Table 3.
Methods of extraction, separation, and identification of Veratrum alkaloids.
| Alkaloid | Plant(s) | Sample Preparation * | Separation Technique | Identification | References |
|---|---|---|---|---|---|
| Cyclopamine (1) | V. californicum | Soxhlet extraction with ethanol/ammonium hydroxide | HPLC | LC-MS, 1H and 13C NMR | [1,50] |
| Ethanol soak | [48,49] | ||||
| Veratramine (2) | V. viride | Ethanol and chloroform extraction | Flash chromatography with silica gel | 1H and 13C NMR, HPLC-MS, crystallization, melting point, and HPLC-CAD. | [65] |
| V. viride | Benzene, ammonia, acetic acid, and NaOH extractions | High-speed counter-current chromatography | HPLC, MS and NMR | [66] | |
| V. oxysepalum | Diethyl ether and dichloromethane extractions | N/A | HPLC-MS | [67] | |
| V. nigrum L. | Ethanol and then chloroform extraction | Column chromatography | Crystallization | [68] | |
| V. grandiflorum | Crystallization and filtration using 2 N-calcium acetate and acetic acid (Unk plant part) | N/A | Crystallization, melting point, and NMR | [69] | |
| V. californicum | Dried and ground, ethanol then chloroform extraction | HPLC | HPLC, CAD and MS | [70] | |
| Isorubijervine (3) | V. eschscholtzii Gray | Chloroform extraction (Unknown plant part) | Craig countercurrent distribution | N/A | [71] |
| V. taliense | Methanol extraction | Silica gel column chromatography and MPLC | NMR and ESI-MS. | [32] | |
| V. viride Aiton | Ethanol and chloroform extraction (Unk plant part) | Flash chromatography with silica gel | IR, LC-MS, 1H and 13C NMR | [65] | |
| Muldamine (4) | V. californicum | Benzene and 5% NH4OH soak (Unk plant part) | Column chromatography with silica gel/benzene/methanol slurry | HPLC-ELSD, MS m/z = 458.37 | [72] |
| Cycloposine (5) | V. californicum | Dried and ground, ethanol then chloroform extraction | HPLC-ELSD | HPLC-MS spectra confirmation | [70,72,73] |
| Veratrosine (6) | V. patulum | Ethanol soak, chloroform extraction, alkaloid residue | Silica gel, recrystallization in acetone | HPLC-MS m/z and elution times | [70,72,73] |
| V. californicum | Dried and ground, ethanol then chloroform extraction | HPLC-ELSD | |||
| Verazine (7) | Zygadenus sibiricus | N/A (From aerial plant) | N/A | N/A | [74] |
| Solanaceae Solanum hypomalacophyllum | Dried, ground and refluxed with CHCl3 | Vacuum liquid chromatography and column chromatography | N/A | [75] | |
| Asteraceae Eclipta alba | EtOAc and MeOH extraction from leaves | Silica gel columns and preparative TLC | MeOH crystallization and DEPT, HETCOR, HMQC, and HMBC NMR | [76] | |
| V. nigrum | Ethanol extraction followed by two CHCl3 extractions (Unknown plant part) | Alkali-treated silica gel and TLC | Specific TLC fractions were recrystallized | [77] | |
| V. nigrum | Three methanol extractions | Silica gel column chromatography twice and HPLC | Recrystallization, ESI-MS, IR, 1H and 13C NMR | [28] | |
| Etioline (8) | Solanum spirale | Dried and ground, Soxhlet extraction with ethanol, chloroform/methanol extraction | Silica gel | 13C NMR and atom probe chromatography | [78] |
| Lilium candidum L. | Ethanol extraction from bulbs and then CHCl3 extraction | TLC with chloroform and methanol | TLC with chloroform and methanol | [79] | |
| Tetrahydrojervine (9) | N/A | Synthesized only | |||
| Dihydrojervine (10) | N/A | Synthesized only | |||
| 22-Keto-26-amino cholesterol (11) | N/A | Cholesterol metabolite, proposed | [80,81] |