Secondary Metabolites from the Roots of Beilschmiedia tsangii and Their Anti-Inflammatory Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation
2.2. Anti-inflammatory Activities
3. Experimental Section
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
4. Conclusions
Acknowledgments
- Conflict of InterestThe authors declare no conflict of interest.
References
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position | 1 | 2 | ||
---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 41.6 (CH) | 2.36, m | 42.0 (CH) | 2.41, br dd (12.0, 6.0) |
2 | 31.5 (CH2) | 1.56, td (12.0, 6.0) 1.65, br dd (12.0, 5.4) | 31.0 (CH2) | 1.57, td (12.0, 6.0) 1.62, br dd (12.0, 5.4) |
3 | 50.5 (CH) | 3.05, ddd (13.5, 12.0, 5.4) | 54.3 (CH) | 2.94, ddd (13.2, 12.0, 5.2) |
4 | 201.6 (C) | - | 203.7 (C) | - |
5 | 135.8 (CH) | 6.70, d (1.2) | 132.3 (CH) | 6.54, s |
6 | 151.5 (C) | - | 158.5 (C) | - |
7 | 36.2 (CH) | 3.51, br s | 71.2 (C) | - |
8 | 123.5 (CH) | 5.56, ddd (10.2, 3.0, 1.8) | 125.9 (CH) | 6.01, br d (10.2) |
9 | 131.5 (CH) | 5.85, ddd (10.2, 4.2, 3.0) | 132.6 (CH) | 5.87, dd (10.2, 4.2) |
10 | 35.8 (CH) | 2.40, m | 35.9 (CH) | 2.47, m |
11 | 48.0 (CH) | 1.47, m | 47.9 (CH) | 1.45, m |
12 | 35.2 (CH) | 2.87, m | 32.9 (CH) | 2.97, br dd (8.4, 6.0) |
13 | 44.8 (CH) | 2.35, m | 51.9 (CH) | 2.24, ddd (13.2, 8.4, 1.2) |
14 | 168.3 (C) | - | - | - |
1′ | 38.4 (CH2) | 1.54, m | 38.2 (CH2) | 1.54, m |
2′ | 28.3 (CH2) | 1.28, m | 28.0 (CH2) | 1.25, m |
3′ | 31.0 (CH2) | 1.28, m | 30.4 (CH2) | 1.28, m |
4′ | 33.2 (CH2) | 1.28, m | 33.0 (CH2) | 1.28, m |
5′ | 23.9 (CH2) | 1.28, m | 23.7 (CH2) | 1.30, m |
6′ | 15.0 (CH3) | 0.88, t (7.2) | 14.4 (CH3) | 0.90, t (6.9) |
position | 3 | 4 | ||
---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 41.9 (CH) | 2.37, m | 43.7 (CH) | 2.72, br dd (12.0, 5.4) |
2 | 31.8 (CH2) | 1.28, m 1.99, ddd (14.4, 9.6, 4.8) | 41.3 (CH) | 2.45, dt (9.0, 5.4) |
3 | 132.3 (CH) | 5.50, ddd (15.6, 9.6, 6.0) | 41.1 (CH) | 1.72, m |
4 | 130.1 (CH) | 5.24, ddd (15.6, 9.6, 5.4) | 41.2 (CH) | 2.25, br t (7.8) |
5 | 31.2 (CH2) | 2.38, m | 41.0 (CH) | 2.36, m |
6 | 34.3 (CH2) | 2.29, ddd (11.4, 5.4, 2.4) 2.22, m | 39.9 (CH2) | 1.63, br d (12.3) 1.87, br dd (12.3, 5.4) |
7 | 173.5 (C) | - | 43.4 (CH) | 1.89, br dd (9.0, 5.4) |
8 | - | - | 48.2 (CH) | 2.91, br dd (8.2, 3.6) |
9 | 70.1 (CH) | 4.87, dt (5.6, 2.4) | 38.8 (CH) | 2.53, m |
10 | 67.2 (CH) | 3.96, br d (7.2) | 134.2 (CH) | 6.19, br t (7.2) |
11 | 40.8 (CH) | 2.21, m | 131.9 (CH) | 6.25, br t (7.2) |
12 | 33.3 (CH) | 3.18, br dt (15.6, 7.5) | - | - |
13 | 30.9 (CH) | 3.02, m | - | - |
14 | 136.0 (CH) | 6.16, dd (10.4, 6.0) | - | - |
15 | 123.9 (CH) | 6.25, dd (10.4, 5.6) | - | - |
1′ | 36.3 (CH2) | 1.47, q (7.5) | 43.1 (CH2) | 2.78, dd (15.6, 7.8) 2.81, br d (7.8) |
2′ | 27.7 (CH2) | 1.27–1.33, m | 136.5 (C) | - |
3′ | 29.5 (CH2) | 1.27–1.33, m | 110.5 (CH) | 6.75, d (1.8) |
