Antioxidant and Anti-Aging Phytoconstituents from Faucaria tuberculosa: In Vitro and In Silico Studies
Abstract
:1. Introduction
2. Results and Discussion
2.1. Evaluation of TPC and TFC of Ethanolic Extract
2.2. Spectroscopic Data of Isolated Compounds
2.3. Antioxidant Activities of Isolated Compounds
2.4. Anti-Aging Activities of Isolated Compounds
2.4.1. Tyrosinase Inhibitory Assay
2.4.2. Hyaluronidase Inhibitory Assay
2.5. In Silico Molecular Docking
2.5.1. Anti-Tyrosinase Activity
2.5.2. Anti-Hyaluronidase Activity
3. Materials and Methods
3.1. Plant Material and Extraction
3.2. General Experimental Materials and Procedures
3.3. Evaluation of the Total Phenolic Content (TPC) of Ethanolic Extract
3.4. Evaluation of the Total Flavonoid Content (TFC) of Ethanolic Extract
3.5. Chromatographic Isolation of Phytoconstituents
3.6. Antioxidant Activities of the Isolated Compounds
3.6.1. ABTS Radical Scavenging
3.6.2. Ferric Reducing/Antioxidant Power (FRAP)
3.7. Anti-Aging Activities of the Isolated Compounds
3.7.1. Tyrosinase Inhibitory Assay
3.7.2. Hyaluronidase Inhibitory Assay
3.8. In Silico Molecular Docking Studies
3.8.1. Anti-Tyrosinase Activity
3.8.2. Anti-Hyaluronidase Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Position | δH (mult, J) | δC | HMBC (H→C) |
---|---|---|---|
Flavanol moiety | |||
2 | ---- | 100.3 | ---- |
3 | 4.05 (d, 3.6) | 68.08 | C-4a |
4 | 4.64 (d, 4) | 29.5 | C-4a, C-2, C-2′, C-3′ |
4a | ---- | 104.5 | ---- |
5 | ---- | 155.5 | ---- |
6 | 6.03(d, 2.4) | 98.6 | C-4a |
7 | ---- | 156.2 | ---- |
8 | 6.10 (d, 2.4) | 96.9 | ---- |
8a | ---- | 158.6 | ----- |
9 | ---- | 132.1 | ----- |
10 | 7.13 (d, 2.4) | 115.65 | C-2, C-9, C-11, C-12, C-14 |
11 | ---- | 146.7 | ---- |
12 | ---- | 145.7 | ---- |
13 | 6.81 (d, 8.4) | 115.67 | C-2, C-11, C-12, C-14 |
14 | 7.01 (dd, 2, 8.4) | 119.8 | C-2, C-9, C-10, C-12, C-13 |
Phloroglucinol moiety | |||
2′ | ---- | 108.1 | |
3′ | ---- | 154.5 | |
4′ | 6.08 (d, 2) | 98.1 | C-2′, C-5′ |
5′ | ---- | 154.9 | |
6′ | 6.23 (d, 2.4) | 96.8 | C-1′, C-2′ |
1′ | ---- | 158.1 | ---- |
β-glucopyranoside moiety | |||
1″ | 4.95 (d, 7.6) | 101.9 | C-5′ |
2″ | 3.604 (dd, 1.6, 7.2) | 74.6 | |
3″ | 3.53 (m) | 77.3 | |
4″ | 3.46 (d, 4.8) | 71.2 | |
5″ | 3.46 (d, 4.8) | 78.2 | |
6″ | 3.73 (m, H-6′ a) | 62.3 | |
3.92 (m, H-6′ b) |
Compound No. | Compound Name | IC50 Value (µg/mL) | |
---|---|---|---|
ABTS Assay | FRAP Assay | ||
1 | Phloroglucinol | 6.44 ± 0.47 | 12.89 ± 0.93 |
2 | Phlorin | 43.40 ± 3.18 | 64.52 ± 4.15 |
3 | Isorhamnetin 3-O-rutinoside | 12.24 ± 0.61 | 25.24 ± 2.03 |
4 | (-) Catechin-(2→1′,4→2′)-phloroglucinol | 4.11 ± 0.32 | 7.36 ± 0.57 |
5 | Isorhamnetin 3-O-[α-rhamnopyranosyl-(1→4)-α-rhamnopyranosyl-(1→6)-β-glucopyranoside] | 18.19 ± 2.94 | 35.04 ± 2.89 |
6 | β-sitosterol | 557.46 ± 19.76 | ND |
Positive standard (Ascorbic acid) | 10.67 ± 0.85 | 20.86± 1.28 |
