Rare Syringyl Acylated Flavonol Glycosides from the Aerial Parts of Leonurus japonicus Houtt.
Abstract
:1. Introduction
2. Results and Discussion
No. | 1 | 2 | ||
---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | |
2 | 156.2 | — | 156.3 | — |
3 | 133.2 | — | 133.1 | — |
4 | 177.0 | — | 177.1 | — |
5 | 161.0 | — | 161.0 | — |
6 | 99.1 | 6.14 (1H, br. s) | 98.9 | 6.16 (1H, br. s) |
7 | 165.9 | — | 165.1 | — |
8 | 93.9 | 6.34 (1H, br. s) | 93.8 | 6.34 (1H, br. s) |
9 | 156.5 | — | 156.5 | — |
10 | 103.2 | — | 103.5 | — |
1' | 120.8 | — | 120.8 | — |
2',6' | 130.7 | 8.02 (2H, d, 8.5) | 130.7 | 7.96 (2H, d, 8.5) |
3',5' | 114.9 | 6.81 (2H, d, 8.5) | 114.9 | 6.83 (2H, d, 8.5) |
4' | 159.8 | — | 159.8 | — |
1'' | 102.2 | 5.30 (1H, d, 7.5) | 101.5 | 5.32 (1H, d, 7.5) |
2'' | 71.0 | 3.57 (1H, dd, 7.5, 9.0) | 74.1 | 3.18 (1H, dd, 7.5, 9.0) |
3'' | 72.9 | 3.43 (1H, dd, 3.0, 9.0) | 76.3 | 3.23 (1H, dd, 9.0, 9.0) |
4'' | 67.9 | 3.65 (1H, m, overlapped) | 69.7 | 3.08 (1H, dd, 9.0, 9.0) |
5'' | 73.2 | 3.63 (1H, m, overlapped) | 75.6 | 3.29 (1H, m) |
6'' | 65.3 | 3.32 (1H, dd, 5.0, 9.0) | 66.8 | 3.38 (1H, dd, 5.0, 9.0) |
3.66 (1H, m, overlapped) | 3.73 (1H, br. d, ca. 11) | |||
5-OH | 12.53 (1H, br. s) | 12.54 (1H, br. s) | ||
1''' | 96.9 | 4.57 (1H, br. s) | 97.6 | 4.53 (1H, br. s) |
2''' | 72.5 | 4.92 (1H, br. d, ca. 3) | 72.5 | 4.95 (1H, br. d, ca. 3) |
3''' | 68.4 | 3.63 (1H, m, overlapped) | 68.6 | 3.61 (1H, dd, 3.0, 9.0) |
4''' | 72.4 | 3.26 (1H, dd, 9.5, 9.5) | 72.4 | 3.24 (1H, dd, 9.0, 9.5) |
5''' | 68.6 | 3.52 (1H, m) | 68.4 | 3.41 (1H, m) |
6''' | 18.0 | 1.15 (3H, d, 6.0) | 17.8 | 1.07 (3H, d, 6.0) |
1'''' | 119.2 | — | 119.4 | — |
2'''',6'''' | 107.0 | 7.19 (2H, s) | 107.1 | 7.19 (2H, s) |
3'''',5'''' | 147.4 | — | 147.4 | — |
4'''' | 140.9 | — | 140.7 | — |
7'''' | 164.7 | — | 164.7 | — |
-OCH3 | 55.9 | 3.81 (6H, s) | 56.0 | 3.82 (6H, s) |
No. | 3 | 4 | ||
---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | |
2 | 156.4 | — | 156.7 | — |
3 | 133.2 | — | 133.2 | — |
4 | 177.3 | — | 177.2 | — |
5 | 161.1 | — | 161.1 | — |
6 | 98.7 | 6.18 (1H, br. s) | 98.7 | 6.16 (1H, d, 1.5) |
7 | 164.3 | — | 164.3 | — |
8 | 93.7 | 6.42 (1H, br. s) | 93.7 | 6.38 (1H, d, 1.5) |
9 | 156.3 | — | 156.4 | — |
10 | 103.7 | — | 103.8 | — |
1' | 120.7 | — | 120.8 | — |
2',6' | 130.9 | 8.06 (2H, d, 8.0) | 130.7 | 7.98 (2H, d, 8.5) |
3',5' | 115.0 | 6.87 (2H, d, 8.0) | 115.0 | 6.88 (2H, d, 8.5) |
4' | 159.9 | — | 159.8 | — |
1'' | 102.0 | 5.34 (1H, d, 8.0) | 101.5 | 5.32 (1H, d, 7.5) |
2'' | 71.0 | 3.57 (1H, dd, 8.0, 9.0) | 74.1 | 3.19 (1H, dd, 7.5, 8.5) |
3'' | 72.8 | 3.43 (1H, dd, 3.0, 9.0) | 76.3 | 3.24 (1H, dd, 8.5, 8.5) |
4'' | 67.7 | 3.67 (1H, m, overlapped) | 69.9 | 3.07 (1H, dd, 8.5, 9.0) |
5'' | 73.1 | 3.64 (1H, m, overlapped) | 75.6 | 3.33 (1H, m) |
6'' | 65.0 | 3.29 (1H, dd, 5.0, 9.0) | 67.3 | 3.37 (1H, dd, 5.5, 12.0) |
3.67 (1H, m, overlapped) | 3.75 (1H, dd, 2.0, 12.0) | |||
5-OH | 12.57 (1H, br. s) | 12.51 (1H, br. s) | ||
