Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H10O5 |
| Molecular Weight | 210.1834 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)C1=C(O)C(C(C)=O)=C(O)C=C1O
InChI
InChIKey=PIFFQYJYNWXNGE-UHFFFAOYSA-N
InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3
| Molecular Formula | C10H10O5 |
| Molecular Weight | 210.1834 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
2,4-Diacetylphloroglucinol (DAPG) is a secondary metabolite of the P. Fluorescens strain CHAo which inhibits bacteria, fungi, and plants and suppresses pathogens. 2,4-Diacetylphlo roglucinol also displays antiviral activity against DNA and RNA viruses with envelopes. 2,4-Diacetylphloroglucinol exhibited a broad-spectrum of anti-leukemic, anti-lung, and anti-breast cancer properties. The anticancer and antimetastatic activities of DAPG were mediated by the inhibition of ROS, NF-κB, Bcl-2, MMP-2, VEGF and primary inflammatory mediators such as TNF-α, IL-6, IL-1β and NO. The DAPG induced apoptosis in cancer cells by intrinsic and extrinsic pathways via the release of cytochrome-C, upregulation of Bax and the activation of caspases and also, exhibited anti-inflammatory activity by the inhibition of LPS-inflammed cell proliferation of macrophage (Raw 264.7), monocytic cells (THP-1) and peripheral blood mononuclear cells (PBMCs). Results further confirmed that the DAPG inhibited the primary inflammatory mediators in cancer cells and inflammed immune cells through the down regulation of NF-κB.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Computational prediction of the Crc regulon identifies genus-wide and species-specific targets of catabolite repression control in Pseudomonas bacteria. | 2010-11-25 |
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| Composts containing fluorescent pseudomonads suppress fusarium root and stem rot development on greenhouse cucumber. | 2010-11 |
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| Immense essence of excellence: marine microbial bioactive compounds. | 2010-10-15 |
|
| The structure of SSO2064, the first representative of Pfam family PF01796, reveals a novel two-domain zinc-ribbon OB-fold architecture with a potential acyl-CoA-binding role. | 2010-10-01 |
|
| Effect of the hfq gene on 2,4-diacetylphloroglucinol production and the PcoI/PcoR quorum-sensing system in Pseudomonas fluorescens 2P24. | 2010-08-01 |
|
| Combination of fluorescent reporters for simultaneous monitoring of root colonization and antifungal gene expression by a biocontrol pseudomonad on cereals with flow cytometry. | 2010-07 |
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| Cutaneous bacteria of the redback salamander prevent morbidity associated with a lethal disease. | 2010-06-04 |
|
| Isolation, characterization, and sensitivity to 2,4-diacetylphloroglucinol of isolates of Phialophora spp. from Washington wheat fields. | 2010-05 |
|
| Novel anti-infective compounds from marine bacteria. | 2010-03-05 |
|
| The Pseudomonas fluorescens secondary metabolite 2,4 diacetylphloroglucinol impairs mitochondrial function in Saccharomyces cerevisiae. | 2010-03 |
|
| Crystal structure and computational analyses provide insights into the catalytic mechanism of 2,4-diacetylphloroglucinol hydrolase PhlG from Pseudomonas fluorescens. | 2010-02-12 |
|
| The resistance-nodulation-division efflux pump EmhABC influences the production of 2,4-diacetylphloroglucinol in Pseudomonas fluorescens 2P24. | 2010-01 |
|
| The chloride ion is an environmental factor affecting the biosynthesis of pyoluteorin and 2,4-diacetylphloroglucinol in Pseudomonas sp. YGJ3. | 2010 |
|
| Expanding the paradigms of plant pathogen life history and evolution of parasitic fitness beyond agricultural boundaries. | 2009-12 |
|
| Biosynthesis of the proteasome inhibitor syringolin A: the ureido group joining two amino acids originates from bicarbonate. | 2009-10-28 |
|
| Impact of antifungals producing rhizobacteria on the performance of Vigna radiata in the presence of arbuscular mycorrhizal fungi. | 2009-10 |
|
| Evaluation of an antibiotic-producing strain of Pseudomonas fluorescens for suppression of plant-parasitic nematodes. | 2009-09 |
|
| Phenazine antibiotics produced by fluorescent pseudomonads contribute to natural soil suppressiveness to Fusarium wilt. | 2009-08 |
|
| Transcriptional activity of antifungal metabolite-encoding genes phlD and hcnBC in Pseudomonas spp. using qRT-PCR. | 2009-05 |
|
| Seed treatment with 2,4-diacetylphloroglucinol-producing pseudomonads improves crop health in low-pH soils by altering patterns of nutrient uptake. | 2009-05 |
|
| Diversity, virulence, and 2,4-diacetylphloroglucinol sensitivity of Gaeumannomyces graminis var. tritici isolates from Washington state. | 2009-05 |
|
| Effect of long-term vineyard monoculture on rhizosphere populations of pseudomonads carrying the antimicrobial biosynthetic genes phlD and/or hcnAB. | 2009-04 |
|
| Influence of host plant genotype, presence of a pathogen, and coinoculation with Pseudomonas fluorescens strains on the rhizosphere expression of hydrogen cyanide- and 2,4-diacetylphloroglucinol biosynthetic genes in P. fluorescens biocontrol strain CHA0. | 2009-02 |
|
