Journal of Food Bioactives, ISSN 2637-8752 print, 2637-8779 online
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Original Research

Volume 23, September 2023, pages 58-67

In Silico Evaluation of Nutri-Pharmacological Potentials of Phytochemicals in Sorghum (Sorghum bicolor) Grains


Figure 1.
Figure 1. Overall target genes network.
Figure 2.
Figure 2. Interaction of the binding poses. (a) gallic acid and alpha-(1,3)-fucosyltransferase 7. (b) p-coumaric acid and aldose reductase. (c) p-coumaric acid and carbonic anhydrase 1. (d) trans-resveratrol and carbonic anhydrase 1. (e) Apigenin and aldose reductase. (f) Luteolinidin and aldose reductase. (g) Apigenin and xanthine dehydrogenase. (h) Naringenin and estrogen receptor
Figure 3.
Figure 3. Protein-ligand complex simulation results (a) RMSD of gallic acid and alpha-(1,3)-fucosyltransferase. (b) RMSF of alpha-(1,3)-fucosyltransferase. (c) Interaction profile of the contact between gallic acid and alpha-(1,3)-fucosyltransferase. (d) RMSD of p-coumaric acid and aldose reductase. (e) RMSF of aldose reductase. (f) Interaction profile of the contact between p-coumaric acid and aldose reductase.


Table 1. Predicted ADME for phytochemical constituents of sorghum grain
Physicochemical properties: Molecular weight (MW), Molar Refractivity (MR), Total polar surface area (TPSA). Pharmacokinetics: Gastrointestinal absorption (GIA), Blood-brain barrier (BBB), P-glycoprotein (P-gp) substrate, Inhibition of Cytochrome P450 (CYPs) type CYP1A2, CYP2C19, CYP2C9, CYP2D6, and CYP3A4, Skin permeation (Log Kp). Water Solubility: ESOL Log S, ESOL Class. Lipophilicity: Consensus Log P. Medicinal Chemistry: Synthetic accessibility (SA). Druglikeness: Bioavailability Score (BS).
1Protocatechuic acid528594154.1237.4577.760.65−1.85Very SolubleHighNoNoCYP3A4−6.420.561.07
2p-hydroxybenzoic acid135138.1235.4257.531.05−2.07SolubleHighYesNoNone−6.020.851.00
3Vanillic acid8468168.1541.9266.761.08−2.02SolubleHighNoNoNone−6.310.851.42
4p-coumaric acid.1549106164.1645.1357.531.26−2.02SolubleHighYesNoNone−6.260.851.61
5Ferulic acid445858194.1851.6366.761.36−2.11SolubleHighYesNoNone−6.410.851.93
6Gallic acid24721416170.1239.4797.990.21−164SolubleHighNoNoNone−6.840.561.22
7Caffeic acid154911180.1647.1677.760.93−1.89Very SolubleHighNoNoNone−6.580.561.81
8Cinnamic acid53729554148.1643.1137.301.79−2.37SolubleHighYesNoNone−5.690.851.67
9Salicyclic acid.46782907138.1235.4257.531.24−2.50SolubleHighYesNoNone−5.540.851.00
10Syringic acid1074275.990.99−1.84Very SolubleHighNoNoNone−6.770.561.70
11Sinapic acid637775224.2158.1275.991.31−2.16SolubleHighNoNoNone−6.000.562.17
13Luteolinidin.441701270.2473.9990.902.11−3.94SolubleHighNoNoCYP1A2, CYP2D6−5.800.552.96
14Apigenin.528044272.2571.5786.991.84−3.49SolubleHighNoYesCYP1A2, CYP2D6, CYP3A4−6.170.553.01
15Luteolin5280445288.2573.591.451.45−3.26SolubleHighNoYesCYP1A2, CYP2D6, CYP3A4−6.620.553.11
17Naringenin932272.2571.5786.991.84−3.49SolubleHighNoYesCYP1A2, CYP3A4−6.170.553.01


