Efficient Preparation of Sophorolipids and Functionalization with Amino Acids to Furnish Potent Preservatives

The development of new preservatives is an ongoing investigation in the food industry, especially those which are safe and environmentally friendly. In this study, biosurfactant sophorolipids (SLs) functionalized with amino acids were developed as efficient preservative agents. SLs were first isolated from fermentation broth by Candida bombicola ATCC 22214, hydrolyzed, and purified by extraction. The typical recovery is around 70%, while the extracted material consists of over 90% deacetylated acidic SLs (SL-COOH). Four types of SL derivatives were then synthesized via dicyclohexylcarbodiimide amidation reactions from prepared SL-COOH. Among the derivatives produced, the arginine SL conjugates (SL-d-Arg) displayed the highest activity against Gram-positive bacteria and fungi and even inhibited the cell growth of Gram-negative bacteria and mildew. Furthermore, the arginine conjugates performed the broadest antimicrobial activity among the derivatives evaluated. The sterilization dosage of the arginine conjugates against the food-spoilage pathogen Bacillus spp. was 63-125 mg/L, in contrast to 250 mg/L for the enterotoxin producer Staphylococcus aureus and 500 mg/L for fungi. More importantly, SL-d-Arg displayed excellent biocompatibility, with a therapeutic index of over 7.94. SL-d-Arg has excellent potential as an alternative to traditional chemical preservatives.