Hydrogen/deuterium exchange, a unique and effective method for MS fragmentation behavior elucidation of ginkgolides and its application to systematic research in Ginkgo biloba

J Pharm Biomed Anal. 2017 Feb 5:134:181-186. doi: 10.1016/j.jpba.2016.11.043. Epub 2016 Nov 26.

Abstract

Ginkgolides, the main active constituents of Ginkgo biloba, possess significant selectively inhibition on platelet-activating factor and pancreatic lipase and attract wide attention in pharmacological research area. In our study, an effective hydrogen/deuterium (H/D) exchange method was developed by exchanging the α-Hs of lactone groups in ginkgolides with Ds, which was very useful for the elucidation of the fragmentation patterns of ginkgolides in Quadrupole Time-of-flight Mass Spectrometry (Q-TOF-MS), especially in accurately distinguishing the type and position of substituent in framework of ginkgolides. Then, a systematic research strategy for qualitative and quantitative analysis of ginkgolides, based on H/D exchange, tandem solid-phase extraction and LC-Q-TOF-MS, was developed, which was successfully applied in each medicinal part of G. biloba, which indicated that ginkgolide B was the most abundant ginkgolide in the seeds of G. biloba (60.6μg/g). This research was the successful application of H/D exchange in natural products, and proved that H/D exchange is a potential method for analysis research of complex TCMs active constituents.

Keywords: Fragmentation pathway; Ginkgo biloba; Ginkgolides; H/D exchange; LC/Q-TOF-MS/MS; Tandem solid-phase extraction.

MeSH terms

  • Deuterium Exchange Measurement / methods*
  • Ginkgo biloba*
  • Ginkgolides / analysis*
  • Ginkgolides / chemistry
  • Mass Spectrometry / methods
  • Plant Extracts / analysis*
  • Plant Extracts / chemistry
  • Seeds
  • Solid Phase Extraction / methods*

Substances

  • Ginkgolides
  • Plant Extracts