| Mobile genetic elements in the genome of the beneficial rhizobacterium Pseudomonas fluorescens Pf-5. | 2009-01-13 |
|
| Antifungal activity of selected indigenous pseudomonas and bacillus from the soybean rhizosphere. | 2009 |
|
| Influence of mineral amendment on disease suppressive activity of Pseudomonas fluorescens to Fusarium wilt of chickpea. | 2009 |
|
| Assessment of genetic and functional diversity of phosphate solubilizing fluorescent pseudomonads isolated from rhizospheric soil. | 2008-12-20 |
|
| [Regulation of gacA, dsbA and phoP/phoQ genes on the transcription of small RNA gene RsmZ in Pseudomonas fluorescens]. | 2008-12 |
|
| 2,4-diacetylphloroglucinol alters plant root development. | 2008-10 |
|
| A new DGGE protocol targeting 2,4-diacetylphloroglucinol biosynthetic gene phlD from phylogenetically contrasted biocontrol pseudomonads for assessment of disease-suppressive soils. | 2008-06 |
|
| Involvement of the ABC transporter BcAtrB and the laccase BcLCC2 in defence of Botrytis cinerea against the broad-spectrum antibiotic 2,4-diacetylphloroglucinol. | 2008-05 |
|
| Genome-wide search reveals a novel GacA-regulated small RNA in Pseudomonas species. | 2008-04-13 |
|
| The identification of 2,4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus. | 2008-01 |
|
| Influence of Nitrogen Source on 2,4-diacetylphloroglucinol Production by the Biocontrol Strain Pf-5. | 2008 |
|
| Exploration of intraclonal adaptation mechanisms of Pseudomonas brassicacearum facing cadmium toxicity. | 2007-11 |
|
| Multilocus sequence analysis of biocontrol fluorescent Pseudomonas spp. producing the antifungal compound 2,4-diacetylphloroglucinol. | 2007-08 |
|
| Co-inoculation of an antibiotic-producing bacterium and a lytic enzyme-producing bacterium for the biocontrol of tomato wilt caused by Fusarium oxysporum f. sp. lycopersici. | 2007-03 |
|
| Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols. | 2007-01-01 |
|
| Is the ability of biocontrol fluorescent pseudomonads to produce the antifungal metabolite 2,4-diacetylphloroglucinol really synonymous with higher plant protection? | 2007 |
|
| Host Crop Affects Rhizosphere Colonization and Competitiveness of 2,4-Diacetylphloroglucinol-Producing Pseudomonas fluorescens. | 2006-07 |
|
| Minimal changes in rhizobacterial population structure following root colonization by wild type and transgenic biocontrol strains. | 2004-08-01 |
|
| Transformation of Pseudomonas fluorescens with genes for biosynthesis of phenazine-1-carboxylic acid improves biocontrol of rhizoctonia root rot and in situ antibiotic production. | 2004-08-01 |
|
| Signaling between bacterial and fungal biocontrol agents in a strain mixture. | 2004-06-01 |
|
| Effect of 2,4-diacetylphloroglucinol on pythium: cellular responses and variation in sensitivity among propagules and species. | 2003-08 |
|
| Prevalence of fluorescent pseudomonads producing antifungal phloroglucinols and/or hydrogen cyanide in soils naturally suppressive or conducive to tobacco black root rot. | 2003-05-01 |
|
| Frequency, Diversity, and Activity of 2,4-Diacetylphloroglucinol-Producing Fluorescent Pseudomonas spp. in Dutch Take-all Decline Soils. | 2003-01 |
|
| Comparison of Three Methods for Monitoring Populations of Different Genotypes of 2,4-Diacetylphloroglucinol-Producing Pseudomonas fluorescens in the Rhizosphere. | 2002-02 |
|
| Biotic Factors Affecting Expression of the 2,4-Diacetylphloroglucinol Biosynthesis Gene phlA in Pseudomonas fluorescens Biocontrol Strain CHA0 in the Rhizosphere. | 2001-09 |
|
| A rapid polymerase chain reaction-based assay characterizing rhizosphere populations of 2,4-diacetylphloroglucinol-producing bacteria. | 2001-01 |
|
| Genetic Diversity of phlD from 2,4-Diacetylphloroglucinol-Producing Fluorescent Pseudomonas spp. | 2001-01 |
Patents
Sample Use Guides
2,4-Diacetylphloroglucinol inhibited MMP-2, MMP-9, and NF-κB activities with the low IC50 concentration of 5.82 ± 1.6, 6.74 ± 1.2, and 10.7 ± 1.5 uM respectively. DAPG inhibited the Bcl-2, Bcl-xL and Bcl-w activities with the high IC50 concentration of 29.8 ± 1.9, 85.9 ± 2.7, and 97.4 ± 1.5 uM, respectively. These results correlate with the relatively high IC50 concentration of 16.3 ± 1.76, 7.67 ± 0.78, and 10.7 ± 0.96 uM in the Bcl-2-overexpressing HL-60, K562 and Raji leukemic cells than the metastatic A549 and MDA MB-231 cancer cells with the low IC50 concentration of 0.06 ± 0.02 and 0.08 ± 0.01 uM, respectively, compared to the healthy, human embryonic kidney (HEK-293) cells with the high IC50 concentration of 54.7 ± 1.43 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
Mon Mar 31 19:51:34 GMT 2025
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| Record UNII |
8XV4YYO3WN
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| Record Status |
Validated (UNII)
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| Record Version |
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C059817
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140662
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2,4-DIACETYLPHLOROGLUCINOL
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8XV4YYO3WN
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