Enzymatic synthesis, emulsifying properties and structure-activity relationships of certain lactulose fatty acid
Mengfei Xie1, Haocong Wang1, Yangjiao Ye1
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou 510632, China; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, China.
Abstract:
The condensation of certain sugars with fatty acids affords esters that can act as versatile surfactants. Given the prebiotic properties of lactulose, various derived mono-esters incorporating C8 to C18 acyl side-chains were prepared and their performance as emulsifiers evaluated. These esters exhibited HLB values between 11 and 17. As the hydrophobic side-chain length increased from C8 to C16, the critical micelle concentrations of these esters decreased from 61,380.33 to 159.47 μmol/L, while the corresponding interfacial activities and emulsification capacities increased. The mixture of mono-esters embodying C18 side-chains formed stable Pickering emulsions with shelf lives of ≥15 days. During simulated (in vitro) digestion, such emulsions maintain droplet integrity in the oral and gastric phases but were "consumed" under intestinal conditions, with free fatty acid release rates reaching 60%-90%. This study establishes a structure-activity relationship profile for lactulose mono-esters, providing a valuable foundation for their deployment in bioactive delivery systems.
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