Synthesis, characterization, antibacterial and antifungal activities of 1-O-alkylglycerols

Abstract

1-O-alkylglycerols are a class of natural existing lipids with broad biological activities. However, their use in food or agricultural fields remains to be investigated, especially for their antimicrobial activity. In this work, three 1-O-alkylglycerols, 1-O-octanylglycerol (C8Gly1), 1-O-dodecylglycerol (C12Gly1), and 1-O-hexadecylglycerol (C16Gly1), were synthesized in the isolated yields of 71.3–89.8 % and characterized by 1H NMR, 13C NMR, FITR, mass spectra, and HPLC-ESLD. The critical micelle concentration (CMC) of 1-O-alkylglycerols was determined to be 1.65 mmol/L (C8Gly1), 0.33 mmol/L (C12Gly1), and 0.23 mmol/L (C16Gly1) using the pyrene method. C12Gly1 and C16Gly1 had similar surface tensions that are lower than C8Gly1. C8Gly1 can form micelles in aqueous solution with excellent nano-dispersed uniformity and stability. Furthermore, C8Gly1 and C12Gly1 not only displayed good antibacterial activity against Staphylococcus aureus, but they also inhibited the growth of Botryosphaeria dothidea, Monilia fructigena, and Phytophthora capsicum at 400 μg/mL. Thus, the C8Gly1 and C12Gly1 can serve as novel antimicrobial agents in food preservation.

Keywords

• 1-O-Alkylglycerol
• Synthesis
• Surface property
• Antibacterial activity
• Antifungal activity