Phytochemical Profiling, Antimicrobial and α-Glucosidase Inhibitory Potential of Phenolic-Enriched Extracts of the Aerial Parts from Echium humile Desf.: In Vitro Combined with In Silico Approach
Abstract
:1. Introduction
2. Results
2.1. Biological Properties
2.1.1. Antimicrobial Activity
2.1.2. Antidiabetic Activity
2.2. HPLC–MS Analysis
2.3. Computational Study
2.3.1. Binding Energies
2.3.2. Receptor–Ligand Interaction Analysis
3. Discussion
4. Materials and Methods
4.1. Plant Material and Extraction
4.2. Antimicrobial Activity
4.3. α-Glucosidase Inhibitory Assay
4.4. HPLC–MS Analysis of Phenolic Compounds
4.5. Molecular Docking Approach
4.6. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Strains | IZD (mm) | ||||||
---|---|---|---|---|---|---|---|
Extracts | Hexane | Dichloromethane | Ethyl Acetate | Methanol | Aqueous | Chloramphenicol | |
Gram-positive bacteria | |||||||
Staphylococcus aureus | – | 11.50 ± 1.00 cdC | 14.00 ± 2.00 abB | 10.00 ± 0.00 dCD | 9.00 ± 0.00 cD | 16.50 ± 1.00 dA | |
Enterococcus faecalis | 10.50 ± 1.00 cC | 13.00 ± 1.00 bcB | 12.50 ± 1.00 bcBC | 15.50 ± 1.00 aA | 10.50 ± 1.00 bC | 12.00 ± 1.00 eBC | |
Bacillus cereus | 14.00 ± 1.00 bB | 14.00 ± 1.00 bB | 12.00±1.00 cC | 14.00±1.00 bB | 11.50 ±1.00 bC | 26.00 ± 1.00 aA | |
Bacillus subtilis | 11.50 ± 1.00 cC | 14.50 ± 1.00 bB | 15.00 ± 1.00 aB | 12.50 ± 1.00 cC | – | 24.00 ± 0.00 bA | |
Micrococcus luteus | 18.50 ± 0.86 aA | _ | 14.5 ± 1.00 aB | 14.00 ± 0.00 bB | 15.00 ± 0.00 aB | 20.00 ± 2.00 cA | |
Gram-negative bacteria | |||||||
Escherichia coli | 10.33 ± 0.76 cC | 18.00 ± 1.00 aB | 8.00 ± 0.00 eD | – | – | 23.50 ± 1.50 bA | |
Klebsiella pneumoniae | 11.00 ± 0.00 c | 11.00 ± 0.00 dB | 11.50 ± 1.50 cdB | – | 10.50±0.50 bB | 22.00 ± 1.00 bA | |
Salmonella Enteritidis | 8.00 ± 0.00 dE | 11.50 ± 0.50 cdB | 10.00 ± 0.00 dC | 11.50 ± 0.50 cB | 9.00 ± 0.00 cD | 16.00 ± 0.00 dA | |
Fungal strains | Cycloheximide | ||||||
Fusarium sp. | – | – | 11.5 ± 0.71 bC | 14.5 ± 0.71 bB | – | 18.00 ± 1.50 abA | |
Pythium catenulatum | – | – | 9.00 ± 0.00 cB | 10.50 ± 0.71 cB | – | 17.50 ± 1.50 bA | |
Fusarium oxysporum | – | – | 13.00 ± 1.00 aB | 20.00 ± 0.00 aA | – | 20.00 ± 2.00 aA |
Strains | Hexane | Dichloromethane | Ethyl Acetate | Methanol | Aqueous |
---|---|---|---|---|---|
Gram-positive bacteria | |||||
Staphylococcus aureus | – | 12.5 (25) {2} | 1.56 (12.5) {8} | 3.12 (6.25) {2} | 3.12 (6.25) {2} |
Enterococcus faecalis | 6.25 (12.5) {2} | 12.5 (50) {4} | 1.56 (12.5) {8} | 0.19 (3.12) {16} | 0.19 (6.25) {32} |
Bacillus cereus | 0.39 (6.25) {16} | 6.25 (25) {4} | 12.5 (100) {8} | 6.25 (12.5) {2} | – |
Bacillus subtilis | 6.25 (25) {4} | 50 (100) {2} | 1.56 (12.5) {8} | 0.39 (6.25) {16} | 0.19 (3.12) {16} |
Micrococcus luteus | 12.5 (50) {4} | – | 1.56 (6.25) {4} | 6.25 (25) {4} | 3.12 (6.25) {2} |
Gram-negative bacteria | |||||
Escherichia coli | 3.12 (12.5) {4} | 1.56 (6.25) {4} | 1.56 (12.5) {8} | – | – |
