Table 2. 1H NMR data for antiaritoxioside A-G (1–7) and antiarotoxinin B (8).
| Proton | 1 | 2‡ | 3 | 4 | 5 | 6 | 7 | 8 |
|---|---|---|---|---|---|---|---|---|
| 1a/b | 1.76 (br d, 13.6)/3.29 (ddd, 13.6, 13.6, 5.7) | 1.90 (m)/2.19 (m) | 2.04 (m)/2.44 (m) | 1.95 (m)/2.27 (br dd, 8.4, 2.3) | 1.92 (m)/2.46 (br s dd, 14.5, 2.9) | 1.23 (m)/2.07 (m) | 1.32 (ddd, 13.5, 13.5, 3.8)/2.21 (m) | 1.45 (t, 11.7)/2.21 (td, 12.5, 4.4) |
| 2a/b | 2.19 (m)/2.27 (m) | 1.67 (m)/2.04 (m) | 1.81 (m)/2.14 (m) | 1.69 (br d, 14.8)/2.00 (m) | 1.81 (br d, 13.1)/2.17 (m) | 1.52 (m) | 1.92 (m)/2.07 (m) | 1.81 (m) |
| 3 | 4.81 (dddd, 11.0, 11.0, 5.4, 5.4) | 4.29 (br s, 6.6)† | 4.40 (br s, 15.7)† | 4.27 (br s, 7.9)† | 4.48 (br s, 7.7)† | 4.18 (br s, 9.9)† | 4.52 (br s, 9.8)† | 4.44 (br s, 11.3) |
| 4a/b | 2.19 (m)/2.45 (br d, 12.8) | 1.90 (m)/2.11 (m) | 1.81 (m)/2.04 (m) | 1.97 (m)/2.15 (m) | 1.92 (m)/2.09 (br d, 9.7) | 1.23 (m)/1.48 (br t, 4.0) | 1.56 (m)/1.97 (m) | 1.78 (m)/2.32 (dd, 14.9, 2.5) |
| 5 | 2.07 (m) | |||||||
| 6a/b | 2.19 (m)/2.27 (m) | 1.55 (m)/2.25 (m) | 1.65 (m)/2.14 (m) | 1.56 (dd, 11.2, 6.3)/1.97 (m) | 1.63 (br d, 13.0)/2.28 (m) | 1.78 (m)/2.02 (m) | 1.49 (m)/2.07 (m) | 1.62 (br d, 13.0)/2.03 (m) |
| 7a/b | 2.27 (m)/2.68 (br d, 11.8) | 1.23 (m)/2.33 (br. d, 9.8) | 1.65 (m)/2.15 (m) | 1.32 (br d, 13.2)/ 2.29 (br s dd, 9.9, 3.3) | 2.12 (m)/2.32 (m) | 1.55 (m)/1.78 (m) | 1.30 (m)/1.64 (br t, 13.5) | 1.40 (m)/2.36 (td, 13.3, 2.0) |
| 8 | 2.27 (m) | 2.36 (d, 12.3) | 2.15 (m) | 2.48 (br t, 11.8) | 2.48 (br dd, 12.8, 2.9) | 1.29 (m) | 1.99 (m) | 1.76 (dt, 12.2, 11.8) |
| 9 | 2.27 (m) | 1.63 (m) | 1.65 (m) | 1.78 (ddd, 8.7, 8.7, 3.0) | 1.81 (br d, 13.1) | 1.24 (m) | 2.39 (m) | 2.03 (m) |
| 10 | 1.43 (m) | |||||||
| 11a/b | 1.88 (m) | 1.55 (m)/1.90 (m) | 1.38 (m)/2.26 (m) | 2.15 (m)/2.24 (m) | 2.12 (m)/2.25 (m) | 1.66 (br d, 2.3)/1.84 (m) | 1.84 (br t, 13.9)/2.25 (m) | 1.40 (m) |
| 12a/b | 1.46 (m) | 1.40 (m) | 1.38 (m) | −/3.74 (br t, 7.8) | −/3.76 (br t, 9.7) | 1.31 (m) | 2.17 (m)/ 2.39 (m) | 1.42 (t, 11.9) |
