Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore
Abstract
:1. Introduction
2. Results and Discussion
C | 1 | 2 | 3 | 4 | 5 | |||||
---|---|---|---|---|---|---|---|---|---|---|
δC | δH (m, J Hz) | δC | δH (m, J Hz) | δC | δH (m, J Hz) | δC | δH (m, J Hz) | δC | δH (m, J Hz) | |
1 | 38.2 | 0.98, 1.56 m | 38.3 | 1.00, 1.60 m | 38.8 | 1.44, 0.88 m | 38.9 | 0.92, 1.46 m | 39.0 | 0.95, 1.48 m |
2 | 25.5 | 1.85, 2.09 m | 25.5 | 1.89, 2.09 m | 26.7 | 2.02, 1.81 m | 26.7 | 1.85, 2.06 m | 26.7 | 1.88, 2.10 m |
3 | 81.6 | 4.05 m | 81.7 | 4.08 m | 88.6 | 3.23 dd (4.0, 11.6) | 88.7 | 3.27 dd (3.9, 11.6) | 88.7 | 3.29 dd (3.8, 11.6) |
4 | 55.5 | − | 55.7 | − | 39.5 | − | 39.5 | − | 39.5 | − |
5 | 47.9 | 1.36 m | 48.0 | 1.37 m | 56.0 | 0.75 d (11.5) | 56.0 | 0.78 d (11.5) | 56.0 | 0.79 d (11.5) |
6 | 20.6 | 0.96, 1.38 m | 20.6 | 0.98, 1.42 m | 18.5 | 1.42, 1.24 m | 18.5 | 1.25, 1.43 m | 18.5 | 1.26, 1.47 m |
7 | 32.5 | 1.18, 1.42 m | 32.5 | 1.19, 1.42 m | 33.1 | 1.40, 1.23 m | 33.1 | 1.24, 1.40 m | 33.2 | 1.25, 1.41 m |
8 | 40.2 | − | 40.3 | − | 39.8 | − | 39.8 | − | 39.8 | − |
9 | 48.2 | 1.68 m | 48.2 | 1.71 m | 48.0 | 1.60 m | 48.1 | 1.66 m | 48.1 | 1.67 m |
10 | 36.3 | − | 36.3 | − | 37.0 | − | 37.0 | − | 37.1 | − |
11 | 23.4 | 1.91, 1.99 m | 23.5 | 1.90, 2.02 m | 23.7 | 1.93, 1.86 m | 23.7 | 1.87, 1.93 m | 23.7 | 1.86, 1.94 m |
12 | 122.6 | 5.40 br s | 122.6 | 5.41 br s | 122.8 | 5.39 br s | 122.8 | 5.43 br s | 122.9 | 5.45 br s |
13 | 144.1 | − | 144.2 | − | 144.1 | − | 144.2 | − | 144.3 | − |
14 | 42.2 | − | 42.2 | − | 42.1 | − | 42.3 | − | 42.3 | − |
15 | 28.3 | 1.14, 2.03 m | 28.3 | 1.15, 2.06 m | 28.3 | 2.27, 1.14 m | 28.5 | 1.16, 2.30 m | 28.6 | 1.18, 2.30 m |
16 | 23.4 | 1.76, 2.01 m | 23.4 | 1.77, 2.04 m | 23.4 | 2.05, 1.91 m | 27.0 | 2.36, 3.08 m | 27.0 | 2.33, 3.10 m |
17 | 47.1 | − | 47.2 | − | 46.9 | − | 47.3 | − | 47.3 | − |
18 | 41.7 | 3.13 dd (3.8, 13.5) | 41.7 | 3.15 dd (3.9, 13.5) | 41.6 | 3.16 dd (3.8, 13.4) | 41.7 | 3.36 dd (3.2, 14.0) | 41.8 | 3.35 dd (3.3, 13.9) |
19 | 46.1 | 1.23, 1.74 m | 46.1 | 1.23, 1.75 m | 46.2 | 1.71, 1.21 m | 41.3 | 1.71, 1.20 m | 41.5 | 1.75, 1.22 m |
