title: Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation.
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.
authors.affiliation: Molecular Interaction Ecology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands; Department of Microbiology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands. Electronic address: exorest@science.ru.nl.
authors.forename: Rob M
authors.initials: RM
authors.lastname: de Graaf
authors.affiliation: Molecular Interaction Ecology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Krosse
authors.affiliation: Synthetic Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Ad E M
authors.initials: AE
authors.lastname: Swolfs
authors.affiliation: Physical Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Esra
authors.initials: E
authors.lastname: te Brinke
authors.affiliation: Department of Plant Sciences, University of Oxford, South Parks Road, OX1 3RB, UK.
authors.forename: Nadine
authors.initials: N
authors.lastname: Prill
authors.affiliation: Department of Plant Sciences, University of Oxford, South Parks Road, OX1 3RB, UK.
authors.forename: Roosa
authors.initials: R
authors.lastname: Leimu
authors.affiliation: Bio-Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Peter M
authors.initials: PM
authors.lastname: van Galen
authors.affiliation: Laboratory of Genetics, Wageningen University, Droevendaalsesteeg 1, 6708 PB Wageningen, The Netherlands.
authors.forename: Yanli
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Laboratory of Genetics, Wageningen University, Droevendaalsesteeg 1, 6708 PB Wageningen, The Netherlands.
authors.forename: Mark G M
authors.initials: MG
authors.lastname: Aarts
authors.affiliation: Molecular Interaction Ecology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands; German Centre for Integrative Biodiversity Research (iDiv) Halle-Jena-Leipzig, Deutscher Platz 5e, 04103 Leipzig, Germany; Friedrich Schiller University Jena, Institute of Ecology, Dornburger-Str. 159, 07743 Jena, Germany.
authors.forename: Nicole M
authors.initials: NM
authors.lastname: van Dam
mesh_terms: D019607:Brassicaceae / Q000737:chemistry* / Q000235:genetics; D005060:Europe; D005961:Glucosinolates / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D006026:Glycoside Hydrolases; D017879:Isothiocyanates / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: C000596496:4-alpha-rhamnosyloxy benzyl glucosinolate; D005961:Glucosinolates; D017879:Isothiocyanates; C037152:isothiocyanic acid; D006026:Glycoside Hydrolases; C022739:thioglucosidase
keywords: Chemotypes; Glucosinolates; Intraspecific variation; Isothiocyanate; Noccaea caerulescens; Populations; Thlaspi