Chemical profile of phenolic extracts from rapeseed meal and inhibitory effects on α-glucosidase: UPLC-MS/MS analysis, multispectral approaches, molecular simulation and ADMET analysis

Abstract

Rapeseed meal (RSM) is the by-product of rapeseed processing that enriches phenolic compounds. However, the comprehensive characterization of its phenolic substances in terms of composition and potential activities remains incomplete, leading to limited utilization in the food industry. In this study, the phenolic profile from RSM (referred to as RMP) was identified, and their inhibitory effects on α-glucosidase were investigated. UPLC-MS/MS analysis showed that a total of 466 phenolic compounds were detected in RMP. The primary components were sinapic acid (SA), caffeic acid (CA), salicylic acid (SAA), and astragalin (AS). Multispectral approaches demonstrated significant inhibitory capacity of RMP against α-glucosidase with a half inhibition value (IC₅₀) of 0.32 mg/mL, with a stronger inhibition compared to CA/SAA/AS (IC₅₀: 4.0, 5.9, and 0.9 mg/mL) in addition to the previously reported SA, suggesting a synergistic effect. Both RMP and CA/SAA/AS altered the secondary structure of α-glucosidase to quench its intrinsic fluorescence. Molecular simulation results revealed that hydrogen bonds and van der Waals forces primarily contributed to the interaction between CA/SAA/AS and α-glucosidase, as well as verified the stability of the binding process over the entire simulation duration. The ADMET analysis showed that CYP2D6 was not inhibited by CA/SAA/AS, which had no AMES toxicity, hepatotoxicity, and skin sensitization. This finding suggests the potential of RMP against α-glucosidase for the treatment of diabetes.

Keywords: ADMET analysis; Inhibitory activity; Phenolic compounds; Rapeseed meal; α-Glucosidase.