Table 1.
NMR (600 MHz, CDCl3) data for 3.
| Position | δC, Mult. | δH (J in Hz) § | 1H, 1H-COSY | HMBC | ROESY |
|---|---|---|---|---|---|
| aglycone | |||||
| 1 | 165.6, C | – | – | – | – |
| 2 | 121.4, CH | 5.75 d (15.4) | 3 | 4 | 4, 17 |
| 3 | 151.7, CH | 6.62 dd (15.4, 9.5) | 2, 4 | 1 | 5, 6, 17 |
| 4 | 41.0, CH | 2.66 | 3, 5, 17 | 2, 3 | 2, 6, 7a, 7b |
| 5 | 88.1, CH | 3.19 | 4, 6 | 3, 4, 6, 7, 17, 18, 1′ | 3, 6, 17, 18, 1′ |
| 6 | 34.0, CH | 1.30 | 5, 7a, 7b, 18 | – | 3, 4, 5, 7a, 10 |
| 7 | 37.4, CH2 | 1.89, Ha | 6, 7b | 6, 8, 9, 18 | 4, 6, 10, 19 |
| 1.83, Hb | 6, 7a | 6, 18 | 4, 18, 19 | ||
| 8 | 78.3, C | – | – | – | – |
| 9 | 202.0, C | – | – | – | – |
| 10 | 122.0, CH | 6.18 d (15.1) | 11 | 8, 9, 11, 12 | 6, 7a, 19 |
| 11 | 144.1, CH | 7.30 dd (15.1, 10.1) | 10, 12 | 9, 12, 13 | – |
| 12 | 133.0, CH | 6.15 dd (14.1, 10.1) | 11, 13 | 10, 11, 13, 14 | – |
| 13 | 143.3, CH | 6.14 dd (14.1, 9.2) | 12, 14 | 11, 12, 14, 20 | 15, 20b |
| 14 | 51.2, CH | 2.47 | 13, 15, 20a, 20b | 12, 13, 15 | 16, 20a |
| 15 | 69.2, CH | 5.06 dq (10.2, 6.2) | 14, 16 | 1, 13, 14 | 13, 20a, 20b |
| 16 | 18.6, CH3 | 1.36 d (6.3) | 15 | 14, 15 | 14, 20a, 20b |
| 17 | 19.2, CH3 | 1.18 d (6.9) | 4 | 3, 4, 5 | 2, ,3, 5, 1′ |
| 18 | 19.3, CH3 | 1.00 d (6.9) | 6 | 5, 6, 7 | 5, 7b |
| 19 | 27.9, CH3 | 1.38 s | – | 7, 8, 9 | 7a, 7b, 10 |
| 20 | 68.4, CH2 | 4.04 dd (9.6, 3.7), Ha | 14, 20b | 13, 14, 15, 1″ | 14, 15, 16, 20b, 1″ |
| 3.57 dd (9.6, 6.1), Hb | 14, 20a | 13, 14, 15, 1″ | 13, 15, 16, 20a, 1″ | ||
| β-d-chalcose unit | |||||
| 1′ | 103.0, CH | 4.19 d (7.6) | 2′ | 5, 5′ | 5, 17, 3′, 5′ |
| 2′ | 75.1, CH | 3.32 dd (8.8, 7.6) | 1′, 3′ | 1′, 3′, 4′ | 4′b |
| 3′ | 80.4, CH | 3.22 | 2′, 4′a, 4′b | 1′, 2′, 4′, 7′ | 1′, 4′a, 5′ |
| 4′ | 36.8, CH2 | 2.04 ddd (12.7, 4.9, 1.9), Ha | 3′, 4′b, 5′ | 2′, 3′ | 3′, 5′, 6′ |
| 1.25, Hb | 3′, 4′a, 5′ | 2′, 3′, 5′ | 2′, 6′ | ||
| 5′ | 67.8, CH | 3.48 | 4′a, 4′b, 6′ | 1′ | 1′, 3′, 4′a |
| 6′ | 20.9, CH3 | 1.23 d (6.2) | 5′ | 4′, 5′ | 4′a, 4′b |
| 7′ | 56.7, CH3 | 3.41 s | – | 3′ | – |
| β-d-mycinose unit | |||||
| 1″ | 101.1, CH | 4.58 d (7.8) | 2″ | 20, 3″, 5″ | 20a, 20b, 5″, 8″ |
| 2″ | 81.9, CH | 3.04 dd (7.8, 3.1) | 1″, 3″ | 1″, 7″ | 3″, 4″, 7″ |
| 3″ | 79.8, CH | 3.76 t (3.1) | 2″, 4″ | 1″, 2″, 4″, 5″, 8″ | 2″, 4″, 8″ |
| 4″ | 72.7, CH | 3.18 | 3″, 5″ | 2″ | 2″, 3″, 6″ |
| 5″ | 70.6, CH | 3.52 | 4″, 6″ | 3″, 4″ | 1″ |
| 6″ | 17.8, CH3 | 1.27 d (6.2) | 5″ | 4″, 5″ | 4″ |
| 7″ | 59.8, CH3 | 3.52 s | – | 2″ | 2″ |
| 8″ | 61.8, CH3 | 3.62 s | – | 3″ | 1″, 3″ |
§ Indiscernible signals owing to overlapping or having complex multiplicity are reported without designating multiplicity. NMR: nuclear magnetic resonance; 1H, 1H COSY: 1H, 1H chemical shift correlated spectroscopy; HMBC: heteronuclear multiple-bond correlation; ROESY: rotating frame overhauser effect spectroscopy.