4′ | 31.9 (CH2) | 2.24, m | 149.2 (C) | - |
5′ | 22.7 (CH2) | 1.27–1.33, m | 147.3 (C) | - |
6′ | 14.1 (CH3) | 0.90, t (6.9) | 109.3 (CH) | 6.74, d (7.8) |
7′ | - | - | 123.1 (CH) | 6.68, dd (7.8, 1.8) |
1″ | - | - | 155.3 (CH) | 6.72, dd (15.6, 8.2) |
2″ | - | - | 121.3 (CH) | 5.71, dd (15.6, 0.9) |
3″ | - | - | 168.4 (C) | - |
OCH2O | - | - | 102.3 (CH2) | 5.94, s |
position | 6 | 7 | ||
---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 36.9 (CH2) | 1.37, br d (12.0) 1.69, dd (12.0, 4.2) | 56.9 (CH) | 1.65, ddd (10.2, 3.6, 1.8) |
2 | 42.8 (CH) | 2.64, d (4.2) | 23.2 (CH2) | 1.33, m 1.66, m |
3 | 147.7 (C) | - | 40.8 (CH2) | 1.56, ddd (15.0, 8.4, 1.8) 1.93, ddd (15.0, 11.1, 2.1) |
4 | 147.5 (CH) | 6.60, dd (3.6, 0.6) | 75.1 (C) | - |
5 | 71.2 (CH) | 4.09, d (3.6) | 73.3 (CH) | 3.60, br dd (6.0, 2.4) |
6 | 48.7 (C) | - | 32.6 (CH2) | 1.57, m 1.75, m |
7 | 56.9 (C) | - | 34.7 (CH2) | 2.05, m 2.43, ddd (13.2, 9.0, 4.2) |
8 | 36.2 (CH2) | 1.10, m 1.58, m | 151.8 (C) | - |
9 | 38.6 (CH2) | 1.25, m | 42.3 (CH) | 2.37, q (10.2) |
10 | 27.1 (CH2) | 1.32, br dd (6.9, 0.9) 1.54, m | 36.0 (CH2) | 1.58, m 1.74, t (10.2) |
11 | 54.9 (C) | - | 34.1 (C) | - |
12 | 26.9 (CH3) | 1.089, s | 21.5 (CH3) | 1.14, s |
13 | 24.2 (CH3) | 0.96, s | 110.5 (CH2) | 4.92, d (1.2) 4.94, d (1.2) |
14 | 18.7 (CH3) | 1.087, s | 22.1 (CH3) | 0.98, s |
15 | 193.3 (CH) | 9.54, s | 30.1 (CH3) | 1.00, s |
OH | - | - | - | 2.07, br s |
OH | - | - | - | 2.29, br d (3.0) |
Compounds | Emax (%) a | IC50 (μM) b |
---|---|---|
endiandric acid M (4) | 97.03 ± 1.30 | 31.70 ± 0.25 |
beilschminol B (5) | 55.62 ± 1.96 | 95.37 ± 0.52 |
ursolic acid (11) | 36.55 ± 4.66 | >100 |
6β-hydroxystigmast-4-en-3-one c | 11.69 ± 2.91 | >100 |
rel-(7S,8S,7′R,8′R)-3,4,5,3′,4′,5′-hexmethoxylignanc | 52.67 ± 5.05 | 98.26 ± 0.13 |
aminoguanidine d (a selective iNOS inhibitor) | 80.35 ± 0.26 | 26.55 ± 0.48 |
Nω-nitro-L-arginine d (a nonselective iNOS inhibitor) | 43.72 ± 0.76 | 152.46 ± 10.53 |
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Huang, Y.-T.; Chang, H.-S.; Wang, G.-J.; Lin, C.-H.; Chen, I.-S. Secondary Metabolites from the Roots of Beilschmiedia tsangii and Their Anti-Inflammatory Activities. Int. J. Mol. Sci. 2012, 13, 16430-16443. https://doi.org/10.3390/ijms131216430
Huang Y-T, Chang H-S, Wang G-J, Lin C-H, Chen I-S. Secondary Metabolites from the Roots of Beilschmiedia tsangii and Their Anti-Inflammatory Activities. International Journal of Molecular Sciences. 2012; 13(12):16430-16443. https://doi.org/10.3390/ijms131216430
Chicago/Turabian StyleHuang, Yun-Ting, Hsun-Shuo Chang, Guei-Jane Wang, Chu-Hung Lin, and Ih-Sheng Chen. 2012. "Secondary Metabolites from the Roots of Beilschmiedia tsangii and Their Anti-Inflammatory Activities" International Journal of Molecular Sciences 13, no. 12: 16430-16443. https://doi.org/10.3390/ijms131216430