Table 3. 1H, 13C, HMBC and COSY NMR spectroscopic data (500 MHz, DMSO-d6) of compounds 2, 4, 6 and 8.
Position | Compound 2 | Compound 4 | Compound 6 | Compound 8 | ||||||||
δ1H | δ13C | HMBC | COSY | δ1H | δ13C | δ1H | δ13C | COSY | δ1H | δ13C | COSY | |
2 | 156.97 | 156.83 | 156.90 | 164.41 | ||||||||
3 | 134.70 | 133.71 | 134.67 | 6.78 s | 102.94 | |||||||
4 | 178.20 | 178.01 | 178.21 | 182.54 | ||||||||
5 | 12.63 s | 161.77 | C5, C6, C10 | 12.62 s | 161.69 | 12.66 s | 161.76 | 13.17 s | 156.48 | |||
6 | 6.21 d (1.6) | 99.19 | C8, C10, C5,C7 | H8 | 6.21 d (1.9) | 99.17 | 6.21 br s | 99.14 | H8 | 6.27 s | 98.67 | |
7 | 10.86 s | 164.68 | 164.63 | 164.66 | 10.83 s | 162.91 | ||||||
8 | 6.42 d (1.6) | 94.21 | C6, C10, C9,C7 | H6 | 6.44 d (1.9) | 94.14 | 6.40 br s | 94.08 | H6 | 6.78 s | 105.26 | |
9 | 157.70 | 156.85 | 157.76 | 160.89 | ||||||||
10 | 104.62 | 104.43 | 104.54 | 104.55 | ||||||||
1′ | 121.00 | 121.34 | 121.18 | 122.11 | ||||||||
2′ | 7.77 dd (8.58) | 131.06 | C6′, C2, C4′ | H3′ | 8.07 d (8.8) | 131.45 | 7.30 d (1.5) | 115.91 | 8.02 d (8.7) | 129.39 | H3′ | |
3′ | 6.93 dd (8.58) | 115.87 | C5′, C1′, C4′ | H2′ | 6.87 d (8.8) | 115.53 | 148.90 | 6.91 d (8.7) | 116.32 | H2′ | ||
4′ | 10.2 s | 160.46 | 160.43 | 145.67 | 10.35 s | 161.61 | ||||||
5′ | 6.93 dd (5.58) | 115.87 | C3′, C1′, C4′ | H6′ | 6.87 d (8.8) | 115.53 | 6.88 d (8.4) | 116.10 | H6′ | 6.91 d (8.7) | 116.32 | H6′ |
6′ | 7.77 dd (8.58) | 131.06 | C2′, C2, C4′ | H5′ | 8.07 d (8.8) | 131.45 | 7.25 d (8.4) | 121.57 | H5′ | 8.02 d (8.7) | 129.39 | H5′ |
3′- OCH3 | 3.19 s | 49.06 | ||||||||||
1″ | 5.31 d (1.8) | 102.27 | C3, C2″ | H2″ | 5.40 d (7.5) | 102.14 | 5.26 s | 102.29 | H2″ | 4.70 d (9.8) | 73.88 | H2″ |
2″ | 3.99 dd (3.6, 1.5) | 70.55 | H1″, H3″ | 71.68 | 3.98 dd | 70.51 | H1″, H3″ | 3.85 dd | 71.39 | |||
3″ | 3.48 dd | 71.08 | H2″, H4″ | 73.57 | 3.50 dd | 71.05 | H2″, H4″ | 3.29 dd | 79.18 | |||
4″ | 3.15 dd | 71.61 | H3″ | 68.35 | 3.17 dd | 71.63 | H3″ | 3.52 dd | 71.09 | |||
5″ | 3.17 dd | 70.83 | H6″ | 76.25 | 3.23 dd | 70.80 | H6″ | 3.26 dd | 82.29 | |||
6″ | 0.81 d (6.09) | 17.93 | H5″ | 60.67 | 0.82 d (6.0) | 17.96 | H5″ | 3.76 dd | 61.82 |
Assignments were done by 1D (1H, 13C, DEPT) and 2D (COSY, HSQC, HMBC) NMR experiments.