1''' | 99.9 | 4.51 (1H, br. s) | 100.8 | 4.46 (1H, d, 1.5) |
2''' | 68.0 | 3.75 (1H, br. d, ca. 3) | 67.8 | 3.77 (1H, dd, 1.5, 3.5) |
3''' | 74.7 | 4.84 (1H, dd, 3.0, 9.5) | 74.7 | 4.78 (1H, dd, 3.5, 9.5) |
4''' | 68.9 | 3.49 (1H, dd, 9.5, 9.5) | 68.8 | 3.49 (1H, dd, 8.5, 9.5) |
5''' | 68.3 | 3.58 (1H, m) | 68.3 | 3.47 (1H, m) |
6''' | 17.8 | 1.14 (3H, d, 6.0) | 17.6 | 1.11 (3H, d, 6.0) |
1'''' | 119.8 | — | 119.9 | — |
2'''',6'''' | 107.2 | 7.27 (2H, s) | 107.2 | 7.28 (2H, s) |
3'''',5'''' | 147.3 | — | 147.3 | — |
4'''' | 140.4 | — | 140.4 | — |
7'''' | 165.3 | — | 165.2 | — |
-OCH3 | 56.0 | 3.81 (6H, s) | 56.0 | 3.82 (6H, s) |
δC | δH (J in Hz) | δC | δH (J in Hz) | ||
---|---|---|---|---|---|
2 | 156.2 | — | 3'' | 72.9 | 3.43 (1H, dd, 3.0, 9.5) |
3 | 133.4 | — | 4'' | 67.8 | 3.68 (1H, m, overlapped) |
4 | 177.2 | — | 5'' | 73.2 | 3.64 (1H, m, overlapped) |
5 | 161.1 | — | 6'' | 65.1 | 3.33 (1H, dd, 5.5, 9.5) |
6 | 98.6 | 6.20 (1H, br. s) | 3.67 (1H, m, overlapped) | ||
7 | 164.3 | — | 1''' | 96.8 | 4.62 (1H, d, 1.0) |
8 | 93.5 | 6.39 (1H, br. s) | 2''' | 72.6 | 4.93 (1H, dd, 1.0, 3.0) |
9 | 156.2 | — | 3''' | 68.6 | 3.65 (1H, m, overlapped) |
10 | 103.7 | — | 4''' | 72.4 | 3.28 (1H, dd, 9.0, 9.5) |
1' | 121.0 | — | 5''' | 68.4 | 3.54 (1H, m) |
2' | 115.9 | 7.54 (1H, d, 2.0) | 6''' | 18.0 | 1.16 (3H, d, 6.0) |
3' | 144.7 | — | 1'''' | 119.2 | — |
4' | 148.4 | — | 2'''',6'''' | 107.0 | 7.20 (2H, s) |
5' | 115.0 | 6.80 (1H, d, 8.5) | 3'''', 5'''' | 147.4 | — |
6' | 121.7 | 7.63 (1H, d, 2.0, 8.5) | 4'''' | 140.7 | — |
5-OH | 12.58 (1H, br. s) | 7'''' | 164.7 | ||
1'' | 101.9 | 5.35 (1H, d, 8.0) | -OCH3 | 55.9 | 3.81 (6H, s) |
2'' | 71.0 | 3.60 (1H, dd, 8.0, 9.0) |
Concentration ( μM) | Inhibitory rate (%) | |
---|---|---|
Control | 0 | 0.0 ± 1.2 |
Orlistat | 1 | 43.3 ± 4.1 * |
1 | 10 | 61.4 ± 10.0 ** |
2 | 10 | 52.8 ± 4.2 * |
3 | 10 | 56.9 ± 9.6 ** |
4 | 10 | 51.7 ± 6.9 * |
5 | 10 | 49.1 ± 4.9 * |
6 | 10 | 44.3 ± 4.3 * |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
Acid Hydrolysis of 1–5
3.4. TG Accumulation Inhibitory Effects Assay
Statistical Analysis
4. Conclusions
Acknowledgments
References
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Zhang, Y.; Deng, S.; Qu, L.; An, Y.-T.; Wu, C.-H.; Han, L.-F.; Gao, X.-M.; Wang, T. Rare Syringyl Acylated Flavonol Glycosides from the Aerial Parts of Leonurus japonicus Houtt. Molecules 2013, 18, 2967-2977. https://doi.org/10.3390/molecules18032967
Zhang Y, Deng S, Qu L, An Y-T, Wu C-H, Han L-F, Gao X-M, Wang T. Rare Syringyl Acylated Flavonol Glycosides from the Aerial Parts of Leonurus japonicus Houtt. Molecules. 2013; 18(3):2967-2977. https://doi.org/10.3390/molecules18032967
Chicago/Turabian StyleZhang, Yi, Shen Deng, Lu Qu, Ya-Ting An, Chun-Hua Wu, Li-Feng Han, Xiu-Mei Gao, and Tao Wang. 2013. "Rare Syringyl Acylated Flavonol Glycosides from the Aerial Parts of Leonurus japonicus Houtt." Molecules 18, no. 3: 2967-2977. https://doi.org/10.3390/molecules18032967