Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik
Abstract
:1. Introduction
2. Results
3. Discussion
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Plant Material
4.3. Extraction and Isolation
4.4. Physical and Spectral Data of Isolated Compounds 1 to 9
4.5. Protein-Ligand Docking
5. 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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1 | 2 | 3 | 4 | 5 | 6 | |
---|---|---|---|---|---|---|
H–Atom | δH, ppm | δH, ppm | δH, ppm | δH, ppm | δH, ppm | δH, ppm |
1 | 5.53 d (3.8) | 5.52 d (3.8) | 5.45 d (3.4) | 5.45 d (3.5) | 5.44 d (3.6) | 5.46 d (3.6) |
2 | 3.51 dd (3.8/9.7) | 3.51 dd (3.8/9.7) | 3.46 (3.4/9.8) | 3.48 dd (3.5/9.5) | 3.45 dd (3.6/9.5) | 3.49 dd (3.6/9.5) |
3 | 3.70 t (9.2) | 3.69 t (9.2) | 3.68 t (9.3) | 3.68 t | 3.67 t (9.5) | 3.70 t (9.5) |
4 | 3.34 t (9.3) | 3.34 t (9.3) | 3.43 t (9.3) | 3.43 t (9.5) | 3.42 t (9.5) | 3.45 t (9.5) |
5 | 4.29 gdd (9.3/7.3) | 4.28 gdd (9.3/7.3) | 3.92 m | 3.92 m | 3.92 m | 3.94 m |
6 | 4.23 dd (11.7/7.3) 4.69 gd (11.7) | 4.23 dd (11.7/7.3) 4.69 gd (11.7) | 3.84 † 3.78 dd (12.2/4.4) | 3.85/3.79 | 3.84 dd (12.0/2.1) 3.78 dd (12.0/4.6) | 3.86 † 3.81 † |
1′ | 3.65 d (12.2) | 3.65 d (12.2) | 3.68 d (12.3) | 3.64 d (12.1) | 3.66 d (12.2) | 3.69 d (12.2) |
3.61 d (12.2) | 3.60 d (12.2) | 3.61 d (12.3) | 3.60 d (12.1) | 3.60 d (12.2) | 3.62 d (12.2) | |
2′ | - | - | - | - | - | - |
3′ | 5.53 d (8.1) | 5.54 d (8.1) | 5.49 d (7.8) | 5.49 d (7.8) | 5.49 d (7.8) | 5.50 d (7.8) |
4′ | 4.52 t (8.1) | 4.52 t (8.1) | 4.40 t (7.8) | 4.40 t | 4.39 t (7.8) | 4.41 t (7.8) |
5′ | 4.00 ddd (3.1/8.1/10.0) | 4.00 ddd (3.1/8.1/10.0) | 3.97 m | 3.97 m | 3.95 m | 3.97 m |
6′ | 3.91 dd (12.1/6.9) 3.84 † | 3.90 dd (12.1/6.9) 3.84 † | 3.85 † | 3.85 † | 3.86 † | 3.86 † |
Acyl→Glu-6(OH) | SA | SA | - | - | - | - |
2″ | 6.88 s | 6.84 s | - | - | - | - |
6″ | 6.88 s | 6.84 s | - | - | - | - |
7″ | 7.57 d (15.7) | 7.56 d (15.9) | - | - | - | - |
8″ | 6.44 d (15.7) | 6.44 d (15.9) | - | - | - | - |
3″&5″-OMe | 3.85 s | 3.82 s | - | - | - | |
Acyl→Fru-3′(OH) | SA | TMC | MFA | SA | TMC | FA |
2‴ | 6.84 s | 6.90 s | 7.22 d (2.0) | 6.93 s | 6.96 s | 7.22 d (2.0) |
5‴ | - | - | 6.95 d (8.0) | - | - | 6.8 d (8.2) |
6″″ | 6.84 s | 6.90 s | 7.21 dd (8.0/2.0) | 6.93 s | 6.96 s | 7.14 dd (8.2/2.0) |
7‴ | 7.65 d (15.7) | 7.67 d (15.9) | 7.71 d (15.9) | 7.69 d (15.9) | 7.72 d (16.0) | 7.71 d (15.9) |
8‴ | 6.42 d (15.7) | 6.53 d (15.9) | 6.47 d (15.9) | 6.44 d (15.9) | 6.54 d (16.0) | 6.44 d (15.9) |
3‴&5‴-OMe | 3.82 s (6H) | 3.84 s (6H) | 3.85 s (3H) | 3.87 s (6H) | 3.88 s (6H) | 3.89 s (3H) |
4‴-OMe | - | 3.77 s (3H) | 3.86 s (3H) | - | 3.80 s (3H) | - |
1 | 2 | 3 | 4 | 5 | 6 | ||
---|---|---|---|---|---|---|---|
C/H | DEPT | δC, ppm | δC, ppm | δC, ppm | δC, ppm | δC, ppm | δC, ppm |
Glu | |||||||
1 | CH | 92.59 | 92.61 | 93.19 | 93.18 | 93.23 | 93.20 |
2 | CH | 72.99 | 72.97 | 72.94 | 72.79 | 73.00 | 72.94 |
3 | CH | 75.00 | 75.01 | 74.86 | 74.87 | 74.93 | 74.42 |
4 | CH | 71.83 | 71.81 | 71.02 | 70.99 | 71.07 | 71.01 |
5 | CH | 72.41 | 72.42 | 74.42 | 74.42 | 74.51 | 74.87 |
6 | CH2 | 65.60 | 65.58 | 62.20 | 62.20 | 62.28 | 62.18 |
Fru | |||||||
