Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation

Rob M. De Graaf*, Sebastian Krosse, Ad E.M. Swolfs, Esra Te Brinke, Nadine Te Prill, Roosa Leimu, Peter M. Van Galen, Yanli Wang, Mark G.M. Aarts, Nicole M. Van Dam

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

28 Citations (Scopus)

Abstract

Glucosinolates are secondary plant compounds typically found in members of the Brassicaceae and a few other plant families. Usually each plant species contains a specific subset of the ∼130 different glucosinolates identified to date. However, intraspecific variation in glucosinolate profiles is commonly found. Sinalbin (4-hydroxybenzyl glucosinolate) so far has been identified as the main glucosinolate of the heavy metal accumulating plant species Noccaea caerulescens (Brassicaceae). However, a screening of 13 N. caerulescens populations revealed that in 10 populations a structurally related glucosinolate was found as the major component. Based on nuclear magnetic resonance (NMR) and mass spectrometry analyses of the intact glucosinolate as well as of the products formed after enzymatic conversion by sulfatase or myrosinase, this compound was identified as 4-α-rhamnosyloxy benzyl glucosinolate (glucomoringin). So far, glucomoringin had only been reported as the main glucosinolate of Moringa spp. (Moringaceae) which are tropical tree species. There was no apparent relation between the level of soil pollution at the location of origin, and the presence of glucomoringin. The isothiocyanate that is formed after conversion of glucomoringin is a potent antimicrobial and antitumor agent. It has yet to be established whether glucomoringin or its breakdown product have an added benefit to the plant in its natural habitat.

Original languageEnglish
Pages (from-to)166-171
Number of pages6
JournalPhytochemistry
Volume110
DOIs
Publication statusPublished - 2015
Externally publishedYes

Keywords

  • Chemotypes
  • Glucosinolates
  • Intraspecific variation
  • Isothiocyanate
  • Noccaea caerulescens
  • Populations
  • Thlaspi

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