Metabolomics

, 13:85

Profiling, isolation and structure elucidation of specialized acylsucrose metabolites accumulating in trichomes of Petunia species

  • Xiaoxiao Liu
  • Mollie Enright
  • Cornelius S. Barry
  • A. Daniel Jones
Original Article

Abstract

Introduction

Acylsugar specialized metabolites function as defenses against insect herbivores, and are the most abundant specialized metabolites produced in Solanaceous trichomes. Metabolite profiling provides the foundation for determining the genetic basis of specialized metabolism and its evolution.

Objectives

To profile and identify acylsugar specialized metabolites in three Petunia species: P. axillaris, P. integrifolia and P. exserta.

Methods

Metabolites were profiled using ultra-high performance liquid chromatography/time-of-flight mass spectrometry (UHPLC/TOF MS). Metabolites were purified using solid phase extraction and HPLC, and structures were established using NMR spectroscopy.

Results

Twenty-eight distinct acylsucrose formulas, representing a sampling of more than 100 different detected chemical forms, were purified from three Petunia species and structures have been proposed based on one- and two-dimensional NMR data. 15 of the 28 purified acylsugars were sucrose pentaesters that possess a malonyl group on the fructose ring. These malonate esters can be readily distinguished from other acylsugars based on distinct masses of pseudomolecular ions and fragment ions generated using multiplexed collision-induced dissociation. Chemical diversity of acylsugars was observed between Petunia species, particularly with respect to the lengths of acyl chains and specific acylation positions.

Conclusions

These findings suggest substrate selectivity of various acyltransferases in Petunia species.

Keywords

Nuclear magnetic resonance (NMR) spectroscopy Petunia axillaris Petunia integrifolia Petunia exserta Specialized metabolite profiling Ultra-high performance liquid chromatography/time-of-flight mass spectrometry (UHPLC/TOF MS) 

Supplementary material

11306_2017_1224_MOESM1_ESM.pdf (21.6 mb)
Supplementary material 1 (PDF 22080 KB)

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Department of ChemistryMichigan State UniversityEast LansingUSA
  2. 2.Department of ChemistryGordon CollegeWenhamUSA
  3. 3.Department of HorticultureMichigan State UniversityEast LansingUSA
  4. 4.Department of Biochemistry and Molecular BiologyMichigan State UniversityEast LansingUSA

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