Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. Physical and Spectroscopic Data of Isatisindigoticanines E–G and Isatindigoside D
3.2. Absolute Configuration Determination of Sugar
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the Compounds 1–23 are available from the authors. |
No. | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δH | δC | δH | δC | δH | δC | |
1 | 10.19, s | 12.06, brs | ||||
2 | 169.5 | 168.3 | 156.8 | |||
3 | 7.48, s | 136.7 | 8.63, s | 130.6 | ||
4 | 126.1 | 118.8 | 160.5 | |||
4a | 122.5 | 116.8 | 120.3 | |||
5 | 7.20, d (2.2) | 110.1 | 155.0 | 8.13, d (8.0) | 126.3 | |
6 | 152.2 | 6.67, d (7.5) | 102.6 | 7.47, dd (8.0, 7.2) | 126.0 | |
7 | 6.63, dd (8.3, 2.2) | 110.7 | 7.15, overlap | 123.9 | 7.82, dd (8.1, 7.2) | 134.9 |
8 | 6.66, d (8.3) | 116.5 | 6.85, d (7.3) | 106.2 | 7.72, d (8.1) | 126.2 |
8a | 135.4 | 138.0 | 148.8 | |||
1’ | 125.4 | 10.51, s | 11.98, brs | |||
2’ | 7.57, d (8.5) | 132.1 | 112.5 | 7.84, d (2.2) | 128.3 | |
3’ | 6.90, d (8.5) | 116.1 | 9.45, s | 133.5 | 112.5 | |
3’a | 126.3 | 127.4 | ||||
4’ | 159.6 | 7.50, d (7.5) | 117.9 | 7.87, d (7.5) | 118.5 | |
5’ | 6.90, d (8.5) | 116.1 | 7.15, overlap | 121.1 | 7.22, dd (8.1, 7.5) | 120.9 |
6’ | 7.57, d (8.5) | 132.1 | 7.00, dd (7.5, 7.4) | 127.0 | 7.25, dd (8.1, 7.5) | 123.0 |
7’ | 7.14, overlap | 109.5 | 7.50, d (7.5) | 112.6 | ||
7’a | 139.4 | 136.4 | ||||
1’’ | 8.13, s | 122.6 | ||||
2’’ | 125.6 | |||||
3’’ | 3.17, 2H, m | 26.2 | ||||
4’’ | 4.25, 2H, t (7.0) | 44.7 | ||||
OMe | 4.04, s | 55.9 | ||||
6-OH | 10.12, s | |||||
4’-OH | 8.96, s |
No. | 23 | No. | 23 | ||
---|---|---|---|---|---|
δH (J in Hz) | δC | δH (J in Hz) | δC | ||
1a | 7.45, brs | 172.9 | 3’’ | 112.1 | |
1b | 7.14, brs | 3’’a | 126.7 | ||
2 | 5.68, s | 38.7 | 4’’ | 7.56, d (8.0) | 118.4 |
1’ | 10.35, brs | 5’’ | 6.93, dd (8.0, 7.1) | 118.9 | |
2’ | 126.8 | 6’’ | 7.04, dd (8.1, 7.1) | 120.5 | |
3’ | 133.0 | 7’’ | 7.32, d (8.1) | 111.4 | |
3’a | 121.2 | 7’’a | 136.0 | ||
4’ | 7.77, d (8.0) | 118.1 | Glc-1 | 4.63, d (7.8) | 106.6 |
5’ | 6.92, dd (8.0, 7.2) | 118.4 | 2 | 3.38, overlap | 74.1 |
6’ | 6.97, dd (8.1, 7.2) | 120.8 | 3 | 3.26, m | 76.8 |
7’ | 7.26, d (8.1) | 111.6 | 4 | 3.28, m | 69.8 |
7’a | 133.3 | 5 | 3.14, m | 77.2 | |
1’’ | 10.94, brs | 6a | 3.56, dd (10.8, 5.6) | 61.0 | |
2’’ | 7.38, s | 123.9 | 6b | 3.67, dd (10.8, 1.8) |
Compounds | IC50 a | Cytotoxicity | Compounds | IC50 a | Cytotoxicity |
---|---|---|---|---|---|
1 | >100 | >100 | 13 | >100 | >100 |
2 | >100 | >100 | 14 | >100 | >100 |
3 | >100 | >100 | 15 | 5.0 ± 1.3 | >100 |
4 | >100 | >100 | 16 | >100 | >100 |
5 | >100 | >100 | 17 | 74.4 ± 3.8 | >100 |
6 | >100 | >100 | 18 | >100 | >100 |
7 | >100 | >100 | 19 | >100 | >100 |
8 | >100 | >100 | 20 | >100 | >100 |
9 | 1.2 ± 0.9 | >25 | 21 | >100 | >100 |
10 | >100 | >100 | 22 | >100 | >100 |
11 | >100 | >100 | 23 | >100 | >100 |
12 | >100 | >100 | AG b | 22.7 ± 0.4 | >100 |
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Zhang, D.; Shi, Y.; Li, J.; Ruan, D.; Jia, Q.; Zhu, W.; Chen, K.; Li, Y.; Wang, R. Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria. Molecules 2019, 24, 4033. https://doi.org/10.3390/molecules24224033
Zhang D, Shi Y, Li J, Ruan D, Jia Q, Zhu W, Chen K, Li Y, Wang R. Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria. Molecules. 2019; 24(22):4033. https://doi.org/10.3390/molecules24224033
Chicago/Turabian StyleZhang, Dongdong, Yanhong Shi, Jingyi Li, Deqing Ruan, Qi Jia, Weiliang Zhu, Kaixian Chen, Yiming Li, and Rui Wang. 2019. "Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria" Molecules 24, no. 22: 4033. https://doi.org/10.3390/molecules24224033