Isolation and Structural Characterization of Tropolonic Alkaloids Colchicum speciosum Steven bulbs
Keywords:
Colchicum speciosum Steven, tropolonic alkaloids, 1D and 2D NMR, Absolute ConfigurationAbstract
The Colchicum genus, is well-known for its significant biological activities. Among its bioactive constituents, tropolonic alkaloids, particularly colchicine, are widely used in the treatment of gout and have shown potential in treating proinflammatory conditions such as familial Mediterranean fever and Behcet's disease. Furthermore, colchicine has emerging applications in anti-tumor therapies. Colchicum speciosum Steven, a perennial herb native to Iran, is a valuable source of these bioactive compounds. This study investigates the phytochemical profile of C. speciosum bulbs collected from Savadkouh, Iran. Methanol (MeOH) extracts were analyzed using high-performance liquid chromatography with photodiode array detection and mass spectrometry (HPLC-PDA-MS), along with nuclear magnetic resonance (NMR) spectroscopy. The MeOH extract was sequentially partitioned with dichloromethane (CH₂Cl₂), ethyl acetate (EtOAc), and water. Electronic circular dichroism (ECD) spectral calculations were used to determine the absolute configurations of compounds 3, 4, and 5. Chromatographic separation of the CH₂Cl₂ fraction led to the isolation and identification of five tropolonic alkaloids, including four known compoundscolchicine (1), demecolcine (2), speciosamine (4), and N-formyldemecolcine (5) and one novel compound 3. The structures were confirmed by 1D (¹H NMR) and 2D-NMR (COSY, HSQC, and HMBC). ECD analysis confirmed that compounds 3, 4, and 5 exhibited the S configuration. This study expands the chemical profile of C. speciosum, identifying one new tropolonic alkaloid and four known compounds, thereby advancing our understanding of the phytochemistry of this plant.
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