Three new biphenyls were isolated from Garcinia multiflora. The structures of these biphenyls were elucidated by spectroscopic methods, and their rotavirus activity was evaluated.
Keywords:
Garcinia multiflora; biphenyls; anti-rotavirus activity
| No. | 1 | 2 | 3 | |||
|---|---|---|---|---|---|---|
| δC (m) / ppm | δH (m, J , Hz) / ppm | δC (m) / ppm | δH (m, J , Hz) / ppm | δC (m) / ppm | δH (m, J , Hz) / ppm | |
| 1 | 129.6 s | 132.4 s | 132.3 s | |||
| 2 | 119.7 s | 114.2 s | 112.4 s | |||
| 3 | 144.9 s | 142.0 s | 141.5 s | |||
| 4 | 135.0 s | 131.9 s | 132.7 s | |||
| 5 | 147.2 s | 149.6 s | 144.8 s | |||
| 6 | 105.9 d | 6.26 (s, 1H ) | 106.6 d | 6.44 (s, 1H) | 105.5 d | 6.43 (s, 1H) |
| 7 | 133.8 s | 134.6 s | 132.7 s | |||
| 8 | 131.7 d | 7.00 (dd, 1H, J 8.8 Hz, 2.4) | 131.8 d | 7.11 (dd, 1H, J 8.4 Hz, 1.9) | 130.3 d | 7.16 (d, 1H, J 8.6 Hz) |
| 9 | 115.7 d | 6.74 (dd, 1H, J 8.8 Hz, 2.4) | 116.0 d | 6.82 (dd, 1H, J 8.4 Hz, 1.9) | 114.8 d | 6.86 (d, 1H, J 8.6 Hz) |
| 10 | 157.1 s | 157.7 s | 155.5 s | |||
| 11 | 115.7 d | 6.74 (dd, 1H, J 8.8 Hz, 2.4) | 116.0 d | 6.82 (dd, 1H, J 8.4 Hz, 1.9) | 114.8 d | 6.86 (d, 1H, J 8.6 Hz) |
| 12 | 131.7 d | 7.00 (dd, 1H, J 8.8 Hz, 2.4) | 131.8 d | 7.11 (dd, 1H, J 8.4 Hz, 1.9) | 130.3 d | 7.16 (d, 1H, J 8.6 Hz) |
| 1' | 26.8 t | 3.21 (d, 2H, J 6.7 Hz, CH2) | 124.7 d | 6.41 (d, 1H, J 10.1 Hz) | 21.1 t | 2.59 (t, 2H, J 6.6 Hz, CH2) |
| 2' | 130.7 d | 5.44 (t, 1H, J 6.7 Hz) | 124.4 d | 5.48 (d, 1H, J 10.1 Hz) | 33.0 t | 1.72 (t, 2H, J 6.6 Hz, CH2) |
| 3' | 134.6 s | 77.6 s | 74.7 s | |||
| 4' | 71.5 t | 4.33 (s, 3H, CH3) | 69.0 t | 4.27 (d, 1H, J 11.5 Hz, CH2) | 26.7 q | 1.39 (s, 3H, CH3) |
| 4.14 (d, 1H, J 11.5 Hz, CH2) | ||||||
| 5' | 14.0 q | 1.39 (s, 3H, CH3) | 23.4 q | 1.47 (s, 3H, CH3) | 26.7 q | 1.39 (s, 3H, CH3) |
| 3-OMe | 56.5 q | 3.76 (s, 3H, OCH3) | 56.5 q | 3.85 (s, 3H, OCH3) | 56.1 q | 3.86 (s, 3H, OCH3) |
| 5'- OAc | 172.9 s | 172.6 s | ||||
| 20.8 q | 1.99 (s, 3H, COCH3) | 20.7 q | 2.00 (s, 3H, COCH3) | |||
| No. | CC50b b CC50: mean (50%) value of cytotoxic concentration; / (μg mL-1) | EC50c c EC50: mean (50%) value of effective concentration; / (μg mL-1) | TId d TI: therapeutic index, CC50/EC50. |
|---|---|---|---|
| 1 | 125.72 ± 6.41 | 11.56 ± 1.13 | 10.93 ± 1.27 |
| 2 | 134.65 ± 8.34 | 10.94 ± 1.65 | 12.35 ± 1.75 |
| 3 | 159.83 ± 7.46 | 12.73 ± 1.75 | 12.58 ± 1.68 |
| Ribavirin | 274.27 ± 11.07 | 13.61 ± 1.04 | 20.14 ± 1.16 |
