Table 4.
1H NMR data (δ, ppm; multiplicity; J, Hz; number of H-atoms).
| Pos. | T-2 Toxin-3-O-β-d-glucoside in Methanol-d4 (A) | HT-2 Toxin-3-O-β-d-glucoside in Acetone-d6 | T-2 Triol-3-O-β-d-glucoside in Acetone-d6 | T-2 Tetraol-3-O-β-d-glucoside in Methanol-d4 | 4,15-Diacetoxyscirpenol-3-O-β-d-glucoside in Methanol-d4 | Neosolaniol-3-O-β-d-glucoside in Methanol-d4 | Iso-neosolaniol-3-O-β-d-glucoside in Methanol-d4 | Fusarenon X-3-O-β-d-glucoside in Acetonitrile-d3 |
|---|---|---|---|---|---|---|---|---|
| 2 | 3.72 (d, 5.0, 1H) | 3.54 (d, 4.7, 1H) | 3.48 (d, 4.9, 1H) | 3.57 (d, 4.8, 1H) | 3.70 (d, 4.8, 1H) | 3.69 (d, 5.0, 1H) | 3.68 (d, 5.0, 1H) | 3.81 (d, 4.8, 1H) |
| 3 | 4.48 (dd, 5.0, 3.1, 1H) | 4.31 (b, 1H) | 4.24 (dd, 4.9, 3.2, 1H) | 4.23 (dd, 4.8, 3.3, 1H) | 4.44 (dd, 4.8, 3.3 1H) | 4.46 (m, 1H) | 4.38 (dd, 5.0, 3.2, 1H) | 4.42 (dd, 4.8, 3.5, 1H) |
| 4 | 5.98 (d, 3.1, 1H) | 4.60 (b, 1H) | 4.83 (m, 1H) | 4.36 (d, 3.3, 1H) | 5.79 (d, 3.2, 1H) | 6.06 (d, 3.0, 1H) | 6.09 (d, 3.2, 1H) | 5.80 (d, 3.5, 1H) |
| 4-Ac | 2.09 (s, 3H) | - | - | - | 2.10 (s, 3H) | 2.09 (s, 3H) | 2.10 (s, 3H) (D) | 2.09 (s, 3H) |
| 7 | 2.38 (dd, 15.2, 5.8, 1H) 1.94 (bd, 15.2, 1H) |
2.35 (dd, 15.1, 5.6, 1H) 2.01 (bd, 15.0, 1H) |
2.26 (dd, 15.0, 5.8, 1H) 1.86 (d, 15.0, 1H) |
2.17 (dd, 14.3, 5.1, 1H) 1.99 (bd, 14.3, 1H) |
2.01 (m, 1H) 1.81 (m, 1H) |
2.25 (dd, 14.5, 5.6, 1H) 1.85 (bd, 14.5, 1H) |
2.24 (dd, 15.1, 5.9, 1H) 1.92 (bd, 15.1, 1H) |
4.79 (s, 1H) |
| 8 | 5.33 (d, 5.7, 1H) | 5.28 (d, 5.5, 1H) | 5.26 (d, 5.8, 1H) | 4.02 (bd, 4.9, 1H) | 2.05–1.90 (m, 2H) | 4.06 (d, 5.5, 1H) | 5.24 (d, 5.7, 1H) | - |
| 8-Ac | - | - | - | - | - | - | 2.05 (s, 3H) (D) | - |
| 10 | 5.75 (d, 5.9, 1H) | 5.69 (d, 5.5, 1H) | 5.66 (m, 1H) | 5.55 (bd, 5.6, 1H) | 5.48 (d, 5.5, H) | 5.60 (d, 5.8, 1H) | 5.77 (d, 6.0, 1H) | 6.58 (dd, 5.9, 1.5, 1H) |
| 11 | 4.38 (m, 1H) | 4.20 (d, 5.5, 1H) | 4.18 (d, 5.9, 1H) | 3.87 (bd, 5.6, 1H) | 4.15 (d, 5.5, 1H) | 4.38 (d, 5.8, 1H) | 4.31 (d, 6.0, 1H) | 4.67 (d, 5.9, 1H) |
| 13 | 3.04 (d, 3.8, 1H) 2.87 (d, 3.8, 1H) |
2.95 (d, 4.0, 1H) 2.80 (d, 4.0, 1H) |
2.89 (d, 4.2, 1H) 2.75 (d, 4.2, 1H) |
2.93 (d, 4.1, 1H) 2.80 (d, 4.1, 1H) |
3.02 (d, 3.9, 1H) 2.85 (d, 3.9, 1H) |
3.03 (d, 4.0, 1H) 2.85 (d, 4.0, 1H) |
3.02 (d, 4.0, 1H) 2.85 (d, 4.0, 1H) |
3.05 (d, 4.2, 1H) 2.98 (d, 4.2, 1H) |
| 14 | 0.74 (s, 3H) | 0.83 (s, 3H) | 0.84 (s, 3H) | 0.86 (s, 3H) | 0.75 (s, 3H) | 0.78 (s, 3H) | 0.79 (s, 3H) | 0.94 (s, 3H) |
| 15 | 4.38 (d, 12.6, 1H) 4.09 (d, 12.6, 1H) |
4.24 (d, 12.2, 1H) 3.95 (d, 12.2, 1H) |
