Bio-Guided Isolation of the Cytotoxic Terpenoids from the Roots of Euphorbia kansui against Human Normal Cell Lines L-O2 and GES-1
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of Compounds 1–12
2.2. Cytotoxicity Activity on Human Normal Cell Lines of Extracts and Compounds from Kansui
3. Experimental Section
3.1. Chemicals and Reagents
3.2. Instrumentation
3.3. Plant Material
3.4. Extraction and Isolation
3.5. Cell Line and Cell Culture
3.6. Cell Proliferation Analysis
3.7. Statistical Analysis
4. Conclusions
Acknowledgments
References
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Position | 1 | Position | 2 | 3 |
---|---|---|---|---|
1 | 2.66 (dd, 6.3, 14.1) | 1 | 4.33 (brs) | 4.94 (s) |
2.25 (m) | ||||
2 | 2.10 (m) | 2 | - | - |
3 | 5.60 (brs) | 3 | 5.53 (d, 4.8) | 5.38 (d, 4.7) |
4 | 2.98 (brs) | 4 | 3.63 (dd, 11.4, 5.0) | 3.48 (m) |
5 | 6.15 (s) | 5 | 5.93 (d, 5.85) | 5.95 (s) |
7 | 6.44 (s) | 7 | 5.88 (s) | 5.88(s) |
8 | 6.05 (s) | 8 | 4.66 (brs) | 4.70 (d, 9.3) |
9 | 5.09 (s) | 9 | - | - |
11 | 4.14 (s) | 11 | 3.70 (d, 1.8) | 3.65 (d, 2.04) |
12 | - | 12 | 3.33 (m) | 3.46 (m) |
13 | 2.33 (q, 6.6) | 13 | 3.38 (m) | 3.26 (m) |
16 | 0.936 (d, 6.6) | 16 | 1.29 (s) | 1.32 (s) |
17 | 5.24 (s) | 17 | 6.52 (s) | 6.390 (s) |
5.14 (s) | 5.94 (s) | 5.95 (s) | ||
18 | 1.31 (s) | 18 | 1.35 (s) | 1.33 (s) |
19 | 1.15 (s) | 19 | 0.85 (s) | 0.89 (s) |
20 | 1.32 (d, 6.3) | 20 | 1.53 (d, 6.27) | 1.65 (d, 6.51) |
Acetyls | - | Acetyls | - | - |
COMe-1 | - | COMe-1 | - | 2.14 (s) |
COMe-3 | 2.10 (s) | COMe-3 | 1.90 (s) | 1.95 (s) |
COMe-5 | 2.08 (s) | COMe-5 | - | - |
COMe-7 | 2.19 (s) | COMe-7 | - | - |
COMe-9 | 2.01 (s) | COMe-9 | - | - |
COMe-15 | 1.96 (s) | COMe-15 | 2.32 (s) | - |
Benzoyls | - | Benzoyls | - | - |
COPh-8 -2,6 | 8.05 (m) | COPh-5-2,6 | 7.56 (m) | 7.48 (m) |
-3,5 | 7.44 (m) | -3,5 | 7.03 (m) | 6.88 (m) |
-4 | 7.55 (m) | -4 | 7.22 (m) | 7.06 (m) |
COPh-7-2,6 | - | COPh-7-2,6 | 7.51 (m) | 7.53 (m) |
-3,5 | - | -3,5 | 6.93 (m) | 7.02 (m) |
-4 | - | -4 | 7.10 (m) | 7.25 (m) |
OH-1 | - | OH-1 | 3.94 (brs) | - |
OH-2 | - | OH-2 | 2.53 (m) | 2.33 (s) |
OH-8 | - | OH-8 | 3.59 (m) | 3.50 (m) |
OH-15 | - | OH-15 | - | 4.10 (s) |
