Hydrolysis and Transport Characteristics of Tyrosol Acyl Esters in Rat Intestine

Abstract

Lipophenols such as palmitoyl esters of green-tea polyphenols (GTP) have been allowed for use as food additives for oxidation control. However, their digestive absorption remains unexplored. In this paper, the hydrolysis and transport characteristics of tyrosol acyl esters (TYr-Es) with various fatty acids (C12:0, C14:0, C16:0, C18:0, C18:1, and C18:2) were evaluated using the everted-rat-gut-sac model for the first time. HPLC-UV measurements demonstrated that TYr-Es were hydrolyzed to TYr, which contributed significantly to TYr transport across the sacs. The hydrolysis and transport rates correlated negatively with the chain lengths of their lipid moieties but showed a positive correlation with the degree of unsaturation. In general, all TYr-Es exhibited sustained-release behavior; therefore, the production of TYr-Es may serve as a useful way to prolong the duration of action and further improve the bioactivities of TYr.

The Effects of Acyl Chain Length on Antioxidant Efficacy of Mono- and Multi-Acylated Resveratrol: A Comparative Assessment

“…However, this is not to say that the triester derivatives of resveratrol cannot be used as antioxidant supplement, cosmetic, or pharmaceuticals ingredients. The esterified phenolics may be hydrolysed by the microorganism, biased pH, and enteric/in vivo enzymes under specific physiochemical or physiological environments [ 41 , 46 ]. Depending on the acyl chain length and degree of acylation, they may be rapidly hydrolysed, detoxified, and excreted from the human body before/after entering systemic circulation and act as antioxidants in this process [ 47 , 48 ].…”

Distribution of tyrosol fatty acid esters in the gastrointestinal tracts of mice and their hydrolysis characteristics by gut microbiota

“…Our previous research showed that resveratrol fatty acid esters (RSv-Es) and tyrosol fatty acid esters (TYr-Es) were stable in simulated gastric fluid 15 and could be hydrolyzed to free polyphenol by intestinal lipase in an everted-rat-gut-sacs model. 16,17 Furthermore, when administered orally to rats, TYr-Es exhibited a prolonged plasma half-life compared to that of TYr. 18 Another study indicated that free hydroxytyrosol (HTy) was liberated from hydroxytyrosol acetate (HTy-Ac) by pancreatin.…”

Antiglycative and anti-inflammatory effects of lipophilized tyrosol derivatives

“…Tyrosol is one of the most abundant phenolic compounds found in olive oil (Richard et al 2011) and the presence of tyrosol esters in olive oil was more recently documented (Lee et al 2016). Furthermore, the esters of tyrosol were found to undergo hydrolysis in rat gut sac model, hence releasing tyrosol to render its effects (Yin et al 2018). However, the biological functions of lipophilic tyrosol esters are not yet well elucidated.…”