Antioxidant and Biological Activities of Novel Structured Monoacylglycerol Derivatives with Phenolic Acids

Abstract

Novel structured monoacylglycerol (MAG)-based phenolic lipids are synthesized from11-bromoundecanoic acid, phenolic acids, and solketal. Selected phenolic acids namely 4-hydroxy benzoic, vanillic, syringic, cinnamic, p-coumaric, sinapic, 4-fluorocinnamic, 4-hydroxyphenyl acetic acid, 3-(4-hydroxyphenyl) propanoic and dihydrocaffeic acids are employed for the synthesis of ten novel MAG-based phenolic lipids. The synthesized phenolic lipids are characterized by FT-IR, NMR, and mass spectra analysis. All the compounds are evaluated for antioxidant, antimicrobial, and cytotoxic activities. MAG derivative 8g of sinapic acid exhibits excellent antioxidant activity in both DPPH assay and inhibition of lipid oxidation assay. MAG derivative 8f bearing p-coumaric acid shows good antimicrobial activity against both Gram-positive and Gram-negative bacterial strains with a minimum inhibitory concentration (MIC) value of 6.25 µm mL −1 . All the synthesized compounds are found to exhibit cytotoxicity against B16, DU145, and CHO cell lines, while sinapic and p-coumaric acid derivatives exhibit better activities compared to other derivatives.

Walnut By-Products and Elderberry Extracts—Sustainable Alternatives for Human and Plant Health

“…Like the previous compounds, p-coumaric acid is part of the class of phenols and is reported in the specialized literature to have an antifungal and antibacterial action, both on human and agricultural pathogens [ 139 , 140 , 141 ].…”

Bioprospecting Phenols as Inhibitors of Trichothecene-Producing Fusarium: Sustainable Approaches to the Management of Wheat Pathogens

“…Sinapic acid displays both antioxidant and antibacterial effects and plays an intriguing role as a preservative in foods [201,202]. Furthermore, it has been proposed as a resistance biomarker metabolite in cereals against Fusaria [203].…”

Catalytic Routes to Produce Polyphenolic Esters (PEs) from Biomass Feedstocks

“…These mainly concern acylation with acyl chlorides or anhydrides, which are performed under inadequately green reaction conditions. Among the class of polyphenols, the majority of studies regard PAs (cinnamic acids, ferulic acid, caffeic acid, sinapic acid, vanillic acid, p-coumaric acid, gallic acid, p-hydroxybenzoic acid) [84][85][86][87][88], followed by flavonoids (epigallocatechin gallate, quercetin, catechin) [89][90][91][92][93] with only a few examples concerning stilbenes (resveratrol) [94].…”

“…In the case of phenolic acids, the carboxylic group is converted into a more reactive one, such as acyl chloride and acetyl/vinyl esters, and subsequently is coupled with an alcohol to obtain polyphenolic esters [84][85][86][87]. For example, vinyl vanillate, caffeate, sinapate, and ferulate were synthesized through the vinyl interchange reaction of vinyl acetate with the corresponding phenolic acid in the presence of mercury acetate (4% w/w), sulfuric acid (4 eq) and tetrahydrofuran as solvents, and subsequently coupled with sitosterol to obtain phytosteryl esters under enzymatic conditions [84][85][86].…”