Three new flavonol glycosides from Fissistigma pallens

Biosci Biotechnol Biochem. 2019 Dec;83(12):2177-2182. doi: 10.1080/09168451.2019.1654848. Epub 2019 Aug 25.

Abstract

Three new flavonol glycosides, fissflavosides A-C (1-3), together with six known flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (4), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (6), rhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (7), rutin (8), and isorhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1-9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.

Keywords: Fissistigma pallens; fissflavoside A; fissflavoside B; fissflavoside C; flavonol.

MeSH terms

  • Annonaceae / chemistry*
  • Antioxidants / pharmacology
  • Carbohydrate Conformation
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Flavonols / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Humans
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antioxidants
  • Flavonols
  • Glycosides