Bioactive compounds such as ω-3 fatty acids and terpenes, have been associated with beneficial health effects; however, their solubility in the gastrointestinal tract and its bioavailability in the body are low. Nanoemulsions offer a viable alternative to disperse lipophilic compounds and improve their dissolution, permeation, absorption and bioavailability. Enzyme modified phosphatidylcholine (PC) with ω-3 fatty acids was used as emulsifier to stabilize oil-in-water nanoemulsions generated using ultrasound device. These systems were used as carriers of betulinic acid, which has reported anti-carcinogenic activity. Phospholipase-catalyzed modification of PC allowed the incorporation of 50 mol% of ω-3 fatty acids. Formation variables such as oil type and ultrasound amplitude had effects on nanoemulsion characteristics. Incorporation of betulinic acid affected globule size; however, betulinic acid nanoemulsions below 200 nm could be prepared. The conditions under which betulinic acid nanoemulsions were obtained using the modified phosphatidylcholine with the smaller globule size (91 nm) were 10% PC, 25% glycerol, medium chain oil and 30% amplitude for 12 min in the sonicator. Storage temperature had an effect on the stability of the nanoemulsions, at 5°C we observed the smallest growth in globule size. The use of olive oil decreased the globule size growth during storage of the nanoemulsion stabilized with modified phosphatidylcholine, although globule size obtained was greater than 200 nm. Medium pH had a significant effect on the nanoemulsions; alkaline pH values improved storage stability. These results provide useful information for using this type of carrier system on the formulation of products in the pharmaceutical or food industry.

Curcumin is a natural, oil-soluble polyphenolic compound with potent anticancer, antiinflammatory, and antioxidant activities. In its free form it is very poorly absorbed in the gut due to its very low solubility. The use of nanoemulsions as carrier is a feasible way for improving curcumin bioavailability. To this end, the choice of emulsifying agent for stabilizing the nanoemulsions is of the upmost importance for achieving a desired functionality. In this work, phosphatidylcholine (PC) and phosphatidycholine enriched (PCE) with medium chain fatty acids (42.5 mol %) in combination with glycerol as co-surfactant, were used for preparing oil-in-water nanoemulsions coded as NEPC and NEPCE, respectively. NEPCE displayed significantly smaller mean droplet size (30 nm), equal entrapment efficiency (100 %), better droplet stability and suffered lower encapsulation efficiency loss (3 %) during storage time (120 days, 4 ºC) than NEPC. Bioavailability, measured in terms of area under the curve of curcumin concentration versus time, and maximum curcumin plasma concentration, were in general terms significantly higher for NEPCE than for NEPC, and for curcumin coarse aqueous suspension (CCS). Also NEPCE produced significantly higher curcumin concentrations in liver and lung than NEPC and CCS. These data support the role of phosphatidylcholine enriched with medium chain fatty acids in increasing bioavailability of nanoemulsions for therapeutic applications.

The influence of nano-emulsified curcumin (NEC) added to the hair sheep milk, prior to cheese-making, on the chemical composition, lipolysis, and proteolysis of manchego-style cheeses were evaluated throughout 80 days of ripening. The addition of NEC to the milk resulted in cheeses with the same moisture content (42.23%), total protein (23.16%), and water activity (0.969) (p > 0.05). However, it increased the fat and ash levels from 26.82% and 3.64% in B 10 ppm to 30.08% and 3.85% in C 10 ppm, respectively, at the end of the ripening (p < 0.05). The total phenolic content and antioxidant activity of experimental cheeses increased during ripening, and the fatty acid groups showed significant changes occurred to a greater extent in the first days of ripening (p < 0.05). The lipolysis increased consistently in all cheeses until day 40 of ripening, to decrease at the end, while proteolysis increased during all ripening time in all samples (p < 0.05); the addition of NEC did not alter the primary proteolysis of manchego-style cheeses, but it modified secondary proteolysis and lipolysis (p < 0.05). Principal component analysis was useful for discriminating cheeses according to their chemical composition and classified into four groups according to their ripening time. This research highlights the potential of CNE to fortify dairy foods to enhance their functionality.

Structured phosphatidylcholine was successfully produced by acidolysis between phosphatidylcholine and free medium chain fatty acid, using phospholipase A1 immobilized on Duolite A568. Response surface methodology was applied to optimize the reaction system using three process parameters: molar ratio of substrates (phosphatidylcholine to free medium chain fatty acid), enzyme loading, and reaction temperature. All parameters evaluated showed linear and quadratic significant effects on the production of modified phosphatidylcholine; molar ratio of substrates contributed positively, but temperature influenced negatively. Increased enzyme loading also led to increased production of modified phosphatidylcholine but only during the first 9 hours of the acidolysis reaction. Optimal conditions obtained from the model were a ratio of phosphatidylcholine to free medium chain fatty acid of 1:15, an enzyme loading of 12%, and a temperature of 45°C. Under these conditions a production of modified phosphatidylcholine of 52.98 % were obtained after 24 h of reaction. The prediction was confirmed from the verification experiments; the production of modified phosphatidylcholine was 53.02%, the total yield of phosphatidylcholine 64.28% and the molar incorporation of medium chain fatty acid was 42.31%. The acidolysis reaction was scaled-up in a batch reactor with a similar production of modified phosphatidylcholine, total yield of phosphatidylcholine and molar incorporation of medium chain fatty acid. Purification by column chromatography of the structured phosphatidylcholine yielded 62.53% of phosphatidylcholine enriched with 42.52% of medium chain fatty acid.