Table 1.
NMR spectroscopic data for 7-hydroxydichapetalin P (1), dichapetalins A (2) and X (3).
| No. | 1 (in CDCl3, 600 MHz) | 2 (in CDCl3, 600 MHz) | 3 (in CDCl3, 500 MHz) | |||
|---|---|---|---|---|---|---|
| δc, Type | δH (J/Hz) | δc, Type | δH (J/Hz) | δc, Type | δH (J/Hz) | |
| 1a | 1.68, m | 1.66, m | 1.69, m | |||
| 1b | 40.1, CH2 | 2.03, dd (7.1, 16.1) | 40.1, CH2 | 2.10, dd (7.0, 16.2) | 40.1, CH2 | 2.11, dd (7.1, 16.2) |
| 2 | 117.8, CH | 5.42, d (7.1) | 117.7, CH | 5.40, d (6.9) | 117.8, CH | 5.43, ddd (1.8, 1.8, 7.1) |
| 3 | 140.0, C | 140.1, C | 140.0, C | |||
| 4 | 38.3, C | 38.3, C | 38.3, C | |||
| 5 | 43.7, CH | 2.01, m | 43.8, CH | 2.00, m | 43.8, CH | 2.04, m |
| 6a | 1.62, ddd (2.4, 13.8, 13.8) | 1.62, m | 1.67, m | |||
| 6b | 24.1, CH2 | 1.85, ddd (3.0, 3.0, 13.8) | 24.2, CH2 | 1.85, dd (10.5, 12.7) | 24.2, CH2 | 1.86, ddd (3.0, 3.0, 13.8) |
| 7 | 72.3, CH | 3.95, dd (2.4, 3.0) | 72.3, CH | 3.94, m | 72.3, CH | 3.97, dd (2.4, 3.0) |
| 8 | 36.4, C | 36.4, C | 36.4, C | |||
| 9 | 45.7, CH | 2.01, m | 45.7, CH | 1.98, m | 45.7, CH | 2.02, m |
| 10 | 35.7, C | 35.2, C | 35.7, C | |||
| 11 | 124.1, CH | 5.46, dd (2.5, 10.2) | 124.1, CH | 5.45, dd (2.1, 10.0) | 124.0, CH | 5.48, dd (2.6, 10.2) |
| 12 | 129.1, CH | 6.20, dd (3.1, 10.2) | 129.0, CH | 6.14, dd (2.9, 10.0) | 129.1, CH | 6.21, dd (3.1, 10.2) |
| 13 | 29.9, C | 30.1, C | 30.0, C | |||
| 14 | 36.2, C | 36.2, C | 36.3, C | |||
| 15a | 1.73, m | |||||
| 15b | 24.8, CH2 | 2.05, m | 24.9, CH2 | 2.05, d (12.2) | 24.8, CH2 | 2.08, m |
| 16a | 1.27, m | |||||
| 16b | 23.2, CH2 | 1.78, ddd (9.6, 15.6, 19.2) | 22.8, CH2 | 1.12, m | 23.2, CH2 | 1.78, ddd (9.6, 15.6, 19.2) |
| 17 | 40.3, CH | 2.63, m | 41.0, CH | 2.62, m | 40.3, CH | 2.64, m |
| 18 | 17.5, CH3 | 0.92, s | 17.4, CH3 | 0.90, s | 17.5, CH3 | 0.92, s |
| 19 | 18.2, CH3 | 1.08, s | 18.1, CH3 | 1.08, s | 18.2, CH3 | 1.11, s |
| 20 | 47.1, CH | 3.01, dd (5.1, 10.0) | 42.1, CH | 3.08, ddd (4.9, 8.3, 12.9) | 47.0, CH | 3.05, dd (5.1, 10.0) |
| 21 | 173.9, C | 178.2, C | 173.9, C | |||
| 22 | 71.9, CH | 4.18, t (9.6) | 31.4, CH2 | 2.37, m | 72.1, CH | 4.19, d (9.5) |
| 23 | 111.3, C | 75.1, CH | 5.12, m | 111.4, C | ||
| 24a | 2.51, d (15.1) | 2.53, d (15.2) | ||||
| 24b | 45.7, CH2 | 2.84, d (15.1) | 122.0, CH | 5.52, dd (8.3, 1.0) | 45.8, CH2 | 2.91, d (15.2) |
| 25 | 85.0, C | 141.7, C | 86.0, C | |||
| 26a | 4.09, d (10.2) | 4.09, d (10.2) | ||||
| 26b | 78.9, CH2 | 4.32, d (10.2) | 67.2, CH2 | 4.05, s | 78.3, CH2 | 4.37, d (10.2) |
| 27 | 22.0, CH3 | 1.70, s | 14.1, CH3 | 1.74, s | 21.6, CH3 | 1.74, s |
| 28 | 23.8, CH3 | 1.33, s | 23.8, CH3 | 1.32, s | 23.8, CH3 | 1.36, s |
| 30a | 0.93, d (5.3) | 0.78, d (5.2) | 0.96, d (5.3) | |||
| 30b | 15.4, CH2 | 1.29, m | 15.0, CH2 | 1.18, d (4.6) | 15.5, CH2 | |
| 2′a | 3.62, d (10.5) | 3.59, d (10.6) | 3.63, d (10.5) | |||
| 2′b | 72.5, CH2 | 3.80, d (10.5) | 72.5, CH2 | 3.76, d (10.6) | 72.5, CH2 | 3.80, d (10.5) |
| 5′a | 2.20, dd | 2.19, dd (2.4, 13.4) | 2.23, dd (2.7, 13.7) | |||
| 5′b | 40.7, CH2 | 2.63, m | 40.7, CH2 | 2.62, m | 40.8, CH2 | |
| 6′ | 81.8, CH | 4.28, dd (2.5, 9.1) | 81.8, CH | 4.26, dd (2.3, 11.6) | 81.8, CH | 4.29, dd (3.6, 11.6) |
| 1″ | 142.6, C | 142.6, C | 142.6, C | |||
| 2″,6′′ | 125.8, CH | 7.35, m | 125.8, CH | 7.37, m | 125.8, CH | 7.36, m |
| 3″,5″ | 128.4, CH | 7.33, m | 128.3, CH | 7.33, m | 128.4, CH | 7.40, m |
| 4″ | 127.5, CH | 7.24, m | 127.5, CH | 7.25, m | 127.5, CH | 7.28, m |
| 1′′′ | 170.4, C | 172.1, C | ||||
| 2′′′a | 21.8, CH3 | 2.03, s | 2.40, dd (9.2, 16.2) | |||
| 2′′′b | 43.7, CH2 | 2.47, dd (3.6, 16.2) | ||||
| 3′′′ | 64.6, CH | 4.20, m | ||||
| 4′′′ | 22.7, CH3 | 1.26, d (6.1) | ||||