Polyoxypregnane Glycosides from Root of Marsdenia tenacissima and Inhibited Nitric Oxide Levels in LPS Stimulated RAW 264.7 Cells
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
2.2. NO Inhibitory Evaluations
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Compound Characterization Data
3.5. Cell Culture and Nitric Oxide Inhibitory Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Position | 1 a | 2 a | 3 a | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|---|---|
1 | 37.4 | 37.6 | 38.5 | 37.8 | 38.1 | 37.9 | 37.8 |
2 | 29.1 | 29.1 | 28.9 | 29.8 | 29.6 | 29.8 | 29.7 |
3 | 76.4 | 76.4 | 76.6 | 77.8 | 77.9 | 76.0 | 75.9 |
4 | 34.7 | 34.8 | 34.5 | 35.2 | 35.1 | 35.2 | 35.2 |
5 | 44.0 | 44.0 | 44.5 | 44.0 | 43.9 | 43.9 | 43.9 |
6 | 26.7 | 26.7 | 27.0 | 27.2 | 27.1 | 27.2 | 27.3 |
7 | 31.8 | 31.9 | 32.3 | 25.2 | 25.2 | 25.1 | 25.3 |
8 | 66.9 | 66.9 | 66.0 | 66.8 | 66.8 | 66.7 | 66.9 |
9 | 51.3 | 51.3 | 54.3 | 51.9 | 51.8 | 51.7 | 51.8 |
10 | 39.1 | 39.2 | 39.3 | 39.4 | 39.4 | 39.4 | 39.5 |
11 | 68.8 | 69.5 | 68.6 | 69.1 | 68.8 | 69.0 | 69.9 |
12 | 75.2 | 75.5 | 74.2 | 75.2 | 75.2 | 74.9 | 75.5 |
13 | 46.1 | 46.2 | 47.3 | 44.0 | 46.1 | 46.1 | 46.5 |
14 | 71.5 | 71.6 | 71.6 | 71.7 | 71.6 | 71.7 | 71.9 |
15 | 26.8 | 26.8 | 27.7 | 32.2 | 32.1 | 32.1 | 32.1 |
16 | 25.1 | 25.1 | 25.4 | 27.1 | 27.1 | 27.1 | 27.2 |
17 | 59.8 | 59.9 | 60.3 | 59.7 | 60.0 | 59.9 | 59.9 |
18 | 16.6 | 16.7 | 17.5 | 16.9 | 17.0 | 16.9 | 16.9 |
19 | 12.7 | 12.8 | 12.9 | 13.2 | 13.2 | 13.1 | 13.2 |
20 | 211.1 | 211.1 | 212.6 | 210.3 | 210.0 | 210.1 | 210.4 |
21 | 30.3 | 30.2 | 32.7 | 30.3 | 29.9 | 30.0 | 30.2 |
11-O | Tig | Bz | HPA | Tig | mBu | HPA | Bz |
1 | 167.4 | 166.2 | 172.0 | 167.2 | 175.5 | 171.5 | 166.5 |
2 | 128.5 | 130.0 | 41.1 | 129.2 | 41.5 | 41.4 | 130.6 |
3 | 138.1 | 129.5 | 125.3 | 138.1 | 26.6 | 124.6 | 129.9 |
4 | 11.6 | 128.1 | 130.7 | 12.2 | 11.9 | 131.3 | 128.7 |
5 | 14.2 | 132.9 | 115.6 | 14.3 | 15.7 | 116.4 | 133.5 |
6 | 128.1 | 155.2 | 158.2 | 128.7 | |||
7 | 129.5 | 115.6 | 116.4 | 129.9 | |||
8 | 130.7 | 131.3 | |||||
12-O | Bz | Bz | Ac | Ac | Ac | Bz | |
1 | 166.1 | 166.1 | 170.7 | 170.8 | 170.8 | 166.3 | |
2 | 129.4 | 129.0 | 20.5 | 20.9 | 20.3 | 130.6 | |
3 | 129.7 | 129.5 | 129.8 | ||||
4 | 128.3 | 128.1 | 128.7 | ||||
5 | 133.1 | 132.8 | 133.3 | ||||
6 | 128.3 | 128.1 | 128.7 | ||||
7 | 129.7 | 129.5 | 129.8 |
Position | 1 a | 2 a | 3 a | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|---|---|
Ole | Ole | Ole | Glc-1 | Glc-1 | Ole | Ole | |
1 | 96.9 | 97.0 | 97.0 | 101.2 | 101.1 | 97.5 | 97.4 |
2 | 36.1 | 36.1 | 36.1 | 71.4 | 71.5 | 37.9 | 37.8 |
3 | 78.8 | 78.8 | 78.8 | 78.0 | 78.0 | 79.7 | 79.6 |
4 | 79.1 | 79.1 | 79.1 | 84.7 | 84.7 | 83.4 | 83.3 |
5 | 71.4 | 71.4 | 71.4 | 78.0 | 77.9 | 71.9 | 71.9 |
6 | 18.6 | 18.6 | 18.6 | 62.6 | 62.6 | 19.1 | 19.0 |
3-OMe | 55.6 | 55.6 | 55.7 | 57.3 | 57.3 | ||
Allo | Allo | Allo | Glc-2 | Glc-2 | Allo | Allo | |
1 | 99.1 | 99.1 | 99.2 | 106.7 | 106.7 | 102.0 | 101.9 |
2 | 71.8 | 71.8 | 71.8 | 77.1 | 77.1 | 72.7 | 72.7 |
3 | 81.0 | 81.0 | 81.0 | 78.3 | 78.3 | 83.2 | 83.2 |
4 | 72.8 | 72.8 | 72.8 | 71.4 | 71.5 | 83.4 | 83.3 |
