Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation of Oleanolic Acid Derivatives
2.2. Antibacterial Activity
2.3. Cytotoxic Activity
2.4. Antiviral Activity
3. Materials and Methods
3.1. General Procedures
3.2. Preparation of Oleanolic Derivatives
3.2.1. Synthesis of Compounds 2, 5, 8, and 9
3.2.2. Synthesis of Compound 3
3.2.3. Synthesis of Compound 4
3.2.4. Synthesis of Compounds 6 and 7
3.2.5. Synthesis of Compounds 10–13
3.2.6. Synthesis of Compounds 14 and 15
3.3. Bacterial Strains and Antimicrobial Activity
3.4. Determination of Minimal Inhibitory Concentration
3.5. Cell Culture Condition
3.6. Viruses
3.7. Cell Cytotoxicity Assay
3.8. Antiviral Activity Assays
3.9. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Comp. | 8 | 9 | 12 | 13 | 14 | 15 | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
C/H | C | H | C | H | C | H | C | H | C | H | C | H |
1 | 36.9 | 36.7 | 36.9 | 1.25 m 1.27 m | 34.4 | 34.8 | 1.29 m 1.31 m | 34.7 | ||||
2 | 32.6 | 28.4 | 32.4 | 1.49 m 1.65 m | 33.9 | 31.3 | 1.45 m 1.66 m | 32.4 | ||||
3 | 75.0 | 76.2 | 77.1 | 75.9 | 85.1 | 88.2 | ||||||
4 | 41.2 | 40.6 | 41.7 | 41.7 | 42.0 | 41.7 | ||||||
5 | 50.9 | 1.21 m | 51.1 | 1.19 m | 51.5 | 1.17 m | 51.0 | 1.18 m | 51.6 | 1.24 m | 51.5 | 1.22 m |
6 | 18.8 | 18.9 | 18.8 | 1.37 m 1.43 m | 20.8 | 18.7 | 1.40 m 1.42 m | 18.8 | ||||
7 | 33.8 | 32.9 | 32.7 | 1.20 m 1.29 m | 30.7 | 32.5 | 1.20 m 1.22 m | 32.5 | ||||
8 | 39.2 | 39.3 | 39.2 | 37.0 | 37.1 | 36.8 | ||||||
9 | 47.5 | 47.6 | 47.7 | 1.62 m | 47.6 | 46.5 | 1.62 m | 47.4 | ||||
10 | 30.7 | 37.1 | 36.7 | 36.8 | 31.2 | 30.9 | ||||||
11 | 23.5 | 23.4 | 23.0 | 1.88 m 1.90 m | 23.2 | 23.3 | 1.83 m 1.84 m | 23.2 | ||||
12 | 122.4 | 5.29 t (3.4) | 122.3 | 5.29 t (3.4) | 122.3 | 5.29 t br (3.5) | 122.2 | 5.28 t (3.5) | 122.4 | 5.28 m | 122.4 | 5.28 m |
13 | 143.8 | 143.8 | 143.8 | 143.7 | 143.4 | 143.7 | ||||||
14 | 41.7 | 41.6 | 40.8 | 39.2 | 40.7 | 40.4 | ||||||
15 | 27.6 | 27.7 | 27.9 | 1.04 m 1.60 m | 27.6 | 27.9 | 1.00 m 1.58 m | 27.6 | ||||
16 | 23.2 | 23.1 | 23.5 | 1.61 m 1.96 m | 23.0 | 23.2 | 1.60 m 1.87 m | 23.0 | ||||
17 | 46.7 | 46.0 | 45.8 | 45.8 | 41.5 | 45.8 | ||||||
18 | 40.9 | 2.86 dd (14.4, 4.4) | 41.3 | 2.87 dd (14.0, 4.6) | 41.2 | 2.85 dd (13.4, 4.3) | 41.3 | 2.85 dd (13.9, 4.1) | 41.3 | 2.85 m | 41.2 | 2.84 dd (14.1, 4.3) |
19 | 45.8 | 46.8 | 46.7 | 1.13 m 1.15 m | 46.7 | 46.5 | 1.10 m 1.12 m | 46.7 | ||||
20 | 30.7 | 30.7 | 30.7 | 30.2 | 30.8 | 30.7 | ||||||
21 | 34.3 | 33.9 | 33.8 | 1.17 m 1.32 m | 32.4 | 34.0 | 1.15 m 1.17 m | 33.8 | ||||
22 | 32.4 | 32.4 | 34.4 | 1.20 m 1.45 m | 32.7 | 29.2 | 1.65 m 1.73 m | 29.1 | ||||
