COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material and Fermentation
3.3. Extraction and Isolation
3.4. Biological Assays
3.5. Computational Calculations
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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Position | 1 | 2 | ||
---|---|---|---|---|
δHa (Mult., J in Hz) | δC a, Type | δH b (Mult., J in Hz) | δC c, Type | |
1 | - | 105.1, C | - | 111.0, C |
2 | - | 123.5, C | 5.88 (ddd, 5.7, 1.0, 0.4) | 130.1, CH |
3 | - | 145.1, C | 6.25 (dd, 5.7, 1.7) | 139.3, CH |
4 | - | 147.3, C | 5.07 (ddd, 7.0, 1.8, 1.0) | 85.7, CH |
5 | 6.59 (dd, 7.9, 1.5) | 117.0, CH | 3.14 (td, 8.5, 7.1) | 51.1, CH |
6 | 6.42 (dd, 7.9, 1.5) | 119.8, CH | 1.86–1.73 (m) | 32.7, CH2 |
7 | 6.80 (dd, 7.9, 1.5) | 121.6, CH | 4.24 (dtd, 12.1, 6.1, 5.6) | 78.7, CH |
8 | 4.81 (dd, 14.0, 3.1) | 73.9, CH | 2.52 (d, 6.3) | 39.9, CH2 |
9a | 2.68 (dd, 15.7, 9.4) | 38.0, CH2 | - | 173.5, C |
9b | 2.97 (dd, 15.7, 3.2) | |||
10 | - | 173.1, C | - | 148.2, C |
11 | - | 148.7, C | 6.87 (dd, 8.9, 7.4) | 108.6, CH |
12 | 7.02 (dd, 8.3, 1.3) | 110.2, CH | 7.40 (dd, 8.9, 7.4) | 127.1, CH |
13 | 7.37 (dd, 8.3) | 121.6, CH | 7.47 (dd, 8.9, 7.4) | 120.1, CH |
14 | 7.39 (dd, 8.3, 1.3) | 128.2, CH | - | 134.5, C |
15 | - | 135.5, C | 7.47 (dd, 8.9, 7.4) | 120.1, CH |
16 | 7.39 (dd, 8.3, 1.3) | 128.2, CH | 7.40 (dd, 8.9, 7.4) | 127.1, CH |
17 | 7.37 (dd, 8.3) | 121.6, CH | 6.87 (dd, 8.9, 7.4) | 108.6, CH |
18 | 7.02 (dd, 8.3, 1.3) | 110.2, CH | - | 148.4, C |
19 | - | 148.9, C | - | 114.1, C |
20 | - | 115.5, C | - | - |
21a | 4.10 (td, 11.4, 6.3) | 66.9, CH2 | - | - |
21b | 4.19 (td, 11.4, 4.3) | - | - | |
22 | 3.80 (dt, 15.2, 6.7) | 71.1, CH | - | - |
23 | 3.56 (ddd, 7.3, 5.7, 2.3) | 64.0, CH2 | - | - |
Compound | Antiproliferative Effect GI50 (µM) | Cytotoxicity CC50 (µM) | Cytotoxicity IC50 (µM) | ||
---|---|---|---|---|---|
HUVEC | K-562 | HeLa | L929 | KB3.1 | |
1 | >50 | 97.5 | 85.3 | − | − |
2 | >50 | 80.8 | 124.7 | 22.9 | 21.8 |
3 | >50 | 91.3 | 119.8 | − | − |
Imatinib | 18.5 | 0.17 | 65.8 | N.D. | N.D. |
Epothilone B | N.D. | N.D. | N.D. | 1.57 × 10−3 | 3.9 × 10−3 |
Compound | COX-1 IC50 (µM) | COX-2 IC50 (µM) |
---|---|---|
1 | 8.8 × 10−3 | 0.3 |
2 | 1.8 | 1.5 |
3 | 1.4 | 2.3 |
Celecoxib | 18.09 | 0.656 |
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Garcia, K.Y.M.; Quimque, M.T.J.; Primahana, G.; Ratzenböck, A.; Cano, M.J.B.; Llaguno, J.F.A.; Dahse, H.-M.; Phukhamsakda, C.; Surup, F.; Stadler, M.; et al. COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci. Int. J. Mol. Sci. 2021, 22, 12379. https://doi.org/10.3390/ijms222212379
Garcia KYM, Quimque MTJ, Primahana G, Ratzenböck A, Cano MJB, Llaguno JFA, Dahse H-M, Phukhamsakda C, Surup F, Stadler M, et al. COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci. International Journal of Molecular Sciences. 2021; 22(22):12379. https://doi.org/10.3390/ijms222212379
Chicago/Turabian StyleGarcia, Katherine Yasmin M., Mark Tristan J. Quimque, Gian Primahana, Andreas Ratzenböck, Mark Joseph B. Cano, Jeremiah Francis A. Llaguno, Hans-Martin Dahse, Chayanard Phukhamsakda, Frank Surup, Marc Stadler, and et al. 2021. "COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci" International Journal of Molecular Sciences 22, no. 22: 12379. https://doi.org/10.3390/ijms222212379