Planta Med 2008; 74 - PC116
DOI: 10.1055/s-0028-1084634

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

FQ Alali 1, A Gharaibeh 2, A Ghawanmeh 2, K Tawaha 3, NH Oberlies 4
  • 1Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan
  • 2Department of Applied Chemistry, Faculty of Science and Arts, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan
  • 3Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan
  • 4Natural Products Laboratory, Research Triangle Institute, P.O. Box 12194, Research Triangle Park, North Carolina 27709, USA

As a part of a project designed to investigate Colchicum species in Jordan [1,2], 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 (2mg) 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, β-lumidemecolcine, 2-demethyl-β-lumicolchicine or 3-demethyl-β-lumicolchicine, N,N-dimethyl-N-deacetyl-β-lumicornigerine; (-)-isoandrocymbine; and (-)-autumnaline. Furthermore, a new compound was identified as N,N-dimethyl-N-deacetyl-(-)-cornigerine (Figure 1). Three compounds, which had molecular ions at m/z of 325, 340, and 374, could not be dereplicated into any obvious structural classes that have been isolated in our labs previously or reported in the literature.

Figure 1. The chemical structure of the dereplicated novel colchicinoid N,N-dimethyl-N-deacetyl-(-)-cornigerine

Acknowledgement: The authors thank Ms Tamam El-Elimat, Pharmaceutical Research Center, and Mr Munther Tahtamoni, Princess Haya Biotechnology Center, both of the Jordan University of Science and Technology (JUST), Irbid, Jordan for technical assistance. This research was undertaken via the kind financial support of the Deanship of Scientific Research, JUST.

References: 1. Alali et al. (2005). J. Nat. Prod. 68, 173–178. 2. Alali et al. (2006). Nat. Prod. Comm. 1: 95–99.