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

Liangliang Shi; Chenyue Jia; Jiangtao Feng; Weinong Zhang; Junbo He

doi:10.1016/j.heliyon.2023.e21790

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

Heliyon. 2023 Oct 31;9(11):e21790. doi: 10.1016/j.heliyon.2023.e21790. eCollection 2023 Nov.

Authors

Liangliang Shi¹, Chenyue Jia¹, Jiangtao Feng^{1

2

3}, Weinong Zhang^{1

2

3}, Junbo He^{1

2

3}

Affiliations

¹ Key Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, China.
² Hubei Key Laboratory for Processing and Transformation of Agricultural Products, Wuhan Polytechnic University, Wuhan 430023, China.
³ Engineering Research Center of Lipid-based Fine Chemicals of Hubei Province, Wuhan 430023, China.

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; Antibacterial activity; Antifungal activity; Surface property; Synthesis.