Octyl gallate

From Rhus chinensis Mill.

Antioxidant-based synergistic eradication of methicillin-resistant Staphylococcus aureus (MRSA) biofilms with bacitracin.[Pubmed:29567095]

Int J Antimicrob Agents. 2018 Jul;52(1):96-99.

Biofilms of methicillin-resistant Staphylococcus aureus (MRSA) have serious clinical implications. However, it is difficult to eradicate MRSA biofilms due to the increased tolerance to antimicrobials of biofilms. In this study, we investigated the synergistic anti-biofilm effect of the combination of Octyl gallate (OG), an antioxidant approved by the US Food and Drug Administration (FDA) as a food additive, and bacitracin, an antimicrobial peptide commonly used in topical antimicrobial ointments. The results of biofilm assays showed that OG enabled bacitracin at concentrations as low as 10(-3) U/ml to inhibit biofilm formation in MRSA. A confocal microscopic analysis exhibited that the combination of bacitracin and OG suppressed biofilm formation in MRSA highly effectively compared to the single treatment of either bacitracin or OG. The synergistic anti-biofilm activity of bacitracin and OG was also confirmed in MRSA strains from humans, including USA300, which is the predominant clone of community-associated MRSA in the US. To the best of our knowledge, this is the first report about the synergistic anti-biofilm activity of an antimicrobial peptide and an antioxidant against MRSA.

Cinnamic Acid Analogs as Intervention Catalysts for Overcoming Antifungal Tolerance.[Pubmed:29065462]

Molecules. 2017 Oct 21;22(10). pii: molecules22101783.

Disruption of fungal cell wall should be an effective intervention strategy. However, the cell wall-disrupting echinocandin drugs, such as caspofungin (CAS), cannot exterminate filamentous fungal pathogens during treatment. For potency improvement of cell wall-disrupting agents (CAS, Octyl gallate (OG)), antifungal efficacy of thirty-three cinnamic acid derivatives was investigated against Saccharomyces cerevisiaeslt2Delta, bck1Delta, mutants of the mitogen-activated protein kinase (MAPK), and MAPK kinase kinase, respectively, in cell wall integrity system, and glr1Delta, mutant of CAS-responsive glutathione reductase. Cell wall mutants were highly susceptible to four cinnamic acids (4-chloro-alpha-methyl-, 4-methoxy-, 4-methyl-, 3-methylcinnamic acids), where 4-chloro-alpha-methyl- and 4-methylcinnamic acids possessed the highest activity. Structure-activity relationship revealed that 4-methylcinnamic acid, the deoxygenated structure of 4-methoxycinnamic acid, overcame tolerance of glr1Delta to 4-methoxycinnamic acid, indicating the significance of para substitution of methyl moiety for effective fungal control. The potential of compounds as chemosensitizers (intervention catalysts) to cell wall disruptants (viz., 4-chloro-alpha-methyl- or 4-methylcinnamic acids + CAS or OG) was assessed according to Clinical Laboratory Standards Institute M38-A. Synergistic chemosensitization greatly lowers minimum inhibitory concentrations of the co-administered drug/agents. 4-Chloro-alpha-methylcinnamic acid further overcame fludioxonil tolerance of Aspergillus fumigatus antioxidant MAPK mutants (sakADelta, mpkCDelta). Collectively, 4-chloro-alpha-methyl- and 4-methylcinnamic acids possess chemosensitizing capability to augment antifungal efficacy of conventional drug/agents, thus could be developed as target-based (i.e., cell wall disruption) intervention catalysts.

Octyl gallate, a food additive with potential beneficial properties to treat Helicobacter pylori infection.[Pubmed:28640317]

Food Funct. 2017 Jul 19;8(7):2500-2511.

Helicobacter pylori infection is marked by intense production of reactive oxygen species (ROS) through the activation of neutrophils that are constantly attracted to the infected gastric mucosa. Here, gallic acid and its alkyl esters were evaluated as compounds able to act as antimicrobial agents and inhibitors of ROS released by H. pylori-activated neutrophils simultaneously. We found that the higher hydrophobicity caused by esterification of gallic acid led to a significant increase in its ability as a cytotoxic agent against H. pylori, a scavenger of ROS and an inhibitor of NADPH oxidase in neutrophils. Octyl gallate, a widely used food additive, showed the highest antimicrobial activity against H. pylori, with a minimum inhibitory concentration (MIC) value of 125 mug mL(-1), whereas gallic acid had a MIC value higher than 1000 mug mL(-1). The production of superoxide anion radicals was almost 100% abolished by the addition of 10 muM (2.82 mug mL(-1)) Octyl gallate, whereas gallic acid inhibited around 20%. A similar tendency was also found when measuring the production of hypochlorous acid. The protective effect of the esters was cytochemically confirmed. In conclusion, this study showed that hydrophobicity is a crucial factor to obtain a significant anti-ROS and anti-H. pylori activity. Finally, it highlights Octyl gallate, a food additive widely used in the food industry, as a promising molecule in the treatment of H. pylori infection.

Heavy ion mutagenesis combined with triclosan screening provides a new strategy for improving the arachidonic acid yield in Mortierella alpina.[Pubmed:29716562]

BMC Biotechnol. 2018 May 2;18(1):23.

BACKGROUND: Arachidonic acid (ARA), which is a omega-6 polyunsaturated fatty acid, has a wide range of biological activities and is an essential component of cellular membranes in some human tissues. Mortierella alpina is the best strain for industrial production of ARA. To increase its yield of arachidonic acid, heavy ion beam irradiation mutagenesis of Mortierella alpina was carried out in combination with triclosan and Octyl gallate treatment. RESULTS: The obtained mutant strain F-23 ultimately achieved an ARA yield of 5.26 g L(- 1), which is 3.24 times higher than that of the wild-type strain. In addition, quantitative real-time PCR confirmed that the expression levels of fatty acid synthase (FAS), Delta5-desaturase, Delta6-desaturase, and Delta9-desaturase were all significantly up-regulated in the mutant F-23 strain, especially Delta6- and Delta9-desaturase, which were up-regulated 3- and 2-fold, respectively. CONCLUSIONS: This study confirmed a feasible mutagenesis breeding strategy for improving ARA production and provided a mutant of Mortierella alpina with high ARA yield.

Solid lipid nanoparticles improve octyl gallate antimetastatic activity and ameliorate its renal and hepatic toxic effects.[Pubmed:28746057]

Anticancer Drugs. 2017 Oct;28(9):977-988.

Metastasis is the main cause of cancer-related death and requires the development of effective treatments with reduced toxicity and effective anticancer activity. Gallic acid derivatives have shown significant biological properties including antitumoral activity as shown in a previous study with Octyl gallate (G8) in vitro. Thus, the aim of this work was to evaluate the antimetastatic effect of free and solid lipid nanoparticle-loaded G8 in mice in a lung metastasis model. Animals inoculated with melanoma cells presented metastasis in lungs, which was significantly inhibited by treatment with G8 and solid lipid nanoparticle-loaded G8, named G8-NVM. However, G8-treated mice showed an increase in several toxicological parameters, which were almost completely circumvented by G8-NVM treatment. This study supports the need for pharmacological studies on new potential medicinal plants to treat cancer and can provide new perspectives on using nanotechnology to improve biological activities while decreasing the chemotherapy toxicological effects of anticancer drugs.

Octyl gallate (Progallin O) is widely used as a food additive, with antimicrobial and antioxidant activity. Octyl gallate (Progallin O) shows selective and sensitive fluorescent property. Octyl gallate shows a marked antiviral effect against HSV-1, vesicular stomatitis virus (VSV) and poliovirus.

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