Klebsiella pneumoniae | 50 (100) {2} | 25 (50) {2} | 12.5 (25) {2} | – | 3.12 (6.25) {2} |
Salmonella Enteritidis | 1.56 (3.12) {2} | 3.12 (12.5) {4} | 1.56 (3.12) {2} | 0.39 (3.12) {8} | 1.56 (6.25) {4} |
Fungal strains | |||||
Fusarium sp. | – | – | 0.39 (3.12) {8} | 0.39 (3.12) {8} | – |
Pythium catenulatum | _ | _ | 1.56 (6.25) {4} | 0.195 (0.78) {4} | – |
Fusarium oxysporum | – | – | 0.39 (1.56) {4} | 3.12 (6.25) {2} | – |
Extracts | IC50 (mg/mL) |
---|---|
Hexane | – |
Dichloromethane | – |
Ethyl acetate | 11.17 ± 0.62 a |
Methanol | 0.06 ± 0.29 c |
Aqueous | 0.80 ± 1.81 b |
Acarbose | 0.70 ± 0.67 b |
Peak | Retention Time (min) | MS [M-H]-m/z | Compounds | Concentration (µg/g) |
---|---|---|---|---|
1 | 7.385 | 153.00 | Protocatechuic acid | 4.204 ± 0.06 |
2 | 9.189 | 289.00 | (+)-Catechin | 39.286 ± 2.46 |
3 | 13.795 | 289.00 | Epicatechin | 26.868 ± 0.82 |
4 | 12.993 | 179.00 | Caffeic acid | 9.673 ± 0.1 |
5 | 14.960 | 515.00 | 1,3-di-O-caffeoylquinic acid | 22.367 ± 0.15 |
6 | 17.087 | 163.00 | p-Coumaric acid | 1335.48 ± 5.22 |
7 | 18.744 | 193.00 | Trans-Ferulic acid | 125.522 ± 10.3 |
8 | 21.779 | 515.00 | 3,4-di-O-caffeoylquinic acid | 6.7645 ± 0.41 |
9 | 22.209 | 359.00 | Rosmarinic acid | 41.154 ± 0.12 |
10 | 22.910 | 463.00 | Hyperoside | 2.992 ± 0.01 |
11 | 23.754 | 717.00 | Salvianolic acid B | 47.832 ± 1.51 |
12 | 23.754 | 515.00 | 4,5-di-O-caffeoylquinic acid | 319.373 ± 0.41 |
13 | 24.302 | 431.00 | Apegenin 7-O-glucoside | 2.481 ± 0.48 |
14 | 23.451 | 329.00 | Cirsiliol | 41.623 ± 0.19 |
15 | 31.852 | 269.00 | Apegenin | 0.973 ± 0.25 |
16 | 37.061 | 283.00 | Acacetin | 107.462 ± 17.4 |
Compounds | Interactions Type | Interacting Residues (1JIJ) | Binding Energy (kcal/mol) |
---|---|---|---|
1,3-di-O-caffeoylquinic acid | van der Waals H bond C-H bond Unfavorable Donor-Donor/ Acceptor-Acceptor Pi-Alkyl | Tyr36, Cys37, Ala39, Thr42, His47, Gly49, Leu52, Pro53, Phe54, Lys84, Tyr170, Gln174, Gln190, Gln196, Ile221. His50 (3.03), Thr75 (2.74), Asp177 (1.93), Asn124 (2.96), Gly193 (2.74). Gly192 (3.56), Asp195 (3.38). Gly38 (2.77), Val224 (2.01). Leu70 (5.41), Val224 (5.46). | −9.8 |
3,4-di-O-caffeoylquinic acid | van der Waals H bond C-H bond Unfavorable Donor-Donor Pi-Alkyl | Tyr36, Cys37, Gly38, Ala39, Gly49, His50, Leu52, Pro53, Gly72, Asn124, Tyr170, Gln174, Asp177, Gln190, Val191, Gly193, Ile200, Ile221. Asp40 (1.84) (2.60), Asp80 (2.72) (2.79), Asp195 (2.08), Gln196 (2.38), Val224 (1.99). Gly192 (3.02). Thr75 (1.03) (1.26). Leu70 (4.95). | −10.7 |
4,5-di-O-caffeoylquinic acid | van der Waals H bond C-H bond Unfavorable Donor-Donor Pi-Alkyl | Tyr36, Cys37, Gly38, Ala39, Thr42, His47, Gly49, Leu52, Pro53, Asp80, Asn124, Tyr170, Gln174, Asp177, Gln190, Gly193, Ile221. His50 (2.55) (2.66), Thr75 (2.03) (2.39), Gln196 (2.84), Val224 (1.98) (2.23). Asp195 (3.36) Asp40 (2.98) Leu70 (5.04) | −10.5 |
