Structural Characterization of the Degradation Products of a Minor Natural Sweet Diterpene Glycoside Rebaudioside M under Acidic Conditions
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. Reagents and Chemicals
3.2. Plant Material
3.3. HPLC Conditions
3.4. General Instrumentation
3.5. Degradation of Rebaudioside M (1)
3.5.1. Isolation of Degradation Compounds 2–4
3.5.2. Physical and Spectroscopic Data of Compounds 2–4
3.5.3. General Procedure for Acid Hydrolysis and Determination of Sugar Configuration in 2–4
3.5.4. Enzymatic Hydrolysis of 4
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Position | 2 | 3 | 4 | |||
---|---|---|---|---|---|---|
1H | 13C | 1H | 13C | 1H | 13C | |
1 | 0.77 t (12.8), 1.76 d (12.8) | 40.2 | 0.78 t (13.2), 1.75 d (13.0) | 40.3 | 0.77 td (3.8, 13.2), 1.47 m | 39.4 |
2 | 1.36 m, 2.25 m | 19.3 | 1.34 m, 2.23 m | 19.3 | 2.02 m | 21.6 |
3 | 1.03 m, 2.33 m | 38.0 | 1.00 td (3.9, 12.8), 2.32 d (12.3) | 38.4 | 1.07 m, 2.77 d (13.1) | 37.3 |
4 | - | 44.0 | - | 43.8 | - | 44.1 |
5 | 1.05 d (12.7) | 56.9 | 1.04 d (12.7) | 57.1 | 1.06 m | 57.1 |
6 | 2.21 m, 2.31 m | 21.8 | 2.11 d (13.5), 2.43 m | 23.1 | 1.38 m, 2.04 m | 19.4 |
7 | 1.49 m, 1.89 m | 40.0 | 1.37 m, 1.88 m | 42.8 | 1.34 m, 1.61 m | 41.3 |
8 | - | - | - | |||
9 | 0.83 d (8.4) | 47.0 | 0.84 d (8.1) | 54.8 | 1.04 m | 54.4 |
10 | - | 39.6 | - | - | ||
11 | 1.56 m, 1.67 m | 20.9 | 1.52 m, 1.71 m | 19.8 | 1.04 m, 1.46 m | 20.1 |
12 | 1.84 t (12.2), 2.36 m | 29.9 | 1.85 m, 2.67 m | 31.6 | 1.24 m, 1.51 m | 37.1 |
13 | - | 89.6 | - | 87.6 | - | 54.2 |
14 | 2.17 d (9.8), 2.69 d (9.8) | 47.1 | 2.44 m, 2.58 d (9.9) | 40.3 | 1.83 d (18.5), 2.62 dd (3.1, 18.5) | 48.4 |
15 | 5.03 s | 134.3 | 1.41 d (14.3), 1.83 m | 54.3 | 1.27 m, 1.36 m | 53.8 |
16 | - | 144.4 | - | 77.1 | - | 220.7 |
17 | 1.89 s | 12.7 | 1.32 s | 22.2 | 0.98 s | 19.9 |
18 | 1.35 s | 28.0 | 1.28 s | 27.7 | 1.42 s | 28.8 |
19 | - | 176.7 | - | 176.9 | - | 175.8 |
20 | 1.33 s | 16.4 | 1.31 s | 16.0 | 0.81s | 13.8 |
1′ | 6.33 d (8.4) | 94.5 | 6.35 d (8.3) | 94.5 | 6.19 d (8.1) | 93.0 |
2′ | 4.51 t (8.8) | 76.6 | 4.53 t (8.7) | 76.4 | 4.51 t (8.9) | 76.8 |
3′ | 4.99 m | 88.3 | 4.98 m | 88.5 | 4.27 t m | 88.4 |
4′ | 4.19 m | 69.6 | 4.21 m | 69.7 | 4.17 m | 69.1 |
5′ | 4.10 m | 78.1 | 4.14 m | 78.3 | 3.98 m | 78.1 |
6′ | 4.21 m, 4.33 m | 61.5 | 4.22 m, 4.30 m | 61.5 | 4.24 m, 4.52 m | 62.0 |
1″ | 5.47 d (8.0) | 95.7 | 5.79 d (6.7) | 96.0 | ||
2″ | 4.13 m | 81.1 | 4.14 m | 80.4 | ||
3″ | 4.89 t (8.9) | 87.6 | 5.09 m | 87.9 | ||
4″ | 4.04 t (8.9) | 70.0 | 4.00 m | 69.9 | ||