5 | 71.3 | 71.3 | 71.3 | 78.9 | 78.9 | 69.6 | 69.5 |
6 | 17.9 | 17.9 | 17.9 | 62.6 | 62.6 | 18.4 | 18.3 |
3-OMe | 62.0 | 61.9 | 62.0 | 61.7 | 61.7 | ||
Glc | Glc | ||||||
1 | 106.6 | 106.6 | |||||
2 | 75.5 | 75.5 | |||||
3 | 78.4 | 78.4 | |||||
4 | 72.0 | 72.0 | |||||
5 | 78.5 | 78.4 | |||||
6 | 63.0 | 63.0 |
Position | 1 a | 2 a | 3 a | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|---|---|
Ole | Ole | Ole | Glc-1 | Glc-1 | Ole | Ole | |
1 | 4.58 dd | 4.58 dd | 4.58 dd | 5.01 d | 5.08 d | 4.78 d | 4.73 d |
(9.8, 1.8) | (9.8, 1.9) | (9.7, 1.7) | (7.6) | (7.7) | (8.9) | (9.4) | |
2 | 1.47 m | 1.45 m | 1.49 m | 4.31 m | 4.31 m | 1.26 m | 1.33 m |
2.30 m | 2.30 m | 2.30 m | 2.41 m | 2.36 m | |||
3 | 3.39 m | 3.38 m | 3.38 m | 4.25 m | 4.23 m | 3.61 m | 3.57 m |
4 | 3.33 m | 3.31 m | 3.34 m | 4.09 m | 4.13 m | 3.59 m | 3.52 m |
5 | 3.33 m | 3.31 m | 3.34 m | 3.92 m | 3.92 m | 3.64 m | 3.52 m |
6 | 1.36 d | 1.32 d | 1.37 d | 4.33 m | 4.34 m | 1.67 d | 1.57 d |
(5.5) | (5.5) | (5.5) | 4.50 m | 4.52 m | (5.8) | (5.0) | |
3-OMe | 3.37 s | 3.35 s | 3.37 s | 3.50 s | 3.47 s | ||
Allo | Allo | Allo | Glc-2 | Glc-2 | Allo | Allo | |
1 | 4.79 d | 4.77 d | 4.79 d | 5.22 d | 5.25 d | 5.27 d | 5.24 d |
(8.1) | (8.3) | (8.3) | (7.8) | (7.8) | (8.1) | (8.1) | |
2 | 3.47 m | 3.46 m | 3.47 m | 4.11 m | 4.12 m | 3.84 m | 3.79 m |
3 | 3.79 t | 3.78 t | 3.78 t | 4.35 m | 4.37 m | 4.47 t | 4.45 m |
(3.0) | (3.0) | (3.0) | (2.5) | ||||
4 | 3.17 m | 3.17 m | 3.17 m | 4.21 m | 4.21 m | 3.73 dd | 3.72 dd |
(9.6, 2.5) | (9.4, 2.0) | ||||||
5 | 3.55 m | 3.54 m | 3.55 m | 3.93 m | 3.94 m | 4.27 m | 4.23 m |
6 | 1.25 d | 1.24 d | 1.25 d | 4.33 m | 4.34 m | 1.63 d | 1.61 d |
(6.0) | (6.4) | (6.1) | 4.45 m | 4.43 m | (6.2) | (6.2) | |
3-OMe | 3.66 s | 3.65 s | 3.65 s | 3.81 s | 3.80 s | ||
Glc | Glc | ||||||
1 | 4.97 d | 4.95 d | |||||
(7.8) | (7.7) | ||||||
2 | 4.02 m | 4.00 m | |||||
3 | 4.26 m | 4.22 m | |||||
4 | 4.22 m | 4.19 m | |||||
5 | 4.01 m | 3.97 m | |||||
6 | 4.36 dd | 4.36 dd | |||||
(11.6, 5,4) | (11.6, 5,1) | ||||||
4.54 dd | 4.53 d | ||||||
(11.6, 2.3) | (11.6) |
Compound | Concentration (μM) | NO Inhibition Rate (%) |
---|---|---|
1 | 40 | 48.19 ± 4.14 |
2 | 40 | 70.33 ± 5.39 |
3 | 40 | −4.09 ± 7.28 |
4 | 40 | −0.86 ± 1.59 |
5 | 40 | 0.80 ± 1.91 |
6 | 40 | −5.57 ± 1.15 |
7 | 40 | 7.13 ± 5.00 |
L-NMMA a | 40 | 68.03 ± 0.72 |
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Na, Z.; Gongpan, P.; Fan, Q. Polyoxypregnane Glycosides from Root of Marsdenia tenacissima and Inhibited Nitric Oxide Levels in LPS Stimulated RAW 264.7 Cells. Molecules 2023, 28, 886. https://doi.org/10.3390/molecules28020886
Na Z, Gongpan P, Fan Q. Polyoxypregnane Glycosides from Root of Marsdenia tenacissima and Inhibited Nitric Oxide Levels in LPS Stimulated RAW 264.7 Cells. Molecules. 2023; 28(2):886. https://doi.org/10.3390/molecules28020886
Chicago/Turabian StyleNa, Zhi, Pianchou Gongpan, and Qingfei Fan. 2023. "Polyoxypregnane Glycosides from Root of Marsdenia tenacissima and Inhibited Nitric Oxide Levels in LPS Stimulated RAW 264.7 Cells" Molecules 28, no. 2: 886. https://doi.org/10.3390/molecules28020886