p-Coumaric acid | van der Waals C-H bond Pi-Cation Pi-Alkyl | Tyr36, Gly38, Ala39, Asp40, Thr75, Asp80, Asn124, Tyr170, Gln174, Gln190, Asp195. Asp177 (2.15) Gln196 (2.99) Leu70 (5.22) | −6.4 |
Salvianolic Acid B | van der Waals H bond C-H bond Pi-Cation/Anion Pi-Alkyl | Tyr36, Ala39, Asp40, Thr42, His47, Gly49, Phe54, Ile71, Gly72, Gly79, Asn124, Tyr170, Gln174, Asp177, Gln190, Val191, Gly193, Gln196, Ile200, Val224. Cys37 (3.71), His50 (2.59), Thr75 (2.16), Lys84 (2.02) (2.94), Arg88 (2.36). Gly38 (3.38), His50 (3.46), Gly192 (3.65). Asp80 (4.13), Lys84 (4.28), Asp195 (3.97) Pro53 (5.15), Leu70 (5.24) | −9.8 |
Compounds | Interactions Type | Interacting Residues (5NN8) (Å) | Binding Energy (kcal/mol) |
---|---|---|---|
3,4-di-O-caffeoylquinic acid | van der Waals H bond Pi-Anion Pi-Pi T shaped | Arg281, Leu283, Trp376, Asp404, Trp481, Asp518, Met519, Phe525, Trp516, Arg600, Trp613, Arg672, leu650, His674, Ser676, Leu677. Asp282(2.21), Ala284 (2.36). Asp616 (4.09) Phe649 (4.98) | −8.3 |
p-Coumaric acid | van der Waals Pi-Anion | Asp282, Trp376, Asp404, Trp481, Trp516, Met519, Phe525, Arg600, Trp613, Asp616, Phe649, His674. Asp518 (3.84). | −5.6 |
Salvianolic acid B | van der Waals H bond Unfavorable Donor-Donor/ Acceptor-Acceptor Pi-Anion Pi-Pi T shaped | Trp376, Ile441, Trp481, Trp516, Met519, Asn524, Trp613, Ser676, Leu677. Arg281 (4.80), Ala284 (2.39), Asp404 (2.36), Asp518 (2.02), Ser523 (2.14), Phe525 (2.6), His674 (2.30). Asp282 (2.73), Arg600 (1.99). Asp616 (3.93). Phe649 (4.75) (5.75). | −8.6 |
Apegenin 7-O-glucoside | van der Waals H bond Pi-Pi T shaped Pi-Alkyl | Asp282, Trp376, Ile441, Trp516, Met519, Ser523, Phe525, Ala555, Arg600, Trp613, Gly615, Asp645, Phe649, Arg672, His674. Trp481 (2.50), Asp518 (2.09), Asn524 (2.61), Asp616 (2.36). Trp481 (4.97) (5.02). Leu283 (5.35), Ala555 (5.50), Leu650 (5.30). | −8.5 |
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Aouadi, K.; Hajlaoui, H.; Arraouadi, S.; Ghannay, S.; Snoussi, M.; Kadri, A. Phytochemical Profiling, Antimicrobial and α-Glucosidase Inhibitory Potential of Phenolic-Enriched Extracts of the Aerial Parts from Echium humile Desf.: In Vitro Combined with In Silico Approach. Plants 2022, 11, 1131. https://doi.org/10.3390/plants11091131
Aouadi K, Hajlaoui H, Arraouadi S, Ghannay S, Snoussi M, Kadri A. Phytochemical Profiling, Antimicrobial and α-Glucosidase Inhibitory Potential of Phenolic-Enriched Extracts of the Aerial Parts from Echium humile Desf.: In Vitro Combined with In Silico Approach. Plants. 2022; 11(9):1131. https://doi.org/10.3390/plants11091131
Chicago/Turabian StyleAouadi, Kaïss, Hafedh Hajlaoui, Soumaya Arraouadi, Siwar Ghannay, Mejdi Snoussi, and Adel Kadri. 2022. "Phytochemical Profiling, Antimicrobial and α-Glucosidase Inhibitory Potential of Phenolic-Enriched Extracts of the Aerial Parts from Echium humile Desf.: In Vitro Combined with In Silico Approach" Plants 11, no. 9: 1131. https://doi.org/10.3390/plants11091131