Tyrosinase (PDB ID: 2Y9X) | ||||
---|---|---|---|---|
Compound | Affinity (kcal/mol) | Distance (in Å) from Main Residue | Type of Interaction | |
Phlorin | −10.935 | 2.61 | Cu400 | Metal acceptor |
2.55 | Cu401 | Metal acceptor | ||
2.50 | His85 | H-bond acceptor | ||
2.82 | Asn260 | H-bond donor | ||
2.74 | Met280 | H-bond donor | ||
4.93 | His244 | Hydrophobic | ||
Isorhamnetin 3-O-rutinoside | −12.154 | 2.12 | Cu400 | Metal acceptor |
2.26 | Cu401 | Metal acceptor | ||
2.36 | His85 | H-bond acceptor | ||
2.97 | Met280 | H-bond donor | ||
2.27 | Val283 | H-bond acceptor | ||
2.53 | Asn81 | H-bond acceptor | ||
3.14 | His263 | Hydrophobic | ||
3.45 | Gly281 | Hydrophobic | ||
kojic acid | −9.385 | 2.96 | Cu400 | Metal acceptor |
2.63 | Cu401 | Metal acceptor | ||
2.34 | His85 | H-bond acceptor | ||
2.90 | Asn260 | H-bond acceptor | ||
2.78 | Met280 | H-bond donor | ||
3.89 | His263 | Hydrophobic | ||
3.39 | Val283 | H-bond acceptor | ||
Hyaluronidase (PDB ID: 1FCV) | ||||
Compound | Affinity (kcal/mol) | Distance (in Å) from Main Residue | Type of Interaction | |
Phlorin | −14.979 | 1.91 | Asp111 | H-bond donor |
2.34 | Ser304 | H-bond acceptor | ||
1.93 | Glu113 | H-bond donor | ||
2.98 | Glu113 | H-bond donor | ||
4.11 | Trp301 | Hydrophobic | ||
2.51 | Tyr184 | H-bond acceptor | ||
Isorhamnetin 3-O-rutinoside | −16.578 | 2.15 | Asp111 | H-bond donor |
2.89 | Ser304 | H-bond acceptor | ||
2.36 | Ser303 | H-bond acceptor | ||
2.41 | Ser303 | H-bond acceptor | ||
1.99 | Glu113 | Electrostatic | ||
3.14 | Trp301 | Hydrophobic | ||
3.54 | Tyr55 | Hydrophobic | ||
3.22 | Asp305 | Hydrophobic | ||
Luteolin | −12.404 | 2.66 | Asp111 | H-bond donor |
2.00 | Ser304 | H-bond acceptor | ||
3.57 | Glu113 | Hydrophobic | ||
4.74 | Trp301 | Hydrophobic | ||
4.77 | Tyr55 | Hydrophobic | ||
2.45 | Asp56 | H-bond acceptor | ||
1.95 | Asp305 | H-bond donor |
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Ahmed, H.S.; Abouzeid, H.; Mansour, M.A.; Owis, A.I.; Amin, E.; Darwish, H.W.; Alanazi, A.S.; Naguib, I.A.; Afifi, N. Antioxidant and Anti-Aging Phytoconstituents from Faucaria tuberculosa: In Vitro and In Silico Studies. Molecules 2023, 28, 6895. https://doi.org/10.3390/molecules28196895
Ahmed HS, Abouzeid H, Mansour MA, Owis AI, Amin E, Darwish HW, Alanazi AS, Naguib IA, Afifi N. Antioxidant and Anti-Aging Phytoconstituents from Faucaria tuberculosa: In Vitro and In Silico Studies. Molecules. 2023; 28(19):6895. https://doi.org/10.3390/molecules28196895
Chicago/Turabian StyleAhmed, Hayam S., Hala Abouzeid, Mostafa A. Mansour, Asmaa I. Owis, Elham Amin, Hany W. Darwish, Ashwag S. Alanazi, Ibrahim A. Naguib, and Naglaa Afifi. 2023. "Antioxidant and Anti-Aging Phytoconstituents from Faucaria tuberculosa: In Vitro and In Silico Studies" Molecules 28, no. 19: 6895. https://doi.org/10.3390/molecules28196895