New Phenolic Glycosides from Humulus lupulus and Their Inhibitory Activity Against DGKζ

Abstract

The new chromone derivative 1-[(2-methylpropanoyl)chromone]-β-D-glucopyranoside (1) together with eight known compounds (2–9) were isolated from Humulus lupulus (common hops). The structures of the isolated compounds were confirmed by detailed analyses of NMR and HR-ESI-MS data. The glucose fragment in 1 was determined as the D-glucoside based on GC analysis. Compounds 2, 4, and 5 exhibited significant inhibitory activity against diacylglycerol kinase ζ (DGKζ). Compound 5 demonstrated strong inhibition of DGKζ with an IC₅₀ value of 1.60 μM. Molecular docking studies gave important information about the role of the galloyl group in DGKζ inhibition.