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Comparative study of the oxidative and physical stability of liposomal and nanoliposomal polyunsaturated fatty acids prepared with conventional and Mozafari methods

Rasti B, Jinap S, Mozafari MR, Yazid AM

Food Chem, 2012 Dec 15;135(4):2761-70.
PMID: 22980870 DOI: 10.1016/j.foodchem.2012.07.016

The relative oxidative stability of freshly prepared and stored liposomal and nanoliposomal systems of docosahexaenoic acid (DHA, 22:6 n-3) and eicosapentaenoic acid (EPA, 20:5 n-3) were investigated. The effects of organic solvents on the oxidative stability of liposomal polyunsaturated fatty acids (PUFAs) produced by two methods, the Bangham thin-film hydration (conventional rotary evaporation method and using organic solvents) and Mozafari (direct hydration and without using organic solvents) methods, were compared. The highest physicochemical stability was observed in PUFA liposomes prepared by the Mozafari method, followed by conventional liposomes and bulk PUFAs. There was no significant change in physicochemical stability during 10 months of cold storage (4°C) in the dark. Moreover, the comparison between liposomes (>200 nm) and nanoliposomes (50-200 nm) revealed that the surface charge, physical stability and oxidative stability of liposomal PUFAs increased as the size of the liposomes decreased. The differences in the oxidative stability of PUFAs may be due to the protective effects of aqueous systems, which indicate the advantage of using non-organic solvent (water and CO(2)) techniques in liposome manufacturing.

Matched MeSH terms: Docosahexaenoic Acids/chemistry*
Choline-Chloride-Based Eutectic Solvent for the Efficient Production of Docosahexaenoyl and Eicosapentaenoyl Ethanolamides via an Enzymatic Process

Liang H, Qin X, Tan CP, Li D, Wang Y

J Agric Food Chem, 2018 Nov 21;66(46):12361-12367.
PMID: 30394748 DOI: 10.1021/acs.jafc.8b04804

Docosahexaenoyl and eicosapentaenoyl ethanolamides (DHEA and EPEA) have physiological functions, including immunomodulation, brain development, and anti-inflammation, but their efficient production is still unresolved. In this study, choline-chloride-based natural deep eutectic solvents are used as media to improve the production of DHEA and EPEA. The water content showed a key effect on the reactant conversion. Adding water to choline chloride-glucose (CG, molar ratio of 5:2) led to a significant increase (13.03% for EPEA and 27.95% for DHEA) in the yields after 1 h. The high yields of EPEA (96.84%) and DHEA (90.06%) were obtained under the optimized conditions [fish oil ethyl esters/ethanolamine molar ratio of 1:2, temperature of 60 °C, 1 h, enzyme loading of 2195 units, and CG containing 8.50% water of 43.30% (w/w, relative to total reactants)]. The products could be easily separated using centrifugation. In summary, the research has the potential to produce fatty acyl ethanolamides.

Matched MeSH terms: Docosahexaenoic Acids/chemistry
Phospholipid-Protein Structured Membrane for Microencapsulation of DHA Oil and Evaluation of Its In Vitro Digestibility: Inspired by Milk Fat Globule Membrane

Chen Y, Ge H, Zheng Y, Zhang H, Li Y, Su X, et al.

J Agric Food Chem, 2020 Jun 03;68(22):6190-6201.
PMID: 32379465 DOI: 10.1021/acs.jafc.0c01250

The present study aims to design a milk fat globule membrane (MFGM)-inspired structured membrane (phospholipid- and protein-rich) for microencapsulation of docosahexaenoic acid (DHA) oil. DHA-enriched oil emulsions were prepared using different ratios of sunflower phospholipid (SPL), proteins [whey protein concentrate (WPC), soy protein isolate (SPI), and sodium caseinate (SC)], and maltodextrin and spray-dried to obtain DHA microcapsules. The prepared DHA oil emulsions have nanosized particles. SPLs were found to affect the secondary structure of WPC, which resulted in increased exposure of the protein hydrophobic site and emulsion stability. SPL also reduced the surface tension and viscosity of the DHA oil emulsions. In vitro digestion of the spray-dried DHA microcapsules showed that they were able to effectively resist gastric proteolysis and protect their bioactivity en route to the intestine. The DHA microcapsules have a high lipid digestibility in the small intestine with a high DHA hydrolysis efficiency (74.3%), which is higher than that of commercial DHA microcapsules.

Matched MeSH terms: Docosahexaenoic Acids/chemistry*
Coenzyme Q10-Loaded Fish Oil-Based Bigel System: Probing the Delivery Across Porcine Skin and Possible Interaction with Fish Oil Fatty Acids

Zulfakar MH, Chan LM, Rehman K, Wai LK, Heard CM

AAPS PharmSciTech, 2018 Apr;19(3):1116-1123.
PMID: 29181705 DOI: 10.1208/s12249-017-0923-x

Coenzyme Q10 (CoQ10) is a vitamin-like oil-soluble molecule that has anti-oxidant and anti-ageing effects. To determine the most optimal CoQ10 delivery vehicle, CoQ10 was solubilised in both water and fish oil, and formulated into hydrogel, oleogel and bigel. Permeability of CoQ10 from each formulation across porcine ear skin was then evaluated. Furthermore, the effects of the omega-3 fatty eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids from fish oil on skin permeation were investigated by means of nuclear magnetic resonance (NMR) and computerised molecular modelling docking experiments. The highest drug permeation was achieved with the bigel formulation that proved to be the most effective vehicle in delivering CoQ10 across the skin membrane due to a combination of its adhesive, viscous and lipophilic properties. Furthermore, the interactions between CoQ10 and fatty acids revealed by NMR and molecular modelling experiments likely accounted for skin permeability of CoQ10. NMR data showed dose-dependent changes in proton chemical shifts in EPA and DHA. Molecular modelling revealed complex formation and large binding energies between fatty acids and CoQ10. This study advances the knowledge about bigels as drug delivery vehicles and highlights the use of NMR and molecular docking studies for the prediction of the influence of drug-excipient relationships at the molecular level.

Matched MeSH terms: Docosahexaenoic Acids/chemistry*
Docosahexaenoic acid-concentrated fish oil supplementation in subjects with mild cognitive impairment (MCI): a 12-month randomised, double-blind, placebo-controlled trial

Lee LK, Shahar S, Chin AV, Yusoff NA

Psychopharmacology (Berl), 2013 Feb;225(3):605-12.
PMID: 22932777 DOI: 10.1007/s00213-012-2848-0

RATIONALE: Epidemiological studies have suggested a beneficial effect of fish oil supplementation in halting the initial progression of Alzheimer's disease. However, it remains unclear whether fish oil affects cognitive function in older people with mild cognitive impairment (MCI).
OBJECTIVES: This study investigated the effects of fish oil supplementation on cognitive function in elderly person with MCI.
METHODS: This was a 12-month, randomised, double-blind, placebo-controlled study using fish oil supplementation with concentrated docosahexaenoic acid (DHA). Thirty six low-socioeconomic-status elderly subjects with MCI were randomly assigned to receive either concentrated DHA fish oil (n = 18) or placebo (n = 18) capsules. The changes of memory, psychomotor speed, executive function and attention, and visual-constructive skills were assessed using cognitive tests. Secondary outcomes were safety and tolerability of the DHA concentrate.
RESULTS: The fish oil group showed significant improvement in short-term and working memory (F = 9.890; ηp (2) = 0.254; p

Matched MeSH terms: Docosahexaenoic Acids/chemistry