New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

Nat Prod Res. 2015;29(10):926-32. doi: 10.1080/14786419.2014.960413. Epub 2014 Sep 18.

Abstract

A new chalcanonol glycoside dimer, bis-O-[(I-4') → (II-6')]-α-hydroxyphloretin-2'-O-β-glucoside (1), in addition to six known compounds, namely (-)-epicatechin (2) and (-)-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.

Keywords: ( − )-epiafzelechin; ( − )-epicatechin; Serenoa repens; chalcanonol glycoside; methylgallate; saw palmetto seeds.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Cell Line, Tumor
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / isolation & purification
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Humans
  • Male
  • Molecular Structure
  • Prostatic Neoplasms
  • Seeds / chemistry
  • Serenoa / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Free Radical Scavengers
  • Glycosides