Three new C-alkylated flavonoids from Desmodium oblongum

J Asian Nat Prod Res. 2017 Oct;19(10):954-959. doi: 10.1080/10286020.2017.1285910. Epub 2017 Feb 1.

Abstract

Three new C-alkylated flavonoids, 4'-hydroxy-8-isobutyryl-7-methoxy-6-methyl-flavone (1), 4',7-dimethoxy-8-isobutyryl-6-methyl-flavone (2), and 4',7-dimethoxy-8-isobutyryl-flavone (3), together with three know ones luteolin (4), kaemferol (5), and quercetin (6), were isolated from Desmodium oblongum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compound 1 showed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC50 values of 8.5, 6.5, and 7.8 μM; compound 2 showed cytotoxicity against SHSY5Y and PC3 cell lines with IC50 values of 5.0 and 6.8 μM; compound 3 displayed cytotoxicity against SHSY5Y and MCF7 cell lines with IC50 values of 6.4 and 9.4 μM, respectively.

Keywords: Desmoditum oxyphyllum; Leguminosae; cytotoxicity; isoflavanone.

MeSH terms

  • Alkylating Agents
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Drug Screening Assays, Antitumor
  • Fabaceae / chemistry*
  • Flavones / chemistry
  • Flavones / isolation & purification*
  • Flavones / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • 4',7-dimethoxy-8-isobutyryl-6-methyl-flavone
  • 4',7-dimethoxy-8-isobutyryl-flavone
  • 4'-hydroxy-8-isobutyryl-7-methoxy-6-methyl-flavone
  • Alkylating Agents
  • Antineoplastic Agents, Phytogenic
  • Flavones
  • flavone