The Structural, Biological, and In-Silico Profiling of Novel Capryloyl Tetra-Glucoside and Aliphatic Ester Constituents from the Abutilon indicum Offers New Perspectives on the Treatment of Pain and Inflammation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Collection of Plant Material
2.2. Extraction and Isolation
2.3. General Experimental Procedures
2.4. Animals
2.4.1. Safety Profile Study
2.4.2. Administration of Drugs
2.4.3. Carrageenan-Induced Rat Hind Paw Edema
2.4.4. Analgesic Activity
Hot Plate Test
Acetic Acid-Induced Writhing Test
2.5. ADMET Analysis
2.6. Molecular Docking
2.6.1. Ligand Preparation
2.6.2. Protein Preparation
2.7. Statistical Analysis
3. Results
3.1. Structural Profiling of Isolated Phytoconstituents
3.1.1. Compound (AB-01)- 5′ Hydoxyl Palmitate
3.1.2. Compound (AB-02)- Capryloyl Diglucoside
3.1.3. Compound (AB-03)- Capryl Diglucoside
3.1.4. Compound (AB-04)- Palmityl Diglucoside
3.1.5. Compound (AB-05)- Capryloyl Tetraglucoside
3.2. Safety Profile Study
3.3. Carrageenan-Induced Rat Paw Edema
3.4. Hot Plate Test
3.5. Acetic Acid-Induced Writhing Methods
3.6. ADMET Analysis
3.7. Molecular Docking
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | AB 01 | AB 02 | AB 03 | AB 04 | AB 05 |
---|---|---|---|---|---|
Mol. Wt. | 356.591 | 468.497 | 496.551 | 580.712 | 792.781 |
Rot bond | 18 | 18 | 20 | 26 | 30 |
H-bond donor | 1 | 7 | 7 | 7 | 13 |
H-bond acceptor | 3.7 | 19 | 19 | 19 | 36 |
Dipole | 1.712 | 4.111 | 1.514 | 3.253 | 3.36 |
QPlogPo/w | 5.922 | −2.055 | −1.487 | 0.334 | −6.255 |
QPlogHERG | −5.85 | −4.589 | −4.972 | −5.887 | −4.01 |
QPPCaco (nm/s) | 1193.933 | 25.694 | 26.629 | 25.667 | 5.006 |
QPlogBB | −1.723 | −3.359 | −3.617 | −4.479 | −4.523 |
QPPMDCK (nm/s) | 599.178 | 9.453 | 9.825 | 9.442 | 1.272 |
QPlogKp | −1.599 | −5.655 | −5.697 | −4.852 | −7.971 |
Percent Human Oral Absorption | 100 | 15.69 | 19.382 | 17.071 | 0 |
Rule of Five | 1 | 2 | 2 | 3 | 3 |
Compound | Initial Potential Energy (kcal/mol) | Potential Energy (kcal/mol) | Van der Waals Energy (kcal/mol) | Electrostatic Energy (kcal/mol) |
---|---|---|---|---|
Molecule 1 | −10.1874 | −22.8631 | −9.73178 | −19.5173 |
Molecule 2 | 67.315 | 6.36013 | −11.7357 | −37.0988 |
Molecule 3 | 67.3404 | 5.36027 | −13.6227 | −36.3396 |
Molecule 4 | 68.7227 | 4.01368 | −16.9201 | −35.0438 |
Molecule 5 | 169.388 | 55.9117 | −20.5852 | −57.9615 |
Compound | TNF_alpha Interacting Residues | Binding Energy (kcal/mol) |
---|---|---|
Molecule 1 | Pi-Sigma: TYR59. Alkyl: LEU57. Pi-Alkyl: TYR59, TYR119, TYR151. | −4.0 |
Molecule 2 | Conventional Hydrogen Bond: HIS15, TYR59, TYR151. Carbon Hydrogen Bond: HIS15. P-i-Donor Hydrogen Bond: HIS15. Pi-Sigma: TYR119. Pi-Alkyl: TYR119. | −5.3 |
Molecule 3 | Conventional Hydrogen Bond: HIS15, TYR59, TYR151. Pi-Donor Hydrogen Bond: HIS15. Alkyl: LEU57. | −5.1 |
Molecule 4 | Conventional Hydrogen Bond: TYR119, GLY121, SER95. Pi-Sigma: TYR119. Pi-Alkyl: TYR59, TYR119, TYR151. | −4.7 |
Molecule 5 | Conventional Hydrogen Bond: HIS15, TYR59, GLN149, TYR151. Carbon Hydrogen Bond: HIS15. Pi-Alkyl: TYR119, TYR151. | −5.9 |
307 | Pi-Donor: TYR151. Pi-Pi Stacked: TYR59. Pi-Pi T-Shaped: TYR119, TYR151. Alkyl: LEU57, ILE155. Pi-Alkyl: TYR59. | −6.4 |
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Wahab, S.; Alsayari, A.; Muhsinah, A.B.; Almaghaslah, D.; Haque, A.; Khalid, M.; Alnasser, S.M.; Azam, F.; Hussain, M.S. The Structural, Biological, and In-Silico Profiling of Novel Capryloyl Tetra-Glucoside and Aliphatic Ester Constituents from the Abutilon indicum Offers New Perspectives on the Treatment of Pain and Inflammation. Plants 2022, 11, 2583. https://0-doi-org.brum.beds.ac.uk/10.3390/plants11192583
Wahab S, Alsayari A, Muhsinah AB, Almaghaslah D, Haque A, Khalid M, Alnasser SM, Azam F, Hussain MS. The Structural, Biological, and In-Silico Profiling of Novel Capryloyl Tetra-Glucoside and Aliphatic Ester Constituents from the Abutilon indicum Offers New Perspectives on the Treatment of Pain and Inflammation. Plants. 2022; 11(19):2583. https://0-doi-org.brum.beds.ac.uk/10.3390/plants11192583
Chicago/Turabian StyleWahab, Shadma, Abdulrhman Alsayari, Abdullatif Bin Muhsinah, Dalia Almaghaslah, Anzarul Haque, Mohammad Khalid, Sulaiman Mohammed Alnasser, Faizul Azam, and Md. Sarfaraj Hussain. 2022. "The Structural, Biological, and In-Silico Profiling of Novel Capryloyl Tetra-Glucoside and Aliphatic Ester Constituents from the Abutilon indicum Offers New Perspectives on the Treatment of Pain and Inflammation" Plants 11, no. 19: 2583. https://0-doi-org.brum.beds.ac.uk/10.3390/plants11192583