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

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.

The responses and detoxification mechanisms of dark septate endophytes (DSE), Exophiala salmonis, to CuO nanoparticles.

To understand the tolerance mechanisms of dark septate endophytes (DSE), Exophiala salmonis, to CuO nanoparticles (CuO-NPs) with different sizes (40 and 150 nm), we investigated the morphology, antioxidant response, Cu subcellular distribution, and the melanin gene expression in the mycelia of E. salmonis. E. salmonis was cultured in liquid and solid media under the stress of increasing CuO-NP concentrations (0, 50, 100, 150, and 250 mg/L). Results showed that (1) E. salmonis showed good CuO-NP tolerance, and the tolerance to CuO-NPs at 150 nm was stronger than that at 40 nm. A large number of agglomeration structures were observed on the mycelia surface with the exception of 50 mg/L CuO-NPs with a diameter of 150 nm. (2) CuO-NP stress significantly stimulated the production of antioxidant enzymes, particularly the CuO-NPs with small particle size (40 nm). (3) Cu uptaken by E. salmonis increased proportionally with the increase of CuO-NP concentration in the medium. More than 80% Cu was absorbed in cell wall of mycelia treated with a small particle size (40 nm). (4) FTIR analysis revealed that hydroxyl, amine, carboxyl, and phosphate groups were associated with CuO-NP binding regardless of particle size. (5) Fungal melanin content increased with the addition of CuO-NPs; the increase of melanin induced by CuO-NPs with small particle size (40 nm) was more significant. (6) The expression of 1,3,6,8-tetrahydroxynaphthalene reductase (Arp2) in the melanin synthesis pathway increased under the stress of CuO-NPs, and CuO-NPs with a small particle size (40 nm) caused a significant change in the expression level of Arp2 gene than those with a large particle size (150 nm). In conclusion, E. salmonis had a strong tolerance to CuO-NPs and mitigated the toxic effects of CuO-NPs through the antioxidant system, the expression of genes related to melanin synthesis, and the synthesis of melanin.