| 15a/b | 1.93 (m)/2.19 (m) | 1.90 (m)/2.04 (m) | 1.81 (m)/2.04 (m) | 1.73 (m)/1.97 (m) | 1.92 (m) | 1.35 (m) | 1.19 (m)/1.49 (m) | 1.89 (m)/2.09 (dt, 12.6, 9.8) |
| 16a/b | 1.93 (m)/2.03 (dd, 20.0, 10.8) | 2.04 (m) | 1.81 (m)/2.04 (m) | 2.15 (m) | 2.12 (m) | 1.94 (m)/2.07 (m) | 1.97 (m)/2.21 (m) | 1.92 (m)/2.26 (m) |
| 17 | 2.76 (dd, 9.1, 3.2) | 2.78 (br d, 7.7) | 2.79 (br t,2.5) | 3.76 (br t, 7.4) | 3.76 (br t, 9.7) | 2.76 (br d, 8.8) | 2.21 (m) | |
| 18 | 0.98 (s) | 1.05 (s) | 1.15 (s) | 1.28 (s) | 1.29 (s) | 0.99 (s) | 1.26 (s) | 1.31 (s) |
| 19 | 1.17 (s) | 1.19 (s) | ||||||
| 20 | 4.36 (t, 6.5) | |||||||
| 21a/b | 4.98 (d, 18.1)/5.27 (d, 18.1) | 5.13 (d, 18.2)/5.30 (d, 18.2) | 5.01 (d, 18.0)/5.29 (d, 18.0) | 5.09 (d, 17.9)/5.23 (d, 17.9) | 5.03 (d, 18.1)/5.33 (d, 18.1) | 5.02 (d, 17.8)/5.31 (br d, 17.8) | 5.07 (dd, 18.2, 1.4)/5.21 (dd, 18.2, 1.4) | 3.89 (dd, 10.5, 6.1)/4.08 (dd, 10.5, 7.2) |
| 22 | 6.08 (s) | 6.12 (s) | 6.12 (s) | 6.22 (s) | 6.23 (s) | 6.12 (s) | 6.23 (d, 1.4) | |
| 1′ | 5.44 (br s) | 5.49 (br s) | 5.40 (d, 5.8) | 5.33 (br s) | 5.43 (d, 8.1) | 5.41 (br s) | 5.39 d, 8.1) | |
| 2′ | 4.27 (br s) | 4.54 (br s) | 3.96 (d, 4.7) | 4.48 (br s) | 4.50 (dd, 8.1, 3.1) | 4.54 (m) | 4.46 (br d, 8.1) | |
| 3′ | 4.44 (dd, 8.9, 3.4) | 4.44 (dd, 9.0, 3.2) | 4.67 (m) | 4.38 (dd, 8.6, 2.8) | 4.77 (t, 3.1) | 4.54 (m) | 4.70 (m) | |
| 4′ | 4.19 (dd, 8.9, 8.9) | 4.31 (m) | 3.66 (d, 6.2) | 4.21 (br t, 8.6) | 4.13 (d, 3.1) | 4.29 (m) | 4.11 (br s) | |
| 5′ | 4.32 (dq, 8.9, 6.1) | 4.22 (m) | 4.34 (dq, 6.2, 4.6) | 4.18 (dq, 8.6, 5.9) | 4.61 (q, 6.6) | 4.29 (m) | 4.59 (q, 6.4) | |
| 6′a/b | 1.59 (d, 6.1) | 1.63 (d, 6.0) | 1.59 (d, 4.6) | 1.61 (d, 5.9) | 1.53 (d, 6.6) | 1.67 (d, 4.7) | 1.56 (d, 6.4) |
δ Value in pyridine-d5 (400 MHz), coupling constants in Hz are given in parentheses.
†
W1/2 (Hz): width of 1/2 peak high.
‡
δ Value in pyridine-d5 (300 MHz), coupling constants in Hz are given in parentheses.