Colchicinoids from Colchicum crocifolium Boiss.: A case study in dereplication strategies for (-)-colchicine and related analogues using LC-MS and LC-PDA techniques

As a part of a project designed to investigate Colchicum species in Jordan, the chemical constituents of Colchicum crocifolium Boiss. (Colchicaceae) were investigated using LC-MS and LC-UV/Vis PDA. A decision tree for working with colchicinods has been developed by incorporating data from LC-UV/PDA and LC-MS. This dereplication strategy draws upon the UV/PDA spectra to classify compounds into one of four structural groups and combines this with retention time and mass spectra/molecular weight to identify the compounds. This strategy was applied on a small amount of extract (2 mg) of Colchicum crocifolium to dereplicate 10 known compounds from four different structural groups, namely (-)-demecolcine, 2-demethyl-(-)-colchicine or3-demethyl-(-)-colchicine, N-deacetyl-(-)-colchicine, (-)-colchiciline, (-)-colchicine, -lumidemecolcine, 2-demethyl--lumicolchicine or 3-demethyl--lumicolchicine, N,N-dimethyl-N-deacetyl--lumicornigerine, (-)-isoandrocymbine and (-)-autumnaline. Furthermore, a new compound was identi?ed as N,N-dimethyl-N-deacetyl-(-)-cornigerine. Three compounds, which had molecular ions at m/z 325, 340 and 374, could not be dereplicated into any obvious structural classes that have been isolated in our laboratories previously or reported in the literature.

Alali, F., Gharaibeh, A., Ghawanmeh, A., Tawaha, K., & Oberlies, N. (2008). Colchicinoids from Colchicum crocifolium Boiss.: A case study in dereplication strategies for (-)-colchicine and related analogues using LC-MS and LC-PDA techniques. Phytochemical Analysis, 19(5), 385-394. DOI: 10.1002/pca.1060