Table 1.
NMR Spectroscopic Data (500 MHz, CDCl3) for Bromophycolides R–U (1–4)a
| bromophycolide R (1) |
bromophycolide S (2) |
bromophycolide T (3) |
bromophycolide U (4) |
|||||
|---|---|---|---|---|---|---|---|---|
| no. | δ C | δH (J in Hz) | δ C | δH (J in Hz) | δ C | δH (J in Hz) | δ C | δH (J in Hz) |
| 1 | 166.8 | 168.0 | 164.2 | 164.9 | ||||
| 2 | 124.0 | 124.1 | 124.0 | 122.8 | ||||
| 3 | 131.4 | 8.30, br s | 129.7 | 8.03, br s | 133.9 | 7.96, d 2.0 | 131.9 | 7.94, s |
| 4 | 127.4 | 127.2 | 125.8 | 129.8 | ||||
| 5a | 24.2 | 2.70, d (15.5) | 24.6 | 2.66, d (16.0) | 33.3 | 3.17, d (16.5) | 26.7 | 2.65, d (16.0) |
| 5b | 3.16, dd (15.5, 12.0) | 3.25, dd (16.0, 11.5) | 4.01, d (16.5) | 2.84, dd (16.0, 12.5) | ||||
| 6 | 46.0 | 3.45, d (11.5) | 43.7 | 3.54, d (11.0) | 131.9 | 48.1 | 2.61, m | |
| 7 | 43.8 | 43.8 | 43.2 | 41.3 | ||||
| 8a | 36.0 | 1.91, m | 36.0 | 1.90, m | 31.8 | 1.54, m | 38.5 | 1.54, m |
| 8b | 1.96, m | 1.90, m | 1.91, m | 2.08, m | ||||
| 9a | 25.0 | 1.63, m | 25.0 | 1.59, m | 23.4 | 1.38, m | 24.1 | 2.19, m |
| 9b | 1.98, m | 1.96, m | 1.71, m | 2.41, m | ||||
| 10 | 67.2 | 2.83, d (5.0) | 67.4 | 2.71, d (9.5) | 61.9 | 2.97, dd (9.5, 5.5) | 63.8 | 4.59, dd (7.0, 2.5) |
| 11 | 64.1 | 64.6 | 73.0 | 76.1 | ||||
| 12a | 32.9 | 1.16, m | 32.2 | 0.88, m | 37.4 | 1.68, m | 26.4 | 1.81, m |
| 12b | 1.97, m | 1.92, m | 2.01, m | 2.47, m | ||||
| 13a | 28.9 | 1.96, m | 26.1 | 2.22, m | 30.8 | 2.10, m | 21.7 | 1.84, m |
| 13b | 2.05, m | 2.42, m | 2.22, m | 2.32, m | ||||
| 14 | 78.7 | 4.74, br d (11.0) | 80.4 | 4.80, dd (12.0, 2.0) | 66.8 | 4.00, dd (11.0, 3.0) | 70.5 | 5.15, d (6.5) |
| 15 | 144.3 | 66.9 | 82.4 | 74.5 | ||||
| 16 | 128.8 | 7.66, dd (8.5, 1.5) | 129.1 | 7.61, d (8.0) | 130.2 | 7.83, dd (8.0, 2.0) | 128.8 | 7.75, dd (8.5, 1.5) |
| 17 | 115.4 | 6.72, d (8.0) | 115.5 | 6.77, d (8.0) | 116.2 | 6.82, d (8.0) | 115.7 | 6.77, d (8.5) |
| 18 | 156.7 | 157.0 | 159.8 | 156.5 | ||||
| 19 | 146.2 | 146.2 | 132.8 | 137.0 | ||||
| 20a | 37.9 | 2.23, m | 37.8 | 2.30, m | 33.6 | 2.21, m | 119.9 | 5.17, m |
| 20b | 2.26, m | 2.30, m | 2.28, m | |||||
| 21a | 35.3 | 2.08, m | 35.1 | 2.09, m | 29.4 | 2.20, m | 34.4 | 2.53, m |
| 21b | 2.28, m | 2.29, m | 2.26, m | 2.57, m | ||||
| 22 | 63.3 | 4.61, dd (12.5, 4.0) | 62.9 | 4.96, dd (12.5, 4.0) | 60.8 | 4.26, dd (11.0, 4.0) | 60.0 | 4.29, dd (10.5, 5.5) |
| 23a | 109.5 | 4.76, s | 109.3 | 4.72, s | 20.5 | 1.90, s | 20.9 | 1.50, s |
| 23b | 4.81, s | 4.77, s | ||||||
| 24 | 17.3 | 0.96, s | 17.3 | 0.95, s | 23.5 | 0.73, s | 17.6 | 1.08, s |
| 25 | 17.1 | 1.34, s | 16.6 | 1.35, s | 17.3 | 1.27, s | 26.4 | 1.43, s |
| 26a | 111.6 | 4.90, s | 32.7 | 1.83, s | 27.6 | 1.86, s | 28.0 | 1.07, s |
| 26b | 5.02, s | |||||||
| 27 | 18.4 | 1.78, s | 29.7 | 1.78, s | 23.9 | 1.76, s | 26.5 | 1.08, s |
| OH | 5.29, br s | 5.36, br s | 5.57, br s | 5.33, br s | ||||
a
br = broad; s = singlet; d = doublet; dd = doublet of doublets; m = multiplet.