Thonningia sanguinea Extract: Antioxidant and Cytotoxic Activities Supported by Chemical Composition and Molecular Docking Simulations
Abstract
:1. Introduction
2. Results and Discussion
2.1. Total Phenolic Content
2.2. Biological Activities
2.2.1. Antioxidant Activity
2.2.2. Cytotoxic Activity
2.2.3. Apoptosis Investigation
Annexin-V-FITC/PI Staining and Cell Cycle Analysis
RT-PCR
2.3. LC-ESI-TOF-MS/MS Analysis
2.4. Molecular Docking Studies
3. Materials and Methods
3.1. Plant Material
3.2. Preparation of Plant Extract
3.3. Determination of Total Phenolic Content
3.4. Preparation of Phenolic Extract
3.5. Determination of Antioxidant Activity
3.5.1. Initial Screening Step
3.5.2. Determination of IC50
3.5.3. Trolox Standard Preparation
3.5.4. DPPH• Assay
3.5.5. Data Analysis
3.6. LC-ESI-TOF-MS/MS Analysis
3.7. Biological Evaluation
3.7.1. Cytotoxic Activity
3.7.2. Apoptotic Investigation
Flow Cytometric Analysis
RT-PCR
3.7.3. Molecular Docking
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Tested Samples | IC50 (μg/mL) * | |||
---|---|---|---|---|
A549 | HepG2 | MDA-MB-231 | MCF-7 | |
Crude extract | 13.25 ± 0.46 | 18.76 ± 0.98 | 56.53 ± 1.32 | 34.65 ± 1.76 |
Phenolic extract | ≥50 | 13.51 ± 0.54 | ≥50 | 16.67 ± 0.87 |
5-FU | 7.47 ± 0.35 | 15.8 ± 0.86 | 20.76 ± 0.76 | 26.98 ± 0.43 |
Compound | RT (min) | Measured m/z [M−H]− | Expected m/z [M−H]− | Relative Error * | Molecular Formula | Fragments |
---|---|---|---|---|---|---|
gentisic acid [41] | 1.31 | 153.0155 | 153.0188 | −21.56 | C7H6O4 | 153, 108 |
ferulic acid [42] | 2.06 | 193.0528 | 193.0501 | 13.98 | C10H10O4 | 178, 134 |
Scopoletin [42] | 5.01 | 191.0332 | 191.0344 | −6.28 | C10H8O4 | 176, 147 |
Isookanin-7-glucoside [43] | 5.23 | 449.1062 | 449.1084 | −4.89 | C21H22O11 | 287, 151, 135, |
(+)-epicatechin [44] | 7.06 | 289.0716 | 289.0712 | 1.38 | C15H14O6 | 125, 123 |
4-deoxyphloridzin [45] | 7.85 | 419.1382 | 419.1342 | 9.54 | C21H24O9 | 419, 257 |
(isorhapontin) [44] | 9.95 | 419.1328 | 419.1342 | −3.34 | C21H24O9 | 281,257 |
(+)-eriodictyol [46] | 9.97 | 287.0565 | 287.0556 | 3.13 | C15H12O6 | 151, 135 |
3, 5, 7-trihydroxy-4’-methoxyflavone [47] | 11.74 | 299.0541 | 299.0556 | −5.01 | C16H12O6 | 299, 284, 256 |
Daidzein [48] | 18.78 | 253.0524 | 253.0501 | 9.08 | C15H10O4 | 225, 224 |
Compound | RT (min) | Measured m/z [M−H]− | Expected m/z [M−H]− | Relative Error * | Molecular Formula | Fragments |
---|---|---|---|---|---|---|
Maritimetin-6-O-glucoside [50] | 6.50 | 449.1066 | 449.1084 | −4.00 | C21H20O11 | 449, 287 |
Phlorizin [51] | 6.78 | 437.1446 | 437.1448 | −0.45 | C21H24O10 | 437, 275 |
3,4-dimethoxycinnamic acid [52] | 6.91 | 209.081 | 209.0814 | −1.91 | C11H12O4 | 209, 191, 163 |
Resveratrol [53] | 7.39 | 229.0853 | 229.0865 | −5.23 | C14H12O3 | 229, 185, 157 |
trans ortho Coumaric acid [54] | 7.45 | 165.054 | 165.0552 | −7.27 | C9H8O3 | 165, 147, 91 |
(-)-Epicatechin [55] | 7.46 | 291.0873 | 291.0869 | 1.37 | C15H14O6 | 165, 123 |
Daphnetin [56] | 8.08 | 179.0342 | 179.0344 | −1.11 | C9H6O4 | 179, 133 |
Compound | Ligand-Receptor Interactions (HB and Van Der Waals Interactions) | |||
---|---|---|---|---|
Thonningianin-A | Arg 66 Ala 59 Gly 104 Tyr 161 Asn 102 | 1 HB-Acceptor 1 HB-donor 1 HB-Acceptor 1 HB-Acceptor 1 HB-Acceptor | ||
Thonningianin-B | Arg 105 Gly 104 Asp 70 Glu 95 | 1 HB-Acceptor 1 HB-Donor 1 HB-Donor 1 HB-Donor | 1 arene-cation with Arg 66 1 arene-arene with Tyr 161 | |
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Abdelhameed, R.F.A.; Elhady, S.S.; Sirwi, A.; Samir, H.; Ibrahim, E.A.; Thomford, A.K.; El Gindy, A.; Hadad, G.M.; Badr, J.M.; Nafie, M.S. Thonningia sanguinea Extract: Antioxidant and Cytotoxic Activities Supported by Chemical Composition and Molecular Docking Simulations. Plants 2021, 10, 2156. https://doi.org/10.3390/plants10102156
Abdelhameed RFA, Elhady SS, Sirwi A, Samir H, Ibrahim EA, Thomford AK, El Gindy A, Hadad GM, Badr JM, Nafie MS. Thonningia sanguinea Extract: Antioxidant and Cytotoxic Activities Supported by Chemical Composition and Molecular Docking Simulations. Plants. 2021; 10(10):2156. https://doi.org/10.3390/plants10102156
Chicago/Turabian StyleAbdelhameed, Reda F. A., Sameh S. Elhady, Alaa Sirwi, Hanan Samir, Elsayed A. Ibrahim, Ama Kyeraa Thomford, Alaa El Gindy, Ghada M. Hadad, Jihan M. Badr, and Mohamed S. Nafie. 2021. "Thonningia sanguinea Extract: Antioxidant and Cytotoxic Activities Supported by Chemical Composition and Molecular Docking Simulations" Plants 10, no. 10: 2156. https://doi.org/10.3390/plants10102156