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Desulfation followed by sulfation: Metabolism of benzylglucosinolate in Athalia rosae (Hymenoptera: Tenthredinidae)

Opitz, S. E. W.; Mix, A.; Winde, Inis LU and Müller, Cheng-Hua (2011) In ChemBioChem 12. p.1252-1257
Abstract
The sawfly species Athalia rosae (L.) (Hymenoptera: Tenthredinidae) is phytophagous on plants of the family Brassicaceae and thus needs to cope with the plant defence, the glucosinolate-myrosinase system. The larvae sequester glucosinolates in their haemolymph. We investigated how these compounds are metabolized by this specialist. When larvae were fed with ([ 14C]-labelled) benzylglucosinolate, one major degradation metabolite, with the same sum formula as benzylglucosinolate, was defecated. This metabolite was also found in the haemolymph along with desulfobenzylglucosinolate, which continuously increased in concentration. NMR spectroscopy in conjunction with LC-TOF-MS measurements revealed the major degradation metabolite to be... (More)
The sawfly species Athalia rosae (L.) (Hymenoptera: Tenthredinidae) is phytophagous on plants of the family Brassicaceae and thus needs to cope with the plant defence, the glucosinolate-myrosinase system. The larvae sequester glucosinolates in their haemolymph. We investigated how these compounds are metabolized by this specialist. When larvae were fed with ([ 14C]-labelled) benzylglucosinolate, one major degradation metabolite, with the same sum formula as benzylglucosinolate, was defecated. This metabolite was also found in the haemolymph along with desulfobenzylglucosinolate, which continuously increased in concentration. NMR spectroscopy in conjunction with LC-TOF-MS measurements revealed the major degradation metabolite to be desulfobenzylglucosinolate-3-sulfate, probably converted from desulfobenzylglucosinolate after sulfation at the sugar moiety. The enzymes responsible must be located in the haemolymph. Additionally, a putative sulfotransferase forms benzylglucosinolate sulfate in the gut from intact, non-sequestered glucosinolate. The corresponding desulfoglucosinolate sulfates were also detected in faeces after feeding experiments with phenylethylglucosinolate and prop-2-enylglucosinolate, which indicates a similar degradation mechanism for various glucosinolates in the larvae. This is the first report on glucosinolate metabolism of a glucosinolate-sequestering insect species (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Brassicaceae, Biotransformations, Conjugation, Glucosinolates, Metabolism, Tenthredinidae
in
ChemBioChem
volume
12
pages
1252 - 1257
publisher
John Wiley & Sons
external identifiers
  • scopus:79955946339
ISSN
1439-4227
DOI
10.1002/cbic.201100053
language
English
LU publication?
no
id
515a0a51-36a7-46ea-b691-4db54448dc36 (old id 3405527)
date added to LUP
2013-01-22 14:33:07
date last changed
2017-07-02 03:21:19
@article{515a0a51-36a7-46ea-b691-4db54448dc36,
  abstract     = {The sawfly species Athalia rosae (L.) (Hymenoptera: Tenthredinidae) is phytophagous on plants of the family Brassicaceae and thus needs to cope with the plant defence, the glucosinolate-myrosinase system. The larvae sequester glucosinolates in their haemolymph. We investigated how these compounds are metabolized by this specialist. When larvae were fed with ([ 14C]-labelled) benzylglucosinolate, one major degradation metabolite, with the same sum formula as benzylglucosinolate, was defecated. This metabolite was also found in the haemolymph along with desulfobenzylglucosinolate, which continuously increased in concentration. NMR spectroscopy in conjunction with LC-TOF-MS measurements revealed the major degradation metabolite to be desulfobenzylglucosinolate-3-sulfate, probably converted from desulfobenzylglucosinolate after sulfation at the sugar moiety. The enzymes responsible must be located in the haemolymph. Additionally, a putative sulfotransferase forms benzylglucosinolate sulfate in the gut from intact, non-sequestered glucosinolate. The corresponding desulfoglucosinolate sulfates were also detected in faeces after feeding experiments with phenylethylglucosinolate and prop-2-enylglucosinolate, which indicates a similar degradation mechanism for various glucosinolates in the larvae. This is the first report on glucosinolate metabolism of a glucosinolate-sequestering insect species},
  author       = {Opitz, S. E. W. and Mix, A. and Winde, Inis and Müller, Cheng-Hua},
  issn         = {1439-4227},
  keyword      = {Brassicaceae,Biotransformations,Conjugation,Glucosinolates,Metabolism,Tenthredinidae},
  language     = {eng},
  pages        = {1252--1257},
  publisher    = {John Wiley & Sons},
  series       = {ChemBioChem},
  title        = {Desulfation followed by sulfation: Metabolism of benzylglucosinolate in <i>Athalia rosae</i> (Hymenoptera: Tenthredinidae)},
  url          = {http://dx.doi.org/10.1002/cbic.201100053},
  volume       = {12},
  year         = {2011},
}