5″ | 3.90 m | 77.4 | 4.17 m | 77.2 | ||
6″ | 4.17 m, 4.31 m | 62.4 | 4.13 m, 4.34 m | 62.0 | ||
1″′ | 5.45 d (7.0) | 104.5 | 5.63 d (7.3) | 103.8 | ||
2″′ | 4.15 m | 75.6 | 4.13 m | 75.6 | ||
3″′ | 4.14 m | 78.1 | 4.09 m | 78.0 | ||
4″′ | 4.02 m | 72.8 | 4.08 m | 72.2 | ||
5″′ | 3.77 m | 77.3 | 3.70 m | 77.5 | ||
6″′ | 4.31 m, 4.53 d (10.9) | 63.5 | 4.32 m, 4.49 m | 63.2 | ||
1″″ | 5.44 d (7.5) | 103.9 | 5.53 d (7.9) | 103.8 | ||
2″″ | 3.98 m | 75.3 | 4.02 m | 75.3 | ||
3″″ | 4.46 t (9.0) | 77.6 | 4.55 t (9.0) | 77.6 | ||
4″″ | 4.14 m | 71.0 | 4.22 m | 71.0 | ||
5″″ | 3.99 m | 77.8 | 4.09 m | 78.0 | ||
6″″ | 4.12 m, 4.33 m | 61.8 | 4.13 m, 4.34 m | 62.0 | ||
1″″′ | 5.81 d (6.9) | 103.8 | 5.76 d (7.8) | 104.0 | 5.79 d (7.9) | 103.4 |
2″″′ | 4.20 m | 75.2 | 4.28 m | 74.8 | 3.99 m | 75.7 |
3″″′ | 4.20 m | 78.2 | 4.20 m | 78.1 | 4.32 m | 78.3 |
4″″′ | 4.10 m | 73.1 | 4.13 m | 73.5 | 4.13 m | 72.4 |
5″″′ | 3.89 m | 77.8 | 3.92 | 77.6 | 4.02 m | 78.4 |
6″″′ | 4.31 m, 4.62 d (11.1) | 63.6 | 4.29 m, 4.64 dd (2.6, 11.6) | 63.8 | 4.36 m, 4.56 m | 63.2 |
1″″′ | 5.33 d (7.7) | 103.9 | 5.22 d (7.8) | 104.0 | 5.35 d (7.9) | 104.5 |
2″″′ | 3.97 m | 75.1 | 3.95 m | 75.1 | 4.04 t (8.2) | 75.2 |
3″″′ | 4.35 t (8.3) | 77.7 | 4.28 m | 77.7 | 4.21 m | 78.3 |
4″″′ | 4.11 m | 70.9 | 4.08 m | 70.8 | 4.14 m | 71.2 |
5″″′ | 3.85 m | 77.7 | 3.76 m | 77.8 | 3.85 m | 78.7 |
6″″′ | 4.12 m, 4.33 m | 61.8 | 4.13 m, 4.34 m | 62.0 | 4.24 m, 4.33 m | 61.6 |
Time (min) | % of Mobile Phase A | % of Mobile Phase B |
---|---|---|
0.0 | 75 | 25 |
20.0 | 69 | 31 |
20.5 | 50 | 50 |
25.0 | 40 | 60 |
25.1 | 75 | 25 |
30.0 | 75 | 25 |
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Prakash, I.; Chaturvedula, V.S.P.; Markosyan, A. Structural Characterization of the Degradation Products of a Minor Natural Sweet Diterpene Glycoside Rebaudioside M under Acidic Conditions. Int. J. Mol. Sci. 2014, 15, 1014-1025. https://doi.org/10.3390/ijms15011014
Prakash I, Chaturvedula VSP, Markosyan A. Structural Characterization of the Degradation Products of a Minor Natural Sweet Diterpene Glycoside Rebaudioside M under Acidic Conditions. International Journal of Molecular Sciences. 2014; 15(1):1014-1025. https://doi.org/10.3390/ijms15011014
Chicago/Turabian StylePrakash, Indra, Venkata Sai Prakash Chaturvedula, and Avetik Markosyan. 2014. "Structural Characterization of the Degradation Products of a Minor Natural Sweet Diterpene Glycoside Rebaudioside M under Acidic Conditions" International Journal of Molecular Sciences 15, no. 1: 1014-1025. https://doi.org/10.3390/ijms15011014