Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
Abstract
:Introduction
Results and Discussion
Extract and fractions | IC50 (μg/ml ± SD)a | ||
---|---|---|---|
A549 | DLD-1 | WS1 | |
Methanol | 15 ± 3 | 19.6 ± 0.9 | 10.6 ± 0.8 |
Spirostanol | 8.8 ± 0.4 | 11.1 ± 0.6 | 6.3 ± 0.3 |
Furostanol | 92 ± 19 | > 200 | 32 ± 2 |
Aglycone | Sugar moities | ||||
---|---|---|---|---|---|
Position | δCb | δHc | Position | δCb | δHc |
1 | 46.9 t | 2.20 m | Galactose | ||
1.25 m | 1 | 102.7 d | 5.00 d (7.8) | ||
2 | 70.5 d | 4.11 m | 2 | 72.4 d | 4.53 m |
3 | 84.2 d | 4.06 m | 3 | 75.1 d | 4.18 m |
4 | 31.5 t | 2.39 q-like (12.6) | 4 | 79.5 d | 4.56 m |
2.16 m | 5 | 75.5 d | 4.11 m | ||
5 | 47.6 d | 1.15 m | 6 | 60.9 d | 4.54 m, 4.30 m |
6 | 69.9 d | 4.01 m | Glucose A | ||
7 | 40.4 t | 2.05 m | 1 | 103.9 d | 5.10 d (7.8) |
1.16 m | 2 | 80.4 d | 4.26 m | ||
8 | 31.9 d | 2.11 m | 3 | 88.0 d | 4.13 m |
9 | 54.3 d | 0.71 m | 4 | 70.2 d | 3.80 m |
10 | 36.9 s | - | 5 | 77.2 d | 3.82 m |
11 | 21.3 t | 1.52 m | 6 | 62.5 d | 4.43 m, 4.00 m |
1.37 m | Glucose B | ||||
12 | 40.0 t | 1.67 m | 1 | 103.5 d | 5.64 d (7.9) |
1.08 m | 2 | 74.4 d | 4.09 m | ||
13 | 40.8 s | - | 3 | 87.6 d | 4.24 m |
14 | 56.1 d | 1.13 m | 4 | 69.5 d | 3.92 m |
15 | 32.1 t | 1.46 m | 5 | 77.5 d | 3.89 m |
1.23 m | 6 | 62.1 d | 4.38 m, 4.29 m | ||
16 | 81.2 d | 4.58 m | Glucose C | ||
17 | 62.8 d | 1.85 t (7.3) | 1 | 104.0 d | 5.22 d (7.8) |
18 | 16.6 q | 0.82 s | 2 | 75.1 d | 4.02 m |
19 | 17.0 q | 1.24 s | 3 | 77.9 d | 4.21 m |
20 | 42.0 d | 1.94 quint. (6.7) | 4 | 71.3 d | 4.07 m |
21 | 15.0 q | 1.15 d (6.9) | 5 | 78.3 d | 4.01 m |
22 | 109.4 s | - | 6 | 62.1 d | 4.54 m, 4.18 m |
23 | 31.7 t | 1.66 m | Glucose D | ||
24 | 29.1 t | 1.57 m | 1 | 105.0 d | 5.17 d (7.8) |
25 | 30.5 d | 1.58 m | 2 | 75.3 d | 4.03 m |
26 | 66.9 t | 3.62 m | 3 | 77.6 d | 4.19 m |
3.51 m | 4 | 71.3 d | 4.07 m | ||
27 | 17.3 q | 0.69 d (5.3) | 5 | 78.1 d | 3.93 m |
6 | 62.2 d | 4.50 m, 4.17 m |
Aglycone | Sugar moities | ||||
---|---|---|---|---|---|
Position | δCb | δHc | Position | δCb | δHc |
1 | 47.3 t | 1.90 m | Galactose | ||
0.92 m | 1 | 102.9 d | 4.39 d (7.8) | ||
2 | 71.4 d | 3.66 m | 2 | 72.9 d | 3.66 m |
3 | 85.3 d | 3.48 m | 3 | 75.6 d | 3.52 m |
4 | 31.6 t | 1.83 m | 4 | 80.4 d | 4.02 br d (3.2) |
1.76 m | 5 | 75.5 d | 3.52 m | ||
5 | 48.5 d | 1.20 m | 6 | 61.2 d | 3.89 m |
6 | 71.6 d | 3.80 m | 3.65 m | ||
7 | 40.8 t | 1.83 m | Glucose A | ||
