Spectaflavoside A, a new potent iron chelating dimeric flavonol glycoside from the rhizomes of Zingiber spectabile Griff

Bioorg Med Chem Lett. 2012 Jun 1;22(11):3831-6. doi: 10.1016/j.bmcl.2012.02.064. Epub 2012 Mar 7.

Abstract

The rhizomes of Zingiber spectabile yielded a new dimeric flavonol glycoside for which the name kaempferol-3-O-(4″-O-acetyl)-α-L-rhamnopyranoside-(I-6,II-8)-kaempferol-3-O-(4″-O-acetyl)-α-L-rhamnopyranoside; spectaflavoside A (1) was proposed, along with kaempferol and its four acetylrhamnosides (2-6), demethoxycurcumin (7) and curcumin (8). The structure of spectaflavoside A was elucidated by spectroscopic methods including, 1D and 2D NMR techniques. This is the first report on the occurrence of a dimeric flavonol glycoside in the Zingiberaceae and the second in nature. Spectaflavoside A was found to be a potent iron chelating agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Dimerization
  • Flavones / chemistry*
  • Flavones / isolation & purification
  • Flavonols / chemistry*
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / toxicity
  • HT29 Cells
  • Hep G2 Cells
  • Humans
  • Iron Chelating Agents / chemistry*
  • Iron Chelating Agents / isolation & purification
  • Iron Chelating Agents / toxicity
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Rhizome / chemistry
  • Zingiberaceae / chemistry*

Substances

  • 3-O-(4'-O-acetyl)rhamnopyranoside-(I-6,II-8)-kaempferol-3-O-(4'-O-acetyl)rhamnopyranoside
  • Flavones
  • Flavonols
  • Glycosides
  • Iron Chelating Agents