Identification of Glycoside Compounds from Tobacco by High Performance Liquid Chromatography/Electrospray Ionization Linear Ion-Trap Tandem Mass Spectrometry Coupled with Electrospray Ionization Orbitrap Mass Spectrometry

Chunxiao Jia,Duobin Mao,Jing Yang,Yonghua Zhu,Jinjie Zhang,Chunping Xu

doi:10.21577/0103-5053.20160211

Abstract

In order to comprehensively screen and identify the glycoside compounds in tobacco, a simple, rapid and sensitive method of high performance liquid chromatography/electrospray ionization linear ion-trap tandem mass spectrometry (HPLC-ESI-LIT/MSn) coupled with electrospray ionization orbitrap mass spectrometry (ESI-Orbitrap-MS) was developed for the first time. As a result, twenty-two glycoside compounds, including eleven alcoholic glycosides, eight phenolic glycosides, two ester glycosides and an indole glycoside, were reliably identified from tobacco with high mass accuracy (within 5 mDa). Among them, four compounds were confirmed as novel molecules and other four compounds, as far as we know, were not reported previously in tobacco. This study provided a useful tool to identify the new structures of glycoside compounds in natural products, especially when there were no reference compounds available.

Highlights

Glycosides are a large class of low-molecular-weight secondary metabolites formed in the process of growth and development of plants
Various analytical techniques used for separation and identification of glycosides in tobaccos include enzymatic hydrolysis or acid hydrolysis coupled with gas chromatography-mass spectrometry (GC-MS) method,[9,14,15,16,17] and liquid chromatography-mass spectrometry (LC-MS) or liquid chromatography-tandem mass spectrometry (LC/MSn) method.[18,19,20,21]
The authentic glycosides I-V were analyzed by LC‐ESI-LIT/MSn and ESI-Orbitrap-MS in positive and negative ion mode, respectively

Summary

Introduction

Glycosides are a large class of low-molecular-weight secondary metabolites formed in the process of growth and development of plants. The LC-ESI-LIT/MSn analyses were carried out in data-dependent scan mode and neutral loss scan mode (glu, rha, and glu-rha, 162, 146 and 308 Da, respectively) in order to screen out the glycosides compounds (including unknown glycosides) comprehensively form tobaccos. Among the 22 compounds detected in this study, compounds 2, 3, 8, 9 and 10 were unambiguously identified as benzyl β-D-glucopyranoside, 2-phenylethyl β-Dglucopyranoside, rutin, 3-oxo-α-ionyl β-D-glucopyranoside and kaempferyl-3-rutinoside, respectively, by comparing the retention time (tR) and fragmentation patterns with those of the authentic glycosides I-V.

Results

Conclusion