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. 2021 Nov 20;10(11):1844.
doi: 10.3390/antiox10111844.

Chemical Constituents, In Vitro Antioxidant Activity and In Silico Study on NADPH Oxidase of Allium sativum L. (Garlic) Essential Oil

Oscar Herrera-Calderon  1 , Luz Josefina Chacaltana-Ramos  2 , Irma Carmen Huayanca-Gutiérrez  2 , Majed A Algarni  3 , Mohammed Alqarni  4 , Gaber El-Saber Batiha  5
Affiliations

Chemical Constituents, In Vitro Antioxidant Activity and In Silico Study on NADPH Oxidase of Allium sativum L. (Garlic) Essential Oil

Oscar Herrera-Calderon et al. Antioxidants (Basel). .

Abstract

Allium sativum L., also known as garlic, is a perennial plant widely used as a spice and also considered a medicinal herb since antiquity. The aim of this study was to determine by gas chromatography-mass spectrometry (GC-MS) the chemical profile fingerprint of the essential oil (EO) of one accession of Peruvian A. sativum (garlic), to evaluate its antioxidant activity and an in- silico study on NADPH oxidase activity of the volatile phytoconstituents. The antioxidant activity was tested using DPPH and β-carotene assays. An in-silico study was carried out on NADPH oxidase (PDB ID: 2CDU), as was ADMET prediction. The results indicated that diallyl trisulfide (44.21%) is the major component of the EO, followed by diallyl disulfide (22.08%), allyl methyl trisulfide (9.72%), 2-vinyl-4H-1,3-dithiine (4.78%), and α-bisabolol (3.32%). Furthermore, the EO showed antioxidant activity against DPPH radical (IC50 = 124.60 ± 2.3 µg/mL) and β-carotene bleaching (IC50 = 328.51 ± 2.0). The best docking score on NADPH oxidase corresponds to α-bisabolol (ΔG = -10.62 kcal/mol), followed by 5-methyl-1,2,3,4-tetrathiane (ΔG = -9.33 kcal/mol). Additionally, the volatile components could be linked to the observed antioxidant activity, leading to potential inhibitors of NADPH oxidase.

Keywords: allyl compounds; antioxidant enzyme; molecular dynamic; oxidative stress; phytochemical study.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Molecular interaction studies of the most active phytochemical constituents of garlic essential oil with NADPH oxidase (PDB ID: 2CDU). (A): 4H-1,2,3-trithiine, (B): 5-methyl-1,2,3,4-tetrathiane, and (C): α-bisabolol. Surface view (left panel), and 2D (right panel) interactions.
Figure 1
Figure 1
Molecular interaction studies of the most active phytochemical constituents of garlic essential oil with NADPH oxidase (PDB ID: 2CDU). (A): 4H-1,2,3-trithiine, (B): 5-methyl-1,2,3,4-tetrathiane, and (C): α-bisabolol. Surface view (left panel), and 2D (right panel) interactions.
Figure 2
Figure 2
(A) RMSD plot of Cα atoms of NADPH oxidase displaying deviations from the mean with α-bisabolol (dark cyan) and diallyl trisulfide (orange) over a 100 ns time scale simulation. (B) RMSF plot of amino acids of NADPH oxidase bound to α-bisabolol (dark cyan) and diallyl trisulfide (orange) over a 100 ns time scale simulation.
Figure 2
Figure 2
(A) RMSD plot of Cα atoms of NADPH oxidase displaying deviations from the mean with α-bisabolol (dark cyan) and diallyl trisulfide (orange) over a 100 ns time scale simulation. (B) RMSF plot of amino acids of NADPH oxidase bound to α-bisabolol (dark cyan) and diallyl trisulfide (orange) over a 100 ns time scale simulation.
Figure 3
Figure 3
(A) Radius of gyration (Rg) plot of Cα atoms of NADPH oxidase complexed with α-bisabolol (dark cyan) and diallyl trisulfide (orange). (B) Number of hydrogen bonds formed between NADPH oxidase and α-bisabolol throughout a simulation time of 100 ns.
Figure 3
Figure 3
(A) Radius of gyration (Rg) plot of Cα atoms of NADPH oxidase complexed with α-bisabolol (dark cyan) and diallyl trisulfide (orange). (B) Number of hydrogen bonds formed between NADPH oxidase and α-bisabolol throughout a simulation time of 100 ns.
Figure 4
Figure 4
Energy plots of NADPH oxidase complexed with (A) α-bisabolol and (B) diallyl trisulfide.
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