Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of the Compounds
2.2. Biological Evaluation
3. Experimental Section
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Compound Characterization Data
3.5. ECD Calculation for Compounds 1–4
3.6. MTPA Esterification of 4
3.7. Bioactivity Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1‒13 are available from the authors. |
1 | 2 | ||||
---|---|---|---|---|---|
no. | δH | δC | no. | δH | δC |
1 | Ha: 1.50 (m) | 34.2, CH2 | 1 | Ha: 1.38 (m) | 33.2, CH2 |
Hb: 1.40 (m) | Hb: 1.33 (overlap) | ||||
2 | Ha: 1.97 (m) | 25.6, CH2 | 2 | Ha: 1.96 (m) | 25.3, CH2 |
Hb: 1.57 (m) | Hb: 1.56 (m) | ||||
3 | 3.42 (t-like, 2.63) | 76.3, CH | 3 | 3.42 (t-like, 2.8) | 76.3, CH |
4 | 37.8, C | 4 | 37.6, C | ||
5 | 1.36 (m) | 49.7, CH | 5 | 1.33 (overlap) | 49.7, CH |
6 | Ha: 1.48 (m) | 18.4, CH2 | 6 | Ha: 1.48 (m) | 18.3, CH2 |
Hb: 1.38 (m) | Hb: 1.44 (m) | ||||
7 | Ha: 1.84 (m) | 37.3, CH2 | 7 | Ha: 1.62 (m) | 34.5, CH2 |
Hb: 1.51 (overlap) | Hb: 1.31 (m) | ||||
8 | 41.4, C | 8 | 37.6, C | ||
9 | 1.51 (overlap) | 51.2, CH | 9 | 1.83 (dd, 10.6, 7.1) | 48.2, CH |
10 | 37.9, C | 10 | 37.5, C | ||
11 | Ha: 1.70 (m) | 23.1, CH2 | 11 | Ha: 2.13 (m) | 23.6, CH2 |
Hb: 1.34 (m) | Hb: 1.93 (m) | ||||
12 | Ha: 2.61 (ddd, 13.6, 4.7, 1.7) | 26.4, CH2 | 12 | 5.40 (t, 3.7) | 114.7, CH |
Hb: 2.16 (tdd, 13.6, 5.2, 1.7) | |||||
13 | 156.7, C | 13 | 151.9, C | ||
14 | 61.4, C | 14 | 49.4, C | ||
15 | 6.16 (d, 5.4) | 142.7, CH | 15 | Ha: 2.59 (brd,17.4) | 41.4, CH2 |
Hb: 1.85 (brdt,17.4, 1.8) | |||||
16 | 6.21 (dd, 5.4, 1.7) | 129.6, CH | 16 | 5.83 (dt, 5.7, 2.6) | 133.5, CH |
17 | 5.79 (q-like, 1.7) | 120.2, CH | 17 | 6.04 (dt, 5.7, 1.8) | 131.3, CH |
18 | 0.64 (s) | 15.5, CH3 | 18 | 0.71 (s) | 17.6, CH3 |
19 | 0.84 (s) | 16.3, CH3 | 19 | 0.93 (s) | 15.2, CH3 |
20 | 0.98 (s) | 28.5, CH3 | 20 | 0.97 (s) | 28.5, CH3 |
21 | 0.84 (s) | 22.4, CH3 | 21 | 0.86 (s) | 22.3, CH3 |
22 | 1.05 (s) | 17.3, CH3 | 22 | 1.08 (s) | 24.9, CH3 |
3 | 4 | ||||
---|---|---|---|---|---|
no. | δH | δC | no. | δH | δC |
1 | 3.18 (m) | 56.7, CH | 1 | 3.61 (dd, 11.4, 4.6) | 76.6, CH |
2 | Ha: 1.99 (m) | 23.7, CH2 | 2 | 1.72 (m) | 26.7, CH2 |
Hb: 1.93 (m) | |||||
3 | Ha: 2.45 (m) | 39.0, CH2 | 3 | 2.19 (m) | 32.4, CH2 |
Hb: 2.36 (m) | |||||
4 | 158.3, C | 4 | 139.0, C | ||
5 | 135.3, C | 5 | 138.2, C | ||
6 | 202.1, C | 6 | 205.8, C | ||
7 | 2.46 (m) | 45.2, CH2 | 7 | Ha: 2.49 (m) | 43.2, CH2 |
Hb: 2.29 (m) | |||||
8 | Ha: 1.86 (m) | 21.4, CH2 | 8 | Ha: 1.94 (m) | 20.8, CH2 |
Hb:1.49 (m) | Hb: 1.90 (m) | ||||
9 | Ha: 1.95 (m) | 46.8, CH2 | 9 | Ha: 2.09 (ddd, 13.2, 5.2, 3.3) | 36.7, CH2 |
Hb: 1.72(m) | Hb: 1.53 (ddd, 13.2, 11.1, 6.4) | ||||
10 | 75.1, C | 10 | 42.7, C | ||
11 | 0.99 (s) | 20.8, CH3 | 11 | 1.74 (s) | 21.2, CH3 |
12 | 2.07 (brs) | 17.2, CH3 | 12 | 0.81 (s) | 18.8, CH3 |
10 -OH | 4.83 (s) a | 1 -OH | 4.67 (d, 4.8) a |
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Liu, Y.-Y.; Huang, D.-L.; Dong, Y.; Qin, D.-P.; Yan, Y.-M.; Cheng, Y.-X. Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins. Molecules 2019, 24, 4379. https://doi.org/10.3390/molecules24234379
Liu Y-Y, Huang D-L, Dong Y, Qin D-P, Yan Y-M, Cheng Y-X. Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins. Molecules. 2019; 24(23):4379. https://doi.org/10.3390/molecules24234379
Chicago/Turabian StyleLiu, Yun-Yun, Dan-Ling Huang, Yun Dong, Da-Peng Qin, Yong-Ming Yan, and Yong-Xian Cheng. 2019. "Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins" Molecules 24, no. 23: 4379. https://doi.org/10.3390/molecules24234379