Suppression of TNF-α induced NFκB activity by gallic acid and its semi-synthetic esters: possible role in cancer chemoprevention

Morais, Mauro César Cafundó de; Luqman, Suaib; Kondratyuk, Tamara P.; Petrônio, Maicon Segalla; Regasini, Luís Octávio; Silva, Dulce Helena Siqueira; Bolzani, Vanderlan da Silva; Soares, Christiane Pienna; Pezzuto, John M.

doi:10.1080/14786410903335232

Cited by 44 publications

(29 citation statements)

References 24 publications

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“…Gallic acid represents a benzenoid compound found in many plants, either in the free-form or as part of tannins. This molecule is known to possess anti-microbial, antioxidant, and cytotoxic properties, and a previous study has shown that gallic acid was able to suppress TNF-α-induced NF-κB activity (Morais et al 2010). In vitro studies on the mode of action of gallic acid revealed that this compound interferes with the functioning of polymorphonuclear leukocytes, scavenging of superoxide anions, inhibition of myeloperoxidase release, and activity (Kroes et al 1992).…”

Section: Introductionmentioning

confidence: 94%

Effects of the hydroalcoholic extract of Phyllanthus niruri and its isolated compounds on cyclophosphamide-induced hemorrhagic cystitis in mouse

Boeira

Leite

Santos

et al. 2011

Naunyn-Schmiedeberg's Arch Pharmacol

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The effects of Phyllanthus niruri hydroalcoholic extract and the isolated compounds quercetin, rutin, and gallic acid were examined in the mouse model of cyclophosphamide (CYP)-induced hemorrhagic cystitis (HC). HC was induced by a single CYP injection (300 mg/kg, IP), and the animals were evaluated 4 and 6 h after. Some animals were orally treated with the reference compound 2-mercaptoethane sodium sulfonate (Mesna) 80 mg/kg (30 min before CYP) and 160 mg/kg (2 h after CYP). Other groups were treated with P. niruri extract (30 and 50 mg/kg), or quercetin, rutin, and gallic acid (10 and 20 mg/kg), given orally, at the same intervals described for Mesna. P. niruri extract and its active components produced a significant attenuation of the nociception, edema, and hemorrhage evoked by CYP, which was similar to that seen for Mesna. Gallic acid and rutin displayed greater anti-inflammatory effects, whereas quercetin presented superior antinociceptive activities. Noteworthy is that P. niruri extract and compounds significantly reduced CYP-induced liver lipid peroxidation. Our results shed new light on the beneficial effects of P. niruri extract and its active compounds in attenuating the collateral effects elicited by the chemotherapeutic agent CYP.

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Section: Introductionmentioning

confidence: 94%

Effects of the hydroalcoholic extract of Phyllanthus niruri and its isolated compounds on cyclophosphamide-induced hemorrhagic cystitis in mouse

Boeira

Leite

Santos

et al. 2011

Naunyn-Schmiedeberg's Arch Pharmacol

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“…The crude products were purified over a silica gel column eluted with mixtures of hexanes and EtOAc, furnishing alkyl gallates (compounds 2 to 16) ( Table 1). The molecular structures of these compounds were established by 1 H and 13 C nuclear magnetic resonance (NMR) spectral analysis (16,17).…”

Section: Methodsmentioning

confidence: 99%

“…Synthetic esters of gallic acid were prepared as described previously, with minor modifications (16,17). A 3.0-ml solution of N,N=-dicyclohexylcarbodiimide (DCC) (1.0 mmol) in dried p-dioxane was added to a cooled (5°C) solution of 0.2 mmol gallic acid (Sigma) (compound 1) (Table 1) and 20 mmol alkyl alcohol in 6.0 ml of dried p-dioxane.…”

Section: Methodsmentioning

confidence: 99%

“…citri subsp. citri activity of gallic acid (3,4,5-trihydroxybenzoic acid), an intermediate of the hydrolysable tannin biosynthesis pathway in plants ( [13][14][15] which, together with its natural and semisynthetic derivatives, has been associated with a broad spectrum of biological actions (16)(17)(18)(19)(20)(21). Moreover, gallic acid and derivatives demonstrated antimicrobial properties.…”

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confidence: 99%

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Antibacterial Activity of Alkyl Gallates against Xanthomonas citri subsp. citri

et al. 2013

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The plant-pathogenic bacterium Xanthomonas citri subsp. citri is the causal agent of Asiatic citrus canker, a serious disease that affects all the cultivars of citrus in subtropical citrus-producing areas worldwide. There is no curative treatment for citrus canker; thus, the eradication of infected plants constitutes the only effective control of the spread of X. citri subsp. citri. Since the eradication program in the state of São Paulo, Brazil, is under threat, there is a clear risk of X. citri subsp. citri becoming endemic in the main orange-producing area in the world. Here we evaluated the potential use of alkyl gallates to prevent X. citri subsp. citri growth. These esters displayed a potent anti-X. citri subsp. citri activity similar to that of kanamycin (positive control), as evaluated by the resazurin microtiter assay (REMA). The treatment of X. citri subsp. citri cells with these compounds induced altered cell morphology, and investigations of the possible intracellular targets using X. citri subsp. citri strains labeled for the septum and centromere pointed to a common target involved in chromosome segregation and cell division. Finally, the artificial inoculation of citrus with X. citri subsp. citri cells pretreated with alkyl gallates showed that the bacterium loses the ability to colonize its host, which indicates the potential of these esters to protect citrus plants against X. citri subsp. citri infection.

