TABLE 2.
No. | [6]-Shogaola |
M10b |
M12b |
5-N-acetylcysteinyl-[6]-shogaola |
||||
---|---|---|---|---|---|---|---|---|
δH multi (J in Hz) | δC | δH multi (J in Hz) | δC | δH multi (J in Hz) | δC | δH multi (J in Hz) | δC | |
1′ | 132.6 | 132.9 | 134.0 | 134.0 | ||||
2′ | 6.80 d (1.8) | 111.8 | 6.71 d (1.5) | 111.0 | 6.73 d (2.2) | 111.0 | 6.81 d (1.8) | 111.7 |
3′ | 147.6 | 146.4 | 146.4 | 149.0 | ||||
4′ | 144.5 | 143.9 | 143.7 | 145.9 | ||||
5′ | 6.71 d (8.0) | 114.7 | 6.84 d (8.0) | 114.3 | 6.84 d (7.9) | 114.2 | 6.71 d (8.0) | 114.6 |
6′ | 6.63 dd (8.0, 1.8) | 120.4 | 6.69 dd (8.0, 1.5) | 120.8 | 6.71 dd (7.9, 2.2) | 120.9 | 6.65 dd (8.0, 1.8) | 120.2 |
1 | 2.88 m | 31.1 | 2.86 t (7.5) | 29.3 | 2.64 m; 2.75 m | 31.7 | 2.80 m | 27.5 |
2 | 2.66 m | 41.3 | 2.75 m | 45.5 | 1.79 m; 1.74 m | 39.8 | 2.74 dd (17.1, 6.3); 2.67 dd (17.1, 6.3) | 49.7 |
3 | 201.5 | 208.4 | 4.00 m | 68.9 | 211.2 | |||
4 | 6.12 br d (15.9) | 130.0 | 2.59 dd (16.6, 6.5); 2.69 dd (16.6, 6.5) | 48.5 | 1.71 m; 1.62 m | 40.6 | 2.74 m | 46.1 |
5 | 6.90 dt (15.9, 7.02) | 148.7 | 3.04 m | 41.6 | 2.75 m | 43.2 | 3.14 m | 42.6 |
6 | 2.22 m | 32.1 | 1.50 m | 34.4 | 1.61m | 34.8 | 1.51 m | 33.7 |
7 | 1.48 m | 27.6 | 1.42 m; 1.38 m | 26.5 | 1.44 m | 26.6 | 1.34 m | 26.6 |
8 | 1.34 m | 29.8 | 1.27 m | 31.6 | 1.31 m | 31.9 | 1.27 m | 30.9 |
9 | 1.34 m | 22.1 | 1.31 m | 22.6 | 1.31 m | 22.6 | 1.33 m | 22.2 |
10 | 0.93 t (7.1) | 13.0 | 0.90 t (7.1) | 14.0 | 0.91 t (7.1) | 14.1 | 0.92 | 14.4 |
3′-OMe | 3.84 s | 3.89 s | 55.9 | 3.90 s | 55.7 | 56.4 | ||
5-SMe | 2.04 s | 13.3 | 2.05 | 12.3 | ||||
4′-OH | 5.45 s | 5.47 s | ||||||
3-OH | 2.25 d (4.9) | |||||||
1′′ | 3.00 dd (4.7, 13.7); 2.92 dd (7.1, 13.7) | 30.4 | ||||||
2′′ | 4.58 dd (7.1, 4.7) | 54.6 | ||||||
3′′ | 173.1 | |||||||
4′′ | 173.1 | |||||||
5′′ | 2.01 s | 22.6 |
Data were measured in CD3OD at 600 (1H) and 150 MHz (13C).
Data were measured in CDCl3 at 600 (1H) and 150 MHz (13C). Chemical shifts (δ) are in ppm being relative to CD3OD and CDCl3.