Position | 4 | 5 | 6 | 7 | 8 | 9 |
---|---|---|---|---|---|---|
1 | 6.14 (brs) | 6.05 (s) | 6.04 (s) | 6.07 (s) | 6.14 (s) | 6.02 (s) |
3 | 5.07 (s) | 5.60 (s) | 5.57 (s) | 5.53 (s) | 5.67 (s) | 3.73 (s) |
5 | 5.51 (brs) | 3.88 (s) | 3.88 (s) | 3.68 (s) | 3.76 (brs) | 5.41 (s) |
7 | 5.88 (d, 1.5) | 6.12 (d, 3.7) | 6.12 (d, 3.7) | 5.76 (m) | 5.78 (m) | 5.91 (m) |
8 | 4.26 (dd, 9.5, 1.5) | 4.08 (dd, 4.0, 11.7) | 4.08 (dd, 4.0, 11.7) | 4.02 (dd, 9.9, 3.0) | 4.03 (m) | 4.13 (dd, 7.0, 14.2) |
11 | 2.31 (m) | 2.49 (m) | 2.48 (m) | 2.46 (m) | 2.54 (m) | 2.41 (m) |
12 | 2.54 (m) | 2.26 (m) | 2.26 (m) | 2.26 (m) | 2.28 (m) | 2.34 (m) 1.77 |
1.73 (m) | 1.75 (m) | 1.76 (m) | 1.74 (m) | 1.75 (m) | (m) | |
13 | 0.74 (m) | 0.72 (m) | 0.72 (m) | 0.67 (m) | 0.67 (m) | 0.70 (m) |
14 | 0.88 (m) | 0.98 (m) | 0.98 (m) | 0.90 (m) | 0.93 (m) | 0.94 (m) |
16 | 1.07 (s) | 1.06 (s) | 1.06 (s) | 1.05 (s) | 1.04 (s) | 1.07 (s) |
17 | 1.13 (s) | 1.08 (s) | 1.08 (s) | 1.08 (s) | 1.06 (s) | 1.17 (s) |
18 | 1.00 (d, 4.7) | 1.00 (d, 7.3) | 1.00 (d, 7.3) | 0.99 (d, 7.2) | 1.05 (d, 4.2) | 0.98 (d, 5.61) |
19 | 1.78 (brs) | 1.8 (d, 1.1) | 1.8 d (1.1) | 1.80 (brs) | 1.83 (d, 1.5) | 1.83 (s) |
20 | 1.56 (s) | 4.75, 4.49 (Abq, 12.5) | 4.75, 4.49 (Abq, 12.5) | 1.79 (s) | 1.81 (s) | 1.60 (s) |
3-R, 2′ | 8.13 (m) | 5.95 (d, 15.3) | 5.86 (d, 15.3) | 5.95 (d, 5.1) | 8.04 (d, 7.3) | - |
3′ | 7.48 (m) | 7.70 (m) | 7.31 (m) | 7.68 (dd, 15.3, 11.4) | 7.48 (t, 7.6) | - |
4′ | 7.60 (m) | 6.16 (m) | 6.21 (m) | 6.16 (m) | 7.61 (t, 7.3) | - |
5′ | - | 5.95 (m) | 6.21 (m) | 5.94 (m) | - | - |
6′ | - | 2.29 (m) | 2.20 (m) | 2.34 (m) | - | - |
7′ | - | 1.43 (m) | 1.43 (m) | 1.43 (m) | - | - |
8′ | - | 1.31 (m) | 1.31 (m) | 1.29 (m) | - | - |
9′ | - | 1.28 (m) | 1.28 (m) | - | - | |
10′ | - | 0.89 (t, 7.0) | 0.72 (t, 7.0) | 0.89 (m) | - | - |
OAc | - | 2.06 (s) | 2.05 (s) | - | - | - |
5-R, 2′ | 2.05 (s) | - | - | - | - | 8.10 (m) |
3′ | - | - | - | - | - | 7.46 (m) |
4′ | - | - | - | - | - | 7.60 (m) |
Position | 10 | 11 |
---|---|---|
1α | 1.44 (m) | 1.44 (m) |
1β | 1.86 (m) | 1.86 (m) |
2 | 1.76 (m) | 1.75 (m) |
1.67 (m) | 1.66 (m) | |
3α | 3.29 (dd, 4.6,11.6) | 3.29 (dd, 4.6,11.6) |
