Table 4.
Purification and biophysical properties of oleanes gem-dimethylated isolated from Gymnema sylvestre.
| No. | Chromatographic conditions | Melting point (°C) | IR analysis (cm−1) | Mass analysis | [α]D (Concentration, Solvent) | Reference |
|---|---|---|---|---|---|---|
| 1 | - | 247–249 | - | - | +53 (Acetone) | [80] |
| Preparative TLC (CH2Cl2/Me2CO, 17:3) | - | - | - | - | [81] | |
| - | 216–218 | - | EI: [M]+ 458 | +38.7 (c2.5, CHCl3) | [82] | |
| HR-ESI: [M]+ 458.3755 | ||||||
| - | 218–220 | - | - | +51.0 (CHCl3) | [83] | |
| - | 244–245 | - | - | - | [84] | |
| 2 | By synthesis | 315–317 | - | HR-ESI: [M-H2O]+ 456.3580 | +35.4 (c1.2, CHCl3) | [85] |
| - | 321–323 | - | - | +43 (c1, CHCl3) | [86] | |
| HPLC (RP-C18; CH3OH/CH3CN/H2O, 2:7:1) | - | - | - | - | [81] | |
| 3 | HPLC (RP-C18; CH3OH/CH3CN/H2O, 2:5:3) | - | - | - | - | [81] |
| HPLC (S-5; H2O/CH3CN, 63:37) | 333–335 | - | HR-ESI: [M-H2O]+ 456.3628 | +57.0 (c0.9, CHCl3:CH3OH 1:1) | [82,87] | |
| 4 | - | - | - | ESI: [M+H]+ 505, [M+Na]+ 527 | - | [88] |
| 5 | Silica gel column chromatography using as eluent CHCl3/CH3OH | 198–202 | 3414 (OH), 1724 | FAB: [M+Na]+ 657 | +16.08 (c0.10, CH3OH). | [89] |
| (COOH), 1636 (C=C), 1458, 1380, 1054. | ||||||
| 6 | Silica gel column chromatography using as eluent CHCl3/CH3OH | 192–195 | 3444 (OH), 1724, 1700, 1635 (C=C), 1457, 1388, 1280, 1074, 720. | FAB: [M+Na]+ 777 | +27.2 (c0.15, CH3OH). | [89] |
| 7 | - | - | - | - | - | [90] |
| 8 | HPLC (RP-C18; CH3OH/H2O, 4:1) and Si-60 (CHCl3/CH3OH, 10:1 to 5:2) | - | - | HR-ESI: [M+Na]+ 687.4085 | −6.5 (c0.01, CH3OH) | [91] |
| 9 | HPLC (RP-C18; CH3OH/H2O, 1:4 to 7:3) | 305–310 | 3440, 2948, 1636, 1420, 1078, 1028 | HR-ESI: [(M.K)+H]+ 835.4065 | +18.1 (c0.08, CH3OH) | [92] |
| 10 | HPLC (ODS S-5, H2O/CH3CN, 4:1) | 213–215 | 3460, 1720, 1655, 1155 | FAB: [M−H]− 811 | +9.1 (c4.5, CH3OH) | [93] |
| 11 | HPLC (RP-C18; CH3OH/H2O, 1:4 to 7:3) | 226–228 | 3422, 2948, 1702, 1636, 1460, 1388, 1282, 1160, 1076, 1026 | FAB: [M+H]+ 917, [M+Na]+ 939 | +15.4 (c0.16, CH3OH) | [92] |
| 12 | HPLC (RP-C18; CH3OH/H2O, 1:4 to 7:3) | 290–293 | 3422, 2928, 1618, 1430, 1028 | FAB: [(M.K)+H]+ 851 | +10.3 (c0.12, CH3OH) | [92] |
| 13 | HPLC (RP-C18; CH3OH/H2O, 4:1) and Si-60 (CHCl3/CH3OH, 10:1 to 5:2) | - | - | ESI: [M-H]− 943 | −26.6 (c0.004, CH3OH) | [91] |
| [M-Glc]− 781, [M-2×Glc]− 619 | ||||||
| [M-3×Glc]− 457, [M+Na]+ 967 | ||||||
| HR-ESI: [M]+ 944.5290 | ||||||
| 14 | HPLC (YMC; S-5; H2O/CH3CN 3:1 to 13:7) | 187–189 | 3450, 1155 | FAB: [M-H]− 1075 | −23.4 (c3.1, CH3OH) | [94] |
| 15 | - | - | - | - | - | [95] |
| 16 | HPLC (RP-C18; CH3OH/H2O, 1:4 to 7:3) | 294–296 | 3418, 2948, 1738, 1713, 1621, 1430, 1374, 1266, 1076, 1031 | FAB: [(M.K)+H]+ 1023 | +1.5 (c0.19, CH3OH) | [92] |
| HPLC (ODS S-5; H2O/CH3CN, 4:1) | 230–232 | 3400, 1730, 1665, 1240, 1160 | FAB: [M-H]− 999 | +2.3 (2.4, CH3OH) | [93] |