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

J Nat Prod. 2017 Apr 28;80(4):1187-1191. doi: 10.1021/acs.jnatprod.6b01024. Epub 2017 Feb 17.

Abstract

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-β-d-glucopyranosyl-(1→4)-3-O-β-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-β-d-glucopyranoside (1), 3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→6)-3-O-β-d-glucopyranoside (2), N-deacetyl-N-formyl-3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→6)-3-O-β-d-glucopyranoside (3), and 3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→3)-3-O-β-d-glucopyranoside (5). The structure elucidation was performed by means of NMR (COSY, HSQC, and HMBC), HRESIMS/MS, and GCMS data analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Colchicaceae* / chemistry
  • Colchicine* / analogs & derivatives
  • Colchicine* / chemistry
  • Colchicine* / isolation & purification
  • Glycosides* / chemistry
  • Glycosides* / isolation & purification
  • India
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Saponins* / chemistry
  • Saponins* / isolation & purification
  • Seeds* / chemistry

Substances

  • Colchicine
  • Glycosides
  • Saponins