In Vitro Gastrointestinal Digestion and Microbial Hydrolysis of Hydroxytyrosol-SCFA and Tyrosol-SCFA Acyl Esters: Controlled-Release of SCFAs and Polyphenols

Abstract

Phenolipids such as hydroxytyrosol-SCFA acyl esters (HTy-SEs) and tyrosol-SCFA acyl esters (TYr-SEs) with various alkyl chains lengths (C1–C4) and different isomers (branched-chain and straight-chain) were successfully synthesized. All esters were hydrolyzed by pancreatic lipase to produce polyphenols (HTy and TYr) and SCFAs (iso-butyric acid, acetic acid, propionic acid, and n-butyric acid). Moreover, HTy-SEs (and TYr-SEs) could also be hydrolyzed to free HTy (and TYr) and SCFAs by gut microbiota and Lactobacillus from mice feces. Especially, the hydrolysis rates showed positive correlation with the carbon skeleton length, and the hydrolysis degree (DH) of ester with a branched-chain fatty acid was weaker than that of ester with a straight-chain fatty acid. Besides, the DH values of TYr -SEs were significantly higher than those of HTy-SEs. Therefore, through regulating the structures of polyphenols, carbon skeleton lengths, and isomers, controlled-release of polyphenols and SCFAs from phenolipids will be easily achieved.

Hydrolysis and Transport Characteristics of Phospholipid Complex of Alkyl Gallates: Potential Sustained Release of Alkyl Gallate and Gallic Acid

“…Obviously, the hydrolysis of A-GAs significantly promoted the transport of GA across the gut sac. Similarly, tyrosol acyl esters (TYr-Es) and hydroxytyrosol acyl esters (HTy-Es) were synthesized in our previous studies. , A linear relationship between the transport rates of TYr (or HTy) and the hydrolysis rate coefficients of various TYr-Es (or HTy-Es) was also found.…”

“…In contrast, the structures of A-GAs are different from those of tyrosol fatty acid esters (TYr-Es) and hydroxytyrosol fatty acid esters (HTy-Es) (Figure S1), which necessarily leads to different digestion and absorption characteristics. Our previous research results showed that TYr-Es, HTy-Es and A-GAs can be slowly hydrolyzed by intestinal lipase, and their hydrolysis rates from small to large are as follows: A-GAs, HTy-Es and TYr-Es. , This is mainly due to the fact that compared to the fatty acid chains, the fatty alcohol chains have a lower affinity for binding to hydrophobic canyon of lipase, hindering the access of the backbone to the oxyanion hole, which is not conductive to play a catalytic role through the binding of hydrophobic canyon of lipase to the interface . Therefore, it may be possible to achieve two-step sustained-release of polyphenols through synthesizing phenolipid-phospholipid complexes, further enhancing their bioavailability.…”

Preparation, Structural Analysis, and Intestinal Probiotic Properties of a Novel Oligosaccharide from Enzymatic Degradation of Huangshui Polysaccharide

“…Metabolites produced by gut microbiota, such as short-chain fatty acids (SCFAs) and indoles acting as "messengers" of the gut microbiota, influence the host's appetite, inflammatory response, and endocrine function, and ultimately regulate the host's metabolic activities. 12 Current research has shown that nondigestible components in food can affect the composition and activity of host gut microbiota, thereby impacting the host's health and physical functions. 13 Even so, there is no information on the intestinal probiotic properties of HS oligosaccharides (HSOs), the nondigestible substances.…”

“…The gut microbiota plays a crucial role in the balance of the intestinal microecosystem to promote host health. Metabolites produced by gut microbiota, such as short-chain fatty acids (SCFAs) and indoles acting as “messengers” of the gut microbiota, influence the host’s appetite, inflammatory response, and endocrine function, and ultimately regulate the host’s metabolic activities . Current research has shown that nondigestible components in food can affect the composition and activity of host gut microbiota, thereby impacting the host’s health and physical functions .…”