Table 3.
1H-NMR (400 MHz, CDCl3) and 13C-NMR (101 MHz) of compound 7 and NMR data reported for threo-carolignan E.
| C no. | Compound 7 | Threo-carolignan E [28] | |
|---|---|---|---|
| δ 1H (J in Hz) | δ 13C | δ 13C | |
| 1 | — | 127.1 | 126.9 |
| 2 | 7.02–7.07 (m, 1H) | 109.5 | 109.3 |
| 3 | — | 147.0 | 146.8 |
| 4 | — | 148.2 | 148.0 |
| 5 | 6.79–6.95 (m, 1H) | 114.9 | 114.7 |
| 6 | 7.02–7.07 (m, 1H) | 123.3 | 123.2 |
| 7 | 7.51 (d, J = 15.9, 1H) | 145.6 | 145.5 |
| 8 | 6.28 (d, J = 15.9, 1H) | 114.9 | 114.7 |
| 9 | — | 167.0 | 166.8 |
| 1′ | — | 131.3 | 131.1 |
| 2′ | 6.79–6.95 (m, 1H) | 109.4 | 109.2 |
| 3′ | — | 146.9 | 146.7 |
| 4′ | — | 145.8 | 145.6 |
| 5′ | 6.79–6.95 (m, 1H) | 114.5 | 114.3 |
| 6′ | 6.79–6.95 (m, 1H) | 120.6 | 120.4 |
| 7′ | 4.94 (br. s, 1H) | 74.6 | 74.4 |
| 8′ | 4.18–4.27 (m, 1H) | 86.5 | 86.3 |
| 9′ | 4.09–4.17 (m, 1H) 4.35–4.38 (m, 1H) |
63.2 | 63.0 |
| 1″ | — | 137.6 | 137.4 |
| 2″ | 6.77 (m, 1H) | 112.5 | 112.3 |
| 3″ | — | 150.9 | 150.7 |
| 4″ | — | 146.2 | 146.0 |
| 5″ | 7.02–7.07 (m, 1H) | 120.8 | 120.6 |
| 6″ | 6.72–6.79 (m, 1H) | 121.2 | 121.0 |
| 7″ | 2.70 (t, J = 7.8, 2H) | 32.2 | 32.0 |
| 8″ | 2.00–2.04 (br. s, 2H) | 30.6 | 30.4 |
| 9″ | 4.23 (t, J = 6.2, 2H) | 63.8 | 63.6 |
| 1‴ | — | 127.0 | 126.7 |
| 2‴ | 7.02–7.07 (m, 1H) | 109.5 | 109.3 |
| 3‴ | — | 147.0 | 146.8 |
| 4‴ | — | 148.3 | 148.1 |
| 5‴ | 6.79–6.95 (m, 1H) | 114.9 | 114.7 |
| 6‴ | 7.08 (br. s, 1H) | 123.2 | 123.0 |
| 7‴ | 7.62 (d, J = 15.9, 1H) | 145.3 | 145.0 |
| 8‴ | 6.32 (d, J = 15.9, 1H) | 115.5 | 115.3 |
| 9‴ | — | 167.5 | 167.3 |
| 3-OCH3 | 3.85 (br. s, 3H) | 56.1 | 55.9 |
| 3′-OCH3 | 3.93 (br. s, 3H) | 56.1 | 55.9 |
| 3″-OCH3 | 3.90 (br. s, 3H) | 56.0 | 55.8 |
| 3‴-OCH3 | 3.94 (br. s, 3H) | 56.1 | 55.9 |
| 4-OH | 5.89 (br. s, 1H) | — | — |
| 4′-OH | 5.61 (br. s, 1H) | — | — |
| 4″-OH | 5.89 (br. s, 1H) | — | — |