Table 2.
1H-NMR Data for Ginsenosides Re (1), Rf (2), Rg2 (3), and 20-gluco-Rf (4) (400 MHz, pyridine-d5, δH)
| H-No. | Ginsenoside Re |
Ginsenoside Rf |
Ginsenoside Rg2 |
20-gluco-ginsenoside Rf |
||
|---|---|---|---|---|---|---|
| PGB16+17-9-15 | Refs3) | PGB16+17-7-16 | PGB9+10-10+11-5-13 | Refs3) | PGB16+17-9-12 | |
| 1 | 0.92 1.631) | – | 0.98, 1.68 | 0.84, 1.57 | 0.95, 1.62 [5] 0.96, 1.65 [8] |
0.76, 1.67 |
| 2 | 1.78, 1.85 | – | 1.62, 1.79 | 1.79, d, 12.4 1.88, d, 7.6 |
1.81, 1.86 | |
| 3 | 3.41, dd, 11.2, 4.82) | 3.44, dd, 4.4, 10.8 | 3.40, dd, 10.8, 4.8 | 3.43, dd, 10.8, 4.4 | ||
| 5 | 1.35, d, 10.4 | 1.35 | 1.33, d, 10.0 | 1.34 | ||
| 6 | 4.66 | 4.39 | 4.59 | 4.68 [5], 4.69 [8] | 4.29 | |
| 7 | 1.97, 2.23 | 1.92, 2.39 | 0.88, 2.19 | 1.97, 2.26 [5] 1.98, 2.26 [8] |
1.89, 2.34 | |
| 9 | 1.48 | 1.50 | 1.48 | 1.45 | ||
| 11 | 1.48, 2.04 | 1.49, 2.03 | 1.51, 1.96 | 1.44, 2.02 | ||
| 12 | 4.13 | 3.87, m | 3.83 | 4.10, m | ||
| 13 | 1.91 | 2.01 | 1.93 | 1.96 | ||
| 15 | 0.82, 1.48 | 1.04, 1.60 [8] | 1.13, 1.63 | 0.83, br.dd, 5.6 1.41 |
0.92, 1.53 [8] | 1.09, 1.44 |
| 16 | 1.19, 1.72 | 1.32, 1.38 | 1.38, 1.73 | 1.26, 1.78 [5] 1.29, 1.77 [8] |
1.26, 1.72 | |
| 17 | 2.48 | 2.28 | 2.21 | 2.49 | ||
| 18 | 1.14, s | 1.14, s | 1.13, s | 1.09, s | ||
| 19 | 0.93, s | 0.94, s | 0.91, s | 0.92, s | ||
| 21 | 1.56, s | 1.37, s | 1.35, s | 1.57, s | ||
| 22 | 1.75, 2.34 | 1.71 [5] | 1.69, 1.99 | 1.57, 1.91 | 1.78, 2.36 | |
| 23 | 2.20, 2.45, br.dd, 19.6, 9.2S | 2.26, 2.58 | 2.18, 2.52 | 2.28, 2.59 [5] 2.27, 2.59 [8] |
2.19, 2.46 | |
| 24 | 5.22, dd, 6.4, 6.4 | 5.31, dd, 6.8, 6.8 | 5.27, dd, 6.8, 6.8 | 5.22, dd, 6.4, 6.8 | ||
| 26 | 1.58, s | 1.65, s | 1.64, s | 1.57, s | ||
| 27 | 1.58, s | 1.62, s | 1.59, s | 1.57, s | ||
| 28 | 2.04, s | 2.03, s | 1.99, s | 2.11 [5], 2.10 [8] | 2.04, s | |
| 29 | 1.33, s | 1.42, s | 1.29, s | 1.44, s | ||
| 30 | 0.92, s | 0.81, s | 0.89, s | 0.76, s | ||
| 6-O-glc-1′ | 5.22, d, 6.4 | 4.90, d, 7.6 | 5.17, d, 6.0 | 4.86, d, 7.2 | ||
| 2′ | 4.32 | 4.38 | 4.24 | 4.34 [5, 8] | 4.43 | |
| 3′ | 4.37 | 4.31 | 4.29 | 4.33 | ||
| 4′ | 4.15 | 4.09 | 4.10 | 4.21 [5], 4.20 [8] | 4.13 ∗ | |
| 5′ | 3.89 | 3.90 | 3.86 | 3.97 [5], 3.96 [8] | 4.21 | |
| 6′ | 4.28, 4.49 | 4.26, 4.42 | 4.30, 4.47 | 4.31, 4.43 ∗ | ||
| 2′-O-rha-1′′ | 6.47, br. s | 6.40, br.s | ||||
| 2′′ | 4.77, br.d, 3.2 | 4.73 | ||||
| 3′′ | 4.64 | 4.59 | ||||
| 4′′ | 4.28 | 4.25 | ||||
| 5′′ | 4.90, dq, 9.2, 6.0 | 4.85, dq, 10.4, 6.4 | 4.98 [5], 4.92 [8] | |||
| 6′′ | 1.74, d, 6.0 | 1.72, d, 6.4 | ||||
| 2′-O-glc-1′′ | – | 5.84, d, 7.2 | – | 5.89 d, 7.2 | ||
| 2′′ | – | 4.13 | – | 4.17 | ||
| 3′′ | – | 4.18 | – | 4.20 | ||
| 4′′ | – | 4.12 | – | 4.12 ∗ | ||
| 5′′ | – | 3.81 | – | 3.81 ∗ | ||
| 6′′ | – | 4.29, 4.42 | – | 4.27, 4.44 ∗ | ||
| 20-O-glc-1′′′ | 5.13, d, 8.4 | – | – | 5.13 d, 7.6 | ||
| 2′′′ | 3.95 | – | – | 3.97 | ||
| 3′′′ | 4.19 | – | – | 4.19 | ||
| 4′′′ | 4.12 | – | – | 4.11 ∗ | ||
| 5′′′ | 3.88 | – | – | 3.90 ∗ | ||
| 6′′′ | 4.23, 4.44 | – | – | 4.27, 4.44 ∗ | ||
br, broad; d, doublet; dd, doublet of doublet; dq, doublet of quartet; s, singlet; NMR, nuclear magnetic resonance.
1)
Signals, the coupling pattern of which was not described, overlapped with other signals.
2)
Chemical shift, coupling pattern, J in Hz.
3)
The chemical shifts showing the difference bigger than 0.1 ppm from those of this study were exhibited. * Assignments with the same superscript in a single column might be reversed.