Isolation, Synthesis and Structures of Cytotoxic Ginsenoside Derivatives
Abstract
:Introduction
Results and Discussion
Characterizations of compounds 1 – 8
Position | Rb1 (1) | Rb3 (2) | Rd (3) | Re (4) | M1 (5) | DM1 (6) | PM1 (7) | SM1 (8) |
---|---|---|---|---|---|---|---|---|
1 | 39.2 | 39.3 | 39.2 | 39.7 | 39.3 | 38.9 | 39.5 | 39.1 |
2 | 26.3 | 26.3 | 26.7 | 26.6 | 28.1 | 27.3 | 28.2 | 28.0 |
3 | 88.9 | 89.0 | 89.0 | 78.1 | 77.9 | 78.8 | 78.0 | 77.8 |
4 | 39.6 | 39.6 | 39.1 | 39.9 | 39.4 | 38.9 | 39.4 | 39.3 |
5 | 56.1 | 56.7 | 56.3 | 60.7 | 56.2 | 55.8 | 56.4 | 56.1 |
6 | 18.6 | 18.6 | 18.5 | 74.2 | 18.6 | 18.2 | 18.7 | 18.5 |
7 | 35.1 | 35.2 | 35.1 | 45.8 | 35.0 | 34.7 | 35.2 | 34.9 |
8 | 39.8 | 39.9 | 40.4 | 41.3 | 39.9 | 39.7 | 39.5 | 39.8 |
9 | 50.0 | 50.2 | 50.2 | 49.5 | 50.2 | 49.8 | 50.3 | 50.0 |
10 | 36.7 | 37.0 | 37.1 | 39.6 | 37.2 | 37.0 | 37.3 | 37.1 |
11 | 30.8 | 31.0 | 31.1 | 30.7 | 30.7 | 30.3 | 30.7 | 30.7 |
12 | 70.1 | 70.1 | 70.2 | 70.1 | 70.1 | 70.6 | 70.1 | 69.8 |
13 | 49.3 | 49.5 | 49.6 | 49.4 | 49.3 | 47.8 | 49.5 | 49.3 |
14 | 51.3 | 51.4 | 51.5 | 51.3 | 51.3 | 51.7 | 51.4 | 51.3 |
15 | 30.8 | 30.8 | 30.7 | 30.9 | 30.7 | 30.6 | 31.0 | 30.5 |
16 | 26.6 | 26.8 | 26.6 | 26.6 | 26.5 | 26.6 | 26.7 | 26.5 |
17 | 51.5 | 51.6 | 51.6 | 51.6 | 51.5 | 51.3 | 51.6 | 51.2 |
18 | 16.0 | 16.0 | 17.7 | 17.7 | 16.2 | 16.1 | 16.3 | 16.1 |
19 | 16.1 | 16.2 | 16.4 | 17.8 | 15.9 | 15.7 | 16.0 | 15.8 |
20 | 83.1 | 83.5 | 83.1 | 83.3 | 83.2 | 84.3 | 83.4 | 83.1 |
21 | 22.3 | 22.3 | 22.4 | 22.4 | 22.3 | 21.2 | 22.9 | 22.7 |
22 | 36.2 | 36.1 | 36.2 | 35.8 | 36.0 | 35.4 | 36.1 | 35.9 |
23 | 23.0 | 23.0 | 23.2 | 23.3 | 23.1 | 22.0 | 23.0 | 22.8 |
24 | 125.8 | 126.0 | 125.8 | 126.0 | 125.8 | 124.5 | 126.0 | 125.8 |
25 | 131.1 | 131.0 | 131.0 | 130.9 | 130.8 | 131.5 | 130.9 | 130.7 |
26 | 25.8 | 25.8 | 25.7 | 25.8 | 25.7 | 25.7 | 25.8 | 25.5 |
27 | 17.9 | 17.9 | 18.0 | 17.6 | 17.7 | 17.6 | 17.8 | 17.6 |
28 | 28.0 | 28.3 | 28.1 | 32.3 | 28.6 | 28.0 | 28.6 | 28.4 |
29 | 16.6 | 16.5 | 16.3 | 17.3 | 16.2 | 15.3 | 16.3 | 16.1 |
30 | 17.1 | 17.4 | 17.7 | 17.3 | 17.3 | 16.9 | 17.4 | 17.2 |
Position | M1 (5) | DM1 (6) | PM1 (7) | SM1 (8) | ||||
---|---|---|---|---|---|---|---|---|
δC | δH | δC | δH | δC | δH | δC | δH | |
20-O-Glc | ||||||||
1’ | 98.1 | 5.14 (d, 7.5) | 96.8 | 4.51 (d, 7.6) | 98.0 | 5.11 (d, 7.5) | 97.8 | 5.14 (d, 7.5) |
2’ | 75.0 | 3.96 (t, 8.0) | 73.3 | 3.36 (m) | 75.0 | 3.95 (d. 8.0) | 74.7 | 3.92 (d. 8.0) |
3’ | 79.2 | 4.19 (m) | 76.7 | 3.55 (m) | 79.2 | 4.18 (m) | 79.0 | 4.19 (m) |
