Chemical Constituents with Leishmanicidal Activity from a Pink-Yellow Cultivar of Lantana camara var. aculeata (L.) Collected in Central Mexico
Abstract
:1. Introduction
2. Results and Discussion
2.1. Leishmanicidal and Cytotoxic Activity of the Crude Extract and the Chromatographic Fractions Obtained from L. camara
2.2. GC–MS and NMR Analysis for the Identification of the Active Compounds Contained in FII, FX, FXI, and FXV
2.3. Leishmanicidal Activity of the Compounds Identified in the Fractions FII, FX, FXI, and FXV
3. Materials and Methods
3.1. Chemicals
3.2. Biological Material
3.3. Plant Material
3.4. Extraction and Isolation
3.5. GC–MS Analysis of FII
3.6. HPLC-PDA Analysis of Fractions FX, FXI, and FXV
3.7. NMR Analysis for the Identification of the Triterpenes Isolated from Fractions FX, FXI, and FXV
3.8. In Vitro Biological Testing
3.8.1. Cytotoxicity Assay on BALB/c Mice Peritoneal Macrophages
3.8.2. In Vitro Anti-Amastigote Activity on Leishmania amazonensis
3.8.3. In Vitro Anti-Promastigote Activity on Leishmania mexicana
3.8.4. In Vitro Anti-Amastigote Activity on Leishmania mexicana
3.8.5. Selectivity Index
3.9. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Extract/Fraction | CC50 ± SD (μg/mL) BALB/c Peritoneal Macrophages | IC50 ± SD (μg/mL) Leishmania amazonensis Amastigotes | SI on L. amazonensis | IC50 ± SD (μg/mL) L. mexicana Promastigotes | SI on L. mexicana |
---|---|---|---|---|---|
Crude extract | >100 | 21.8 ± 2.4 | >5 | 42.6 ± 1.9 | >2 |
FI | 65.2 ± 2.3 | 12.2 ± 1.8 | 5 | >200 | <0.5 |
FII | >100 | 9.1 ± 3.4 | >11 | 132.1 ± 7.9 | 0.49 |
FIII | >100 | 18.3 ± 1.5 | >5 | >200 | N.C. |
FIV | >100 | 30.2 ± 3.5 | >3 | >200 | <0.5 |
FV | >100 | 17.9 ± 3.8 | >6 | >200 | <0.5 |
FVI | >100 | 21.5 ± 4.3 | >5 | >200 | <0.5 |
FVII | 96.8 ± 2.2 | 17.9 ± 2.5 | >5 | >200 | <0.5 |
FVIII | 92.3 ± 3.1 | 24.7 ± 2.9 | >4 | >200 | <0.5 |
FIX | >100 | 18.6 ± 1.5 | >5 | 96.0 ± 1.6 | >1 |
FX | >100 | 7.9 ± 0.3 | >13 | 11.2 ± 2.2 | >9 |
FXI | >100 | 8.0 ± 1.1 | >13 | 22.0 ± 9.3 | >4 |
FXII | >100 | 16.7 ± 3.7 | >6 | 87.3 ± 2.1 | >1 |
FXIII | 82.2 ± 2.6 | 12.1 ± 0.7 | >7 | 83.3 ± 6.9 | 1 |
FXIV | 60.8 ± 1.4 | 15.1 ± 1.0 | >4 | 89.4 ± 2.4 | N.C. |
FXV | >100 | 23.6 ± 2.6 | >4 | 2.8 ± 0.5 | >35 |
FXVI | >100 | 8.5 ± 1.7 | >12 | 16.5 ± 1.6 | >6 |
FXVII | >100 | 19.8 ± 3.9 | >5 | 157.8 ± 15.5 | <0.6 |
FXVIII | >100 | 15.6 ± 4.7 | >6 | >200 | <0.5 |
Pentamidine | 11.7 ± 1.7 | 1.3 ± 0.1 | 9 | N.D. | N.D. |
Glucantime® | 60.0 ± 3.0 | N.D. | N.D. | 4019.7 ± 140.4 | 0.015 |
Fraction | Compound | IC50 ± SD (μM) L. mexicana promastigotes |
---|---|---|
FII | Eicosane (1) | >500 a |
Squalene (2) | >500 a | |
β-ionone (3) | 80.80 ± 7.09 b | |
Caryophyllene oxide (4) | 81.62 ± 2.16 b | |
β-caryophyllene (5) | 74.43 ± 4.38 b | |
Hexanoic acid (6) | 42.96 ± 6.02 c | |
Tiglic acid (7) | >500 a | |
FX, FXV | Lantanilic acid (8)/Camaric acid (9) (79%/21%) | 12.02 ± 0.36 d (9.50 ± 0.28 lantanilic acid, 8) (2.52 ± 0.08 camaric acid, 9) |
FX, FXI | Lantadene B (10) | 23.45 ± 2.15 d |
Glucantime® | 11,000.00 ± 2.15 e |
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Delgado-Altamirano, R.; López-Palma, R.I.; Monzote, L.; Delgado-Domínguez, J.; Becker, I.; Rivero-Cruz, J.F.; Esturau-Escofet, N.; Vázquez-Landaverde, P.A.; Rojas-Molina, A. Chemical Constituents with Leishmanicidal Activity from a Pink-Yellow Cultivar of Lantana camara var. aculeata (L.) Collected in Central Mexico. Int. J. Mol. Sci. 2019, 20, 872. https://doi.org/10.3390/ijms20040872
Delgado-Altamirano R, López-Palma RI, Monzote L, Delgado-Domínguez J, Becker I, Rivero-Cruz JF, Esturau-Escofet N, Vázquez-Landaverde PA, Rojas-Molina A. Chemical Constituents with Leishmanicidal Activity from a Pink-Yellow Cultivar of Lantana camara var. aculeata (L.) Collected in Central Mexico. International Journal of Molecular Sciences. 2019; 20(4):872. https://doi.org/10.3390/ijms20040872
Chicago/Turabian StyleDelgado-Altamirano, Ronna, Rosa Isela López-Palma, Lianet Monzote, José Delgado-Domínguez, Ingeborg Becker, José Fausto Rivero-Cruz, Nuria Esturau-Escofet, Pedro A. Vázquez-Landaverde, and Alejandra Rojas-Molina. 2019. "Chemical Constituents with Leishmanicidal Activity from a Pink-Yellow Cultivar of Lantana camara var. aculeata (L.) Collected in Central Mexico" International Journal of Molecular Sciences 20, no. 4: 872. https://doi.org/10.3390/ijms20040872