23 | 20.7 | 0.91 s | 19.5 | 0.87 s | 16.8 | 0.73 s | 16.8 | 0.71 s | 17.2 | 0.71 s | 16.8 | 0.70 s |
24 | 23.0 | 0.82 s | 24.1 | 0.95 s | 23.6 | 0.93 s | 23.8 | 0.92 s | 23.7 | 0.91 s | 23.4 | 0.92 s |
25 | 14.9 | 0.91 s | 15.8 | 0.91 s | 14.9 | 0.90 s | 14.9 | 0.90 s | 15.1 | 0.93 s | 15.0 | 0.90 s |
26 | 16.8 | 0.73 s | 16.9 | 0.73 s | 20.7 | 0.78 s | 18.8 | 0.79 s | 20.4 | 0.76 s | 20.5 | 0.75 s |
27 | 26.1 | 1.15 s | 26.0 | 1.16 s | 26.0 | 1.14 s | 26.1 | 1.14 s | 26.2 | 1.12 s | 26.1 | 1.14 s |
28 | 178.3 | 178.3 | 178.3 | 178.4 | 178.4 | 178.3 | ||||||
29 | 33.1 | 0.93 s | 33.1 | 0.91 s | 33.1 | 0.90 s | 33.1 | 0.90 s | 33.2 | 0.91 s | 33.1 | 0.89 s |
30 | 23.6 | 0.94 s | 23.6 | 0.93 s | 23.7 | 0.94 s | 23.6 | 0.92 s | 23.8 | 0.76 s | 23.6 | 0.92 s |
1′ | 40.5 | 2.11 dd (13.8, 6.8) 2.41 dd (13.8, 8.2) | 41.1 | 2.23 dd (13.5, 7.2) 2.48 dd (14.0, 7.4) | 36.8 | 1.25 m 1.87 m | 40.9 | 1.85 m 1.90 m | 43.8 | 2.00 m 2.24 dd m (14.1, 6.6) | 39.2 | 1.67 m 1.70 m |
2′ | 134.7 | 5.93 ddt (17.1, 10.0, 7.3) | 135.0 | 5.91 ddt. (17.0, 10.2, 7.5) | 69.0 | 4.11 m | 69.6 | 4.04 m | 67.3 | 4.44 m | 82.1 | 5.02 m |
3′ | 118.9 | 5.12 m 5.16 m | 118.0 | 5.10 dd (17.0, 2.3) 5.16 dd (10.2, 2.3) | 67.4 | 3.44 dd (11.2, 6.7) 3.59 m | 67.6 | 3.48 dd (10.9, 6.5) 3.58 m | 78.2 | 3.81 m | 72.3 | 3.81 m 3.90 m |
1″ | 133.9 | |||||||||||
2″ = 6″ | 129.9 | 7.34 d (8.5) | ||||||||||
3″ = 5″ | 127.7 | 7.79 m | ||||||||||
4″ | 144.8 | |||||||||||
Tosyl-CH3 | 21.6 | 2.45 s | ||||||||||
-OMe | 51.5 | 3.63 s | 51.5 | 3.62 s | 50.7 | 3.63 s | 51.6 | 3.62 s | 51.5 | 3.62 s | 51.5 | 3.62 s |
Strain | Compounds | MIC100 [mg/mL] |
---|---|---|
E. coli DH5α | 1 | >10 |
3 | >10 | |
4 | >10 | |
6 | >10 | |
7 | 10 | |
8 | >10 | |
9 | >10 |
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Fontana, G.; Badalamenti, N.; Bruno, M.; Maggi, F.; Dell’Annunziata, F.; Capuano, N.; Varcamonti, M.; Zanfardino, A. Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3. Int. J. Mol. Sci. 2024, 25, 8480. https://doi.org/10.3390/ijms25158480
Fontana G, Badalamenti N, Bruno M, Maggi F, Dell’Annunziata F, Capuano N, Varcamonti M, Zanfardino A. Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3. International Journal of Molecular Sciences. 2024; 25(15):8480. https://doi.org/10.3390/ijms25158480
Chicago/Turabian StyleFontana, Gianfranco, Natale Badalamenti, Maurizio Bruno, Filippo Maggi, Federica Dell’Annunziata, Nicoletta Capuano, Mario Varcamonti, and Anna Zanfardino. 2024. "Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3" International Journal of Molecular Sciences 25, no. 15: 8480. https://doi.org/10.3390/ijms25158480