1′ | CH2 | 63.72 | 63.72 | 65.19 | 65.20 | 65.24 | 65.19 |
2′ | C | 104.78 | 104.76 | 104.69 | 104.70 | 104.71 | 104.71 |
3′ | CH | 79.19 | 79.32 | 79.59 | 79.52 | 79.70 | 79.54 |
4′ | CH | 74.07 | 74.09 | 73.74 | 73.76 | 73.80 | 73.75 |
5′ | CH | 84.18 | 84.21 | 83.96 | 83.94 | 84.06 | 83.96 |
6′ | CH2 | 65.60 | 65.58 | 62.84 | 62.82 | 62.85 | 62.84 |
Acyl→Glu-6(OH) | SA | SA | |||||
1″ | C | 126.46 | 126.48 | ||||
2″ | CH | 106.89 | 106.75 | ||||
3″ | C | 149.25 | 149.24 | ||||
4″ | C | 139.42 | 139.33 | ||||
5″ | C | 149.25 | 149.24 | ||||
6″ | CH | 106.89 | 106.75 | ||||
7″ | CH | 147.33 | 147.23 | ||||
8″ | CH | 115.65 | 115.66 | ||||
9″ | C | 169.16 | 169.10 | ||||
3″&5″-OMe | CH3 | 56.79 | 56.73 | ||||
Acyl→Fru-3′(OH) | SA | TMC | MFA | SA | TMC | FA | |
1‴ | C | 126.51 | 131.34 | 128.56 | 126.49 | 131.46 | 127.60 |
2‴ | CH | 106.74 | 106.78 | 111.63 | 106.95 | 106.85 | 112.00 |
3″ | C | 149.24 | 154.59 | 150.47 | 149.27 | 154.66 | 150.49 |
4″″ | C | 139.30 | 141.10 | 152.68 | 139.43 | 141.17 | 149.21 |
5‴ | C/CH | 149.24 | 154.59 | 112.45 | 149.27 | 154.66 | 116.43 |
6‴ | CH | 106.74 | 106.78 | 124.10 | 106.95 | 106.85 | 124.15 |
7‴ | CH | 147.97 | 147.29 | 147.30 | 147.95 | 147.22 | 147.73 |
8‴ | CH | 115.29 | 117.63 | 115.83 | 115.32 | 117.74 | 114.89 |
9‴ | C | 168.31 | 167.85 | 168.17 | 168.26 | 167.82 | 168.39 |
3‴&5‴-OMe | CH3 | 56.84 | 56.79 | 56.51 | 56.90 | 56.79 | 56.88 |
4‴-OMe | CH3 | 61.18 | 61.39 | 61.20 |
Protein | Ligand | JAMDA Score | All-Atom RMSD |
---|---|---|---|
MPO (PDB ID: 5QJ2) | PDB chemical ID: JXS | −2.32663 | 0.632 Å |
Compound 1 | −3.78280 | ||
Compound 2 | −3.57348 | ||
Compound 3 | −2.90840 | ||
Compound 4 | −3.13930 | ||
Compound 5 | −2.97990 | ||
Compound 6 | −2.83140 | ||
Compound 7 | −2.50225 | ||
Compound 8 | −3.03640 | ||
Compound 9 | −3.52060 | ||
iNOS (PDB ID: 3E7G) | PDB chemical ID: AT2 | −2.62362 | 0.682 Å |
Compound 1 | −2.85444 | ||
Compound 2 | −3.14240 | ||
Compound 3 | −2.66980 | ||
Compound 4 | −2.34210 | ||
Compound 5 | −2.54230 | ||
Compound 6 | −3.02600 | ||
Compound 7 | −2.67380 | ||
Compound 8 | −3.47560 | ||
Compound 9 | −2.78550 | ||
COX-2 (PDB ID: 5KIR) | PDB chemical ID: RCX | −2.52030 | 0.532 Å |
Compound 1 | Positive | ||
Compound 2 | Positive | ||
Compound 3 | Positive | ||
Compound 4 | Positive | ||
Compound 5 | Positive | ||
Compound 6 | Positive | ||
Compound 7 | −2.56960 | ||
Compound 8 | Positive | ||
Compound 9 | Positive |
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Ünlü, A.; Teralı, K.; Uğurlu Aydın, Z.; Dönmez, A.A.; Yusufoğlu, H.S.; Çalış, İ. Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik. Molecules 2022, 27, 684. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030684
Ünlü A, Teralı K, Uğurlu Aydın Z, Dönmez AA, Yusufoğlu HS, Çalış İ. Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik. Molecules. 2022; 27(3):684. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030684
Chicago/Turabian StyleÜnlü, Ayşe, Kerem Teralı, Zübeyde Uğurlu Aydın, Ali A. Dönmez, Hasan Soliman Yusufoğlu, and İhsan Çalış. 2022. "Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik" Molecules 27, no. 3: 684. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030684