A Fragmentation Study on Four Oligostilbenes by Electrospray Tandem Mass Spectrometry

Chen-Chen Zhang,Chang-An Geng,Ji-Jun Chen

doi:10.1007/s13659-019-0212-3

Abstract

Oligostilbenes have attracted much interest due to their intricate structures and diverse bioactivities. In this study, two stilbene dimers, (−)-7,8-cis-ε-viniferin (1) and carasiphenol A (2), and two trimers, suffruticosol A (3) and suffruticosol C (4), were investigated by electrospray ionization ion-trap time-of-flight multistage mass spectrometry (ESI-IT-TOF-MSn). Based on the MSn study, the fragmentation pathways and diagnostic ions of four oligostilbenes in both positive and negative modes were proposed. The consecutive elimination of phenol (C6H6O) and resorcinol (C6H6O2) moieties were the particular dissociation for oligostilbenes due to the presence of 1,2-diphenylethylene nucleus. The present MSn fragmentation study will provide valuable information for the fast characterization of oligostilbenes from complicated natural mixtures.Graphical

Highlights

Natural stilbenes are an important group of polyphenols characterized by the presence of 1,2-diphenylethylene nucleus [1]
We report the MSn fragmentation rules of four oligostilbenes, (−)-7,8-cis-εviniferin (1), carasiphenol A (2), suffruticosol A (3) and suffruticosol C (4), by electrospray ionization ion-trap time-of-flight (ESI-IT-TOF) mass spectrometer to provide reference for their fast characterization from natural sources
It should be noted that alternative ways of fragmentation that can reasonably interpret the product ions are possible in addition to the proposed pathway

Summary

Introduction

Natural stilbenes are an important group of polyphenols characterized by the presence of 1,2-diphenylethylene nucleus [1]. Anti-fungal, anti-diabetic and anti-Alzheimer’s disease effects [3,4,5,6,7], whereas their natural distribution is quite limited, mainly in Cyperaceae, Dipterocarpaceae, Gnetaceae, Iridaceae, Leguminosae, Moraceae, Orchidaceae and Polygonaceae plants [2]. It is necessary to develop and establish a rapid and systematic method to profile stilbenes from natural resources. Mass spectrometry (MS) with high sensitivity and resolution is one of the most efficient method in analyzing natural products [8,9,10]. We report the MSn fragmentation rules of four oligostilbenes, (−)-7,8-cis-εviniferin (1), carasiphenol A (2), suffruticosol A (3) and suffruticosol C (4), by electrospray ionization ion-trap time-of-flight (ESI-IT-TOF) mass spectrometer to provide reference for their fast characterization from natural sources

Results and Discussion

Chemicals and Samples

Conclusion

Apparatus and Analytical Conditions