Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils
Abstract
:1. Introduction
2. Results and Discussion
2.1. Characterization of the Isolated Compounds
Positions | Compound 1 | Compound 2 | Compound 3 | |||
---|---|---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 38.1 | 1.28 (d, 4H, J = 6.6) | 29.8 | 0.94, (m, 2H) | 36.1 | 1.41 (m, 1H) |
1.31 (m,1H) | ||||||
2 | 27.3 | 1.68 (d, 4H, J = 3.0) | 25.7 | 1.01 (m, 2H) | 28.2 | 1.42 (m, 1H) |
1.32 (m, 1H) | ||||||
3 | 80.1 | 3.39 (dd, 1H, J = 10.8, 4.8) | 80.1 | 3.44 (1H, t, J = 18.0), 4.68 (OH) | 36.7 | 1.42 (m, 1H) |
1.33 (m, 1H) | ||||||
4 | 39.6 | - | 43.0 | - | 30.8 | - |
5 | 55.6 | 1.32 (d, 1H, J = 7.2) | 151.0 | - | 59.6 | 1.34 (m, 1H) |
6 | 17.7 | 1.28 (m, 4H, J = 6.6) | 109.3 | 4.79 (t, 1H, J = 6.0) | 18.6 | 1.65 (m, 2H) |
7 | 34.1 | 1.28 (m, 4H) | 31.9 | 1.77 (m, 2H) | 37.4 | 1.46 (m, 1H) |
8 | 40.9 | - | 50.3 | 1.48 (m, 1H) | 40.1 | - |
9 | 50.3 | 0.88 (m, 10H) | 48.2 | - | 51.9 | 1.56 (m, 1H) |
10 | 37.3 | - | 39.9 | - | 36.7 | - |
11 | 21.0 | 1.61 (m, 4H) | 23.7 | 1.34 (m, 2H) | 20.6 | 1.54 (m, 1H) |
1.29 (m, 1H) | ||||||
12 | 25.1 | 1.68 (m, 4H) | 22.7 | 1.31 (m, 2H) | 25.2 | 1.55 (m, 1H) |
1.29 (m, 1H) | ||||||
13 | 37.9 | 1.34 (m, 1H) | 42.8 | - | 37.7 | 1.24 (m, 1H) |
14 | 42.8 | - | 40.9 | - | 42.9 | - |
15 | 27.4 | 1.26 (m, 4H) | 34.5 | 1.57 (m, 2H) | 39.7 | 1.49 (m, 1H) |
1.00 (m, 1H) | ||||||
16 | 35.5 | 1.26 (m, 4H) | 29.4 | 1.63 (m, 2H) | 40.4 | 1.86 (m, 1H) |
1.25 (m,1H) | ||||||
17 | 43.0 | - | 55.6 | 1.48 (m,1H) | 59.6 | - |
18 | 47.9 | 2.04 (m, 1H) | 27.4 | 1.03 (s, 2H) | 46.5 | 1.68 (m, 1H) |
19 | 48.2 | 2.38 (d, 1H, J = 7.2) | 17.7 | 1.04 s, 1H | 37.2 | 2.09 (m, 1H) |
20 | 150.9 | - | 35.3 | 1.68 (m, 1H) | 150.9 | - |
21 | 29.7 | 1.88–1.94 (m, 2H) | 95.1 | 4.80 (m, 1H) | 29.2 | 1.60 (m, 6H) |
22 | 39.9 | 1.34 (m, 4H) | 35.5 | 1.18 (m, 2H) | 23.0 | 1.75 (t, 2H, J = 5.4) |
23 | 14.5 | 0.79 (s, 3H) | 25.0 | 1.35 (m, 2H) | 22.1 | 0.83 (s, 6H) |
24 | 18.0 | 0.83 (s, 3H) | 150.9 | 4.57 (m, 1H) | 16.6 | 0.90 (s, 3H) |
25 | 15.9 | 0.94 (s, 3H) | 109.3 | - | 15.4 | 0.76 (s, 3H) |
26 | 16.1 | 1.01(s, 3H) | 69.2 | 4.03 (d, 1H, J = 12) | 17.6 | 0.89 (s, 3H) |
27 | 14.1 | 1.07 (s, 3H) | 173.8 | - | 13.9 | 0.73 (s, 3H) |
28 | 95.1 | 4.79 (t, 1H, J = 6 Hz) | 14.1 | 0.80 (s, 3H) | 183.5 | - |
29 | 109.3 | 4.69 (br s, 1H) | 15.9 | 0.85 (s, 1H) | 116.3 | 5.32 (brs, 1H) |
4.57 (br s, 1H) | ||||||
30 | 69.2 | 5.14 (m, 1H, H-30) | 16.5 | 0.92 (q, 3H) | 20.1 | 1.10 (s, 3H) |
5.19 (m, 1H, H-30) |
2.2. Chemotactic Activity
Compounds | IC50 Value (μM) | ||
---|---|---|---|
ROS | Chemotaxis | ||
PMNs | WB | ||
28,28,30-Trihydroxylupeol (1) | 9.2 ± 0.5 | 11.5 ± 0.05 | 6.8 ± 0.1 |
3,21,21,26-Tetrahydroxylanostanoic acid (2) | 0.9 ± 0.03 | 0.1 ± 0.3 | 2.8 ± 0.1 |
Dehydroxybetulinic acid (3) | 0.9 ± 0.1 | 1.7 ± 0.1 | 2.5 ± 0.1 |
Taraxerone (4) | 1.3 ± 0.1 | 4.6 ± 0.08 | 4.1 ± 0.5 |
Taraxerol (5) | - | - | - |
Ethyl palmitate (6) | 1.1 ± 0.05 | 0.7 ± 0.05 | 3.7 ± 0.2 |
Herniarin (7) | 0.5 ± 0.5 | 1.6 ± 0.1 | 8.2 ± 0.2 |
Stigmasterol (8) | - | - | - |
Ursolic acid (9) | 0.8 ± 0.5 | 1.3 ± 0.8 | 3.6 ± 0.2 |
Acetylursolic acid (10) | - | - | - |
Aspirin (positive control) | 9.4 ± 0.5 | 11.6 ± 0.3 | - |
Ibuprofen (positive control) | - | - | 6.7 ± 0.5 |
2.3. Reactive Oxygen Species (ROS) Inhibitory Activity of Isolated Pure Compounds on Human Whole Blood (WB) and PMNs
3. Experimental Section
3.1. General Information
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Chemicals, Reagents and Equipment
3.5. Isolation of Polymorphonnuclear Leucocytes (PMNs)
3.6. Cell Viability
3.7. Chemiluminescence Assay
3.8. Chemotaxis Assay
3.9. Statistical Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Mawa, S.; Jantan, I.; Husain, K. Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils. Molecules 2016, 21, 9. https://doi.org/10.3390/molecules21010009
Mawa S, Jantan I, Husain K. Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils. Molecules. 2016; 21(1):9. https://doi.org/10.3390/molecules21010009
Chicago/Turabian StyleMawa, Shukranul, Ibrahim Jantan, and Khairana Husain. 2016. "Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils" Molecules 21, no. 1: 9. https://doi.org/10.3390/molecules21010009
APA StyleMawa, S., Jantan, I., & Husain, K. (2016). Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils. Molecules, 21(1), 9. https://doi.org/10.3390/molecules21010009