Table 1.
NMR spectral dataa of hypoculoside (8) and hypoculine (9).
| Position | 8 | 9 | ||
|---|---|---|---|---|
| 13Cb | 1Hc, mult. (J = Hz) | 13Cb | 1Hc, mult. (J = Hz) | |
| 1 | 12.1 | 1.12, d (6.5) | 18.4 | 1.14, d (6.5) |
| 2 | 75.5 | 3.74, m | 71.8 | 3.68, m |
| 3 | 75.4 | 3.69, m | 76.7 | 3.35, m |
| 4 | 34.1 | 1.44, m, 1.44, m | 33.8 | 1.34, m, 1.54, m |
| 5 | 27.0 | 1.31, m, 1.49, m | 27.0 | 1.33, m, 1.55, m |
| 6–19 | 30.6–30.8 | 1.26–1.34, m | 30.6–30.8 | 1.28, m |
| 20 | 27.2 | 1.32, m, 1.32, m | 27.1 | 1.33, m, 1.33, m |
| 21 | 34.0 | 1.43, m, 1.43, m | 34.0 | 1.44, m |
| 22 | 71.8 | 3.68, m | 71.7 | 3.69 m |
| 23 | 52.6 | 3.25, m | 52.6 | 3.25, ddd (10, 6.7, 3) |
| 24 | 12.2 | 1.20, d (6.5) | 12.2 | 1.20, d (6.5) |
| 1′ | 96.7 | 4.94, d (3.9) | ||
| 2′ | 73.5 | 3.38, dd (9.7, 3.9) | ||
| 3′ | 75.2d | 3.62, m | ||
| 4′ | 74.0d | 3.62, m | ||
| 5′ | 71.9 | 3.27, m | ||
| 6′ | 62.7 | 3.64, m, 3.78, m | ||
aAssignments based on COSY, HSQCED and HMBC. b(8) and (9) were recorded at 100 MHz with CD3OD as internal standard at δ 49.0 Chemical shifts (δ) in ppm. c(8) and (9) was recorded at 400 MHz with CD3OD as internal standard at δ 3.30. dAssignments are interchangeable. s: singlet; d: doublet. q: quartet; m: multiplet; br; broad.