Five New Taraxerene-Type Triterpenes from the Branch Barks of Davidia involucrata
Abstract
:1. Introduction
2. Results and Discussion
Compounds | Cell Lines | ||
---|---|---|---|
SGC-7901 | MCF-7 | BEL-7404 | |
1 | >100 | >100 | >100 |
2 | >100 | >100 | >100 |
3 | 58.23 ± 2.36 | 65.35 ± 3.12 | 70.26 ± 4.21 |
4 | 30.57 ± 1.63 | 41.34 ± 1.24 | 37.29 ± 1.64 |
5 | 32.22 ± 1.22 | 42.54 ± 1.67 | 39.26 ± 1.14 |
6 | >100 | >100 | >100 |
7 | 35.47 ± 1.55 | 55.24 ± 2.28 | 53.82 ± 2.11 |
9 | 37.65 ± 1.85 | 58.93 ± 2.58 | 54.77 ± 2.05 |
Doxorubicin | 0.19 ± 0.032 | 0.08 ± 0.007 | 0.12 ± 0.011 |
3. Experimental Section
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectral Data
Position | 1a [δH (J in Hz)] | 2b [δH (J in Hz)] | 3c [δH (J in Hz)] | 4d [δH (J in Hz)] | 5d [δH (J in Hz)] |
---|---|---|---|---|---|
1 | 0.80, m | 0.84, m | 1.60, d (14.3) | 2.05, m | 1.80, m |
1.53, m | 1.51, m | 1.79, d (14.3) | 2.12, m | 1.85, m | |
2 | – | – | – | 2.30, m | 2.32, m |
2.75, ddd (16.3, 11.2, 4.9) | 2.59, ddd (16.3, 11.2, 6.4) | ||||
3 | 2.01, m | 3.18, dd (9.8, 6.8) | – | – | – |
2.25, m | |||||
4 | – | – | – | – | – |
5 | 1.00, m | 0.98, m | 1.61, d (10.9) | 1.78, d (11.1) | 2.03, d (11.0) |
6 | 1.23, m | 1.21, m | 3.91, ddd (15.0, 10.9, 4.1) | 3.98, ddd (15.2, 11.1, 4.2) | 3.98, ddd (15.2, 11.2, 4.0) |
1.83, d (13.0) | 1.80, d (13.0) | ||||
7 | 1.35, m | 1.27, m | 1.38, t (10.9) | 1.49, t (11.1) | 1.50, t (11.2) |
2.03 dt-like (13.0) | 2.01 dt-like (13.0) | 2.28, dd (10.9, 4.1) | 2.30, dd (11.1, 4.2) | 2.28, dd (11.2, 4.0) | |
8 | – | – | – | – | – |
9 | 1.49, m | 1.51, m | 1.52, m | 1.60, d (7.0) | 1.70, m |
10 | – | – | – | – | – |
11 | 1.51, m | 1.50, m | 1.60, m | 4.28, t (7.0) | 1.85, m |
1.65 m | 1.60, m | 1.72, m | 1.92, m | ||
12 | 1.48, m | 1.46, m | 1.60, m | 1.98, d (14.5) | 1.80, m |
1.60, m | 1.53, m | 1.75, m | 2.12, d (14.5) | 1.92, m | |
13 | – | – | – | – | – |
14 | – | – | – | – | – |
15 | 5.51, dd (8.2, 3.1) | 5.47, dd (8.0, 3.1) | 5.60, dd (8.1, 2.9) | 5.96, br. s | 5.94, br. s |
16 | 1.68, dd (15.2, 3.1) | 1.66, dd (15.2, 3.1) | 1.79, dd (14.5, 8.1) | – | – |
2.13, dd (15.2, 8.2) | 2.09, dd (15.2, 8.0) | 2.05, dd (14.5, 2.9) | |||
17 | – | – | – | – | – |
18 | 0.57, dd (13.5, 3.8) | 0.60, dd (13.5, 3.8) | 1.22, dd (13.5, 5.1) | 1.88, dd (13.5, 5.2) | 1.92, dd (13.5, 5.1) |
19 | 0.91, dd (13.5, 3.8) | 0.96, dd (13.5, 3.8) | 1.44, dd (13.5, 5.1) | 1.63, dd (13.5, 5.2) | 1.65, dd (13.5, 5.1) |
1.37, t (13.5) | 1.32, t (13.5) | 1.88, t (13.5) | 2.54, t (13.5) | 2.49, t (13.5) | |
20 | – | – | – | – | – |
21 | 1.53, m | 1.46, m | – | – | – |
1.65, m | 1.60, m | ||||
22 | 1.24, m | 1.20, m | 1.87, d (12.8) | 2.51, d (13.8) | 2.49, d (13.7) |
2.05, m | 2.03, m | 2.63, d (12.8) | 2.62, d (13.8) | 2.61, d (13.7) | |
23 | 1.22, s | 1.05, s | 1.29, s | 1.35, s | 3.58, d (10.2) |
3.80, d (10.2) | |||||
24 | 0.94, s | 0.91, s | 1.32, s | 1.36, s | 1.27, s |
25 | 0.87, s | 0.84, s | 0.82, s | 0.98, s | 1.13, s |
26 | 1.08, s | 1.02, s | 1.11, s | 1.26, s | 1.30, s |
27 | 1.07, s | 1.01, s | 1.02, s | 1.22, s | 0.96, s |
