Table 1.
1H NMR data of flavonolignans and 7-O-methylflavonolignans in DMSO-d6 (500 MHz, 30 °C)
| Position | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 2 | 5.08, d (11.5) | 5.14, d (11.5) | 5.08, d (11.5) | 5.14, d (11.5) | 5.11, d (10.9) | 5.16, d (10.9) | 5.11, d (11.5) | 5.16, d (11.5) | 5.02, d (11.4) | 5.05, d (11.4) | 5.17, d (11.9) | 5.22, d (11.4) | 4.86, dd (10.4) | 4.91, dd (10.4) |
| 3 | 4.63, dd (11.5, 6.3) | 4.69, dd (11.5, 6.3) | 4.61, dd (11.5, 6.3) | 4.67, dd (11.5, 6.3) | 4.60, dd (10.9, 6.3) | 4.66, dd (10.9, 6.3) | 4.61, dd (11.5, 5.9) | 4.67, dd (11.5, 6.3) | 4.52, dd (11.4, 6.4) | 4.58, dd (11.4, 6.3) | 4.64, dd (11.9, 6.5) | 4.67, dd (11.4, 6.9) | 4.44, dd (10.4, 5.4) | 4.48, dd (10.4, 5.4) |
| 6 | 5.91, d (1.7) | 6.12, d (1.7) | 5.91, d (2.3) | 6.12, d (2.3) | 5.92, d (2.3) | 6.13, d (2.3) | 5.92, d (2.0) | 6.13, d (2.3) | 5.91, d (2.0) | 6.12, d (2.3) | 5.93, d (1.9) | 6.13, d (2.0) | 5.91, d (2.5) | 6.12, d (1.9) |
| 8 | 5.86, d (1.7) | 6.10, d (1.7) | 5.87, d (2.3) | 6.10, d (2.3) | 5.89, d (2.3) | 6.12, d (2.3) | 5.89, d (2.0) | 6.12, d (2.3) | 5.86, d (2.0) | 6.09, d (2.3) | 5.88, d (1.9) | 6.11, d (2.0) | 5.88, d (2.5) | 6.11, d (1.9) |
| 2′ | 7.09, d (1.7) | 7.10, d (1.7) | 7.08, d (1.8) | 7.10, d (2.3) | 7.09, d (2.3) | 7.11, d (2.3) | 7.10, d (1.8) | 7.11, d (1.7) | 6.82, d (1. 5) | 6.84, d (1.2) | — | — | 3.44, dd (4.0, 2.0) | 3.45, dd (4.0, 2.0) |
| 5′ | 6.97, d (8.0) | 6.98, d (8.6) | 6.97, d (8.1) | 6.98, d (8.0) | 6.93, d (8.6) | 6.94, d (8.6) | 6.93, d (8.0) | 6.94, d (8.0) | — | — | 6.75, d (8.1) | 6.74, d (8.1) | 3.17, dd (8.9, 3.0) | 3.19, dd (6.9, 3.0) |
| 6′ | 7.00, dd (8.0, 1.7) | 7.01, dd (8.6, 1.7) | 7.02, dd (8.1, 1.8) | 7.02, dd (8.0, 2.3) | 6.98, dd (8.6, 2.3) | 6.99, dd (8.6, 2.3) | 6.98, dd (8.0, 1.8) | 7.00, dd (8.0, 1.7) | 6.87, br s | 6.88, br s | 6.96, d (8.1) | 6.97, d (8.1) | 5.92, d (8.9) | 6.01, d (6.9) |
| 2″ | 7.01, d (1.8) | 7.03, d (1.8) | 7.02, d (1.7) | 7.04, d (1.7) | 7.00, d (1.7) | 7.00, d (1.7) | 7.00, d (2.3) | 7.01, d (1.8) | 6.96, d (2.0) | 6.96, d (1.8) | 6.86, d (1.5) | 6.86, d (2.0) | 6.75, d (2.0) | 6.76, d (1.9) |
| 5″ | 6.80, d (8.6) | 6.80, d (8.6) | 6.79, d (8.6) | 6.80, d (8.0) | 6.80, d (8.6) | 6.80, d (8.0) | 6.80, d (8.6) | 6.80, d (8.2) | 6.76, d (8.4) | 6.76, d (8.1) | 6.70, d (7.9) | 6.69, d (8.5) | 6.63, d (8.5) | 6.64, d (8.4) |
| 6″ | 6.86, dd (8.6, 1.8) | 6.86, dd (8.6, 1.8) | 6.86, dd (8.6, 1.7) | 6.86, dd (8.0, 1.7) | 6.86, dd (8.6, 1.7) | 6.85, dd (8.0, 1.7) | 6.86, dd (8.6, 2.3) | 6.85, dd (8.2, 1.8) | 6.80, dd (8.4, 2.0) | 6.81, dd (8.1, 1.8) | 6.76, dd (7.9, 1.5) | 6.76, dd (8.5, 2.0) | 6.55, dd (8.5, 2.0) | 6.56, dd (8.4, 1.9) |
