Despite the wide literature describing the biological effects of polyphenols, scarce data are available on their content in the human diet. This study examined total polyphenols content, free and total phenolic acids profile, and antioxidant activity of different commercial beers types (abbey, ale, bock, wheat, lager, pilsner, and dealcoholized). Ferulic acid is by far the most abundant phenolic acid in beers, followed by sinapic, vanillic, caffeic, p-coumaric, and 4-hydroxyphenylacetic acids. Ferulic, caffeic, syringic, sinapic, and, to a lesser extent, vanillic acids are present in beers mainly as bound forms, whereas p-coumaric and 4-hydroxyphenylacetic acids are generally present equally in free and bound forms. Total polyphenols and phenolic acids contents greatly vary among different beer types (i.e., total polyphenols, from 366 μg/mL gallic acid equivalents for dealcoholized beers to 875 μg/mL gallic acid equivalents for bock beers, with higher values measured in bock, abbey, and ale beers and lower values in dealcoholized beers). Similarly, the antioxidant activity measured with the ferric reducing antioxidant power (FRAP) assay is remarkably different depending on beer type (from 1525 μM for dealcoholized beers to 4663 μM for bock beers), with higher values in bock, abbey, and ale beers and lower values in dealcoholized beers. FRAP values strictly correlate with polyphenols and phenolic acids content. The contribution of single phenolic acids to the antioxidant activity measured with FRAP assay was also studied.
The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide.
Cell-penetrating peptides (CPPs) are cationic oligopeptides able to translocate across biological membranes without perturbing them, while antimicrobial peptides (AMPs) kill bacteria mainly by disrupting their membranes. The two peptide classes share several characteristics (charge, amphipathicity, helicity, and length), and therefore the molecular properties discriminating between the two different bioactivities are not clear. Pep-1-K (KKTWWKTWWTKWSQPKKKRKV) is a new AMP derived from the widely studied CPP Pep-1 (KETWWETWWTEWSQPKKKRKV), or 'Chariot', known for its ability to carry large cargoes across biological membranes. Pep-1-K was obtained from Pep-1 by substituting the three Glu residues with Lys, to increase its cationic character. Previous studies showed that these modifications endow Pep-1-K with a potent antimicrobial activity, with MICs in the low micromolar range. Here, we characterized the interaction of Pep-1 and Pep-1-K with model membranes to understand the reason for the antimicrobial activity of Pep-1-K. The data show that this peptide causes vesicle aggregation, perturbs membrane order, and induces the leakage of ions, but not of larger solutes, while these effects were not observed for Pep-1. These differences are likely due, at least in part, to the higher affinity of Pep-1-K toward anionic bilayers, which mimick the composition of bacterial membranes
Aminoethylcysteine ketimine decarboxylated dimer (AECK-DD) is a natural compound with antioxidant properties of a new family of sulfur-containing amino acids. It has been detected in human urine and plasma, in mammalian cerebellum, and in dietary vegetables. In this study, we first demonstrate the absorption of AECK-DD in mice from AECK-DD-supplemented diet, using both liquid chromatography with electrochemical detection and gas chromatography coupled with mass spectrometry. AECK-DD circulates in the plasma of supplemented mice at a micromolar concentration and is incorporated in liver tissue. The absorption of AECK-DD is dose dependent. The dehydrogenation product of AECK-DD was also identified in plasma and liver of mice fed the AECK-DD-supplemented diet. A significant increase in plasma antioxidant potential was measured in mice fed AECK-DD-supplemented diet with respect to mice fed the control diet. These results demonstrate for the first time the absorption of AECK-DD from diet and the physiological relevance of this compound through its antioxidant action in vivo.
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