Gynostemosides A-E, megastigmane glycosides from Gynostemma pentaphyllum

Phytochemistry. 2010 Apr;71(5-6):693-700. doi: 10.1016/j.phytochem.2009.12.017. Epub 2010 Jan 25.

Abstract

Megastigmane glycosides (1-5) together with seven (6-12) related known compounds were isolated from the whole plants of Gynostemma pentaphyllum. The structures were elucidated by means of spectroscopic methods, including 2D NMR, HR-ESIMS, and circular dichroism (CD), as well as chemical transformations to be (3R,4R,5S,6S,7E)-3,4,6-trihydroxymegastigmane-7-en-9-one-3-O-beta-D-glucopyranoside (gynostemoside A, 1), (3S,4S,5R,6R,7E,9R)-3,4,6,9-tetrahydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside B, 2), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-9-O-beta-D-glucopyranoside (gynostemoside C, 3), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside D, 4), and (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-4-O-beta-D-glucopyranoside (gynostemoside E, 5), respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanones / chemistry
  • Cyclohexanones / isolation & purification
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Gynostemma / chemistry*
  • Molecular Structure
  • Norisoprenoids / chemistry
  • Norisoprenoids / isolation & purification*
  • Plant Extracts / chemistry*

Substances

  • (3R,4R,5S,6S,7E)-3,4,6-trihydroxymegastigmane-7-en-9-one-3-O-beta-D-glucopyranoside
  • (3S, 4S, 5R, 6R, 7E, 9R)-3,4,6,9-tetrahydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside
  • (3S, 4S, 5S, 6S, 7E, 9R)-3,4,9-trihydroxymegastigmane-7-en-9-O-beta-D-glucopyranoside
  • Cyclohexanones
  • Glucosides
  • Glycosides
  • Norisoprenoids
  • Plant Extracts
  • megastigmane