Antimicrobial Properties of Mandelic Acid, Gallic Acid and their Derivatives

Abstract

Purpose: Alpha-hydroxy acids (AHAs) are one of the classes of hydroxy acids being beneficial for human health. The manuscript summarizes the biological properties of two popular members of AHAs i.e. mandelic acid (MA) and gallic acid (GA) with particular emphasis on antimicrobial properties. Moreover, attempts to design of new derivatives improving the natural properties of AHAs by using the chemical and physical approach, are discussed. Methods: Antimicrobial properties of MA, an arylalkyl AHA containing phenyl group attached to α-carbon, and GA, an aromatic trihydroxybenzoic acid containing the phenolic ring and carboxylic acid functional group, and their derivatives against common human and plant pathogenic fungi have been reviewed. Results: The antimicrobial activity of MA and GA is a complex phenomenon strictly correlated with other properties exhibited by these acids e.g. pro-oxidative activity, hydrophobicity. In most cases, the acids derivatives exhibited higher antimicrobial activity than acids itself. This is probably because of the higher lipophilicity of moiety that allows better penetration through the cell membrane. Conclusion: MA and GA present an excellent health-promoting tool and are valuable starting materials for the design of new compounds such as metal complexes with alkali, or alkali earth metals. The lipophilic, antimicrobial, and pro-oxidative properties act synergistically supporting the pharmacological and therapeutic effect of acids and their derivatives.

Pathway to Construct α-Acyloxy Esters by B(C6F5)3-Catalyzed O–H Insertion of Carboxylic Acids with Sulfoxonium Ylides

“…2-Arylpropionic acid anti-inflammatory drugs such as naproxen, ibuprofen, and loxoprofen were also suitable for the reaction, yielding products 6ab – 6ad with yields ranging from 63 to 78%. Mandelic acid, with a hydroxyl group in the α-position, selectively offered the product 6ae in 60% yield. Oxaprozin, as a sort of propionic acid-based drug, also was proved to be compatible with our protocol, yielding the product 6af with an acceptable yield.…”

Simultaneous Improvements of Physicochemical Properties and Anti‐Microbial Activity of Berberine via Forming Salt with Gallic Acid

“…Gallic acid (GA, Figure 1c) is a kind of hydroxybenzoic acid derived from gallnut , [ 23 ] showing the similar pharmacological activities as BER with anti‐bacterial, [ 24,25 ] anti‐inflammatory, [ 26 ] anti‐tumor effects etc. [ 27,28 ] Therefore, salt formation of BER with GA may simultaneously optimize the physicochemical properties and the therapeutic effect of BER.…”

Design and Synthesis of Mandelic Acid Derivatives for Suppression of Virulence via T3SS against Citrus Canker

“…35 Mandelic acid, an α-amino acid, possesses significant antibacterial properties and is regarded as a promising substrate and intermediary for the development and synthesis of innovative drugs. 36,37 The utilization of mandelic acid and its derivatives is prevalent in the fields of medicines, aesthetic medicine, and environmental therapy. 38,39 Furthermore, there have been reports in the field of agriculture indicating that they possess the ability to effectively minimize the occurrence of black shank.…”

“…Bismerthiazol and thiadiazole copper are widely utilized bactericides that have demonstrated efficacy in efficiently managing citrus canker . Mandelic acid, an α-amino acid, possesses significant antibacterial properties and is regarded as a promising substrate and intermediary for the development and synthesis of innovative drugs. , The utilization of mandelic acid and its derivatives is prevalent in the fields of medicines, aesthetic medicine, and environmental therapy. , Furthermore, there have been reports in the field of agriculture indicating that they possess the ability to effectively minimize the occurrence of black shank . Although all of the aforementioned compounds possess antiseptic properties, it is possible to develop and synthesize their active structural frameworks using novel methodologies in order to acquire the desired molecules.…”