5α | 1.67 (m) | 1.66 (m) |
6α | 2.40 (m) | 2.41 (m) |
6β | 2.38 (m) | 2.38 (m) |
11α | 2.37 (m) | 2.36 (m) |
11β | 2.24 (m) | 2.24 (m) |
12α | 1.76–1.80 (m) | 1.76–1.80 (m) |
15α | 1.55 (m) | 1.55 (m) |
15β | 2.12 (m) | 2.12 (m) |
16α | 1.34 (m) | 1.34 (m) |
16β | 1.93 (m) | 1.94 (m) |
17 | 1.44 (m) | 1.46 (m) |
18 | 0.73 (s) | 0.73 (s) |
19 | 1.06 (s) | 1.05 (s) |
20 | 1.41 (m) | 1.43 (m) |
21 | 0.88 (d, 6.0) | 0.93 (d, 6.1) |
22 | 1.13 (m), 1.55 (m) | 1.05 (m), 1.48 (m) |
23 | 1.90 (m), 2.04 (m) | 1.82 (m), 2.04 (m) |
24 | 5.09 (m) | 5.10 (m) |
26 | 1.69 (s) | 1.68 (s) |
27 | 1.61 (s) | 1.60 (s) |
28 | 0.99 (s) | 0.99 (s) |
29 | 0.88 (s) | 0.88 (s) |
30 | 0.97 (s) | 0.96 (s) |
Extract/Compounds | IC50 | |
---|---|---|
L-O2 | GES-1 | |
EtOH extract | 42.02 μg/mL | 30.67 μg/mL |
EtOAc extract | 27.08 μg/mL | 21.89 μg/mL |
Water extract | >100 μg/mL | >100 μg/mL |
1 | >100 μM | >100 μM |
2 | >100 μM | >100 μM |
3 | >100 μM | >100 μM |
4 | >100 μM | >100 μM |
5 | 12.40 μM | 8.51 μM |
6 | 8.22 μM | 6.67 μM |
7 | 13.08 μM | 3.53 μM |
8 | 70.78 μM | 23.51 μM |
9 | 34.53 μM | 22.01 μM |
10 | 14.36 μM | 13.44 μM |
11 | 17.82 μM | 8.04 μM |
12 | >100 μM | >100 μM |
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Zhang, L.; Gao, L.; Li, Z.; Yan, X.; Yang, Y.; Tang, Y.; Cao, Y.; Ding, A. Bio-Guided Isolation of the Cytotoxic Terpenoids from the Roots of Euphorbia kansui against Human Normal Cell Lines L-O2 and GES-1. Int. J. Mol. Sci. 2012, 13, 11247-11259. https://doi.org/10.3390/ijms130911247
Zhang L, Gao L, Li Z, Yan X, Yang Y, Tang Y, Cao Y, Ding A. Bio-Guided Isolation of the Cytotoxic Terpenoids from the Roots of Euphorbia kansui against Human Normal Cell Lines L-O2 and GES-1. International Journal of Molecular Sciences. 2012; 13(9):11247-11259. https://doi.org/10.3390/ijms130911247
Chicago/Turabian StyleZhang, Li, Lan Gao, Zhengjun Li, Xiaojing Yan, Yanjing Yang, Yuping Tang, Yudan Cao, and Anwei Ding. 2012. "Bio-Guided Isolation of the Cytotoxic Terpenoids from the Roots of Euphorbia kansui against Human Normal Cell Lines L-O2 and GES-1" International Journal of Molecular Sciences 13, no. 9: 11247-11259. https://doi.org/10.3390/ijms130911247