Table 1. NMR Spectroscopic Data (1H 500 and 13C 125 MHz) of Oblarotenoids E (1), F (2) (CD2Cl2a), and G (CDCl3).
|
1 |
2 |
3 |
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|---|---|---|---|---|---|---|---|---|---|
| position | δC, type | δH (J in Hz) | HMBCb | δC, type | δH (J in Hz) | HMBC | δC, type | δH (J in Hz) | HMBC |
| 1 | 106.6, CH | 6.31 s | C-1a, C-2, C-3, C-4a, C-12a | 105.9, CH | 6.54 s | C-1a, C-2, C-3, C-4a, C-12a | 107.1, CH | 8.32 s | C-2, C-3, C-4a, C-12a |
| 1a | 109.4, C | 109.9, C | 111.8, C | ||||||
| 2 | 138.9, C | 149.5, C | 142.9, C | ||||||
| 3 | 136.3, C | 142.4, C | 147.4, C | ||||||
| 4 | 136.9, C | 99.3, CH | 6.46 s | C-1a, C-2, C-3 | 98.7, CH | 6.53 s | C-1a, C-2, C-3 | ||
| 4a | 133.2, C | 149.5, C | 147.5, C | ||||||
| 6 | 66.8, CH2 | 4.65 dd (12.5, 2.6) | C-4a, C-6a, C-12a | 64.0, CH2 | 4.58 dd (13.5, 2.6) | C-4a, C-6a, C-12a | 65.0, CH2 | 4.96 s | C-4a, C-6a, C-12a |
| 4.21 br d (12.5) | C-4a,C-6a | 4.46 d (13.5, 2.6) | C-4a,C-6a | ||||||
| 6a | 72.7, CH | 4.94 dd (2.6) | C-1a, C-4a, C-6, C-12, C-12a | 76.4, CH | 4.56 br d (3.6) | C-1a, C-4a, C-6, C-12, C-12a | 156.8, C | ||
| 7a | 163.0, C | 157.5, C | 156.7, C | ||||||
| 8 | 100.9, CH | 6.44 d (2.3) | C-7a, C-9, C-10, C-11a | 100.3, CH | 6.40 s | C-7a, C-9, C-10, C-11a | 100.3, CH | 6.83 d (2.2) | C-7a, C-9, C-10, C-11a |
| 9 | 167.0, C | 157.3, C | 164.0, C | ||||||
| 10 | 110.9, CH | 6.59 dd (8.9, 2.3) | C-8, C-9, C-11a | 145.3, C | C-8, C-9, C-11a | 114.7, CH | 7.00 dd (8.9, 2.2) | C-8, C-11a | |
| 11 | 129.6, CH | 7.85 d (8.9) | C-7a, C-9, C-12 | 106.9, CH | 7.25 s | C-7a, C-9, C-12 | 127.9, CH | 8.20 d (8.9) | C-7a, C-9, C-12 |
| 11a | 113.1, C | 109.5, C | 118.7, C | ||||||
| 12 | 189.0, CO | 191.3, CO | 174.2, CO | ||||||
| 12a | 45.0, CH | 3.81c | C-1a, C-4, C-6 | 67.9, C | 112.3, C | ||||
| OCH2O | 102.7, CH2 | 5.97 d (1.4); 5.91 d (1.4) | C-3, C-4 | 101.5, CH2 | 5.83 d (1.4); 5.86 d (1.4) | C-2, C-3 | 101.5, CH2 | 5.96 s | C-2, C-3 |
| OMe-2 | 57.2, CH3 | 3.73 s | C-2 | ||||||
| OMe-9 | 56.2, CH3 | 3.81 s | C-9 | 56.4, CH3 | 3.86 s | C-9 | 56.0, CH3 | 3.92 s | C-9 |
| OMe-10 | 56.5, CH3 | 3.88 s | C-10 | ||||||
CD2Cl2 was used due to the gradual color change observed in the slightly acidic CDCl3.
HMBC correlations, optimized for 6 Hz, are from the stated proton(s) to the indicated carbon.
Signal overlapping with that of OMe-9.