Search Results (5)

Biofilm-dwelling cells endure adverse conditions, including oxidative imbalances. The NADH:quinone oxidoreductase enzyme WrbA has a crucial role in the mechanism of action of antibiofilm molecules such as ellagic and salicylic acids. This study aimed to exploit the potential of the WrbA scaffold as a valuable target for identifying antibiofilm compounds at non-lethal concentrations. A three-dimensional computational model, based on the published WrbA structure, was used to screen natural compounds from a virtual library of 800,000 compounds. Fisetin, morin, purpurogallin, NZ028, and NZ034, along with the reference compound ellagic acid, were selected. The antibiofilm effect of the molecules was tested at non-lethal concentrations evaluating the cell-adhesion of wild-type and WrbA-deprived Escherichia coli strains through fluorochrome-based microplate assays. It was shown that, except for NZ028, all of the selected molecules exhibited notable antibiofilm effects. Purpurogallin and NZ034 showed excellent antibiofilm performances at the lowest concentration of 0.5 μM, in line with ellagic acid. The observed loss of activity and the level of reactive oxygen species in the mutant strain, along with the correlation with terms contributing to the ligand-binding free energy on WrbA, strongly indicates the WrbA-dependency of purpurogallin and NZ034. Overall, the molecular target WrbA was successfully employed to identify active compounds at non-lethal concentrations, thus revealing, for the first time, the antibiofilm efficacy of purpurogallin and NZ034. Full article

Purpurogallin (PPG) is a phenolic compound known for its high antioxidant properties in plant-based food materials. However, there is no easy and reliable method for direct determination of PPG in brewed beverages owing to its hydrophobicity, which makes it hard to separate from the background hydrophobic components. Therefore, a method employing solid-phase extraction (SPE) and liquid chromatography-mass spectrometry (LC-MS) was developed for detection and quantification of PPG in brewed beverages, and PPG content was quantified in commercial coffee, cocoa, and tea samples. The limits of detection and quantification were 71.8 and 155.6 ng/g dry weight (dw), respectively. The recovery with SPE was 26.6%. When combined with acetonitrile extraction (ANE), the recovery was 6.8%, higher than 2.6% with water extraction (WTE). Test tube extractions were better than moka pot brewing (MPB) for PPG quantification. Total PPG content of ground coffees prepared by ANE, WTE, and MPB ranged between 635 and 770, 455 and 630, and 85 and 135 ng/g dw, respectively. PPG was detected in two English breakfast tea samples (335–360 ng/g dw) using WTE, but not in cocoa samples. ANE showed higher (p < 0.05) PPG levels, but WTE (r = 0.55, p < 0.01) correlated better with MPB than ANE (r = 0.43, p < 0.01). The result indicated that WTE is the best method to determine PPG in brewed beverages. This work demonstrated that PPG was significant in brewed coffee, and our pioneer study in developing the method for beverage sample preparation and LC-MS analysis has made possible industrial applications and provided new perspectives for future research. Full article

Purpurogallin or (6E,8Z)-2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one is a benzotropolone possessing a dienic system and known to inhibit the TLR1/TLR2 activation pathway. We have recently described the easy green synthesis of purpurogallin from pyrogallol catalyzed by a copper complex or by vegetable oxidases. The purpurogallin was acetylated and the tetra-acetate derivative thus obtained was engaged in a Diels–Alder reaction with various dienophiles (benzoquinone, maleic anhydride, ethylmaleimide, phenylmaleimide, etc.). The results obtained are presented and discussed. Full article

Purpurogallin, a benzotropolone-containing natural compound, has been reported to exhibit numerous biological and pharmacological functions, such as antioxidant, anticancer, and anti-inflammatory effects. In this study, we enzymatically synthesized purpurogallin from pyrogallol and investigated its role in receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastogenesis. Purpurogallin attenuated the formation of multinucleated tartrate-resistant acid phosphatase (TRAP)-positive osteoclasts from bone marrow macrophages (BMMs) without causing cytotoxicity, and suppressed upregulation of osteoclast-specific markers, including TRAP (Acp5), cathepsin K (Ctsk), and dendritic cell-specific transmembrane protein (Dcstamp). However, purpurogallin did not affect the bone resorbing function of mature osteoclasts evident by the resorption pit assay. Activation of mitogen-activated protein kinases, Akt and IkB pathways in RANK signaling were not altered by purpurogallin, whereas the expression of c-Fos and NFATc1, key transcriptional regulators in osteoclastogenesis, was dramatically inhibited by purpurogallin. Purpurogallin also significantly reduced the expression level of B lymphocyte-induced maturation protein-1 (Blimp1) gene (Prdm1). Further, downregulation of Blimp1 led to forced expression of anti-osteoclastogenic genes, including interferon regulatory factor-8 (Irf8) and B-cell lymphoma 6 (Bcl6) genes. Taken together, our data suggested that purpurogallin inhibits osteoclast differentiation via downregulation of c-Fos and NFATc1. Full article

Biomass-derived phenols have recently arisen as an attractive alternative for building blocks to be used in synthetic applications, due to their widespread availability as an abundant renewable resource. In the present paper, commercial laccase from the thermophilic fungus Myceliophthora thermophila was used to bioconvert phenol monomers, namely catechol, pyrogallol and gallic acid in water. The resulting products from catechol and gallic acid were polymers that were partially characterized in respect to their optical and thermal properties, and their average molecular weight was estimated via solution viscosity measurements and GPC. FT-IR and ¹H-NMR data suggest that phenol monomers are connected with ether or C–C bonds depending on the starting monomer, while the achieved molecular weight of polycatechol is found higher than the corresponding poly(gallic acid). On the other hand, under the same condition, pyrogallol was dimerized in a pure red crystalline compound and its structure was confirmed by ¹H-NMR as purpurogallin. The herein studied green synthesis of enzymatically synthesized phenol polymers or biological active compounds could be exploited as an alternative synthetic route targeting a variety of applications. Full article