1.18 m | 1 | 104.8 d | 4.56 d (7.8) | ||
8 | 30.8 d | 1.96 m | 2 | 84.8 d | 3.48 m |
9 | 55.6 d | 0.78 m | 3 | 78.2 d | 3.56 m |
10 | 37.9 s | - | 4 | 71.7 d | 3.22 m |
11 | 22.2 t | 1.56 m | 5 | 78.0 d | 3.29 m |
1.44 m | 6 | 63.2 d | 3.88 m | ||
12 | 41.1 t | 1.76 m | 3.58 m | ||
1.18 m | Glucose B | ||||
13 | 41.8 s | - | 1 | 106.1 d | 4.67 d (7.6) |
14 | 57.2 d | 1.17 m | 2 | 76.2 d | 3.27 m |
15 | 32.8 t | 2.00 m | 3 | 77.7 d | 3.37 m |
1.29 m | 4 | 70.9 d | 3.37 m | ||
16 | 82.2 d | 4.39 m | 5 | 78.7 d | 3.35 m |
17 | 63.9 d | 1.75 m | 6 | 62.2 d | 3.97 m |
18 | 17.0 q | 0.82 s | 3.80 m | ||
19 | 17.3 q | 1.06 s | |||
20 | 43.0 d | 1.90 m | |||
21 | 14.9 q | 0.96 d (7.0) | |||
22 | 110.6 s | - | |||
23 | 32.5 t | 1.70 m | |||
1.56 m | |||||
24 | 29.9 t | 1.62 m | |||
1.42 m | |||||
25 | 31.5 d | 1.59 m | |||
26 | 67.9 t | 3.44 m | |||
3.32 m | |||||
27 | 17.5 q | 0.79 d (6.4) |
Compounds | IC50 (μM ± SD) | ||
---|---|---|---|
A549 | DLD-1 | WS1 | |
Yayoisaponin C (1) | 3.7 ± 0.7 | 5.6 ± 0.2 | 3.0 ± 0.2 |
Eruboside B (2) | 5.3 ± 0.5 | 8.2 ± 0.4 | 3.6 ± 0.2 |
Aginoside (3) | 5.8 ± 0.9 | 7.9 ± 0.5 | 3.6 ± 0.2 |
Compound 4 | 9 ± 1 | 13 ± 1 | 3.1 ± 0.1 |
Leucospiroside A (5) | 5.0 ± 0.1 | 7.2 ± 0.1 | 4.55 ± 0.07 |
Compound 6 | 22 ± 2 | 22 ± 2 | 14.5 ± 0.5 |
Compound 7 | 7.8 ± 0.4 | 8.9 ± 0.2 | 7.7 ± 0.2 |
Etoposide | 1.1 ± 0.1 | 4.8 ± 0.8 | n.d. |
5-fluorouracil | 48 ± 18 | 11 ± 2 | 20 ± 2 |
Experimental Section
General experimental
Plant material
Extraction and isolation
Spectroscopic data for leucospiroside A (5)
Acid hydrolysis of leucospiroside A (5)
Cell culture
Cytotoxicity assay
Acknowledgements
References and Notes
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Mskhiladze, L.; Legault, J.; Lavoie, S.; Mshvildadze, V.; Kuchukhidze, J.; Elias, R.; Pichette, A. Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum. Molecules 2008, 13, 2925-2934. https://doi.org/10.3390/molecules13122925
Mskhiladze L, Legault J, Lavoie S, Mshvildadze V, Kuchukhidze J, Elias R, Pichette A. Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum. Molecules. 2008; 13(12):2925-2934. https://doi.org/10.3390/molecules13122925
Chicago/Turabian StyleMskhiladze, Lasha, Jean Legault, Serge Lavoie, Vakhtang Mshvildadze, Jumber Kuchukhidze, Riad Elias, and André Pichette. 2008. "Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum" Molecules 13, no. 12: 2925-2934. https://doi.org/10.3390/molecules13122925