Table 2.
1H- and 13C NMR data of sesquiterpene lactones in globe artichoke byproducts [CDCl3/CD3OD 2:1 v/v, 1H 600 MHz, 13C 150 MHz, ppm (J = Hz)]. Multiplicity: d = doublet; dd = doublet of doublets; ddd = doublet of doublets of doublets; dt = doublet of triplets; q = quartet; t = triplet.
| Position | Cynaropicrin | Dehydrocynaropicrin | Grosheimin | |||
|---|---|---|---|---|---|---|
| 1H | 13C | 1H | 13C | 1H | 13C | |
| 1 | 2.99 ddd (10.2; 9.8; 7.2) |
45.4 | 3.30 | 40.9 | 3.21 | 40.3 |
| 2a | 2.17 dt (12.9; 7.1) |
39.1 | 2.64 dd (18.6; 8.4) |
43.7 | 2.58 | 43.7 |
| 2b | 1.74 ddd (12.8;11.6; 8.6) |
39.1 | 2.58 | 43.7 | 2.52 | 43.7 |
| 3 | 4.52 ddt (8.5; 7.3; 2.2) |
73.3 | - | 205.2 | - | 220.8 |
| 4 | - | 152.3 | - | 2.34 | 47.5 | |
| 5 | 2.87 | 51.3 | 3.35 | 49.4 | 2.35 | 51.3 |
| 6 | 4.31 dd (10.6; 9.0) |
79.4 | 4.18 dd (9.9; 8.9) |
80.4 | 4.03 t (9.0) | 83.6 |
| 7 | 3.25 | 47.7 | 3.50 | 46.9 | 3.11 | 49.6 |
| 8 | 5.14 dd (5.1; 3.5) |
74.5 | 5.13 | 74.5 | 3.80 dd (10.0; 6.1) |
73.1 |
| 9a | 2.72 dd (14.8; 5.2) |
37.0 | 2.92 dd( 13.4; 5.7) |
41.5 | 2.85 | 48.5 |
| 9b | 2.41 dd (14.8; 3.6) |
37.0 | 2.38 | 41.5 | 2.29 | 48.5 |
| 10 | - | 142.2 | - | - | 144.2 | |
| 12 | - | 170.2 | - | 170.0 | - | 171.1 |
| 13a | 6.20 d (3.5) |
122.9 | 6.30 d (3.3) |
125.0 | 6.37 dd (2.8; 1.2) |
126.0 |
| 13b | 5.67 * d (3.3) |
122.9 | 5.85 * d (3.0) |
125.0 | 6.33 * dd (3.3; 1.2) |
126.0 |
| 14a | 5.16 | 118.2 | 5.09 | 115.2 | 5.07 | 115.2 |
| 14b | 4.94 d (1.5) |
118.2 | 4.77 | 115.2 | 4.78 | 115.2 |
| 15a | 5.47 t (1.8) |
113.0 | 6.28 dd (2.4; 0.6) |
123.6 | 1.26 | 14.9 |
| 15b | 5.38 t (2.3) |
113.0 | 5.89 dd (2.2; 0.6) |
123.6 | ||
| 1′ | - | 165.7 | - | |||
| 2′ | - | 140.2 | - | |||
| 3′a | 6.35 q (1.2) |
126.0 | 6.37 | 126.3 | ||
| 3′b | 6.01 q (1.6) |
126.0 | 6.04 | 126.3 | ||
| 4′ | 4.35 t (1.3) |
61.0 | 4.36 | 61.0 | ||
* Asterisks indicate signals used for integration and quantification of metabolites.