Table 2. Target prediction results for phytochemical constituents of sorghum grain
SNLigands% Probability of Predicted Targets
A. Carbon anhydrase I/II/VI/VII/XII (P00915/P00918/P23280/P43166/O43570). B. Carbon anhydrase III/IV/VA/VB/IX/XI/XIII/XIV (P07451/P22748/P35218/Q16790/Q8N1Q1/Q9ULX7), C. Aldose reductase (P15121), D. Estrogen receptor (Q92731), E. Macrophage migration inhibitory factor (P14174), F. Alpha (1–3)-fucosyltransferase7 (Q11130), G. Arachidonate 5-lioxygenase (P09917), H. Matrix metaloprotenase9 (P14780), I. Matrix metaloprotenase1 (P03956), J. Matrix metaloprotenase2 (P08253). K. Protein-tyrosine phosphatase 1B (P18031). L. Hydroxycarboxylic acid receptor (Q8TDS4). M. Lymphocyte differentiation antigen (P28907). N. NADPH Oxidase 4 (Q9NPH5). O. Cyclin-dependent kinase 5 (Q00535). P. Xanthine dehydrogenase (P47989).
1Protocatechuic acid9898
2p-hydroxy benzoic acid100100
3Vanillic acid30253025
4p-coumaric acid100100100100
5Ferulic acid9898
6Gallic acid100100100
7Caffeic acid80808080808080
8Trans resveratrol100
9Salicylic acid10025
10Syringic acid100100
11Sinapic acid2525
16Salicyclic acid10040
17Cinnamic acid90


Table 3. Molecular docking results
SNProteinBinding Affinity Score(kcal.mol−1)
p-Coumaric acidGallic acidTrans-ResveratrolApigeninLuteolinidinNaringenin
Docking parameter: Arachidonate 5-lioxygenase [Center: −4.57, 2.552, −4.052; Size: 126, 106, 126; Spacing 0.867]. Aldose reductase [Center: 1.346, 2.385, 0.255; Size:126, 126, 126; Spacing: 0.400]. Carbon anhydrase I [Center: 36.650, 14.797, −13.116; Size:126, 126, 126; Spacing: 0.375]. Alpha (1–3) fucosynltransferase 7 [Center: 0.064, 2.743, 7.051; Size: 76, 70, 126; Spacing: 1.000]. Carbon anhydrase IV [Center: −3.911, 2.015, −4.599; Size: 126, 126, 68; Spacing: 0.844]. Carbon anhydrase XII [Center: −6.047, 0.271, −6.751; Size:126, 120, 126; Spacing: 0.536].
1Arachidonate 5-lioxygenase−5.620
2Aldose reductase−7.759−10.430−10.500
3Carbon anhydrase I−5.554−5.982
4Alpha (1–3) fucosynltransferase 7−5.512
5Carbon anhydrase IV−5.163
6Carbon anhydrase XII−6.328
7Estrogen receptor−7.513−6.648−6.778
8NADPH oxidase 4−8.287
9Cyclin dependent kinase 5−8.366
10Xanthine dehydrogenase−9.196


Table 4. : Prime MMGBSA binding energy of interaction of p-coumaric acid and aldose reductase and gallic acid with alpha-(1,3)-fucosyltransferase 7, before and after molecular dynamics simulation
ComplexSimulation Time (ns)MMGBSA ΔGbind (kcal.mol−1)
CoulombCovalentHbondLipoPackingSolv_GBvdWGbind (Total)
Legend: Covalent: Covalent binding energy. Coulomb: Coulomb energy. Lipo: Lipophilic energy. Hbond: Hydrogen bonding energy. Packing: Pi-pi packing correction. Solv GB: Generalized Born electrostatic solvation energy. vdW: Van der Waals energy. Total: Total energy (Prime energy).
p-Coumaric acid and aldose reductase0−13.9801.333−1.308−22.041−0.00212.445−33.076−56.631
Gallic acid and alpha-(1,3)-fucosyltransferase 70−19.2262.005−0.554−8.601−2.27318.761−19.743−29.632