Hydrolysis and transport characteristics of starch inclusion complexes with long-chain alkyl gallates: Controlled two-step release of gallic acid and retardation of starch digestion.

Corn starch inclusion complexes of alkyl gallates (typical phenololipid representatives), including stearyl gallate, dodecyl gallate, octyl gallate, and hexadecyl gallate, were synthesized by using a heat treatment method. Such inclusion complexes exhibited significantly improved two-step release properties for gallic acid. In other words, gallic acid was generated via the breakdown of alkyl gallates that were released from inclusion complexes in an everted rat intestinal sac model, as determined by HPLC-UV analysis.

Glycosylation of oyster peptides by COS ameliorates zinc deficiency-induced syndromes: intestinal inflammation and imbalance of the gut microbiota .

Zinc is essential for maintaining the integrity and repair of small intestinal epithelial cells while zinc deficiency could induce the inflammatory infiltration and imbalance of intestinal flora in the intestine. In this study, glycosylation between oyster protein hydrolysate (OPH) and chitosan oligosaccharide (COS) was conducted and used as the carrier of zinc ions (OCZn). The results of zeta potential and particle size distribution showed that the OPH-COS successfully bound to zinc ions to form OCZn with a surface zinc content of 0.

Recovery effects of sodium carboxymethylcellulose-xanthan gum hydrogels containing peptide‑iron complexes against iron deficient anemia in vivo.

In this study, the sodium carboxymethylcellulose (CMC) and xanthan gum (XG) were used to prepare the CXM-Fe hydrogels (CMC: 20 mg/mL, XG: 10 mg/mL) with the addition of Mytilus edulis protein hydrolysate‑iron (MEPH-Fe) complexes. The incorporation of MEPH-Fe complexes formed a denser network structure and the CXM-Fe hydrogels had better pH stability as well as gastrointestinal retention ability. Compared with ferrous sulfate and MEPH-Fe complexes, the CXM-Fe hydrogels at moderate doses (Fe:2 mg/kg) showed impressive recovery effects on iron deficiency anemia (IDA) mice in terms of hematological indices, organ coefficients and iron content, antioxidant capacity, and remarkedly attenuated the infiltration of inflammatory cells as well as the levels of inflammatory factors in iron deficiency-induced colonic inflammation.

A soft electronic skin simulating the multi-scale human touch for the detection of fruit freshness.

Realizing biomimicry for human tactile perception is a meaningful challenge. In this work, a soft matter system with multi-scale energy dissipation structure is designed to realize flexible sensing and detection by biomimetic human touch. At the molecular scale, the supramolecular interactions are introduced into the hydrogel system, including the hydrophobic interaction and the ion attraction between macromolecular segments.

Preparation and characterization of white shrimp hydrolysate-xylooligosaccharide Maillard products and their promotive effects of zinc absorption in mice.

The Maillard reaction products, as a kind of glycosylation-based reaction, possess the metal-chelating ability. In this study, the white shrimp hydrolysate (WH) and xylooligosaccharides (XOS) were used to prepare the Maillard reaction product-zinc complex (WH-XOS-MR-Zn) with zinc ions. The Maillard reaction conditions, such as pH level, temperature, reaction time, and the ratio of XOS to WH, were selected by testing the products' zinc-chelating capacity, while the optimized conditions (zinc-chelating capacity = 64.

The change rule of lipid oxidation and hydrolysis driven via water in Antarctic krill oil: Based on association colloid formation.

The residual water and amphiphilic compounds such as phospholipids in bulk oil can form reverse micelles, which affect oxidative stability. In this study, the Antarctic krill oil (AKO) samples with different water contents were subjected to accelerated storage. During storage, AKO exhibited oxidative changes, manifested as increased POV, TBARS values, and volatile compound levels but decreased PUFA percentages.

Influence of lipid oxidation on the digestive efficiency of Antarctic krill oil: insights from a simulated gastrointestinal digestion model.

Lipid oxidation profoundly impacts its digestibility, a topic that has been predominantly investigated in triglyceride (TAG)-based dietary lipids. However, there is a dearth of similar research on lipids with diverse classes, such as Antarctic krill oil (AKO), which encompasses a spectrum of lipids including glycerides and phospholipids. This study aimed to elucidate the influence of lipid oxidation on the digestibility of AKO through a simulated gastrointestinal digestion (SGID) model.

Application of resveratrol on oxidative stability of protein-based Antarctic krill oil high internal phase emulsion.