20 | 30.6 | − | 30.7 | − | 30.7 | − | 35.7 | − | 35.7 | − |
21 | 33.9 | 1.11, 1.34 m | 34.0 | 1.13, 1.36 m | 33.9 | 1.30, 1.08 m | 73.3 | 3.65 br s | 73.3 | 3.66 br s |
22 | 32.5 | 1.72, 1.89 m | 32.5 | 1.72, 1.90 m | 32.5 | 1.82, 1.74 m | 39.6 | 2.25, 2.28 m | 39.7 | 2.23, 2.29 m |
23 | 206.3 | 9.61 s | 206.4 | 9.66 s | 28.1 | 1.30 s | 28.1 | 1.29 s | 28.2 | 1.31 s |
24 | 10.5 | 1.32 s | 10.6 | 1.34 s | 17.2 | 1.15 s | 17.2 | 1.16 s | 17.2 | 1.17 s |
25 | 15.6 | 0.89 s | 15.7 | 0.89 s | 15.5 | 0.83 s | 15.6 | 0.87 s | 15.7 | 0.88 s |
26 | 17.5 | 1.05 s | 17.5 | 1.06 s | 17.4 | 1.06 s | 17.4 | 1.09 s | 17.4 | 1.10 s |
27 | 26.2 | 1.21 s | 26.2 | 1.21 s | 26.1 | 1.23 s | 25.6 | 1.33 s | 25.7 | 1.35 s |
28 | 176.6 | − | 176.5 | − | 176.5 | − | 176.5 | − | 176.5 | − |
29 | 33.1 | 0.86 s | 33.1 | 0.86 s | 33.1 | 0.86 s | 28.3 | 1.14 s | 28.4 | 1.15 s |
30 | 23.7 | 0.88 s | 23.7 | 0.87 s | 23.7 | 0.87 s | 24.9 | 1.00 s | 25.0 | 1.01 s |
C | 1 | 2 | 3 | 4 | 5 | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
δC | δH | δC | δH | δC | δH | δC | δH | δC | δH | |||
3-O-sugar (Confirm here) | ||||||||||||
Ara | ||||||||||||
1 | 104.6 | 4.92 d (7.1) | 104.6 | 4.91 d (7.2) | 105.3 | 4.72 d (6.9) | 105.0 | 4.77 d (6.2) | 105.2 | 4.74 d (6.2) | ||
2 | 75.6 | 4.48 m | 75.5 | 4.50 m | 75.5 | 4.50 m | 76.4 | 4.50 m | 76.1 | 4.49 m | ||
3 | 75.5 | 3.91 d (10.3) | 75.4 | 3.90 m | 75.0 | 4.18 m | 74.1 | 4.26 m | 74.6 | 4.25 m | ||
4 | 80.7 | 4.10 m | 80.8 | 4.08 m | 80.3 | 4.21 m | 79.7 | 4.27 m | 81.0 | 4.26 m | ||
5 | 65.8 | 3.58, 4.35 m | 65.9 | 3.56, 4.32 m | 65.3 | 3.74, 4.38 m | 64.5 | 4.40, 3.80 m | 64.9 | 3.78, 4.41 m | ||
Rha I | ||||||||||||
1 | 101.3 | 6.33 s | 101.2 | 6.34 s | 101.4 | 6.30 s | 101.8 | 6.15 s | 101.7 | 6.26 s | ||
2 | 72.0 | 4.88 br s | 71.9 | 4.87 br s | 71.9 | 4.89 m | 72.3 | 4.71 m | 72.2 | 4.67 m | ||
3 | 82.9 | 4.73 m | 82.9 | 4.75 m | 82.9 | 4.72 m | 72.6 | 4.59 m | 72.4 | 4.60 m | ||
4 | 72.9 | 4.45 m | 73.0 | 4.47 m | 73.0 | 4.48 m | 74.1 | 4.28 m | 74.0 | 4.25 m | ||
5 | 69.5 | 4.71 m | 69.6 | 4.72 m | 69.7 | 4.66 m | 69.8 | 4.62 m | 69.7 | 4.72 m | ||
