The electrochemical oxidative stability of solvent molecules used for lithium ion battery, ethylene carbonate (EC), propylene carbonate, dimethyl carbonate, diethyl carbonate, and ethyl methyl carbonate in the forms of simple molecule and coordination with anion PF(6)(-), is compared by using density functional theory at the level of B3LYP/6-311++G (d, p) in gas phase. EC is found to be the most stable against oxidation in its simple molecule. However, due to its highest dielectric constant among all the solvent molecules, EC coordinates with PF(6)(-) most strongly and reaches cathode most easily, resulting in its preferential oxidation on cathode. Detailed oxidative decomposition mechanism of EC is investigated using the same level. Radical cation EC(*+) is generated after one electron oxidation reaction of EC and there are five possible pathways for the decomposition of EC(*+) forming CO(2), CO, and various radical cations. The formation of CO is more difficult than CO(2) during the initial decomposition of EC(*+) due to the high activation energy. The radical cations are reduced and terminated by gaining one electron from anode or solvent molecules, forming aldehyde and oligomers of alkyl carbonates including 2-methyl-1,3-dioxolane, 1,3,6-trioxocan-2-one, 1,4,6,9-tetraoxaspiro[4.4]nonane, and 1,4,6,8,11-pentaoxaspiro[4.6]undecan-7-one. The calculation in this paper gives a detailed explanation on the experimental findings that have been reported in literatures and clarifies the mechanism on the oxidative decomposition of EC.

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This study compared the loading ability of various carotenoids into liposomal membrane, lipid peroxidation inhibition capacity, storage stability and in vitro release behavior in simulated gastrointestinal (GI) media. It was found that carotenoids exhibited various incorporating abilities into liposomes ranging from the strongest to the weakest: lutein > β-carotene > lycopene > canthaxanthin. A similar trend was also observed in their antioxidant activities against lipid peroxidation during preparation. Storage measurements demonstrated that a liposomal membrane can strongly retain β-carotene and lutein, whereas this effect was not pronounced for lycopene and canthaxanthin. In vitro release experiments showed that lutein and β-carotene were hardly released in a simulated gastric fluid, while displaying a slow and sustained release in a simulated intestinal fluid. By contrast, lycopene and canthaxanthin underwent fast and considerable release in GI media. Dynamic light scattering indicated that carotenoid incorporation strongly affected the particle stability and dispersion during preparation and GI incubation. The differences in molecular release may be attributed to the different modulating effects of carotenoids. Our results may guide the potential application of liposomes as carriers for the controlled delivery of carotenoids in nutraceutical and functional foods.

This study was conducted to understand how carotenoids exerted antioxidant activity after encapsulation in a liposome delivery system, for food application. Three assays were selected to achieve a wide range of technical principles, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging, ferric reducing antioxidant powder (FRAP), and lipid peroxidation inhibition capacity (LPIC) during liposome preparation, auto-oxidation, or when induced by ferric iron/ascorbate. The antioxidant activity of carotenoids was measured either after they were mixed with preformed liposomes or after their incorporation into the liposomal system. Whatever the antioxidant model was, carotenoids displayed different antioxidant activities in suspension and in liposomes. The encapsulation could enhance the DPPH scavenging and FRAP activities of carotenoids. The strongest antioxidant activity was observed with lutein, followed by β-carotene, lycopene, and canthaxanthin. Furthermore, lipid peroxidation assay revealed a mutually protective relationship: the incorporation of either lutein or β-carotene not only exerts strong LPIC, but also protects them against pro-oxidation elements; however, the LPIC of lycopene and canthaxanthin on liposomes was weak or a pro-oxidation effect even appeared, concomitantly leading to the considerable depletion of these encapsulated carotenoids. The antioxidant activity of carotenoids after liposome encapsulation was not only related to their chemical reactivity, but also to their incorporation efficiencies into liposomal membrane and modulating effects on the membrane properties.

Lutein was loaded into liposomes, and their stability against environmental stress was investigated. Subsequently, these findings were correlated with the interactions between lutein and lipid bilayer. Results showed that the liposomes with loaded lutein at concentrations of 1 and 2% remained stable during preparation, heating, storage, and surfactant dissolution. However, with further increase in the loading concentration to 5 and 10%, the stabilization role of lutein on membrane was not pronounced or even opposite. Membrane fluidity demonstrated that at 1 and 2%, lutein displayed less fluidizing properties both in the headgroup region and in the hydrophobic core of the liposome, whereas this effect was not significant at 5 and 10%. Raman spectra demonstrated that lutein incorporation greatly affected the lateral packing order between acyl chains and longitudinal packing order of lipid acyl chains. These results may guide the potential application of liposomes as carriers for lutein in nutraceuticals and functional foods.

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The instability of dietary flavonoids is currently a challenge for their incorporation in functional foods. This study investigated the protective effects of liposome encapsulation on a variety of flavonoids and their interaction mechanisms. It was found that the incorporation of flavonoids into the liposomal membrane was strongly dependent on their structure and loading concentration. Liposomes loading quercetin and luteolin exhibited a relatively small size and homogeneous suspension compared to those loading kaempferol. Additionally, liposomes displayed a stronger retaining ability to quercetin and luteolin than kaempferol during preparation, storage, heating and pH shock. After encapsulation, quercetin displayed the strongest 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging and lipid peroxidation inhibition capacity, followed by kaempferol and luteolin. Raman and IR spectroscopy techniques demonstrated that flavonoids could modulate the dynamic and packing order of lipid chains, which were responsible for the stabilization of liposomes. Our findings should guide the rational design of liposomal encapsulation technology to efficiently deliver flavonoids in nutraceuticals and functional foods.