A Newly Discovered Phenylethanoid Glycoside from Stevia rebaudiana Bertoni Affects Insulin Secretion in Rat INS-1 Islet β Cells

Molecules. 2019 Nov 18;24(22):4178. doi: 10.3390/molecules24224178.

Abstract

The tea-like beverage Stevia rebaudiana Bertoni (Stevia) is popular in China because it reduces blood glucose and has a sweet taste. In this work, a comprehensive quality assessment of Stevia led to the discovery of five phenylethanoid glycosides, namely steviophethanoside (1), cuchiloside (2), salidroside (3), icariside D (4), and tyrosol (5). Of them, compound 1 is a novel compound. Mass spectrometry and NMR spectroscopy were employed to confirm the absolute configuration. A hydrolytic step with 4 N TFA at 95 °C for 4 h was used to confirm the monosaccharides. In addition, Discovery Studio 4.0 was used to predict the ADME and toxicity activity of compound 1. The results suggested that compound 1 was biocompatible and had poor toxicity, which was verified by rat INS-1 islet β cells through an MTT assay. Meanwhile, a significant stimulatory effect on INS-1 cells was observed, which indicated a hypoglycemic effect of compound 1. This is the first report that describes a natural, novel, and hypoglycemic phenylethanoid glycoside in Stevia.

Keywords: DS; Stevia rebaudiana Bertoni; insulin secretion; phenylethanoid glycoside; structure.

MeSH terms

  • Animals
  • Cells, Cultured
  • China
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Insulin Secretion / drug effects*
  • Insulin-Secreting Cells / drug effects*
  • Insulin-Secreting Cells / metabolism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Rats
  • Stevia / chemistry*

Substances

  • Glycosides
  • Plant Extracts