6 | 18.5 | 1.56 d (6.1) | 18.5 | 1.55 d (6.2) | 18.5 | 1.55 d (6.2) | 18.6 | 1.63 d (6.2) | 18.6 | 1.64 d (6.2) | ||
Xyl | ||||||||||||
1 | 107.7 | 5.34 d (7.6) | 107.6 | 5.35 d (7.7) | 107.6 | 5.34 d (7.7) | ||||||
2 | 75.6 | 4.03 m | 75.5 | 4.04 m | 75.6 | 4.05 m | ||||||
3 | 78.5 | 4.13 m | 78.5 | 4.15 m | 78.5 | 4.14 m | ||||||
4 | 71.1 | 4.12 m | 71.0 | 4.13 m | 71.1 | 4.16 m | ||||||
5 | 67.4 | 3.68, 4.45 m | 67.4 | 3.68, 4.23 m | 67.5 | 3.73, 4.32 m | ||||||
Glc I | ||||||||||||
1 | 106.9 | 5.08 d (7.9) | 106.9 | 5.08 d (7.9) | 106.2 | 5.03 d (8.0) | 106.4 | 5.13 d (7.9) | 106.3 | 5.04 d (8.0) | ||
2 | 75.5 | 3.99 m | 75.4 | 4.01 m | 74.9 | 4.00 m | 75.5 | 4.02 m | 74.9 | 3.99 m | ||
3 | 78.5 | 4.18 m | 78.5 | 4.16 m | 76.7 | 4.18 m | 78.6 | 4.19 m | 76.7 | 4.17 m | ||
4 | 71.2 | 4.20 m | 71.1 | 4.22 m | 81.3 | 4.29 m | 71.3 | 4.23 m | 81.3 | 4.28 m | ||
5 | 78.8 | 3.85 m | 78.8 | 3.86 m | 76.7 | 3.83 m | 78.8 | 3.89 m | 76.7 | 3.82 m | ||
6 | 62.5 | 4.33, 4.45 m | 62.4 | 4.36, 4.46 m | 61.8 | 4.41, 4.51 m | 62.6 | 4.37, 4.48 m | 61.8 | 4.40, 4.51 m | ||
Glc IV | ||||||||||||
1 | 105.1 | 5.15 d (7.8) | 105.1 | 5.15 d (7.8) | ||||||||
2 | 74.9 | 4.06 m | 74.9 | 4.05 m | ||||||||
3 | 78.3 | 4.19 m | 78.3 | 4.18 m | ||||||||
4 | 71.6 | 4.17 m | 71.5 | 4.17 m | ||||||||
5 | 78.4 | 3.99 m | 78.4 | 3.98 m | ||||||||
6 | 62.6 | 4.26, 4.52 m | 62.5 | 4.27, 4.53 m | ||||||||
28-O-sugar | ||||||||||||
Glc II | ||||||||||||
1 | 95.6 | 6.31 d (8.2) | 95.6 | 6.23 d (8.1) | 95.7 | 6.32 d (8.2) | 95.6 | 6.25 d (8.2) | 95.7 | 6.23 d (8.1) | ||
2 | 74.1 | 4.19 m | 73.9 | 4.10 m | 74.2 | 4.20 m | 73.8 | 4.08 m | 73.8 | 4.11 m | ||
3 | 79.3 | 4.03 m | 78.7 | 4.18 m | 79.3 | 4.02 m | 78.7 | 4.16 m | 78.7 | 4.17 m | ||
4 | 71.2 | 4.35 m | 70.8 | 4.28 m | 71.2 | 4.37 m | 70.8 | 4.23 m | 70.7 | 4.29 m | ||
5 | 78.9 | 4.27 m | 78.0 | 4.08 m | 78.9 | 4.28 m | 78.0 | 4.06 m | 78.0 | 4.08 m | ||
6 | 62.2 | 4.41, 4.44 m | 69.2 | 4.31, 4.64 m | 62.3 | 4.41, 4.46 m | 69.1 | 4.28, 4.62 m | 69.0 | 4.31, 4.63 m | ||
Glc III | ||||||||||||
1 | 104.9 | 4.97 d (7.7) | 104.8 | 4.97 d (7.8) | 104.9 | 4.98 d (7.8) | ||||||
