16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells
Abstract
:1. Introduction
2. Results and Discussion
2.1. Pharmacological Activity of Tournefortia hirsutissima
2.2. Purification and Characterization of Polyisoprenoid Alcohols
2.3. Effect of Compounds on NO Production in LPS-Stimulated RAW 264.7 Cells
2.4. Antiproliferative Activity of Compounds
2.5. Apoptosis Induced by Compound 1
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Preparation of Extracts
3.4. Isolation and Purification of Polyisoprenoid Alcohol Compounds 1–3
3.5. Preparation of (S)- and (R)-MTPA Esters of Compound 1 (1a and 1b)
3.6. Cell Viability of the RAW 264.7 Cells
3.7. Measurement of Nitrite Concentration
3.8. TPA-Induced Ear Edema in Mice
3.9. Antiproliferative Assay
3.10. Cell Cycle Analysis
3.11. Study of Cell Death by Annexin V-FITC/PI Staining
3.12. Cell Morphology Observation
3.13. RT-PCR
3.14. Caspase 3/7
3.15. Statistical Analysis
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds Compounds 1–3 are available from the authors. |
Position | δH | δC | Position | δH | δC |
---|---|---|---|---|---|
CH3-1 | 1.69 | 25.89 | CH2-21 | 2.21–2.16 | 27.08 |
C-2 | 131.15a | CH-22 | 5.26 | 124.73 | |
CH-3 | 5.25 | 125.00b | C-23 | 135.22e | |
CH2-4 | 2.22–2.16 | 27.29c | CH2-24 | 2.12 | 40.27d |
CH2-5 | 2.12–2.08 | 40.27d | CH2-25 | 2.23–2.15 | 27.18g |
C-6 | 135.05e | CH-26 | 5.30 | 124.82f | |
CH-7 | 5.30 | 124.86f | C-27 | 135.28e | |
CH2-8 | 2.23–2.15 | 27.30g | CH2-28 | 2.12–2.08 | 40.38d |
CH2-9 | 2.12–2.08 | 40.23d | CH2-29 | 2.22–2.16 | 27.17c |
C-10 | 135.09e | CH-30 | 5.25 | 124.98b | |
CH-11 | 5.26 | 124.54 | C-31 | 131.17a | |
CH2-12 | 2.19–2.15 | 26.91 | CH3-32 | 1.69 | 25.89 |
CH2-13 | 2.04 | 40.03 | CH3-33 | 1.57 | 17.78 |
C-14 | 137.29 | CH3-34 | 1.62 | 16.45h | |
CH-15 | 5.36 | 129.04 | CH3-35 | 1.60 | 16.18h |
CH-16 | 4.39 | 68.62 | CH3-36 | 1.61 | 16.76 |
CH2-17 | 2.40, 2.26 | 37.13 | CH3-37 | 1.59 | 16.76 |
CH-18 | 5.34 | 120.92 | CH3-38 | 1.60 | 16.18h |
C-19 | 137.87 | CH3-39 | 1.62 | 16.45h | |
CH2-20 | 2.11–2.09 | 40.25d | CH3-40 | 1.57 | 17.78 |
Treatment | HeLa | PC3 | HepG2 | Hep3B | IHH |
---|---|---|---|---|---|
Th-H | N.D.b | N.D. | 21.6 ± 1.9 | 32.7 ± 0.9 | 77 ± 7 |
Th-D | N.D. | N.D. | 33.6 ± 2.2 | > 100 | > 100 |
Th-HA | N.D. | N.D. | 31 ± 1.4 | 36.1 ± 1.5 | 84 ± 10 |
1 | 37.3 ± 3.5 | 32.0 ± 4.4 | 26.6 ± 3.5 | 21.3 ± 3.5 | 88.8 ± 8.9 |
2 | 95.7 ± 12.0 | 74.2 ± 5.0 | 76.6 ± 6.0 | 50.3 ± 5.9 | 76.6 ± 6.0 |
3 | 84.1 ± 8.9 | 76.4 ± 6.6 | 74.2 ± 5.5 | 69.7 ± 5.5 | 74.1 ± 5.5 |
Paclitaxela | 0.01 ± 0.002 | 0.0154 ± 0.0035 | 0.0065 ± 0.0007 | 0.008 ± 0.001 | 0.08 ± 0.005 |
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Hurtado-Díaz, I.; Sánchez-Carranza, J.N.; Romero-Estrada, A.; González-Maya, L.; González-Christen, J.; Herrera-Ruiz, M.; Alvarez, L. 16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells. Molecules 2019, 24, 2366. https://doi.org/10.3390/molecules24132366
Hurtado-Díaz I, Sánchez-Carranza JN, Romero-Estrada A, González-Maya L, González-Christen J, Herrera-Ruiz M, Alvarez L. 16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells. Molecules. 2019; 24(13):2366. https://doi.org/10.3390/molecules24132366
Chicago/Turabian StyleHurtado-Díaz, Israel, Jessica Nayelli Sánchez-Carranza, Antonio Romero-Estrada, Leticia González-Maya, Judith González-Christen, Maribel Herrera-Ruiz, and Laura Alvarez. 2019. "16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells" Molecules 24, no. 13: 2366. https://doi.org/10.3390/molecules24132366