Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Purification of Compounds 1–5
2.2. Structure Elucidation of Compounds 1–5
2.3. In Vitro Cytotoxic Activities 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 2–4
3.5. X-ray Crystal Structure Analysis of Compound 1
3.6. Cytotoxicity Assays of Compounds 1–5
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1 and 5 are available from the authors. |
No. | 2 a | 3 b | 4 a | |||
---|---|---|---|---|---|---|
δC, Type | δH (J in Hz) | δc, Type | δH (J in Hz) | δc, Type | δH (J in Hz) | |
1 | 25.3 CH2 | 1.79 m, 1.65 m | 25.3 CH2 | 1.83 m, 1.71 m | 25.3 CH2 | 1.87 m, 1.75 m |
2 | 32.8 CH2 | 3.76 br d (7.5), 2.22 m | 32.9 CH2 | 3.81 br d (7.5), 2.16 m | 33.2 CH2 | 3.87 m, 2.29 m |
3 | 217.8 C | 217.6 C | 217.6 C | |||
4 | 80.3 C | 80.4 C | 80.3 C | |||
5 | 78.2 CH | 5.36 dd (8.5, 2.0) | 78.1 CH | 5.37 dd (9.6, 1.2) | 78.1 CH | 5.39 br d (9.5) |
6 | 79.8 CH | 4.60 dd (8.5, 5.0) | 79.9 CH | 4.65 dd (9.6, 6.0) | 79.9 CH | 4.69 dd (9.5,6.5) |
7 | 41.5 CH | 2.97 m | 41.6 CH | 3.01 m | 41.7 CH | 3.02 m |
8 | 70.3 CH | 4.35 d (10.5) | 70.3 CH | 4.43 d (10.2) | 70.5 CH | 4.40 d (10.0) |
9 | 78.7 CH | 5.11 d (10.5) | 79.3 CH | 5.18 d (10.2) | 78.4 CH | 5.15 d (10.0) |
10 | 29.8 CH | 2.15 m | 30.1 CH | 2.21 m | 30.0 CH | 2.23 m |
11 | 132.6 C | 132.7 C | 132.7 C | |||
12 | 169.6 C | 169.6 C | 169.5 C | |||
13 | 123.9 CH2 | 6.27 d (3.0), 5.62 d (3.0) | 123.8 CH2 | 6.30 d (3.0) 5.67 d (3.0) | 123.8 CH2 | 6.32 d (3.0) 5.67 d (3.0) |
14 | 20.0 CH3 | 0.92 d (7.0) | 19.9 CH3 | 0.94 d (6.6) | 20.0 CH3 | 0.98 d (6.5) |
15 | 23.4 CH3 | 1.18 s | 23.3 CH3 | 1.21 s | 23.5 CH3 | 1.24 s |
1′ | 172.5 C | 176.3 C | 175.9 C | |||
2′ | 42.7 CH2 | 2.31 d (7.0), 2.26 o | 33.9 CH | 2.67 m | 41.3 CH | 2.52 m |
3′ | 25.3 CH | 2.09 o c | 18.0 CH3 | 1.21 d (6.6) | 26.3 CH2 | 1.76 o, 1.52 o |
4′ | 21.3 CH3 | 0.96 d (6.0) | 17.9 CH3 | 1.20 d (6.6) | 16.1 CH3 | 1.24 d (7.0) |
5′ | 21.4 CH3 | 0.95 d (6.0) | 10.7 CH3 | 0.98 t (7.0) | ||
1′′ | 173.3 C | 167.2 C | 176.7 C | |||
2′′ | 43.0 CH2 | 2.26 o, 2.06 o | 136.4 C | 41.5 CH | 2.52 m | |
3′′ | 25.4 CH | 2.09 o | 124.7 CH2 | 5.63 dq (3.6, 1.8), 6.13 dq (3.6, 1.8) | 26.2 CH2 | 1.76 o, 1.52 o |
4′′ | 21.4 CH3 | 0.96 d (6.5) | 17.1 CH3 | 1.96 br s | 16.2 CH3 | 1.26 d (7.0) |
5′′ | 21.4 CH3 | 0.95 d (6.5) | 10.6 CH3 | 0.96 t (7.0) |
Compounds | IC50 (μM) | ||
---|---|---|---|
A549 | HepG2 | Hela | |
1 | >40 | 16.98 ± 2.23 | 29.39 ± 0.17 |
2 | 30.70 ± 0.51 | 7.47 ± 0.21 | 16.82 ± 0.27 |
3 | >40 | >40 | >40 |
4 | >40 | >40 | >40 |
5 | >40 | 31.64 ± 0.16 | 11.63 ± 1.00 |
cis-platin | 7.90 ± 0.23 | 13.03 ± 1.49 | 15.34 ± 0.35 |
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Zhang, T.; Si, J.-G.; Zhang, Q.-B.; Chen, J.-H.; Ding, G.; Zhang, H.-W.; Jia, H.-M.; Zou, Z.-M. Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity. Molecules 2018, 23, 1078. https://doi.org/10.3390/molecules23051078
Zhang T, Si J-G, Zhang Q-B, Chen J-H, Ding G, Zhang H-W, Jia H-M, Zou Z-M. Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity. Molecules. 2018; 23(5):1078. https://doi.org/10.3390/molecules23051078
Chicago/Turabian StyleZhang, Tao, Jin-Guang Si, Qiu-Bo Zhang, Jia-Huan Chen, Gang Ding, Hong-Wu Zhang, Hong-Mei Jia, and Zhong-Mei Zou. 2018. "Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity" Molecules 23, no. 5: 1078. https://doi.org/10.3390/molecules23051078