Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii
Abstract
:1. Introduction
2. Results and Discussion
Position | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
1H | 13C | 1H | 13C | 1H | 13C | |
1 | 1.62 m 1.85 m | 22.6 | 1.51 m 1.80 m | 22.6 | 1.61 m 1.92 m | 22.5 |
2 | 1.97 m 2.54 br d (12.0) | 28.9 | 1.91 m 2.38 br d (12.0) | 28.9 | 1.97 m 2.43 br d (11.0) | 28.8 |
3 | 3.73 br s (W1/2 = 7.5) | 87.5 | 3.65 br s (W1/2 = 6.8) | 87.7 | 3.72 br s (W1/2 = 7.1) | 86.6 |
4 | --- | 41.9 | --- | 42.4 | --- | 41.5 |
5 | --- | 143.4 | --- | 143.3 | --- | 142.9 |
6 | 5.49 d (4.2) | 118.8 | 5.50 m | 118.9 | 5.70 br s | 119.2 |
7 | 1.64 m 2.24 m | 24.4 | 1.65 m 2.24 m | 24.5 | 1.67 m 2.43 m | 24.7 |
8 | 1.62 m | 43.6 | 1.62 m | 43.8 | 1.59 m | 43.8 |
9 | --- | 35.1 | --- | 36.6 | --- | 34.4 |
10 | 2.27 m | 38.3 | 2.28 m | 38.4 | 2.28 m | 38.2 |
11 | 1.36 m 1.59 m | 32.4 | 1.37 m 1.58 m | 32.6 | 1.35 m 1.62 m | 32.5 |
12 | 1.45 m 1.62 m | 30.6 | 1.46 m 1.65 m | 30.8 | 1.44 m 1.63 m | 30.9 |
13 | --- | 46.7 | --- | 46.5 | --- | 46.1 |
14 | --- | 49.4 | --- | 49.7 | --- | 49.3 |
15 | 1.09 m 1.19 m | 34.9 | 1.09 m 1.19 m | 35.0 | 1.08 m 1.20 m | 35.1 |
16 | 1.49 m 2.16 m | 28.2 | 1.48 m 2.15 m | 28.4 | 1.50 m 2.16 m | 28.5 |
17 | 1.69 m | 50.8 | 1.68 m | 50.9 | 1.69 m | 50.8 |
18 | 0.85 s | 15.5 | 0.85 s | 15.7 | 0.84 s | 15.8 |
19 | 0.91 s | 28.1 | 0.88 s | 28.2 | 0.99 s | 28.3 |
20 | 1.57 m | 36.2 | 1.56 m | 36.3 | 1.57 m | 36.2 |
21 | 1.11 d (6.0) | 19.1 | 1.10 d (6.3) | 19.2 | 1.10 d (6.1) | 19.3 |
22 | 1.76 m 2.00 m | 33.3 | 1.76 m 1.99 m | 33.4 | 1.75 m 2.00 m | 33.3 |
23 | 1.66 m 1.97 m | 29.0 | 1.65 m 1.93 m | 29.1 | 1.67 m 1.94 m | 29.0 |
24 | 3.80 d (9.0) | 92.4 | 3.80 d (8.9) | 92.6 | 3.80 d (9.4) | 92.6 |
25 | --- | 72.9 | --- | 73.2 | --- | 72.8 |
26 | 1.39 s | 26.7 | 1.39 s | 26.9 | 1.39 s | 26.9 |
27 | 1.52 s | 24.4 | 1.51 s | 24.5 | 1.52 s | 24.6 |
28 | 1.09 s | 28.2 | 1.11 s | 28.3 | 1.06 s | 28.2 |
29 | 1.51 s | 25.6 | 1.52 s | 25.8 | 1.50 s | 25.9 |
30 | 0.84 s | 18.0 | 0.83 s | 18.2 | 0.85 s | 18.2 |
Glc-1 | ||||||
1 | 4.93 d (6.8) | 103.7 | 4.92 d (6.8) | 103.8 | 4.93 d (7.1) | 103.8 |
2 | 4.29 m | 81.1 | 4.27 m | 81.2 | 4.29 m | 81.1 |
3 | 4.30 m | 78.3 | 4.29 m | 78.4 | 4.29 m | 78.2 |
4 | 3.98 m | 71.0 | 3.97 m | 71.1 | 3.98 m | 71.2 |
5 | 4.10 m | 76.1 | 4.09 m | 76.2 | 4.09 m | 76.3 |
6 | 3.98 m 4.89 d (9.7) | 69.9 | 3.97 m 4.88 d (9.4) | 70.0 | 3.98 m 4.89 d (9.5) | 70.0 |
Glc-2 | ||||||
1 | 4.850 d (7.3) | 104.5 | 4.85 d (7.7) | 104.6 | 4.850 d (7.7) | 104.5 |
2 | 4.06 m | 74.9 | 4.06 m | 75.0 | 4.06 m | 75.0 |
3 | 4.27 m | 77.6 | 4.28 m | 77.6 | 4.29 m | 78.2 |
4 | 4.18 m | 71.3 | 4.18 m | 71.4 | 4.18 m | 71.5 |
5 | 3.95 m | 78.0 | 3.94 m | 78.2 | 3.93 m | 78.2 |
6 | 4.30 m 4.50 d (11.0) | 62.2 | 4.30 m 4.50 m | 62.2 | 4.30 m 4.50 dd (1.9, 12.0) | 62.4 |
Glc-3 | ||||||
1 | 5.56 d (7.9) | 104.6 | 5.18 d (7.7) | 104.8 | 5.56 m | 104.7 |
2 | 4.11 m | 75.6 | 4.08 m | 74.7 | 4.11 m | 75.8 |