Antarctic krill oil (KO) is known for its poor oxidative stability, especially in emulsion systems. In this experiment, a complex of scallop water-soluble protein-resveratrol (SWPs-RES) was mixed with KO to create high internal phase emulsions (HIPEs) with varying RES ratios. The addition of RES led to noticeable conformational changes in SWPs, including fluorescence bursts, alterations in secondary structure, and modifications in binding motifs.

Controlled release characteristics of alkyl gallates and gallic acid from β-cyclodextrin inclusion complexes of alkyl gallates.

The freeze-drying approach was used to create inclusion complexes utilizing alkyl gallates and β-cyclodextrin, namely dodecyl gallate, octyl gallate, butyl gallate, and ethyl gallate, which are exemplary examples of phenolic esters. The everted-rat-gut-sac model demonstrated that the inclusion complexes released alkyl gallates, which were subsequently hydrolyzed to generate free gallic acid, as evidenced by HPLC-UV analysis. Both gallic acid and short-chain alkyl gallates were capable of permeating the small intestinal membrane.

Mechanism of discoloration of Antarctic krill oil upon storage: A study based on model systems.

The reddish-orange color of Antarctic krill oil fades during storage, and the mechanism remains unclear. Model systems containing different combinations of astaxanthin (ASTA), phosphatidylethanolamine (PE), and tocopherol were subjected to accelerated storage. Among all groups containing ASTA, only the ones with added PE showed significant fading.

Controlled dual release of phenol compounds from phospholipid complexes of short-chain lipophenols.

Ethanol evaporation method was applied to synthesize phospholipid complexes from phosphatidylcholine (PC) and short-chain alkyl gallates (A-GAs, a typical representative of lipophenols) including butyl-, propyl- and ethyl gallates. H NMR, UV and FTIR showed that A-GAs were interacted with PC through weak physical interaction. Through the analysis of concentrations of A-GAs and gallic acid (GA) by an everted rat gut sac model coupled with HPLC-UV detection, phospholipid complexes were found to gradually release A-GAs.

β-cyclodextrin inclusion complexes with short-chain phenolipids: An effective formulation for the dual sustained-release of phenolic compounds.

The β-cyclodextrin and short-chain alkyl gallates (A-GAs), which are representative of phenolipids, such as butyl, propyl, ethyl, and methyl gallates, were chosen to form inclusion complexes by the use of the freeze-drying process. In the everted rat gut sac model, HPLC-UV analysis demonstrated that the released A-GAs from inclusion complexes were degraded to yield free gallic acid (GA) (sustained-release function 1). The small intestine membrane may be crossed by both the GA and the A-GAs.

Mechanism of color change in Antarctic krill oil during storage.

Antarctic krill oil (AKO) is reddish-orange in color but undergoes changes during storage. To investigate the color deterioration and potential mechanisms involved, the changes in color, endogenous components (astaxanthin, fatty acids, and phospholipids), and reaction products (aldehydes, α-dicarbonyl compounds, and pyrroles) of AKO upon storage were determined. Although the visual color of AKO tended to darken upon storage, the colorimetric analysis and ultraviolet-visible spectrum analysis both indicated a fading in red and yellow due to the oxidative degradation of astaxanthin.

Comparative study on the enzymatic degradation of phenolic esters: The HPLC-UV quantification of tyrosol and gallic acid liberated from tyrosol acyl esters and alkyl gallates by hydrolytic enzymes.

HPLC-UV analysis was used to evaluate the enzymatic degradation characteristics of tyrosol acyl esters (TYr-Es) and alkyl gallates (A-GAs). Among various hydrolytic enzymes, TYr-Es can be hydrolyzed by pancrelipase, while A-GAs cannot be hydrolyzed by pancrelipase. Interestingly, carboxylesterase-1b (CES-1b), carboxylesterase-1c (CES-1c) and carboxylesterase-2 (CES-2) are able to hydrolyze TYr-Es and A-GAs, and thus to liberate tyrosol (TYr) and gallic acid (GA).

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

Phospholipid complexes of alkyl gallates (A-GAs) including ethyl gallate (EG), propyl gallate (PG), and butyl gallate (BG) were successfully prepared by the thin film dispersion method. HPLC-UV analysis in an everted rat gut sac model indicated that A-GAs can be liberated from phospholipid complexes, which were further hydrolyzed by intestinal lipase to generate free gallic acid (GA). Both A-GAs and GA are able to cross the membrane, and the hydrolysis rate of A-GAs and the transport rate of GA are positively correlated with the alkyl chain length.

Characterization of Oyster Protein Hydrolysate-Iron Complexes and their Protective Effects against Iron Deficiency-Induced Symptoms in Mice.

