Four New Sesquiterpenoids from the Roots of Diarthron Tianschanica with Their Antineoplastic Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Purification of Compounds 1–4
2.2. Structure Elucidation of Compounds 1–4
2.3. Antineoplastic Activity of Compounds 1–5
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Isolation and Purification of Compounds 1–5
3.4. Characterization of Compounds 1–4
3.5. Cytotoxicity Assay of Compounds 1–5
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–4 and 5 are available from the authors. |
Position | 1 | Position | 2 | ||
---|---|---|---|---|---|
δc Type | δH (J in Hz) | δc Type | δH (J in Hz) | ||
1 | 172.1 | 1 | 162.6 | ||
2 | 27.6 | 1.50 (1H, dd, 10.8, 9.6) 1.52 (1H, dd, 10.8, 2.4) | 2 | 39.9 | 2.26 (2H, m) |
3 | 39.5 | 1.99 (1H, m) 2.48 (1H, m) | 3 | 34.0 | 2.48 (2H, m) |
4 | 73.9 | 4 | 145.5 | ||
5 | 83.3 | 5 | 144.9 | ||
6 | 34.7 | 2.53 (1H, m) 2.65 (1H, m) | 6 | 39.6 | 2.48 (2H, m) |
7 | 42.2 | 2.67 (1H, m) | 7 | 41.5 | 3.28 (1H, m) |
8 | 47.9 | 2.16 (1H, dd, 12.0, 1.8) 2.60 (1H, dd, 12.0, 10.8) | 8 | 49.6 | 2.81 (2H, m) |
9 | 205.3 | 9 | 199.0 | ||
10 | 136.8 | 10 | 134.1 | ||
11 | 151.0 | 11 | 147.3 | ||
12 | 108.7 | 4.65 (1H, d, 1.8) 4.71 (1H, d, 1.8) | 12 | 110.8 | 4.77 (1H, d, 1.8) 4.79 (1H, d, 1.8) |
13 | 20.1 | 1.72 (3H, s) | 13 | 20.1 | 1.75 (3H, s) |
14 | 7.9 | 1.54 (3H, s) | 14 | 2.3 | 1.80 (3H, s) |
15 OH | 27.5 | 1.19 (3H, s) 4.31 (br s) 5.27 (br s) | 15 OH | 58.8 | 4.15 (1H, dd, 11.5, 5.4) |
Position | 3 | Position | 4 | ||
---|---|---|---|---|---|
δc Type | δH (J in Hz) | δc Type | δH (J in Hz) | ||
1 | 138.2 | 1 | 47.6 | 2.33 (1H, m) | |
2 | 40.4 | 2.90 (1H, m) 3.20 (1H, m) | 2 | 29.1 | 1.09 (1H, m) 1.23 (1H, m) |
3 | 202.8 | 3 | 30.9 | 1.43 (1H, m) 1.85 (1H, m) | |
4 | 137.3 | 4 | 34.7 | 2.56 (1H, m) | |
5 | 165.5 | 5 | 78.4 | ||
6 | 35.3 | 2.63 (1H, m) 2.80 (1H, m) | 6 | 35.5 | 1.76 (2H, m) |
7 | 37.2 | 2.65 (1H, m) | 7 | 154.3 | |
8 | 41.0 | 1.93 (1H, m) 1.89 (1H, m) | 8 | 124.5 | 5.63 (1H, d, 1.2) |
9 | 70.0 | 4.33 (1H, m) | 9 | 202.1 | |
10 | 130.4 | 10 | 84.3 | ||
11 | 149.8 | 11 | 146.3 | ||
12 | 110.1 | 4.71 (1H, s) 4.76 (1H, s) | 12 | 125.6 | 6.09 (1H, d, 1.2) 6.12 (1H, d, 0.6) |
13 | 20.2 | 1.75 (1H, s) | 13 | 165.8 | |
14 | 17.0 | 1.87 (1H, s) | 14 | 15.9 | 1.92 (3H, s) |
15 | 8.2 | 1.66 (1H, s) | 15 MeO | 22.2 51.7 | 0.90 (3H, d, 7.2) 3.62 (3H, s) |
Compound | HepG-2 | MCF-7 | HeLa |
---|---|---|---|
IC50 (μM) * | |||
Paclitaxel | 1.80 ± 0.26 | 3.80 ± 0.31 | 4.25 ± 0.52 |
1 | 18.9 ± 0.02 | 48.7 ± 0.39 | >50 |
2 | 41.3 ± 0.13 | >50 | 39.6 ± 0.53 |
3 | 22.5 ± 0.09 | >50 | >50 |
4 | >50 | >50 | >50 |
5 | 20.3 ± 0.24 | >50 | 29.6 ± 0.61 |
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Sun, D.-X.; Zhao, D.; Wei, H.-Y.; Ma, X.-L.; Shi, L.-L.; Zhang, J. Four New Sesquiterpenoids from the Roots of Diarthron Tianschanica with Their Antineoplastic Activity. Molecules 2018, 23, 1383. https://doi.org/10.3390/molecules23061383
Sun D-X, Zhao D, Wei H-Y, Ma X-L, Shi L-L, Zhang J. Four New Sesquiterpenoids from the Roots of Diarthron Tianschanica with Their Antineoplastic Activity. Molecules. 2018; 23(6):1383. https://doi.org/10.3390/molecules23061383
Chicago/Turabian StyleSun, Dong-Xue, Dan Zhao, Hong-Yan Wei, Xiao-Ling Ma, Lei-Ling Shi, and Jing Zhang. 2018. "Four New Sesquiterpenoids from the Roots of Diarthron Tianschanica with Their Antineoplastic Activity" Molecules 23, no. 6: 1383. https://doi.org/10.3390/molecules23061383