Enzymatic synthesis of stachyose-derived fatty acid mono-esters, the evaluation of their surface and interfacial properties and the capacity of certain derived emulsions to deliver resveratrol.

Food Chem

State 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; Anhui Jinhe Industrial Co., Ltd., Chuzhou 239200, China. Electronic address:

Published: January 2025

The nutritional characteristics of the tetrasaccharide stachyose prompted its incorporation into biosurfactants through esterification with fatty acid derivatives embodying 12-22 carbon chains. The resulting esters were evaluated for their surface active effects, emulsifying properties and capacities to form emulsions capable of the selective delivery of the anti-oxidant resveratrol. While such studies have revealed that those congeners embodying longer side-chains have higher critical micelle concentrations (CMC) and lower interfacial tensions, their hydrophilic-lipophilic balance (HLB) values fell within a tight range. Those emulsions stabilized by esters with medium and longer side-chains exhibited good stabilities over the pH range 6-10 and up to 95 °C. Assessments of the in vitro digestion of the corresponding emulsions charged with resveratrol revealed the bioavailability of the anti-oxidant reached ca. 80 % and so suggesting that the title stachyose esters are distinctive and promising sugar-based surfactants for the targeted delivery of functional foods.

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http://dx.doi.org/10.1016/j.foodchem.2025.142948DOI Listing

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