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Article

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

by
Mohammed Lamine Khenifi
1,2,
Talia Serseg
2,3,
Piotr Migas
4,
Mirosława Krauze-Baranowska
4,
Sadin Özdemir
5,
Chawki Bensouici
6,
Mohammed I. Alghonaim
7,
Khattab Al-Khafaji
8,
Sulaiman A. Alsalamah
7,
Messaoud Boudjeniba
1,
Mohamed Yousfi
3,
Fehmi Boufahja
7,*,
Hamdi Bendif
1,9 and
Mohamed Mahdid
1
1
Laboratoire d’Ethnobotanique et Substances Naturelles, Departement of Biology, Ecole Normale Supérieure de Kouba, B.P 92, Kouba 16308, Algeria
2
Laboratoire des Sciences Appliquées et Didactiques, Ecole Normale Supérieure de Laghouat, B.P 4033 la gare routière, Laghouat 03000, Algeria
3
Fundamental Sciences Laboratory, Amar Telidji University, Laghouat 03000, Algeria
4
Pharmacognosy with Medicinal Plants Garden, Medical University of Gdańsk, 80-416 Gdańsk, Poland
5
Food Processing Programme, Technical Science Vocational School Mersin University, Mersin TR-33343, Turkey
6
Biotechnology Research Center (CRBT), Ali Mendjli New Town UV 03, B.P E73, Constantine 25016, Algeria
7
Biology Department, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia
8
Department of Environmental Science, College of Energy and Environmental Science, Al-Karkh University of Science, Baghdad 10081, Iraq
9
Department of Natural and life Sciences, Faculty of Sciences, University of Msila, Msila 28000, Algeria
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(23), 7798; https://doi.org/10.3390/molecules28237798
Submission received: 20 October 2023 / Revised: 18 November 2023 / Accepted: 20 November 2023 / Published: 27 November 2023
(This article belongs to the Special Issue Extraction and Analysis of New Bioactive Compounds Derived from Natural Products)
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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; Trigonella foenum-graecum; HPLC-DAD-ESIMS; flavonoid glycosides; α-amylase; antioxidant activity; molecular docking; molecular dynamic simulation Fenugreek; Trigonella foenum-graecum; HPLC-DAD-ESIMS; flavonoid glycosides; α-amylase; antioxidant activity; molecular docking; molecular dynamic simulation

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MDPI and ACS Style

Khenifi, M.L.; Serseg, T.; Migas, P.; Krauze-Baranowska, M.; Özdemir, S.; Bensouici, C.; Alghonaim, M.I.; Al-Khafaji, K.; Alsalamah, S.A.; Boudjeniba, M.; et al. HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds. Molecules 2023, 28, 7798. https://doi.org/10.3390/molecules28237798

AMA Style

Khenifi ML, Serseg T, Migas P, Krauze-Baranowska M, Özdemir S, Bensouici C, Alghonaim MI, Al-Khafaji K, Alsalamah SA, Boudjeniba M, et al. HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds. Molecules. 2023; 28(23):7798. https://doi.org/10.3390/molecules28237798

Chicago/Turabian Style

Khenifi, Mohammed Lamine, Talia Serseg, Piotr Migas, Mirosława Krauze-Baranowska, Sadin Özdemir, Chawki Bensouici, Mohammed I. Alghonaim, Khattab Al-Khafaji, Sulaiman A. Alsalamah, Messaoud Boudjeniba, and et al. 2023. "HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds" Molecules 28, no. 23: 7798. https://doi.org/10.3390/molecules28237798

APA Style

Khenifi, M. L., Serseg, T., Migas, P., Krauze-Baranowska, M., Özdemir, S., Bensouici, C., Alghonaim, M. I., Al-Khafaji, K., Alsalamah, S. A., Boudjeniba, M., Yousfi, M., Boufahja, F., Bendif, H., & Mahdid, M. (2023). HPLC-DAD-MS Characterization, Antioxidant Activity, α-amylase Inhibition, Molecular Docking, and ADMET of Flavonoids from Fenugreek Seeds. Molecules, 28(23), 7798. https://doi.org/10.3390/molecules28237798

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