3.84 (d, 12.1, 1H) 3.53 (d, 12.0, 1H) |
3.74 (d, 12.4, 1H) 3.41 (d, 12.4, 1H) |
4.31 (d, 12.3, 1H) 4.04 (d, 12.3, 1H) |
4.39 (d, 12.5, 1H) 4.20 (d, 12.5, 1H) |
3.97 (d, 12.2, 1H) 3.56 (d, 12.2, 1H) |
3.89 (d, 12.3, 1H) 3.66 (d, 12.3, 1H) |
| 15-Ac | 2.06 (s, 3H) | 2.03 (s, 3H) | - | - | 2.05 (s, 3H) | 2.07 (s, 3H) | - | - |
| 16 | 1.75 (s, 3H) | 1.72 (s, 3H) | 1.70 (s, 3H) | 1.83 (s, 3H) | 1.73 (s, 3H) | 1.84 (s, 3H) | 1.76 (s, 3H) | 1.82 (s, 3H) |
| 2′ | 2.15 (m, 2H) | 2.15 (d, 7.0, 2H) | 2.21 (d, 6.9, 2H) | - | - | - | - | - |
| 3′ | ca. 2.06 (m, 1H) | ca. 2.05 (1H) (B) | 2.06 (m, 1H) | - | - | - | - | - |
| 4′ | 0.97 (d, 6.6, 3H) 0.96 (d, 6.6, 3H) |
0.97 (d, 6.4, 3H) 0.96 (d, 6.4, 3H) |
0.95 (d, 6.7, 3H) 0.94 (d, 6.7, 3H) |
- | - | - | - | - |
| 1″ | 4.44 (d, 7.8, 1H) | 4.72 (d, 7.9, 1H) | 4.66 (d, 7.9, 1H) | 4.57 (d, 7.9, 1H) | 4.42 (d, 7.9, 1H) | 4.45 (d, 7.8, 1H) | 4.45 (d, 7.8, 1H) | 4.39 (d, 7.8, 1H) |
| 2″ | 3.21 (m, 1H) | 3.29 (t, 8.2, 1H) | 3.26 (dd, 8.6, 7.9, 1H) | 3.25 (b, 1H) | 3.24 (dd, 8.9, 7.9, 1H) | 3.25 (dd, 9.0, 7.9, 1H) | 3.25 (m, 1H) | 3.16 (m, 1H) |
| 3″ | 3.35 (t, 9.0, 1H) | 3.43 (t, 8.8, 1H) | 3.42 (t, 8.7, 1H) | 3.37 (bt, 7.2, 2H) (C) | 3.35 (t, 8.9, 1H) | 3.35 (t, 9.0, 1H) | 3.35 (m, 1H) | 3.30 (m, 1H) |
| 4″ | ca. 3.26 (m, 1H) | 3.40 (t, 9.1, 1H) | 3.37 (dd, 9.3, 8.7, 1H) | 3.37 (bt, 7.2, 2H) (C) | 3.31 (1H) (B) | 3.30 (t, 9.0, 1H) | 3.30 (m, 1H) | 3.25 (m, 1H) |
| 5″ | 3.21 (ddd, 9.7, 5.7, 2.2, 1H) | 3.34 (b, 1H) | 3.32 (dd, 9.4, 5.4, 1H) | 3.27 (b, 1H) | 3.21 (ddd, 9.5, 5.6, 2.2, 1H) | 3.21 (ddd, 9.5, 5.7, 2.2, 1H) | 3.22 (m, 1H) | 3.25 (m, 1H) |
| 6″ | 3.83 (dd, 12.1, 2.2, 1H) 3.65 (dd, 12.1, 5.7, 1H) |
3.84 (bd, 10.6, 1H) 3.70 (m, 1H) |
3.82 (m, 1H) 3.66 (m, 1H) |
3.83 (dd, 12.1, 2.0, 1H) 3.68 (dd, 12.1, 5.0, 1H) |
3.83 (dd,12.0, 2.3, 1H) 3.65 (dd, 12.0, 5.6, 1H) |
3.83 (dd, 12.0, 2.2, 1H) 3.65 (dd, 12.0, 5.7, 1H) |
3.82 (dd, 12.2, 2.4, 1H) 3.65 (m, 1H) |
3.6 (m, 2H) |
Ac, acetyl-group; Multiplicities are abbreviated as s (singlet), d (doublet), bd (broad doublet), bt (broad triplet), dd (doublet of doublets), t (triplet), m (multiplet), and b (broad signal). (A)—Only 1H- and 13C-spectra were acquired and compared to the already published spectra acquired on an Agilent 600 MHz NMR-spectrometer [50]. (B)—Overlapping with solvent signal. (C)—In this case it was not possible to assign the specific position of the two protons with the chosen measurement conditions. (D)—Indicates that shifts for positions 4-Ac and 8-Ac may be reversed.