Two new flavonol glycosides and a metabolite profile of Bryophyllum pinnatum, a phytotherapeutic used in obstetrics and gynaecology

Planta Med. 2013 Nov;79(16):1565-71. doi: 10.1055/s-0033-1350808. Epub 2013 Sep 26.

Abstract

Bryophyllum pinnatum is a succulent perennial plant native to Madagascar which is used in anthroposophical medicine to treat psychiatric disorders and as a tocolytic agent to prevent premature labour. We performed a metabolite profiling study in order to obtain a comprehensive picture of the constituents in B. pinnatum leaves and to identify chromatographic markers for quality control and safety assessment of medicinal preparations. Preliminary HPLC-PDA-ESIMS analyses revealed that flavonoid glycosides were the main UV-absorbing constituents in the MeOH extract of B. pinnatum. Two phenolic glucosides, syringic acid β-D-glucopyranosyl ester (1) and 4'-O-β-D-glucopyranosyl-cis-p-coumaric acid (2), as well as nine flavonoids (3-11) including kaempferol, quercetin, myricetin, acacetin, and diosmetin glycosides were unambiguously identified by 1H and 2D NMR analysis after isolation from a MeOH extract. The flavonol glycosides quercetin 3-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside 7-O-β-D-glucopyranoside (3) and myricetin 3-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside (4) were new natural products. With the aid of HPLC-PDA-APCIMS and authentic references isolated from the related species B. daigremontianum, the presence of four bufadienolides, bersaldegenin-1-acetate (12), bryophyllin A (13), bersaldegenin-3-acetate (14), and bersaldegenin-1,3,5-orthoacetate (15) was detected in B. pinnatum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomarkers, Pharmacological / analysis
  • Bufanolides / chemistry*
  • Bufanolides / isolation & purification
  • Chemical Fractionation
  • Chromatography, High Pressure Liquid
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Kalanchoe / chemistry*
  • Mass Spectrometry
  • Nuclear Magnetic Resonance, Biomolecular
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Biomarkers, Pharmacological
  • Bufanolides
  • Flavonoids
  • bufadienolide