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Investigation of the hydrolysis of ginsenosides by high performance liquid chromatography-electrospray ionization mass spectrometry.

Zhang X, Song F, Cui M, Liu Z, Liu S

Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun Center of Mass Spectrometry, Changchun, P. R. China.

The hydrolysis of ginsenoside standards and the crude extracts of ginseng has been investigated at different pH values (2.4 - 11.2) using high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS). The experimental results indicated that the pH value of aqueous solutions is an important factor in changing the composition of ginsenosides. For (20 S)-protopanaxadiol ginsenosides, ginsenosides with a large mass hydrolyzed to form hydrolysates (20 S)-Rg (3) and (20 R)-Rg (3) at pH 4.3. There were more hydrolyzed products observed at pH 3.3: (20 S)-F (2), C-25,26 hydrated ginsenoside "C-Y (1)" and "C-Y (2)" (MW = 802 Da) accompanied with (20 S)-Rg (3), (20 R)-Rg (3). At pH 2.4, only (20 R)-Rg (3), (20 S)-F (2), a small quantity of (20 S)-Rg (3) and three C-25,26 hydrated ginsenosides were obtained. For (20 S)-protopanaxatriol Re, no hydrolysates were observed at pH 4.3; it was hydrolyzed at pH 3.3 to form hydrolysates (20 S)-Rg (2), (20 R)-Rg (2) and hydrated C-25,26 (MW = 802 Da) and at pH 2.4 only C-25,26 hydrated ginsenosides "C-Y (1)" and "C-Y (2)" (MW = 802 Da) were left in the solution. Similar hydrolysis reactions could be also observed for the crude extracts of ginseng. It showed that HPLC/ESI-MS is a fast and convenient method to study the hydrolysis of ginseng.

Published 1 October 2007 in Planta Med, 73(11): 1225-9.
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