ABSTRACT
Polyphenols, as secondary metabolites from plants, possess a natural antioxidant capacity and biological activities attributed to their chemical and structural characteristics. Due to their mostly polar character, polyphenols present a low solubility in less polar environments or hydrophobic matrices. However, in order to make polyphenols able to incorporate in oils and fats, a transformation strategy is necessary. For the above, the functionalization of polyphenols through chemical or enzymatic lipophilization has allowed the synthesis of phenolipids. These are amphipilic molecules that preserve the natural phenolic core to which an aliphatic motif is attached by esterification or transesterification reactions. The length of the aliphatic chain in phenolipids allows them to interact with different systems (such as emulsions, oily molecules, micelles and cellular membranes), which would favor their use in processed foods, as vehicles for drugs, antimicrobial agents, antioxidants in the cosmetic industry and even in the treatment of degenerative diseases related to oxidative stress.
Subject(s)
Antioxidants , Phenols , Antioxidants/pharmacology , Antioxidants/chemistry , Phenols/pharmacology , Polyphenols/pharmacology , Polyphenols/chemistry , Oxidative Stress , OilsABSTRACT
Enzymatic lipophilization is an important process to extend the use of anthocyanins in lipidic media. In this work delphinidin 3-O-sambubioside (Dp3sam) isolated from Hibiscus sabdariffa L. flower was esterified with octanoic acid using Candida antarctica lipase B. The physical-chemical properties of the new lipophilic pigment were studied by UV-vis spectroscopy. Dp3sam with chloride, acetate and formate as counter ions were employed to study the lipophilization reaction. The hydrolysis of the reagent was avoided with a formate counter ion and the expected product was achieved with a noteworthy change of solubility. 1D and 2D NMR characterization of Dp3sam-C8 confirmed that the lipophilization took place at the primary alcohol of the glucoside moiety. Overall, the Dp3sam-C8 ester presents a stabilization of the quinoidal base (blue color) at neutral or moderate alkaline pH, which foresees a potential use of this pigment as a broad kind of industries on lipo-soluble formulations.
Subject(s)
Anthocyanins/analysis , Fatty Acids/metabolism , Fungal Proteins/metabolism , Hibiscus/chemistry , Lipase/metabolism , Acylation , Anthocyanins/isolation & purification , Anthocyanins/metabolism , Biocatalysis , Chromatography, High Pressure Liquid , Color , Disaccharides/chemistry , Hibiscus/metabolism , Hydrogen-Ion Concentration , Mass Spectrometry , Plant Extracts/chemistry , Solid Phase ExtractionABSTRACT
Los aceites esenciales son conocidos por sus numerosas actividades biológicas y organolépticas, pero su empleo suele verse limitado por su alta volatilidad y tendencia a degradarse. La microencapsulación es una estrategia válida para superar estos inconvenientes. En este trabajo se empleó almidón de ñame (D. rotundata), el cual fue sometido a procesos de hidrólisis y lipofilización, empleando anhídrido dodecenilsuccínico (DDSA); esto incrementó significativamente las capacidades captadora de aceite y emulsificante (tensoactiva) del almidón nativo, el cual se empleó para microencapsular aceite esencial de tomillo, que en estudios previos demostró potente actividad antibacteriana sobre las cepas involucradas en el desarrollo del acné. La microencapsulación se llevó a cabo por microparticulación lipídica sólida, seguida de emulsificación. Esta alcanzó una eficiencia superior al 98%, y el producto obtenido, desafiado en diversas pruebas, demostró capacidad de retener más del 90% del aceite esencial en condiciones de evaporación, evitando su oxidación y el cambio en su perfil de composición. Finalmente, las microcápsulas de aceites esenciales de tomillo, al ponerse en contacto con las bacterias del acné, mantuvieron su actividad bactericida. Los resultados de este trabajo aportan al desarrollo de formulaciones farmacéuticas, cosméticas y alimentarias estables y funcionales de aceites esenciales, al protegerlos de la evaporación y degradación.
Essential oils are known for their numerous biological and organoleptic activities, but their use is often limited by high volatility and tendency to degrade. Microencapsulation is a valid strategy to overcome these drawbacks. In this paper starch yam (D. rotundata) was used, which was subjected to hydrolysis processes and lipophilization using dodecenyl succinic (DDSA) anhydride, this significantly increased the scavenging capacity of oil and emulsifier (surfactant) of native starch, which was used to microencapsulate thyme essential oil, that in previous studies showed potent antibacterial activity on strains involved in the development of acne. Microencapsulation was conducted by microparticulation solid lipid, followed by emulsification. This reached an efficiency of over 98%, and the product obtained, challenged by various trials, demonstrated ability to hold more than 90% of essential oil under evaporation conditions, avoiding oxidation and change in composition profile. Finally, the microcapsules of essential oil of thyme at contact the acne bacteria, maintained its bactericidal activity. The results of this study contribute to the development of pharmaceutical, cosmetic and food formulations stable and functional based on essential oils, to protect degradation and evaporation.
ABSTRACT
The antifungal activities of 5-O-caffeoyl quinic acid (5-CQA) and of methyl, butyl, octyl, and dodecyl esters or 5-CQA, were tested on five toxigenic moulds from the Aspergillus genus (Aspergillus flavus, Aspergillus nomius, Aspergillus ochraceus, Aspergillus parasiticus, Aspergillus westerdijkiae). These mycotoxin producers' moulds may contaminate many types of food crops throughout the food chain posing serious health hazard to animals and humans. The use of chemical methods to decrease mycotoxin producer moulds contamination on food crops in the field, during storage, and/or during processing, has been proved to be efficient. In this work, the antifungal effect of 5-CQA and a homologous series of 5-CQA esters (methyl, butyl, octyl, dodecyl), was investigated using the microdilution method and the minimum inhibitory concentrations (MIC50 and MIC80). All molecules presented antifungal activity, and two esters showed a MIC for all fungi: octyl (MIC50 ≤ 0.5-0.75 mg/mL, MIC80 = 1.0-1.5 mg/mL) and dodecyl (MIC50 = 0.75-1.25 mg/mL) chlorogenates. Dodecyl chlorogenate showed a MIC80 (1.5 mg/mL) only for A. parasiticus. The maximum percent of growth inhibition on aspergillii was observed with octyl (78.4-92.7%) and dodecyl (54.5-83.7%) chlorogenates, being octyl chlorogenate the most potent antifungal agent. It was thus concluded that lipophilization improved the antifungal properties of 5-CQA, which increased with the ester alkyl chain length, exhibiting a cut-off effect at 8 carbons. As far as we know, it is the first report demonstrating that lipophilization may improve the antifungal activity of 5-CQA on five toxigenic moulds from the Aspergillus genus. Lipophilization would be a novel way to synthesize a new kind of antifungal agents with a good therapeutic value or a potential use as preservative in food or cosmetics.