Isolation and Structure Elucidation of Glucosylated Colchicinoids from the Seeds of Gloriosa superba by LC-DAD-SPE-NMR

Four new colchicinoids were isolated from the seeds of Gloriosa superba together with the known compounds colchicoside (4) and 3-de-O-methylcolchicine-3-O-beta-D-glucopyranosyl-(1 -> 4)-3-O-beta-D-glucopyranoside (6), by means of conventional column chromatography and LC-DAD-SPE-NMR. The new compounds were identified as N-deacetyl-N-formyl-3-de-O-methylcolchicine-3-O-beta-dD-glucopyranoside (1), 3-de-O-methylcolchicine-3-O-beta-D-glucopyranosyl-(1 -> 6)-3-O-beta-d-glucopyranoside (2), N-deacetyl-N-formyl-3-de-O-methylcolchicine-3-O-beta-D-glucopyranosyl-(1 -> 6)-3-O-beta-D-glucopyranoside (3), and 3-de-O-methylcolchicine-3-O-beta-D-glucopyranosyl-(1 -> 3)-3-O-beta-D-glucopyranoside (5). The structure elucidation was performed by means of NMR (COSY, HSQC, and HMBC), HRESIMS/MS, and GCMS data analysis.