3 | 4.23 m | 77.9 | 4.27 m | 77.8 | 4.23 m | 78.0 |
4 | 4.07 m | 71.9 | 4.16 m | 71.4 | 4.07 m | 72.2 |
5 | 4.00 m | 78.1 | 4.02 m | 78.3 | 4.01 m | 78.2 |
6 | 4.32 m 4.60 d (12.0) | 63.1 | 4.23 m 4.53 m | 62.2 | 4.32 m 4.60 dd (2.3, 12.0) | 63.3 |
Glc-4 | ||||||
1 | 4.845 d (7.3) | 106.6 | 4.84 d (7.7) | 106.7 | 4.86 d (7.7) | 104.5 |
2 | 3.95 m | 75.1 | 3.98 m | 74.8 | 4.28 m | 81.3 |
3 | 4.23 m | 77.9 | 4.27 m | 76.5 | 4.29 m | 78.2 |
4 | 4.13 m | 77.0 | 4.27 m | 81.4 | 3.98 m | 71.2 |
5 | 4.06 m | 74.9 | 3.92 m | 76.2 | 4.07 m | 76.8 |
6 | 4.35 m 4.83 m | 69.9 | 4.30 m 4.50 m | 62.1 | 4.32 m 4.78 m | 69.8 |
Glc-5 | ||||||
1 | 5.18 d (7.9) | 104.9 | 5.57 d (8.1) | 104.8 | 5.34 d (7.7) | 104.7 |
2 | 4.06 m | 74.9 | 4.10 m | 75.8 | 4.09 m | 76.8 |
3 | 4.31 m | 78.0 | 4.23 m | 77.8 | 4.24 m | 77.7 |
4 | 4.19 m | 71.3 | 4.07 m | 72.2 | 4.30 m | 71.3 |
5 | 4.00 m | 78.1 | 4.00 m | 78.3 | 3.92 m | 78.2 |
6 | 4.35 m 4.54 d (12.0) | 62.5 | 4.31 m 4.59 m | 63.2 | 4.46 m 4.55 m | 62.5 |
Glc-6 | ||||||
1 | 5.16 d (7.8) | 105.0 | ||||
2 | 4.07 m | 74.9 | ||||
3 | 4.29 m | 78.2 | ||||
4 | 4.19 m | 71.5 | ||||
5 | 4.01 m | 78.3 | ||||
6 | 4.35 m4.57 m | 62.6 |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Isolation
HPLC Method | Time (min) | % of Mobile Phase A | % of Mobile Phase B |
---|---|---|---|
Method 1 | 0.0 | 90 | 10 |
15.0 | 75 | 25 | |
20.0 | 54 | 46 | |
21.0 | 10 | 90 | |
26.0 | 10 | 90 | |
26.5 | 90 | 10 | |
31.0 | 90 | 10 | |
Method 2 | 0.0 | 75 | 25 |
15.0 | 75 | 25 | |
16.0 | 70 | 30 | |
30.0 | 70 | 30 | |
31.0 | 10 | 90 | |
36.0 | 10 | 90 | |
37.0 | 75 | 25 | |
45.0 | 75 | 25 | |
Method 3 | 0.0 | 18 | 82 |
15.0 | 18 | 82 | |
20.0 | 50 | 50 | |
21.0 | 95 | 5 | |
25.0 | 95 | 5 | |
26.0 | 18 | 82 | |
31.0 | 18 | 82 | |
Method 4 | 0.0 | 75 | 25 |
15.0 | 75 | 25 | |
30.0 | 65 | 35 | |
31.0 | 30 | 70 | |
35.0 | 30 | 70 | |
36.0 | 75 | 25 | |
40.0 | 75 | 25 | |
Method 5 | 0.0 | 75 | 25 |
8.5 | 75 | 25 | |
10.0 | 71 | 29 | |
16.5 | 70 | 30 | |
18.5 | 66 | 34 | |
24.5 | 66 | 34 | |
26.5 | 48 | 52 | |
29.0 | 48 | 52 | |
Method 5 | 31.0 | 30 | 70 |
37.0 | 30 | 70 | |
37.1 | 75 | 25 | |
45.0 | 75 | 25 | |
Method 6 | 0.0 | 15 | 85 |
20.0 | 15 | 85 | |
30.0 | 95 | 5 | |
31.0 | 95 | 5 | |
36.0 | 15 | 85 | |
37.0 | 15 | 85 |
4. Conclusions
Supplementary Materials
Acknowledgments
Conflictts of Interest
References
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Prakash, I.; Chaturvedula, V.S.P. Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii. Molecules 2014, 19, 3669-3680. https://doi.org/10.3390/molecules19033669
Prakash I, Chaturvedula VSP. Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii. Molecules. 2014; 19(3):3669-3680. https://doi.org/10.3390/molecules19033669
Chicago/Turabian StylePrakash, Indra, and Venkata Sai Prakash Chaturvedula. 2014. "Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii" Molecules 19, no. 3: 3669-3680. https://doi.org/10.3390/molecules19033669