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“…To investigate the effects of JEZTC and GA on IL-1β-induced chondrocytes, the cells were grouped as follow: (1) normal control group, chondrocytes treated with culture medium only; (2) IL-1β (OA model) group, chondrocytes treated with culture medium contained 10 ng/ml IL-1β (Gibco, USA); (3) JEZTC-1 group, chondrocytes pre-incubated with 2.344 µg/ml JEZTC for 1 h followed by stimulation with IL-1β for 24 h; (4) JEZTC-2 group, chondrocytes pre-incubated with 4.688 µg/ml JEZTC for 1 h followed by stimulation with IL-1β for 24 h; (5) JEZTC-3 group, chondrocytes pre-incubated with 9.376 µg/ml JEZTC for 1 h followed by stimulation with IL-1β for 24 h; (6) GA group, chondrocytes pre-incubated with 4.688 µg/ml GA for 1 h followed by stimulation with IL-1β for 24 h. The concentrations of JEZTC were determined according to previous study [26]. The dose of GA was derived from the preliminary cytotoxicity assay, which was optimal for cell growth.…”

Section: Il-1β-induced Chondrocytes and Treatmentmentioning

confidence: 99%

A Novel Synthesized Sulfonamido-Based Gallate-JEZTC Blocks Cartilage Degradation on Rabbit Model of Osteoarthritis: An in Vitro and in Vivo Study

Liu

et al. 2018

Cell Physiol Biochem

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Background/Aims: 3, 4, 5-trihydroxy-N-{4-[(5-methylisoxazol-3-yl) sulfamoyl] phenyl} benzamide (JEZTC), synthesized from gallic acid (GA) and sulfamethoxazole (SMZ), was reported with chondroprotective effects. However, the effects of JEZTC on osteoarthritis (OA) are still unclear. The goal of this study was to investigate the anti-osteoarthritic properties of JEZTC on interleukin-1-beta (IL-1β) stimulated chondrocytes in vitro and a rabbit anterior cruciate ligament transaction (ACLT) OA model in vivo. Methods: Changes in matrix metalloproteinases (MMPs) and apoptosis genes (bax, caspase 3 and tnf-α) and OA-specific protein (MMP-1) expression in vitro and in vivo were detected by real-time quantitative reverse transcription-polymerase chain reaction (qRT-PCR) and immunohistochemistry. The production of reactive oxygen species (ROS) were investigated upon the treatment of JEZTC in chondrocytes processed with IL-1β in vitro and OA in vivo. Effect of JEZTC on OA was further studied by the macroscopic and histological evaluation and scores. The key proteins in signaling pathways inMAPK/P38, PI3KAkt and NF-κB also determined using western blot (WB) analysis. Results: JEZTC could significantly suppress the expression of MMPs and intracellular ROS, while meaningfully increase the gene expression of tissue inhibitor of metalloproteinase-1 (TIMP-1). Moreover, there was less cartilage degradation in JEZTC group compared with the phosphate-buffered saline (PBS) group in vivo. Results also indicated that JEZTC exerts effect on OA by regulating MAPKs and PI3K/Akt signaling pathways to activate NF-κB pathway, leading to the down-regulation of MMPs. The chondro-protective effect of JEZTC may be related with its ability to inhibit chondrocyte apoptosis by reduction of ROS production. Conclusion: JEZTC may be a possible therapeutic agent in the treatment of OA.

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Suppression of TNF-α induced NFκB activity by gallic acid and its semi-synthetic esters: possible role in cancer chemoprevention

Cited by 44 publications

References 24 publications

Effects of the hydroalcoholic extract of Phyllanthus niruri and its isolated compounds on cyclophosphamide-induced hemorrhagic cystitis in mouse

Effects of the hydroalcoholic extract of Phyllanthus niruri and its isolated compounds on cyclophosphamide-induced hemorrhagic cystitis in mouse

Antibacterial Activity of Alkyl Gallates against Xanthomonas citri subsp. citri

A Novel Synthesized Sulfonamido-Based Gallate-JEZTC Blocks Cartilage Degradation on Rabbit Model of Osteoarthritis: An in Vitro and in Vivo Study

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