Synthesis and Evaluation of the Antioxidant Activity of Lipophilic Phenethyl Trifluoroacetate Esters by In Vitro ABTS, DPPH and in Cell-Culture DCF Assays

Abstract

Polyphenols are natural compounds showing a variety of health-promoting effects. Unfortunately, due to low lipid solubility, their applications in the pharmaceutical, food, and cosmetic industries are limited. With the aim of obtaining novel lipophilic derivatives, the present study reports the synthesis of a series of phenethyl trifluoroacetate esters containing up to two hydroxyl groups in the aromatic ring. Experimental logP values confirmed a greater lipophilicity of the novel compounds compared to the parent compounds. The radical scavenging capacity of all phenethyl trifluoroacetate esters was evaluated by in vitro assays (ABTS, DPPH) and in cultured cells (L6 myoblasts and THP-1 leukemic monocytes) using 2′,7′-dichlorodihydrofluorescein diacetate. These data revealed that the esters showed a good antioxidant effect that was strictly dependent on the grade of hydroxylation of the phenyl ring. The lack of toxicity, evaluated by the MTT assay and proliferation curves, makes these trifluoroacetates attractive derivatives for pharmaceutical, food, and cosmetic applications.

Antiwrinkle and Antimelanogenesis Effects of Tyndallized Lactobacillus acidophilus KCCM12625P

“…In addition, treatment with AL prevented cell death by UVB, indicating that AL protects the skin and body from UVB irradiation (Figure 1b). The antioxidant effects of AL were found through ABTS radical-scavenging assays [46][47][48], which again demonstrates that AL exerts antioxidant effects (Figure 1d).…”

Effects of UV-B Radiation on the Content of Bioactive Components and the Antioxidant Activity of Prunella vulgaris L. Spica during Development

“…Phenolic acids and flavonoids are well-known to have beneficial health effects, such as antioxidative, antimicrobial, anti-inflammatory, and antimutagenic properties, for various organisms [ 14 ]. In this study, we measured the antioxidant capacities of two ethanol extracts by the DPPH ● and ABTS•+ assays [ 28 , 29 ]. The antioxidant activity of P. vulgaris spicas showed a similar fluctuation with growth stage as was seen in the phenolic and flavonoid contents since the DPPH ● and ABTS•+ scavenging activities were positively correlated with the contents of bioactive compounds in the spica except in case of the salviaflaside ( Table 2 ).…”

Quantification of Phenolic Compounds and In Vitro Radical Scavenging Abilities with Leaf Extracts from Two Varieties of Psidium guajava L.

“…Jeong et al [ 21 ] measured total phenolic compounds, ABTS, and DPPH in three varieties of Psidium guajava cultivated in Korea. These assays are used due to the versatility of the samples that can be analyzed from cell lines to nutrition lines, since it shows a premise of the structure and its relationship in the antioxidant activity of the compounds contained in the samples [ 25 , 26 ].…”