28 | 3.10 (d, 10.9) | 3.06 (d, 10.9) | 0.78, s | 1.07, s | 1.06, s |
3.23, (d, 10.9) | 3.18, (d, 10.9) | ||||
29 | 1.05, s | 1.02, s | 1.06, s | 3.26, d (10.3) | 3.24, d (10.4) |
3.71, d (10.3) | 3.69, d (10.4) | ||||
30 | 0.94, s | 0.90, s | 1.05, s | 1.06, s | 1.05, s |
Position | 1a (δc mult.) | 2b (δc mult.) | 3c (δc mult.) | 4d (δc mult.) | 5e (δc mult.) |
---|---|---|---|---|---|
1 | 38.2 (CH2) | 38.1 (CH2) | 37.3 (CH2) | 39.3 (CH2) | 36.4 (CH2) |
2 | – | – | – | 34.1 (CH2) | 31.6 (CH2) |
3 | 29.8 (CH2) | 77.3 (CH) | 219.7 (C) | 222.5 (C) | 220.9 (C) |
4 | 47.5 (C) | 47.7 (C) | 47.0 (C) | 49.2 (C) | 54.3 (C) |
5 | 55.7 (CH) | 55.7 (CH) | 58.8 (CH) | 59.9 (CH) | 54.2 (CH) |
6 | 19.9 (CH2) | 19.8 (CH2) | 67.3 (CH) | 67.5 (CH) | 67.2 (CH) |
7 | 40.6 (CH2) | 40.5 (CH2) | 50.4 (CH2) | 50.2 (CH2) | 50.3 (CH2) |
8 | 38.9 (C) | 38.9 (C) | 39.7 (C) | 41.2 (C) | 42.5 (C) |
9 | 48.5 (CH) | 48.5 (CH) | 47.0 (CH) | 55.9 (CH) | 47.2 (CH) |
10 | 40.3 (C) | 40.3 (C) | 38.5 (C) | 40.7 (C) | 40.0 (C) |
11 | 17.3 (CH2) | 17.2 (CH2) | 16.8 (CH2) | 65.9 (CH) | 17.7 (CH2) |
12 | 30.6 (CH2) | 30.5 (CH2) | 33.2 (CH2) | 43.3 (CH2) | 37.4 (CH2) |
13 | 37.6 (C) | 37.6 (C) | 37.3 (C) | 38.9 (C) | 39.3 (C) |
14 | 158.5 (C) | 158.3 (C) | 157.3 (C) | 177.9 (C) | 178.3 (C) |
15 | 116.0 (CH) | 116.1 (CH) | 116.5 (CH) | 118.8 (CH) | 119.4 (CH) |
16 | 32.6 (CH2) | 32.5 (CH2) | 37.5 (CH2) | 206.3 (C) | 206.3 (C) |
17 | 37.9 (C) | 37.9 (C) | 37.3 (C) | 47.1 (C) | 47.2 (C) |
18 | 44.8 (CH) | 44.7 (CH) | 48.8 (CH | 46.4 (CH) | 46.7 (CH) |
19 | 35.7 (CH2) | 35.7 (CH2) | 37.3 (CH2 | 31.4 (CH2) | 31.8 (CH2) |
20 | 28.9 (C) | 28.8 (C) | 43.1 (C) | 48.7 (C) | 48.5 (C) |
21 | 33.3 (CH2) | 33.2 (CH2) | 219.7 (C) | 219.9 (C) | 220.0 (C) |
22 | 27.8 (CH2) | 27.6 (CH2) | 51.5 (CH2) | 48.4 (CH2) | 48.2 (CH2) |
23 | 25.6 (CH3) | 25.9 (CH3) | 31.5 (CH3) | 32.2 (CH3) | 72.5 (CH2) |
24 | 21.3 (CH3) | 21.3 (CH3) | 19.7 (CH3) | 20.6 (CH3) | 16.4 (CH3) |
25 | 14.7 (CH3) | 14.7 (CH3) | 16.0 (CH3) | 17.9 (CH3) | 17.1 (CH3) |
26 | 25.7 (CH3) | 25.7 (CH3) | 25.6 (CH3) | 25.5 (CH3) | 24.6 (CH3) |
27 | 21.6 (CH3) | 21.5 (CH3) | 20.2 (CH3) | 29.1 (CH3) | 26.9 (CH3) |
28 | 65.1 (CH2) | 64.7 (CH2) | 32.5 (CH3) | 33.8 (CH3) | 33.9 (CH3) |
29 | 33.4 (CH3) | 33.3 (CH3) | 28.1 (CH3) | 71.2 (CH2) | 71.2 (CH2) |
30 | 29.8 (CH3) | 29.7 (CH3) | 23.0 (CH3) | 20.2 (CH3) | 20.2 (CH3) |
3.5. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
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Tan, Q.-W.; Ouyang, M.-A.; Chen, Q.-J.; Wu, Z.-J. Five New Taraxerene-Type Triterpenes from the Branch Barks of Davidia involucrata. Molecules 2014, 19, 17619-17631. https://doi.org/10.3390/molecules191117619
Tan Q-W, Ouyang M-A, Chen Q-J, Wu Z-J. Five New Taraxerene-Type Triterpenes from the Branch Barks of Davidia involucrata. Molecules. 2014; 19(11):17619-17631. https://doi.org/10.3390/molecules191117619
Chicago/Turabian StyleTan, Qing-Wei, Ming-An Ouyang, Qi-Jian Chen, and Zu-Jian Wu. 2014. "Five New Taraxerene-Type Triterpenes from the Branch Barks of Davidia involucrata" Molecules 19, no. 11: 17619-17631. https://doi.org/10.3390/molecules191117619