Cytotoxic isoferulic acidamide from Myricaria germanica (Tamaricaceae)

Plant Signal Behav. 2013 Jan;8(1):e22642. doi: 10.4161/psb.22642. Epub 2012 Nov 3.

Abstract

Tamgermanitin, a unique N-trans-Isoferuloyltyramine, together with the hitherto unknown polyphenolics, 2,4-di-O-galloyl-(α/β)-glucopyranose and kaempferide 3,7-disulphate have been isolated from the leaf aqueous ethanol extract of the false tamarisk, Myricaria germanica DESV. In addition, 18 known phenolics were also separated and characterized. All structures were elucidated on the basis of detailed analysis of 1D- (1)H and (13)C NMR, COSY, HSQC, HMBC and HRFTESIMS spectral data. The extract, its chromatographic column fractions and the isolated isoferuloyltyramine, tamgermanetin demonstrated potential cytotoxic effect against three different tumor cell lines, namely liver (Huh-7), breast (MCF-7) and prostate (PC-3). The IC 50''s were found to be substantially low with low-resistance possibility. DNA flow-cytometic analysis indicated that column fractions and tamgermanetin enhanced pre-G apoptotic fraction. Both materials showed inhibiting activity against PARP enzyme activity. In conclusion, we report the isolation and identification of a novel compound, tamgermanitin, from the aqueous ethanol extract of Myricaria germanica leaves. Further, different fractions of the extract and tamgermanitin exhibit potent cytotoxic activities which warrant further investigations.

Keywords: 2,4-di-O-galloyl-(α/β)-glucopyranose; Myricaria germanica; N-trans-Isoferuloyltyramine; cytotoxicity; kaempferide 3,7-disulphate; tamgermanitin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis
  • Breast Neoplasms / drug therapy*
  • Cell Proliferation
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification
  • Coumaric Acids / pharmacology
  • Coumaric Acids / therapeutic use*
  • Humans
  • Inhibitory Concentration 50
  • Liver Neoplasms / drug therapy*
  • MCF-7 Cells
  • Male
  • Molecular Structure
  • Phytotherapy*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Plant Extracts / therapeutic use*
  • Plant Leaves
  • Poly(ADP-ribose) Polymerase Inhibitors
  • Polyphenols / chemistry
  • Polyphenols / isolation & purification
  • Polyphenols / pharmacology
  • Polyphenols / therapeutic use
  • Prostatic Neoplasms / drug therapy*
  • Tamaricaceae / chemistry*
  • Tyramine / analogs & derivatives*
  • Tyramine / chemistry
  • Tyramine / isolation & purification
  • Tyramine / pharmacology
  • Tyramine / therapeutic use

Substances

  • Coumaric Acids
  • N-(3-hydroxy-4-methoxycinnamoyl)tyramine
  • Plant Extracts
  • Poly(ADP-ribose) Polymerase Inhibitors
  • Polyphenols
  • Tyramine