2 | 75.3 | 3.92 m | 75.3 | 3.93 m | 75.3 | 3.93 m | ||||||
3 | 76.5 | 4.12 m | 76.5 | 4.12 m | 76.4 | 4.14 m | ||||||
4 | 78.2 | 4.40 m | 78.2 | 4.39 m | 78.0 | 4.39 m | ||||||
5 | 77.1 | 3.62 m | 77.1 | 3.64 m | 77.1 | 3.63 m | ||||||
6 | 61.2 | 4.07, 4.18 m | 61.2 | 4.07, 4.17 m | 61.1 | 4.08, 4.18 m | ||||||
Rha II | ||||||||||||
1 | 102.7 | 5.84 s | 102.7 | 5.84 s | 102.7 | 5.85 s | ||||||
2 | 72.6 | 4.66 m | 72.5 | 4.65 m | 72.6 | 4.65 m | ||||||
3 | 72.7 | 4.53 m | 72.7 | 4.52 m | 72.7 | 4.53 m | ||||||
4 | 74.0 | 4.31 m | 74.0 | 4.30 m | 74.0 | 4.32 m | ||||||
5 | 70.3 | 4.95 m | 70.3 | 4.94 m | 70.2 | 4.95 m | ||||||
6 | 18.5 | 1.68 d (6.2) | 18.5 | 1.68 d (6.2) | 18.5 | 1.62 d (6.2) |
Compounds a | Cytotoxic activity (IC50, μM; mean ± SD, n = 3) | |||
---|---|---|---|---|
HL-60 | HepG2 | A549 | HeLa | |
1 | 82.16 ± 2.79 | >100 | >100 | >100 |
3 | 45.32 ± 1.74 | 55.79 ± 2.57 | 75.68 ± 2.79 | >100 |
6 | 12.32 ± 0.41 | 13.25 ± 0.38 | 19.42 ± 0.67 | 22.20 ± 0.42 |
7 | 9.57 ± 0.54 | 10.64 ± 0.47 | 22.38 ± 0.72 | 17.31 ± 0.81 |
8 | 7.25 ± 0.31 | 12.11 ± 0.87 | 9.89 ± 0.57 | 15.47 ± 0.73 |
Doxorubicin b | 0.35 ± 0.05 | 0.50 ± 0.04 | 0.68 ± 0.10 | 0.66 ± 0.07 |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Acid Hydrolysis and GC Analysis of the Sugar Moieties in 1–5
3.5. Assays for in Vitro Antitumor Activity
4. Conclusions
Supplementary Materials
Acknowledgments
Conflicts of Interest
References
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Wang, X.; Wang, M.; Xu, M.; Wang, Y.; Tang, H.; Sun, X. Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore. Molecules 2014, 19, 2121-2134. https://doi.org/10.3390/molecules19022121
Wang X, Wang M, Xu M, Wang Y, Tang H, Sun X. Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore. Molecules. 2014; 19(2):2121-2134. https://doi.org/10.3390/molecules19022121
Chicago/Turabian StyleWang, Xiaoyang, Minchang Wang, Min Xu, Yi Wang, Haifeng Tang, and Xiaoli Sun. 2014. "Cytotoxic Oleanane-Type Triterpenoid Saponins from the Rhizomes of Anemone rivularis var. flore-minore" Molecules 19, no. 2: 2121-2134. https://doi.org/10.3390/molecules19022121