Table 1. NMR Spectroscopic Data [CDCl3, 800 MHz (1H), 200 MHz (13C), δ (ppm)] for Neurolobatins A (1) and B (2).
neurolobatin
A (1) |
neurolobatin
B (2) |
|||||||
---|---|---|---|---|---|---|---|---|
position | δH (J in Hz) | δC | HMBCa | NOESY | δH (J in Hz) | δC | HMBCa | NOESY |
1 | 194.8 | 194.7 | ||||||
2a | 2.77 dd (16.4, 3.2) | 34.5 | C-1, C-3 | H-3, H-5a, H-15, H-6 | 2.81 dd (16.9, 2.5) | 35.9 | C-1, C-3 | H-3, H-9 |
2b | 3.27 dd (16.4, 9.9) | C-1, C-3 | H-3, H-5a, H-6 | 3.22 dd (16.9, 10.1) | C-1, C-3 | H-3, H-9 | ||
3 | 4.07 dd (9.7, 2.7) | 79.0 | C-1, C-4, C-5, C-15 | H-2a, H-2b, H-9, H-14, H-15 | 4.14 dd (10.1, 2.6) | 80.7 | C-1, C-2, C-4, C-5, C-15 | H-2a, H-2b, H-9, H-14, H-15 |
4 | 81.9 | 79.0 | ||||||
5a | 2.40 dd (14, 4.1) | 40.7 | C-6, C-7 | H-2a, H-2b, H-6, H-15 | 2.45 dd (13.8, 5.1) | 38.5 | C-3, C-4, C-6, C-7, C-15 | H-6 |
5b | 1.84 dd (14.0, 11.8) | C-3, C-6, C-7, C-15 | H-6, H-15 | 2.01 dd (13.8, 11.8) | C-6, C-7 | |||
6 | 4.91 ddd (11.8, 9.4, 3.9) | 73.7 | C-7 | H-2a, H-2b, H-5b | 4.71 td (10.5, 5.1) | 74.1 | C-7 | H-5a, H-9, H-15 |
7 | 3.45 dddd (9.0, 4.1, 3.7, 3.1) | 46.3 | C-5, C-6, C-12 | H-5a, H-8 | 3.23 dq (9.9, 3.1) | 46.2 | C-5, C-6, C-12 | H-13a |
8 | 5.40 t (4.1) | 68.4 | C-6, C-1′ | H-9 | 5.43 t (2.5) | 67.1 | C-6, C-1′ | |
9 | 5.62 d (4.1) | 98.9 | C-4, C-7 | H-3, H-8, H-15 | 5.35 d (1.9) | 102.0 | C-4, C-7, C-8 | H-2a, H-2b, H-3, H-6 |
10 | 196.4 | 196.4 | ||||||
11 | 134.1 | 134.7 | ||||||
12 | 169.2 | 169.2 | ||||||
13a | 5.38 d (3.1) | 121.3 | C-7, C-11 | 5.47 d (3.4) | 121.3 | C-7, C-11 | H-7 | |
13b | 6.26 d (3.7) | C-7, C-11, C-12 | 6.25 d (3.4) | C-7, C-11, C-12 | ||||
14 | 2.37 s | 23.5 | C-10 | H-3 | 2.40 s | 23.5 | C-10 | H-3 |
15 | 1.40 s | 23.0 | C-3, C-4, C-5 | H-2a, H-3, H-5a, H-5b, H-9 | 1.48 s | 26.0 | C-3, C-4, C-5 | H-3, H-6 |
1′ | 172.5 | 172.2 | ||||||
2′ | 2.16 m | 42.9 | C-3′, C-4′, C-5′ | 2.20 m | 43.0 | C-3′, C-4′, C-5′ | ||
3′ | 2.01 m | 25.6 | C-2′, C-4′, C-5′ | 2.04 m | 25.6 | C-2′, C-4′, C-5′ | ||
4′ | 0.92 d (6.6) | 22.3 | C-2′, C-3′ | 0.93 d (6.7) | 22.3 | C-2′, C-3′ | ||
5′ | 0.93 d (6.6) | 22.3 | C-2′, C-3′ | 0.92 d (6.7) | 22.3 | C-2′, C-3′ |
HMBC correlations are from proton(s) stated to the indicated carbon.