Table 1.
1H NMR, 13C NMR and HMBC data for Compounds TC-16R identified as tinosporide and TC-19R identified as 8-hydroxy tinosporide.
| Sl. |
TC-16R |
TC-19R |
||||
|---|---|---|---|---|---|---|
| δC | δH | HMBC | δC | δH | HMBC | |
| 1 | 71.0 | 5.23 d (2.6) | 34.9 (C-9),41.6 (C-5), 52.1 (3), 50.0 (2), 172.5 (C-18) | 70.9 | 5.37br s | 41.6 (C-5), 52.3 (3), 172.6 (C-18) |
| 2 | 50.0 | 3.97 dd (2.6, 4.3) | 52.1 (3), 71.0 (1) | 50.2 | 4.10 m | – |
| 3 | 52.1 | 4.01 d (4.3) | 50.1 (2), 81.3 (C-4), 172.5 (C-18), 71.0 (1) | 52.3 | 4.03br s | 50.2 (2), 81.6 (C-4), 172.6 (C-18) |
| 4 | 81.3 | – | – | 81.6 | – | – |
| 5 | 41.6 | – | – | 41.6 | – | – |
| 6 | 26.5 | 1.99 m, 1.75 m | 17.0 (C-7),23.3 (C-19), 41.6 (C-5), 81.3 (4) | 27.7 | 2.04 m | 23.7 (C-19),27.2 (C-7), 41.6 (C-5), 47.4 (C-10), 72.8 (C-8) |
| 7 | 17.0 | 2.88 m, 2.03 m | 26.5 (C-6), 34.9 (C-9), 44.0 (C-8), 173.8 (C-17), | 27.2 | 3.43 m, 2.03 m | 27.7 (C-6), 40.0 (C-9), 72.8 (C-8), 174.3 (C-17), |
| 8 | 44.0 | 2.55 dd (11.1, 1.5) | 17.0 (C-7), 26.5 (C-6), 27.9 (C-20), 34.9 (C-9), 46.3 (C-10), 173.8(C-17) | 72.8 | – | – |
| 9 | 34.9 | – | – | 40.0 | – | – |
| 10 | 46.3 | 2.31 s | 23.3 (C-19), 27.9 (C-20), 34.9 (C-9), 41.6 (C-5), 50.0 (C-2), 81.3 (C-4) | 47.4 | 2.41 s | 21.0 (C-20), 23.7 (C-19), 27.7 (C-6), 36.3 (C-11), 40.0 (C-9), 41.6 (C-5), 50.2 (C-2), 70.9 (C-1), 81.6 (C-4) |
| 11 | 41.2 | 2.46 dd (14.7, 4.1) 2.01 m |
27.9 (C-20), 34.9 (C-9), 44.0 (C-8), 46.3 (C-10), 70.9 (C-12),125.9 (C-13) | 36.3 | 2.80dd (14.5, 11.6) 2.32 dd (14.5, 5.5) |
21.0 (C-20), 40.0 (C-9), 47.4 (C-10), 71.4 (C-12), 72.8 (C-8), 126.5 (C-13) |
| 12 | 70.9 | 5.96 dd (12.2, 4.1) | 41.2 (C-11), 109.1 (C-14), 125.9 (C-13), 140.3 (C-16) | 71.4 | 6.00 dd (11.6, 5.5) | 36.3 (C-11), 109.3 (C-14), 126.5 (C-13), 140.3 (C-16) |
| 13 | 125.9 | – | – | 126.5 | – | – |
| 14 | 109.1 | 6.65 br s | 125.9 (C-13), 140.3 (C-16), 144.1 (C-15) | 109.3 | 6.69br s | 126.5 (C-13), 140.3 (C-16), 144.1 (C-15) |
| 15 | 144.1 | 7.62 br s | 109.1(C-14), 125.9 (C-13), 140.3 (C-16) | 144.1 | 7.59br s | 109.3(C-14), 126.5 (C-13), 140.3 (C-16) |
| 16 | 140.3 | 7.69 br s | 109.1(C-14), 125.9 (C-13), 144.1 (C-15) | 140.3 | 7.71br s | 109.3(C-14), 126.5 (C-13), 144.1 (C-15) |
| 17 | 173.8 | – | – | 174.3 | – | – |
| 18 | 172.5 | – | – | 172.6 | – | – |
| 19 | 23.3 | 1.48, 3H s | 26.5 (C-6), 41.6 (C-5), 46.3 (C-10), 81.3 (C-4) | 23.7 | 1.64, 3H s | 27.7 (C-6), 41.6 (C-5), 47.4 (C-10), 81.6 (C-4) |
| 20 | 27.9 | 1.29, 3H s | 34.9 (C-9), 41.2 (C-11), 44.0 (C-8), 46.3 (C-10), | 21.0 | 1.53, 3H s | 36.3 (C-11), 40.0 (C-9), 47.4 (C-10), 72.8 (C-8) |