An unusual 2- O -glyceryl-glycosyl-γ-pyrone from Erigeron annuus (L.) with potential antifungal activity: in-vitro and in-silico study.

Phytochemical characterisation of the polar fraction of Erigeron annuus extract led to the isolation of glycerylerigeroside ( 1 ), a unique γ-pyrone derivative. Structure of 1 was decided by intensive study of NMR and mass spectra as 3- O -[4'-((1,3-dihydroxypropan-2-yl)oxy)-β-D-glucopyranoside)]-4H-pyran-4-one, with uncommon glyceroxy side chain attached to 4' position of pyromeconic acid β -D-glucopyranoside. Antimicrobial potential of 1 was tested against Staphylococcus aureus , Salmonella enterica , and Candida albicans . Compound 1 strongly inhibited growth of Candida albicans (MIC = 17.24 µM/disc), compared to fluconazole (MIC = 16.33 µM/disc). Meanwhile, it moderately inhibited the growth of Staphylococcus aureus (MIC = 71.84 µM/disc) and Salmonella enterica (MIC = 71.84 µM/disc), as compared with thiophenicol (MIC = 14.05 µM/disc) and (MIC = 14.05 µM/disc), respectively. The binding mode of 1 with the active site of sterol 14α-demethylase (CYP51) from Candida albicans (PDB ID: 5TZ1), in combination with fluconazole, was predicted by molecular docking study and supported the antifungal activity.