Cytotoxicity and Nitric Oxide Production Inhibitory Activities of Compounds Isolated from the Plant Pathogenic Fungus Curvularia sp.
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Fungal Material and Identification
2.3. Fermentation, Extraction, and Isolation
2.4. Bioassays
2.4.1. Nitric Oxide (NO) Production Inhibitory Assay
2.4.2. Cytotoxicity Assay in Mammalian Cells (RAW 264.7 Cells)
2.4.3. Cytotoxicity Assay against Lung Cancer A549, Colorectal Cancer SW480, and Leukemic K562 Cells
2.5. Computational Methods
3. Results and Discussion
3.1. Isolated Compounds from Curvularia sp.
3.2. Structural Characterization of a New Compound
3.3. Cytotoxicity against the Three Cancer Cell Lines, including Lung Cancer A549, Colorectal Cancer SW480, and Leukemic K562 Cells and Mammalian Cells (RAW 264.7 Cells)
3.4. Nitric Oxide Production Inhibitory Activity of Isolated Compounds 1–6
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Position | δC | δH [mult, J in Hz] | HMBC (1H→13C) |
---|---|---|---|
1 | 142.7 | ||
2 | 146.9 | ||
3 | 40.4 | 2.82 (td, 10.5, 2.7) | 1, 2, 4, 10, 3′ |
4 | 46.3 | 2.68 (m) | 3 |
5 | 148.3 | 6.46 (d, 11.7) | 4, 6, 13, 2″ |
6 | 131.2 | ||
7 | 44.9 | 3.49 (d, 12.0) | 5, 6, 8, 9, 12, 13 |
8 | 24.3 | 2.61 (m); 1.76 (dd, 13.0, 12.6) | 5, 6, 7, 9, 12 |
9 | 24.4 | 2.93 (dd, 13.0, 7.3); 2.46 (t, 13.0) | 1, 2, 7, 8, 11 |
10 | 165.9 | ||
11 | 165.7 | ||
12 | 177.6 | ||
13 | 169.8 | ||
1’ | 14.0 | 0.92 (t, 7.6) | 2’, 3’ |
2’ | 21.0 | 1.25 (m) | 3, 1’, 3’ |
3’ | 34.9 | 1.89 (m); 1.53 (m) | 1’ |
1” | 12.3 | 0.93 (t, 7.2) | 4, 2” |
2” | 25.9 | 1.98 (ddd, 13.2, 7.2, 2.5); 1.38 (m) | 4, 5, 1” |
Samples (100 µg/mL) | Cell Viability (%) | |||
---|---|---|---|---|
RAW 264.7 | A549 (Lung Cancer) | SW480 (Colorectal Cancer) | K562 (Leukemic Cells) | |
1 | 97.14 ± 0.81 | 88.51 ± 1.19 | 82.60 ± 1.68 | 81.07 ± 3.80 |
2 | 10.80 ± 0.09 | 13.37 ± 0.48 | 14.95 ± 0.57 | 12.54 ± 1.24 |
3 | 71.38 ± 2.67 | 96.32 ± 3.70 | 75.59 ± 2.00 | 79.23 ± 1.86 |
4 | 11.07 ± 0.43 | 8.40 ± 0.58 | 14.39 ± 0.40 | 10.56 ± 0.20 |
5 | 82.59 ± 1.72 | 84.08 ± 3.01 | 97.87 ± 1.70 | 75.65 ± 1.19 |
6 | 99.34 ± 2.51 | 92.03 ± 3.75 | 97.69 ± 1.04 | 99.15 ± 3.84 |
5% DMSO (control) | 100.00 ± 2.47 | 100.00 ± 0.41 | 100.00 ± 2.49 | 100.00 ± 1.89 |
Sample | Concentration | Cell Viability (%) | |||
---|---|---|---|---|---|
RAW 264.7 | A549 (Lung Cancer) | SW480 (Colorectal Cancer) | K562 (Leukemic Cells) | ||
2 | 100 | 10.80 ± 0.09 | 13.37 ± 0.48 | 14.95 ± 0.57 | 12.54 ± 1.24 |
50 | 11.67 ± 0.08 | 14.77 ± 2.54 | 15.64 ± 0.77 | 13.35 ± 0.89 | |
25 | 15.00 ± 0.29 | 17.92 ± 1.93 | 17.56 ± 0.70 | 21.01 ± 2.61 | |
12.5 | 16.61 ± 0.52 | 23.07 ± 1.84 | 23.41 ± 0.25 | 38.42 ± 3.18 | |
6.25 | 28.48 ± 1.98 | 73.11 ± 1.09 | 30.75 ± 0.40 | 70.95 ± 1.69 | |
IC50 (µM) | <11.73 | 14.34 | <11.73 | 17.59 | |
4 | 100 | 11.07 ± 0.43 | 8.40 ± 0.58 | 14.39 ± 0.40 | 10.56 ± 0.20 |
50 | 12.79 ± 0.70 | 9.35 ± 0.52 | 14.71 ± 0.24 | 11.27 ± 0.40 | |
25 | 12.14 ± 0.42 | 10.16 ± 0.17 | 15.37 ± 0.42 | 12.88 ± 0.34 | |
12.5 | 12.45 ± 0.47 | 11.58 ± 1.05 | 15.59 ± 0.39 | 14.03 ± 2.31 | |
6.25 | 14.32 ± 0.73 | 12.39 ± 0.17 | 17.29 ± 0.33 | 19.48 ± 2.62 | |
IC50 (µM) | <12.14 | <12.14 | <12.14 | <12.14 |
Samples | NO Production Inhibition | |
---|---|---|
% of NO Inhibition at 100 µg/mL | IC50 (µM) | |
1 | 51.30 ± 1.65 | 53.7 |
2 | not tested * | not tested * |
3 | 73.41 ± 0.44 | 32.8 |
4 | not tested * | not tested * |
5 | 74.01 ± 1.14 | 12.8 |
6 | 41.03 ± 3.36 | inactive |
Indomethacin | 77.45 ± 0.28 | 73.4 |
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Suthiphasilp, V.; Raksat, A.; Maneerat, T.; Hadsadee, S.; Jungsuttiwong, S.; Pyne, S.G.; Chomnunti, P.; Jaidee, W.; Charoensup, R.; Laphookhieo, S. Cytotoxicity and Nitric Oxide Production Inhibitory Activities of Compounds Isolated from the Plant Pathogenic Fungus Curvularia sp. J. Fungi 2021, 7, 408. https://doi.org/10.3390/jof7060408
Suthiphasilp V, Raksat A, Maneerat T, Hadsadee S, Jungsuttiwong S, Pyne SG, Chomnunti P, Jaidee W, Charoensup R, Laphookhieo S. Cytotoxicity and Nitric Oxide Production Inhibitory Activities of Compounds Isolated from the Plant Pathogenic Fungus Curvularia sp. Journal of Fungi. 2021; 7(6):408. https://doi.org/10.3390/jof7060408
Chicago/Turabian StyleSuthiphasilp, Virayu, Achara Raksat, Tharakorn Maneerat, Sarinya Hadsadee, Siriporn Jungsuttiwong, Stephen G. Pyne, Putarak Chomnunti, Wuttichai Jaidee, Rawiwan Charoensup, and Surat Laphookhieo. 2021. "Cytotoxicity and Nitric Oxide Production Inhibitory Activities of Compounds Isolated from the Plant Pathogenic Fungus Curvularia sp." Journal of Fungi 7, no. 6: 408. https://doi.org/10.3390/jof7060408