Iron is one of the trace mineral elements, and iron deficiency is a common phenomenon that negatively influences human health. Food-derived iron supplements were considered excellent candidates for improving this syndrome. In this work, oyster-protein hydrolysates (OPH) and ferrous chloride successfully formed the OPH-Fe complex (6 mg/mL, 40 °C, 30 min), where the main binding sites involved were the carboxyl and amino groups.

In vitro plasma hydrolysis of phenolic esters and their absorption kinetics in rats: Controlled release of phenolic compounds and enhanced health benefits.

Phenolic esters are considered as promising functional food ingredients. However, their digestion, absorption and metabolism are still unclear. Tyrosol acyl esters (TYr-Es), hydroxytyrosol acyl esters (HTy-Es) and alkyl gallates (A-GAs) were hydrolyzed by carboxylesterase in plasma and exhibited slow release of polyphenols (phenolic acids).

Bioinspired Adhesive Antibacterial Hydrogel with Self-Healing and On-Demand Removability for Enhanced Full-Thickness Skin Wound Repair.

Adhesive-caused injury is a great threat for extensive full-thickness skin trauma because extra-strong adhesion can incur unbearable pain and exacerbate trauma upon removal. Herein, inspired by the mussel, we designed and fabricated an adhesive antibacterial hydrogel dressing based on dynamic host-guest interaction that enabled on-demand stimuli-triggered removal to effectively care for wounds. In contrast with most hard-to-removable dressing, this adhesive antibacterial hydrogel exhibited strong adhesion property (85 kPa), which could achieve painless and noninvasive on-demand separation within 2 s through a host-guest competition mechanism (amantadine).

Encapsulation Alleviates the Auto-browning of Epigallocatechin-3-gallate in Aqueous Solutions through Regulating Molecular Self-Aggregation Behavior.

Catechins are widely recognized for superb antioxidant capability, but their application as food antioxidants is hindered by susceptibility to auto-browning under high-moisture conditions. Here, we proposed a strategy of ordered encapsulation with cyclodextrin-based metal-organic frameworks (CD-MOFs) to alleviate the auto-browning phenomenon of catechins while preserving their antioxidant capability and demonstrated the feasibility of this strategy via selecting epigallocatechin-3-gallate (EGCG) as a model. Even in aqueous solutions, EGCG@CD-MOFs still possessed delayed browning, in contrast with pristine EGCG, characterized by suppressed efficiencies on the generation of oxidative dimers (theasinensin A) and semiquinone radicals.

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

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 from mice feces.

The potential of hydroxytyrosol fatty acid esters to enhance oral bioavailabilities of hydroxytyrosol and fatty acids: Continuous and slow-release ability in small intestine and blood.

HPLC-UV analysis in rat everted gut sac and in vitro simulated digestion models indicated that hydroxytyrosol fatty acid esters (HTy-Es) could be hydrolyzed by pancreatic lipase to slow-release of free fatty acids (FAs) and HTy. Meanwhile, the HTy-Es, the liberated FAs and the HTy could cross the membrane and were transported into blood circulation. HTy-Es were further hydrolyzed by carboxylesterase in in vitro rat plasma hydrolysis model, which also showed slow-release of FAs (C1-C4) and HTy.

Effects of Addition of Tea Polyphenol Palmitate and Process Parameters on the Preparation of High-Purity EPA Ethyl Ester.

High-purity eicosapentaenoic acid (EPA) ethyl ester (EPA-EE) can be produced from an integrated technique consisting of saponification, ethyl esterification, urea complexation, molecular distillation and column separation. In order to improve the purity and inhibit oxidation, tea polyphenol palmitate (TPP) was added before the procedure of ethyl esterification. Furthermore, through the optimization of process parameters, 2:1 (mass ratio of urea to fish oil, g/g), 6 h (crystallization time) and 4:1 (mass ratio of ethyl alcohol to urea, g/g) were found to be the optimum conditions in the procedure of urea complexation.

Hydrolysis and transport characteristics of tyrosol-SCFA esters in rat intestine and blood: Two-step release of tyrosol and SCFAs to enhance the beneficial effects.

The models of rat everted gut sac and hydrolysis by rat plasma were used to clarify the hydrolysis and transport characteristics of tyrosol-SCFA esters (TYr-SEs). HPLC-UV results indicated that TYr-SEs could be hydrolyzed by intestinal lipase, which showed sustained release of SCFAs and TYr. Meanwhile, TYr-SEs and the liberated SCFAs and TYr could cross the membrane and were transported into blood circulation.