HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds

Molecules. 2023 Nov 27;28(23):7798. doi: 10.3390/molecules28237798.

Abstract

Fenugreek (Trigonella foenum-graecum) has a great beneficial health effect; it has been used in traditional medicine by many cultures. Likewise, the α-amylase inhibitors are potential compounds in the development of drugs for the treatment of diabetes. The beneficial health effects of fenugreek lead us to explore the chemical composition of the seeds and their antioxidant and α-amylase inhibition activities. The flavonoid extraction from fenugreek seeds was achieved with methanol through a Soxhlet apparatus. Then, the flavonoid glycosides were characterized using HPLC-DAD-ESI-MS analysis. The antioxidant capacity of fenugreek seed was measured using DPPH, FRAP, ABTS, and CUPRAC assays. Finally, the α-amylase inhibition activity was carried out using in vitro and in silico methods. The methanolic extract was found to contain high amounts of total phenolics (154.68 ± 1.50 μg GAE/mg E), flavonoids (37.69 ± 0.73 μg QE/mg E). The highest radical-scavenging ability was recorded for the methanolic extract against DPPH (IC50 = 556.6 ± 9.87 μg/mL), ABTS (IC50 = 593.62 ± 9.35 μg/mL). The ME had the best reducing power according to the CUPRAC (A 0.5 = 451.90 ± 9.07 μg/mL). The results indicate that the methanolic extracts of fenugreek seed best α-amylase inhibition activities IC50 = 653.52 ± 3.24 μg/mL. Twenty-seven flavonoids were detected, and all studied flavonoids selected have good affinity and stabilize very well in the pocket of α-amylase. The interactions between the studied flavonoids with α-amylase were investigated. The flavonoids from fenugreek seed present a good inhibitory effect against α-amylase, which is beneficial for the prevention of diabetes and its complications.

Keywords: Fenugreek; HPLC-DAD-ESIMS; Trigonella foenum-graecum; antioxidant activity; flavonoid glycosides; molecular docking; molecular dynamic simulation; α-amylase.

MeSH terms

  • Antioxidants / chemistry
  • Chromatography, High Pressure Liquid
  • Diabetes Mellitus*
  • Flavonoids / analysis
  • Flavonoids / pharmacology
  • Humans
  • Methanol / chemistry
  • Molecular Docking Simulation
  • Plant Extracts / chemistry
  • Seeds / chemistry
  • Trigonella* / chemistry
  • alpha-Amylases

Substances

  • Antioxidants
  • fenugreek seed meal
  • Flavonoids
  • alpha-Amylases
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Plant Extracts
  • Methanol

Grants and funding

The authors extend their appreciation to the Deputyship for Research & Innovation, Ministry of Education in Saudi Arabia, for funding this research through project number IFP-IMSIU-2023015. The authors also appreciate the Deanship of Scientific Research at Imam Mohammad Ibn Saud Islamic University (IMSIU) for supporting and supervising this project.