Two new flavonoid glucosides from the fruits of Sinopodophyllum hexandrum

Nat Prod Res. 2021 Jul;35(13):2164-2169. doi: 10.1080/14786419.2019.1663518. Epub 2019 Sep 12.

Abstract

Two new flavonoid glucosides, sinoflavonoidgs A (1) and B (2), along with three known analogues 3-5, were isolated from the fruits of Sinopodophyllum hexandrum. Their structures were established on the basis of extensive spectroscopic (UV, IR, HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC) and chromatographic (HPLC) analysis. The isolation of compounds 1-2 represents the first report of ring B-glucosided flavonoids from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds were evaluated in comparison with etoposide against four cell lines (MCF-7, HepG2, HeLa, KB). The antioxidant activities of all isolated compounds were examined by DPPH free radical-scavenging assay. The preliminary structure-activity relationships showed that the glycosilation of 3-methoxyquercetin at C-3' resulted in a greater decrease of cytotoxic and antioxidant activity.

Keywords: Sinopodophyllum hexandrum; antioxidant; cytotoxic; flavonoid glucoside.

MeSH terms

  • Berberidaceae / chemistry*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Fruit / chemistry*
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Humans
  • Inhibitory Concentration 50
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Flavonoids
  • Glucosides