzymes and transporters that are capable of phosphate assimilation in addition to extracting inorganic phosphate from organic sources. This is an essential process since phosphate plays an important role in cellular membranes, genetic expression, and metabolism within the cell. Under low nutrient availability, the Pho regulon helps the cell survive and thrive despite a depletion of phosphate within the environment. When this occurs, phosphate starvation-inducible (psi) genes activate other proteins that aid in the transport of inorganic phosphate.

References

  1. 1 2 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. Bibcode:1995PNAS...92.4197C. doi: 10.1073/pnas.92.10.4197 . PMC   41910 . PMID   11607544.
  2. 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. Bibcode:1999ApEnM..65.2429D. doi: 10.1128/aem.65.6.2429-2438.1999 . PMC   91358 . PMID   10347023.
  3. 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.
  4. 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. PMC   93771 . PMID   10322017.
  5. 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. Bibcode:1997ApEnM..63.1357C. doi:10.1128/AEM.63.4.1357-1361.1997. PMC   1389549 . PMID   16535571.
  6. 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.
  7. 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. S2CID   18469703.
  8. 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. S2CID   27149357.
  9. Garagulia, AD; Kiprianova, EA; Boĭko, OI (1974). "[Antibiotic action of bacteria of the genus Pseudomonas on phytopathogenic fungi]". Mikrobiolohichnyi Zhurnal (in Ukrainian). 36 (2): 197–202. OCLC   1063241398. PMID   4465652.
  10. Pidoplichko, VN; Garagulya, AD (1974). "[Effect of antagonistic bacteria on development of wheat root rot]". Zhurnal Mikrobiologii (in Ukrainian). Kyiv. 36: 599–602. ISSN   1028-0987. OCLC   1063241398.