Triacetylphloroglucinol
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| Category | Others |
| Catalog number | BBF-04423 |
| CAS | 2161-87-7 |
| Molecular Weight | 252.22 |
| Molecular Formula | C12H12O6 |
| Purity | >98% by HPLC |
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Description
It is the most hydrophobic of a small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5 trihydroxybenzene) family. It is produced by pseudomonas fluoresces and exhibits a broad range of biological activities. It is important for dereplication to eliminate leads due to high amounts of weakly potent actives.
Specification
| Synonyms | Phloroglucinol 2,4,6-Triacetate; 2,4,6-Triacetyl-1,3,5-trihydroxybenzene; 2,4,6-Triacetylphloroglucinol; 1,1',1''-(2,4,6-Trihydroxybenzene-1,3,5-triyl)triethanone |
| Storage | Store at 2-8°C |
| IUPAC Name | 1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethanone |
| Canonical SMILES | CC(=O)C1=C(C(=C(C(=C1O)C(=O)C)O)C(=O)C)O |
| InChI | InChI=1S/C12H12O6/c1-4(13)7-10(16)8(5(2)14)12(18)9(6(3)15)11(7)17/h16-18H,1-3H3 |
| InChI Key | YOQHLDOEJYEQRA-UHFFFAOYSA-N |
| Source | Pseudomonas fluorescens |
Properties
| Appearance | Off-white to Beige Solid |
| Boiling Point | 501.4±50.0°C (Predicted) |
| Melting Point | 145-147°C |
| Density | 1.406±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, DMF, DMSO; Slightly soluble in Chloroform, Methanol |
Reference Reading
1. Characterization of PhlG, a hydrolase that specifically degrades the antifungal compound 2,4-diacetylphloroglucinol in the biocontrol agent Pseudomonas fluorescens CHA0
Christoph Keel, Mélanie Bottiglieri Appl Environ Microbiol . 2006 Jan;72(1):418-27. doi: 10.1128/AEM.72.1.418-427.2006.
The potent antimicrobial compound 2,4-diacetylphloroglucinol (DAPG) is a major determinant of biocontrol activity of plant-beneficial Pseudomonas fluorescens CHA0 against root diseases caused by fungal pathogens. The DAPG biosynthetic locus harbors the phlG gene, the function of which has not been elucidated thus far. The phlG gene is located upstream of the phlACBD biosynthetic operon, between the phlF and phlH genes which encode pathway-specific regulators. In this study, we assigned a function to PhlG as a hydrolase specifically degrades DAPG to equimolar amounts of mildly toxic monoacetylphloroglucinol (MAPG) and acetate. DAPG added to cultures of a DAPG-negative DeltaphlA mutant of strain CHA0 was completely degraded, and MAPG was temporarily accumulated. In contrast, DAPG was not degraded in cultures of a DeltaphlA DeltaphlG double mutant. To confirm the enzymatic nature of PhlG in vitro, the protein was histidine tagged, overexpressed in Escherichia coli, and purified by affinity chromatography. Purified PhlG had a molecular mass of about 40 kDa and catalyzed the degradation of DAPG to MAPG. The enzyme had a kcat of 33 s(-1) and a Km of 140 microM at 30 degrees C and pH 7. The PhlG enzyme did not degrade other compounds with structures similar to DAPG, such as MAPG and triacetylphloroglucinol, suggesting strict substrate specificity. Interestingly, PhlG activity was strongly reduced by pyoluteorin, a further antifungal compound produced by the bacterium. Expression of phlG was not influenced by the substrate DAPG or the degradation product MAPG but was subject to positive control by the GacS/GacA two-component system and to negative control by the pathway-specific regulators PhlF and PhlH.
2. Antibacterial pyrrolidinyl and piperidinyl substituted 2,4-diacetylphloroglucinols from Pseudomonas protegens UP46
Joakim Bjerketorp, Rolf Larsson, Jerry Ståhlberg, Bengt Guss, Jolanta J Levenfors, Bo Öberg, Anders Broberg, Christina Nord J Antibiot (Tokyo) . 2020 Nov;73(11):739-747. doi: 10.1038/s41429-020-0318-1.
