Further New Gypenosides from Jiaogulan (Gynostemma pentaphyllum)

J Agric Food Chem. 2017 Jul 26;65(29):5926-5934. doi: 10.1021/acs.jafc.7b01477. Epub 2017 Jul 11.


Jiaogulan (Gynostemma pentaphyllum) has been widely used as a herbal tea, dietary supplement, and vegetable in Asian countries. In this study, six new gypenosides (1-6) were isolated from the aerial parts of G. pentaphyllum. Their molecular structures were elucidated through spectroscopic analysis and acid hydrolysis. Gypenosides 1 and 2 represented the first example of a dammar-21-O- glucopyranoside without any unsaturated functional group and a dammar-3-O-glucopyranosyl-25-O-glucopyranoside without any cyclization in the side chain, respectively. In addition, gypenosides 5 and 6 exhibited the first example of a 24-hydroperoxy-19-oxo-dammarane triterpenoid and 19-oxo-dammar-21-O-glucopyranoside with a saturated side chain, respectively. Gypenoside 5 was found to possess protein tyrosine phosphatase 1B inhibitory activity, with an IC50 value of 8.2 ± 0.9 μM, and moderate cytotoxicity against human breast cancer cells MCF7, MCF7/ADR, and MDA-MB-231, with IC50 values ranging from 10.5 ± 1.4 to 14.2 ± 2.6 μM. The outcome of the study provided crucial information regarding the structural diversity and health benefits of gypenosides.

Keywords: Gynostemma pentaphyllum; PTP1B inhibitory activity; cytotoxicity; jiaogulan; new gypenosides.

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Gynostemma / chemistry*
  • Humans
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism


  • Enzyme Inhibitors
  • Plant Extracts
  • gypenoside
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1