3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
Abstract
:1. Introduction
2. Results
2.1. Chemistry and Structure Elucidation
2.2. X-ray Crystallographic Analysis
2.3. Plausible Biogenetic Pathway of Fladins B–D (1–3)
2.4. Bioactivity Evaluation of Fladins B–D (1–3)
3. Discussion
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Plant Materials
4.3. Extraction and Isolation
4.3.1. Fladin B (1)
4.3.2. Fladin C (2)
4.3.3. Fladin D (3)
4.4. Single Crystal X-ray Data of Fladin B (1)
4.5. Bioactivity Evaluation
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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No. | 1 a | 2 b | 3 a | |||
---|---|---|---|---|---|---|
δH, (J in Hz) | δC | δH, (J in Hz) | δC | δH, (J in Hz) | δC | |
1α | 1.95 (m) | 27.2 t | 1.73 (m) | 27.4 t | 1.92 (m) | 26.4 t |
1β | 2.45 (m) | 1.91 (m) | 1.94 (m) | |||
2α | 2.40 (ddd, 19.6, 7.3, 1.0) | 27.2 t | 2.47 (dd, 19.1, 7.3) | 26.5 t | 2.41 (m) | 26.7 t |
2β | 3.13 (ddd, 19.6, 11.0, 8.8) | 2.60 (m) | 2.46 (m) | |||
3 | - | 172.7 s | - | 171.0 s | - | 170.8 s |
4 | - | 74.6 s | - | 145.4 s | 1.93 (m) | 25.5 d |
5 | 2.07 (m) | 43.8 d | 2.66 (dd, 8.0, 4.0) | 43.0 d | 1.78 (m) | 38.8 d |
6α | 1.96 (m) | 28.0 t | 1.93 (m) | 28.9 t | 1.97 (m) | 22.2 t |
6β | 2.51 (m) | 2.31 (m) | 2.00 (m) | |||
7 | 5.57 (dt, 5.6, 2.1) | 127.5 d | 5.63 (m) | 127.2 d | 5.66 (dd, 4.2, 3.8) | 127.6 d |
8 | - | 132.8 s | - | 133.1 s | - | 132.8 s |
9 | - | 87.0 s | - | 86.5 s | - | 87.4 s |
10 | - | 37.8 s | - | 36.8 s | - | 37.2 s |
11α | 1.75 (ddd, 13.6, 3.6, 3.6) | 27.2 t | 1.77 (dd, 14.2, 2.7) | 28.5 t | 1.79 (m) | 28.4 t |
11β | 2.07 (m) | 1.98 (m) | 1.95 (m) | |||
12α | 1.33 (m) | 31.6 t | 1.34 (m) | 31.6 t | 1.31 (dt, 8.8, 2.9) | 31.6 t |
12β | 1.83(m) | 1.96 (m) | 1.95 (m) | |||
13 | - | 36.6 s | - | 36.6 s | - | 36.8 s |
14α | 1.82 (m) | 42.6 t | 1.75 (d, 3.0) | 42.6 t | 1.79 (m) | 42.7 t |
14β | 2.51 (m) | 2.57 (d, 3.0) | 2.54 (m) | |||
15 | 5.80 (dd, 17.5, 10.7) | 149.2 d | 5.82 (dd, 17.5, 10.5) | 149.1 d | 5.82 (dd, 17.5, 10.7) | 149.2 d |
16α | 4.89 (dd, 10.7, 1.2) | 110.2 t | 4.89 (d, 10.8) | 110.2 t | 4.90 (dd, 10.8, 1.2) | 110.2 t |
16β | 4.94 (dd, 17.5, 1.2) | 4.95 (d, 10.5) | 4.96 (dd, 17.2, 1.2) | |||
17 | 0.88 (s) | 21.2 q | 0.90 (s) | 21.3 q | 0.89 (s) | 21.2 q |
18 | 1.28 (s) | 34.4 q | 1.84 (s) | 23.1 q | 0.97 (d, 7.2) | 25.0 q |
19α | 1.33 (s) | 26.4 q | 4.92 (br s) | 115.9 t | 0.94 (d, 6.8) | 19.0 q |
19β | 4.98 (br s) | |||||
20 | 1.14 (s) | 19.9 q | 1.08 (s) | 19.1 q | 1.01 (s) | 19.0 q |
D—H···A | D—H | H···A | D···A | D—H···A |
---|---|---|---|---|
O1—H1···O2i | 0.82 | 2.13 | 2.810 (4) | 140.3 |
Symmetry code: (i) −x + 2, y − 1/2, −z + 2. |
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Li, W.-F.; Liang, Z.-M.; Zhao, C.-L.; Tsang, N.Y.; Li, J.-X.; Liu, Y.-H.; He, K.; Pan, L.-T.; Rong, L.; Zou, J.; et al. 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus. Molecules 2022, 27, 3098. https://doi.org/10.3390/molecules27103098
Li W-F, Liang Z-M, Zhao C-L, Tsang NY, Li J-X, Liu Y-H, He K, Pan L-T, Rong L, Zou J, et al. 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus. Molecules. 2022; 27(10):3098. https://doi.org/10.3390/molecules27103098
Chicago/Turabian StyleLi, Wan-Fei, Zheng-Ming Liang, Chen-Liang Zhao, Nga Yi Tsang, Ji-Xin Li, Ya-Hua Liu, Kang He, Lu-Tai Pan, Lijun Rong, Juan Zou, and et al. 2022. "3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus" Molecules 27, no. 10: 3098. https://doi.org/10.3390/molecules27103098