4’ | 71.5 | 4.12 (dd, 9.0, 8.5) | 70.0 | 3.43 (m) | 71.6 | 4.16 (m) | 71.4 | 4.17 (m) |
5’ | 78.2 | 3.88 (m) | 73.4 | 3.44 (m) | 78.0 | 3.98 (m) | 77.8 | 3.98 (m) |
6’ | 62.7 | 4.44, 4.27 (m) | 63.3 | 4.30, 4.38 (m) | 64.6 | 4.63, 5.02 (m) | 64.4 | 4.65, 5.05 (m) |
Glc-6’-O-ester | ||||||||
1’’ | 174.1 | 173.5 | 173.3 | |||||
2’’ | 34.2 | 2.27, 2.35 (m) | 34.4 | 2.43, 2.48 (m) | 34.2 | 2.42, 2.49 (m) | ||
3’’ | 24.8 | 1.27c | 25.3 | 1.42 | 25.0 | 1.45 | ||
4’’ | 29.6 c | 1.27c | 29.4 | 1.27c | 30.7 | 1.27c | ||
5’’ | 29.1 c | 1.27c | 28.2 | 1.27c | 29.2 | 1.27c | ||
6’’ | 29.2 c | 1.27c | 29.6 | 1.27c | 29.3 | 1.27c | ||
7’’ | 29.3 c | 1.27c | 30.0c | 1.27c | 29.4 | 1.27c | ||
8’’ | 29.4 c | 1.27c | 30.0 c | 1.27c | 29.7 c | 1.27c | ||
9’’ | 29.6 c | 1.27c | 30.0 c | 1.27c | 29.7 c | 1.27c | ||
10’’ | 31.9 | 1.36 (m) | 30.0 c | 1.27c | 29.7 c | 1.27c | ||
11’’ | 22.6 | 1.56 (m) | 30.0 c | 1.27c | 29.7 c | 1.27c | ||
12’’ | 14.1 | 0.85 (t, 6.0) | 29.6 | 1.27c | 29.7 c | 1.27c | ||
13’’ | 29.8 | 1.27c | 29.5 | 1.27c | ||||
14’’ | 32.1 | 1.30 (m) | 30.5 | 1.27c | ||||
15’’ | 22.1 | 1.48 (m) | 29.7 | 1.27c | ||||
16’’ | 14.2 | 0.83 (t, 5.6) | 31.9 | 1.36 (m) | ||||
17’’ | 22.7 | 1.48 (m) | ||||||
18’’ | 14.0 | 0.85 (t, 0.56) |
Bioactivity Results
M1 (5) | DM1 (6) | PM1 (7) | SM1 (8) | |
---|---|---|---|---|
MCF-7 | 8.48 | 0.50 | 2.31 | 1.65 |
SK-MEL-2 | 14.71 | 1.46 | 1.88 | 0.17 |
B16 | 6.10 | 6.13 | 5.73 | 0.33 |
COR-L23 | 33.0 | 5.68 | 4.86 | 7.76 |
Conclusions
Experimental
General
Chemicals and reagents
Extraction and isolation
Enzymatic reaction
Synthesis of DM1, PM1 and SM1
In vitro cytotoxicity assays
Acknowledgments
References
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Lei, J.; Li, X.; Gong, X.-j.; Zheng, Y.-n. Isolation, Synthesis and Structures of Cytotoxic Ginsenoside Derivatives. Molecules 2007, 12, 2140-2150. https://doi.org/10.3390/12092140
Lei J, Li X, Gong X-j, Zheng Y-n. Isolation, Synthesis and Structures of Cytotoxic Ginsenoside Derivatives. Molecules. 2007; 12(9):2140-2150. https://doi.org/10.3390/12092140
Chicago/Turabian StyleLei, Jun, Xiang Li, Xiao-jie Gong, and Yi-nan Zheng. 2007. "Isolation, Synthesis and Structures of Cytotoxic Ginsenoside Derivatives" Molecules 12, no. 9: 2140-2150. https://doi.org/10.3390/12092140
APA StyleLei, J., Li, X., Gong, X.-j., & Zheng, Y.-n. (2007). Isolation, Synthesis and Structures of Cytotoxic Ginsenoside Derivatives. Molecules, 12(9), 2140-2150. https://doi.org/10.3390/12092140