| 7″ | 4.90, d (7.5) | 4.91, d (7.5) | 4.90, d (7.5) | 4.91, d (7.5) | 4.91, d (8.1) | 4.91, d (7.5) | 4.91, d (7.5) | 4.92, d (7.5) | 5.46, d (7.0) | 5.46, d (6.9) | 5.58, d (2.5) | 5.57, d (2.5) | 3.31, br s | 3.31, br s |
| 8″ | 4.17, ddd (7.5, 4.6, 2.3) | 4.18, ddd (7.5, 4.6, 2.3) | 4.16, ddd (7.5, 4.1, 2.3) | 4.17, ddd (7.5, 4.6, 2.3) | 4.16, ddd (8.1, 4.6, 2.3) | 4.17, ddd (7.5, 4.0, 2.3) | 4.17, ddd (7.5, 4.6, 2.3) | 4.17, ddd (7.5, 4.6, 1.7) | 3.47, ddd (12.6, 12.0, 7.0) | 3.47, ddd (12.6, 12.0, 6.9) | 3.67, m | 3.67, m | 2.72, br s | 2.73, br s |
| 9″a | 3.53, ddd (10.3, 5.2, 2.3) | 3.53, ddd (10.3, 5.2, 2.3) | 3.53, ddd (9.8, 4.6, 2.3) | 3.54, ddd (12.0, 5.2, 2.3) | 3.53, ddd (12.0, 4.6, 2.3) | 3.53, ddd (12.0, 4.6, 2.3) | 3.54, ddd (11.9, 5.2, 2.3) | 3.53, ddd (12.0, 5.2, 1.7) | 3.72, ddd (12.6, 10.9, 5.0) | 3.72, ddd (12.6, 10.9, 5.2) | 3.68, m | 3.68, m | 4.12, dd (8.0, 3.0) | 4.13, dd (8.0, 3.0) |
| 9″b | 3.33, m | 3.34, m | 3.33, m | 3.33, m | 3.33, m | 3.33, m | 3.33, m | 3.33, m | 3.63, ddd (12.6, 10.9, 5.6) | 3.63, ddd (12.6, 10.9, 5.7) | 3.45, m | 3.44, m | 3.78, d (8.0) | 3.78, d (8.0) |
| 7-OCH3 | — | 3.78, s | — | 3.78, s | — | 3.79, s | — | 3.79, s | — | 3.78, s | — | 3.80, s | — | 3.79, s |
| 3″-OCH3 | 3.77, s | 3.77, s | 3.77, s | 3.77, s | 3.78, s | 3.77, s | 3.77, s | 3.77, s | 3.76, s | 3.76, s | 3.70, s | 3.69, s | 3.73, s | 3.74, s |
| 3-OH | 5.83, d (6.3) | 5.90, d (6.3) | 5.83, d (6.3) | 5.89, d (6.3) | 5.83, d (6.3) | 5.91, d (6.3) | 5.84, d (5.9) | 5.91, d (6.3) | 5.77, d (6.4) | 5.81, d (6.3) | 5.76, d (6.5) | 5.81, d (6.9) | 6.02, d (6.3) | 6.04, d (6.3) |
| 5-OH | 11.90, s | 11.86, s | 11.90, s | 11.87, s | 11.90, s | 11.87, s | 11.90, s | 11.87, s | 11.91, s | 11.87, s | 11.93, s | 11.90, s | 11.81, s | 11.77, s |
| 7-OH | 10.86, s | — | 10.86, s | — | 10.85, s | — | 10.86 s | — | 10.84, s | — | 10.98, s | — | 10.91, s | — |
| 4″-OH | 9.18, s | 9.19, s | 9.17, s | 9.18, s | 9.15, s | 9.18, s | 9.16, s | 9.18, s | 9.03, s | 9.02, s | 9.00, s | 8.99, s | 8.79, s | 8.79, s |
| 9″-OH | 4.97, dd (5.7, 5.2) | 4.98, dd (5.7, 5.2) | 4.98, dd (5.7, 4.6) | 4.98, dd (5.7, 5.2) | 4.95, dd (5.7, 4.6) | 4.97, dd (5.7, 4.6) | 4.96, dd (5.5, 5.0) | 4.97, dd (4.6, 5.2) | 5.01, dd (5.6, 5.0) | 5.01, dd (5.7, 5.2) | 5.07, br dd (4.5, 2.0) | 5.06, dd (6.5, 4.5) | ||
| 3′-OH | — | — | — | — | — | — | — | — | — | — | — | — | 7.19, s | 7.17, s |
Chemical shifts in δ, coupling constants in Hz.