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 or 3-demethyl-(-)-colchicine, N-deacetyl-(-)-colchicine, (-)-colchiciline, (-)-colchicine, beta-lumidemecolcine, 2-demethyl-beta-lumicolchicine or 3-demethyl-beta-lumicolchicine, N,N-dimethyl-N-deacetyl-beta-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
Feras Q
FQ
Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan. falali@just.edu.jo
Gharaibeh
Ahmad
A
Ghawanmeh
Abdullah
A
Tawaha
Khaled
K
Oberlies
Nicholas H
NH
D002853:Chromatography, Liquid / Q000379:methods*; D003078:Colchicine / Q000031:analogs & derivatives* / Q000032:analysis; D003079:Colchicum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet
D003078:Colchicine