Lipid Structure Influences the Digestion and Oxidation Behavior of Docosahexaenoic and Eicosapentaenoic Acids in the Simulated Digestion System

Beltrame, Gabriele; Ahonen, Eija; Damerau, Annelie; Gudmundsson, Haraldur G.; Haraldsson, Guđmundur G.; Linderborg, Kaisa M.

doi:10.1021/acs.jafc.3c02207

Cited by 3 publications

(1 citation statement)

References 48 publications

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“…This is supported by the slower absorption profiles and T max obtained for the Pickering formulations in the fed state. It has been recently shown that n -3 PUFA are most sensitive to oxidation in the stomach. , Initial protection of the oil by the Pickering layer followed by release in the small intestine may thus be beneficial with respect to maximizing bioavailability of n -3 PUFAs and minimize exposure of undesirable oxidation products. Additional in vitro studies combining drug release and degradation may be helpful to further verify this hypothesis in the future.…”

Section: Discussionmentioning

confidence: 99%

In Vitro and In Vivo Performance of Pickering Emulsion-Based Powders of Omega-3 Polyunsaturated Fatty Acids

Nyström,

Mira,

Benjamins

et al. 2023

Mol. Pharmaceutics

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Omega-3 polyunsaturated fatty acids (n-3 PUFA) are essential nutrients for human health and have been linked to a variety of health benefits, including reducing the risk of cardiovascular diseases. In this paper, a spray-dried powder formulation based on Pickering emulsions stabilized with cellulose nanocrystals (CNC) and hydroxypropyl methylcellulose (HPMC) has been developed. The formulation was compared in vitro and in vivo to reference emulsions (conventional Self-Emulsifying Drug Delivery System, SEDDS) to formulate n-3 PUFA pharmaceutical products, specifically in free fatty acid form. The results of in vivo studies performed in fasted dogs showed that Pickering emulsions reconstituted from powders are freely available (fast absorption) with a similar level of bioavailability as reference emulsions. In the studies performed with dogs in the fed state, the higher bioavailability combined with slower absorption observed for the Pickering emulsion, compared to the reference, was proposed to be the result of the protection of the n-3 PUFAs (in free fatty acid form) against oxidation in the stomach by the solid particles stabilizing the emulsion. This observation was supported by promising results from short-term studies of chemical stability of powders with n-3 PUFA loads as high as 0.8 g oil/g powder that easily regain the original emulsion drop sizes upon reconstitution. The present work has shown that Pickering emulsions may offer a promising strategy for improving the bioavailability and stability as well as providing an opportunity to produce environmentally friendly (surfactant free) and patient-acceptable solid oral dosage forms of n-3 PUFA in the free fatty acid form.

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Section: Discussionmentioning

confidence: 99%

In Vitro and In Vivo Performance of Pickering Emulsion-Based Powders of Omega-3 Polyunsaturated Fatty Acids

Nyström,

Mira,

Benjamins

et al. 2023

Mol. Pharmaceutics

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Plant-Based Oil-in-Water Food Emulsions: Exploring the Influence of Different Formulations on Their Physicochemical Properties

Quezada,

Urra,

Mella

et al. 2024

Foods

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The global focus on incorporating natural ingredients into the diet for health improvement encompasses ω-3 polyunsaturated fatty acids (PUFAs) derived from plant sources, such as flaxseed oil. ω-3 PUFAs are susceptible to oxidation, but oil-in-water (O/W) emulsions can serve to protect PUFAs from this phenomenon. This study aimed to create O/W emulsions using flaxseed oil and either soy lecithin or Quillaja saponins, thickened with modified starch, while assessing their physical properties (oil droplet size, ζ-potential, and rheology) and physical stability. Emulsions with different oil concentrations (25% and 30% w/w) and oil-to-surfactant ratio (5:1 and 10:1) were fabricated using high-pressure homogenization (800 bar, five cycles). Moreover, emulsions were thickened with modified starch and their rheological properties were measured. The physical stability of all emulsions was assessed over a 7-day storage period using the TSI (Turbiscan Stability Index). Saponin-stabilized emulsions exhibited smaller droplet diameters (0.11–0.19 µm) compared to lecithin (0.40–1.30 µm), and an increase in surfactant concentration led to a reduction in droplet diameter. Both surfactants generated droplets with a high negative charge (−63 to −72 mV), but lecithin-stabilized emulsions showed greater negative charge, resulting in more intense electrostatic repulsion. Saponin-stabilized emulsions showed higher apparent viscosity (3.9–11.6 mPa·s) when compared to lecithin-stabilized ones (1.19–4.36 mPa·s). The addition of starch significantly increased the apparent viscosity of saponin-stabilized emulsions, rising from 11.6 mPa s to 2117 mPa s. Emulsions stabilized by saponin exhibited higher stability than those stabilized by lecithin. This study confirms that plant-based ingredients, particularly saponins and lecithin, effectively produce stable O/W emulsions with flaxseed oil, offering opportunities for creating natural ingredient-based food emulsions.

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Chemoenzymatic Synthesis of ABC-Type Enantiostructured Triacylglycerols by the Use of the p-Methoxybenzyl Protective Group

Haraldsdottir,

Gudmundsson,

Linderborg

et al. 2024

Molecules

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This report demonstrates the first asymmetric synthesis of enantiopure structured triacylglycerols (TAGs) of the ABC type presenting three non-identical fatty acids, two of which are unsaturated. The unsaturated fatty acids included monounsaturated oleic acid (C18:1 n-9) and polyunsaturated linoleic acid (C18:2 n-6). This was accomplished by a six-step chemoenzymatic approach starting from (R)- and (S)-solketals. The highly regioselective immobilized Candida antarctica lipase (CAL-B) played a crucial role in the regiocontrol of the synthesis. The synthesis also benefited from the use of the p-methoxybenzyl (PMB) ether protective group, which enabled the incorporation of two different unsaturated fatty acids into the glycerol skeleton. The total of six such TAGs were prepared, four constituting the unsaturated fatty acids in the sn-1 and sn-2 positions, with a saturated fatty acid in the remaining sn-3 position of the glycerol backbone. In the two remaining TAGs, the different unsaturated fatty acids accommodated the sn-1 and sn-3 end positions, with the saturated fatty acid present in the sn-2 position. Enantiopure TAGs are urgently demanded as standards for the enantiospecific analysis of intact TAGs in fats and oils.

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Lipid Structure Influences the Digestion and Oxidation Behavior of Docosahexaenoic and Eicosapentaenoic Acids in the Simulated Digestion System

Cited by 3 publications

References 48 publications

In Vitro and In Vivo Performance of Pickering Emulsion-Based Powders of Omega-3 Polyunsaturated Fatty Acids

In Vitro and In Vivo Performance of Pickering Emulsion-Based Powders of Omega-3 Polyunsaturated Fatty Acids

Plant-Based Oil-in-Water Food Emulsions: Exploring the Influence of Different Formulations on Their Physicochemical Properties

Chemoenzymatic Synthesis of ABC-Type Enantiostructured Triacylglycerols by the Use of the p-Methoxybenzyl Protective Group

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