In the search for new antibiotic compounds, fractionation of Pseudomonas protegens UP46 culture extracts afforded several known Pseudomonas compounds, including 2,4-diacetylphloroglucinol (DAPG), as well as two new antibacterial alkaloids, 6-(pyrrolidin-2-yl)DAPG (1) and 6-(piperidin-2-yl)DAPG (2). The structures of 1 and 2 were determined by nuclear magnetic resonance spectroscopy and mass spectrometry. Compounds 1 and 2 were found to have antibacterial activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus cereus, with minimal inhibitory concentration (MIC) 2 and 4 μg ml-1, respectively, for 1, and 2 μg ml-1for both pathogens for 2. The MICs for 1 and 2, against all tested Gram-negative bacteria, were >32 μg ml-1. The half maximal inhibitory concentrations against HepG2 cells for compounds 1 and 2 were 11 and 18 μg ml-1, respectively, which suggested 1 and 2 be too toxic for further evaluation as possible new antibacterial drugs. Stable isotope labelling experiments showed the pyrrolidinyl group of 1 to originate from ornithine and the piperidinyl group of 2 to originate from lysine. The P. protegens acetyl transferase (PpATase) is involved in the biosynthesis of monoacetylphloroglucinol and DAPG. No optical rotation was detected for 1 or 2, and a possible reason for this was investigated by studying if the PpATase may catalyse a stereo-non-specific introduction of the pyrrolidinyl/piperidinyl group in 1 and 2, but unless the PpATase can be subjected to major conformational changes, the enzyme cannot be involved in this reaction. The PpATase is, however, likely to catalyse the formation of 2,4,6-triacetylphloroglucinol from DAPG.
3. Trinuclear vanadium(iv) and vanadium(v) complexes derived from 2,4,6-triacetylphloroglucinol and study of their peroxidase mimicking activity
Nádia Ribeiro, Maxim L Kuznetsov, João Costa Pessoa, Isabel Correia, Mannar R Maurya, Fernando Avecilla, M Fernanda N N Carvalho, Reshu Tomar Dalton Trans . 2020 Feb 25;49(8):2589-2609. doi: 10.1039/c9dt04415a.
Novel dibasic Schiff bases with three tridentate sites were obtained from the condensation of the triketone 2,4,6-triacetylphloroglucinol (H3ptk) with four different hydrazides, benzoyl hydrazide (bhz), furoyl hydrazide (fah), isonicotinoyl hydrazide (inh) and nicotinoyl hydrazide (nah): H6ptk(bhz)3I, H6ptk(fah)3II, H6ptk(inh)3III and H6ptk(nah)3IV. These ligand precursors I-IV, each being an ONO donor, are tricompartmental building blocks able to form trinuclear complexes having C3 symmetry. The reaction of I-IV with [VIVO(acac)2] leads to the formation of [{VIVO(H2O)}3(ptk(bhz)3)] 1, [{VIVO(H2O)}3(ptk(fah)3)] 2, [{VIVO(H2O)}3(ptk(inh)3)] 3, and [{VIVO(H2O)}3(ptk(nah)3)] 4. In methanol/aqueous solutions of M2CO3 (M+ = Na+, K+ and Cs+), these complexes are slowly converted into dioxidovanadium(v) compounds, namely, M3[(VVO2)3{ptk(bhz)3}]·6H2O [M+ = K+5, Na+9, Cs+13], M3[(VVO2)3{ptk(fah)3}]·6H2O [M+ = K+6, Na+10, Cs+14], M3[(VVO2)3{ptk(inh)3}]·6H2O [M+ = K+7, Na+11, Cs+15] and M3[(VVO2)3{ptk(nah)3}]·6H2O [M+ = K+8, Na+12, Cs+16]. All ligand precursors and complexes are characterized by various techniques such as FT-IR, UV/Visible, EPR, NMR (1H, 13C and 51V), elemental analysis, thermal studies, cyclic voltammetry (CV) and single-crystal X-ray analysis. X-ray diffraction studies of complexes K2.7[{(VVO2)3ptk(fah)3}]·11.5H2O·MeOH 6a, Cs3[{(VVO2)3ptk(bhz)3}]·7H2O 13a and Cs3[{(VVO2)3ptk(nah)3}]·7.3H2O 16a reveal their distorted square pyramidal geometry by coordinating through phenolate oxygen (of ptk), azomethine nitrogen and enolate oxygen (of hydrazide) atoms. The reactivity of complexes 5-16 and their catalytic potential were screened towards their peroxidase mimetic activity in the oxidation of dopamine to aminochrome driven by H2O2 as an oxidant. The conversion of dopamine to aminochrome with different catalysts was monitored by HPLC showing high activity under mild conditions with good conversions within 1 h. Kinetic studies using compounds 13-16 as catalyst precursors reveal that the reaction follows a Michaelis-Menten-like kinetics.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
