Lipophenols, phenolic compounds esterified with fatty
alcohols
or fatty acids, provide greater health benefits upon dietary ingestion
of plant-based foods than unesterified (poly)phenols. Based on this
premise, the present study aimed to demonstrate the role of gastrointestinal
enzymes (pepsin, pancreatin, and pancreatic lipase) in releasing alkyl
gallates and trans-caffeates from wine lees, providing
bioactive compounds with enhanced capacities against oxidative stress
(OS) and para-inflammation. The UHPLC–ESI-QqQ-MS/MS-based analysis
revealed ethyl gallate and ethyl trans-caffeate as
the most prominent compounds (1.675 and 0.872 μg/g dw, respectively),
while the bioaccessibility of the derivatives of gallic and caffeic
acids was dependent on the alkyl chain properties. The de
novo formation of alkyl gallates during gastric and intestinal
digestion resulted from intestinal enzyme activity. Moreover, the in vitro capacity of bioaccessible alkyl esters of gallic
and trans-caffeic acids to reduce cyclooxygenase-2
concentration and modulate oxilipins related to OS (8-iso-PGF2α) and inflammation (PGF2α and PGE2) was demonstrated in a time-dependent manner. In conclusion,
the presence of alkyl esters of gallic and trans-caffeic
acids in wine lees and their subsequent formation during digestion
of this byproduct emphasize their value as a source of antioxidant
and anti-inflammatory compounds, encouraging the consideration of
wine lees as a valuable ingredient for health-promoting coproducts.