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

R.M. de Graaf, S. Krosse, A.E.M. Swolfs, E. te Brinke, N. Prill, R. Leimu, P.M. van Galen, Y. Wang, M.G.M. Aarts, N.M. van Dam

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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-a-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
JournalPhytochemistry
Volume110
DOIs
Publication statusPublished - 2015

Keywords

  • hyperaccumulator thlaspi-praecox
  • moringa-oleifera l.
  • mustard oil bomb
  • arabidopsis-thaliana
  • plants
  • isothiocyanates
  • stenopetala
  • accumulation
  • brassicaceae
  • profiles

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    de Graaf, R. M., Krosse, S., Swolfs, A. E. M., te Brinke, E., Prill, N., Leimu, R., van Galen, P. M., Wang, Y., Aarts, M. G. M., & van Dam, N. M. (2015). Isolation and identification of 4-a-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation. Phytochemistry, 110, 166-171. https://doi.org/10.1016/j.phytochem.2014.11.016