Table 1.
NMR data of undescribed compounds 1–3. 1H/400 MHz,13C/100 MHz, δ in ppm, J in Hz.
| Position | 1a,b |
2a,b |
3a,b |
|||
|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | |
| 1 | – | 145.3 | – | 145.3 | – | 145.3 |
| 2 | 6.30 (d, J = 2.2) | 107.6 | 6.30 (d, J = 2.2) | 107.6 | 6.30 (d, J = 2.2) | 107.6 |
| 3 | – | 162.2 | – | 162.2 | – | 162.2 |
| 4 | 6.27 (d, J = 2.2) | 98.9 | 6.27 (d, J = 2.2) | 98.9 | 6.27 (d, J = 2.2) | 98.9 |
| 5 | – | 162.2 | – | 162.2 | – | 162.2 |
| 6 | 6.30 (d, J = 2.2) | 107.6 | 6.30 (d, J = 2.2) | 107.6 | 6.30 (d, J = 2.2) | 107.6 |
| α | 2.80 (m) | 39.5 | 2.80 (m) | 39.5 | 2.80 (m) | 39.5 |
| α′ | 2.81 (m) | 38.1 | 2.81 (m) | 38.1 | 2.81 (m) | 38.1 |
| 1′ | – | 137.1 | – | 137.1 | – | 137.1 |
| 2′ | 7.10 (d, J = 8.6) | 130.5 | 7.10 (d, J = 8.6) | 130.5 | 7.10 (d, J = 8.6) | 130.5 |
| 3′ | 7.00 (d, J = 8.6) | 117.6 | 7.00 (d, J = 8.6) | 117.6 | 7.00 (d, J = 8.6) | 117.6 |
| 4′ | – | 157.4 | – | 157.4 | – | 157.4 |
| 5′ | 7.00 (d, J = 8.6) | 117.6 | 7.00 (d, J = 8.6) | 117.6 | 7.00 (d, J = 8.6) | 117.6 |
| 6′ | 7.10 (d, J = 8.6) | 130.5 | 7.10 (d, J = 8.6) | 130.5 | 7.10 (d, J = 8.6) | 130.5 |
| 3,5-OCH3 | 3.71 (s) | 55.6 | 3.71 (s) | 55.6 | 3.71 (s) | 55.6 |
| Sugar moiety | Glc | Glc | Glc | |||
| 1″ | 4.83 (d, J = 7.3) | 102.5 | 4.85 (d, J = 7.2) | 102.3 | 4.81 (d, J = 7.5) | 102.6 |
| 2″ | 3.43 (m) | 74.9 | 3.43 (m) | 74.9 | 3.43 (m) | 74.9 |
| 3″ | 3.43 (overlapped) | 77.9 | 3.43 (overlapped) | 77.8 | 3.43 (overlapped) | 77.9 |
| 4″ | 3.36 (m) | 71.8 | 3.37 (m) | 71.5 | 3.35 (m) | 71.6 |
| 5″ | 3.59 (m) | 76.8 | 3.62 (m) | 77.3 | 3.59 (m) | 77.0 |
| 6a′′ | 3.60 (m) | 68.2 | 3.62 (overlapped) | 69.3 | 3.61 (m) | 68.8 |
| 6b′′ | 4.05 (dd, J = 5.4, 14.3) | 4.10 (dd, J = 2.1, 11.5) | 4.01 (dd, J = 1.5, 10.6) | |||
| Sugar moiety | Araf | Arap | Apif | |||
| 1‴ | 4.93 (d, J = 1.5) | 110.0 | 4.30 (d, J = 6.8) | 104.9 | 4.98 (d, J = 2.4) | 111.1 |
| 2‴ | 4.00 (dd, J = 3.4, 1.5) | 83.3 | 3.57 (m) | 72.5 | 3.91 (d, J = 2.4) | 78.0 |
| 3‴ | 3.82 (dd, J = 6.0, 3.4) | 78.9 | 3.49 (dd, J = 3.3, 8.9) | 74.1 | – | 80.5 |
| 4‴ | 3.96 (m) | 85.8 | 3.75 (m) | 69.5 | 3.76 (d, J = 9.6) | 75.0 |
| 3.98 (d, J = 9.6) | ||||||
| 5‴ | 3.62 (m) | 63.0 | 3.42 (m) | 66.7 | 3.58 (s) | 65.5 |
| 3.70 (m, overlapped) | 3.82 (dd, J = 3.1, 12.4) | |||||
a) Recorded in CD3OD. b) Multiplicities inferred from DEPT and HSQC experiments. Glc: glucopyranose; Araf: arabinofuranose; Arap: arabinopyranose; Apif: apiofuranose.