Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae)

Opitz S, Mix A, Winde IB, Müller C (2011)
ChemBioChem 12(8): 1252-1257.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Abstract / Bemerkung
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 ([C-14]-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.
Stichworte
Brassicaceae; metabolism; biotransformations; glucosinolates; Tenthredinidae; conjugation
Erscheinungsjahr
2011
Zeitschriftentitel
ChemBioChem
Band
12
Ausgabe
8
Seite(n)
1252-1257
ISSN
1439-4227
Page URI
https://pub.uni-bielefeld.de/record/2289808

Zitieren

Opitz S, Mix A, Winde IB, Müller C. Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae). ChemBioChem. 2011;12(8):1252-1257.
Opitz, S., Mix, A., Winde, I. B., & Müller, C. (2011). Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae). ChemBioChem, 12(8), 1252-1257. https://doi.org/10.1002/cbic.201100053
Opitz, Sebastian, Mix, Andreas, Winde, Inis B., and Müller, Caroline. 2011. “Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae)”. ChemBioChem 12 (8): 1252-1257.
Opitz, S., Mix, A., Winde, I. B., and Müller, C. (2011). Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae). ChemBioChem 12, 1252-1257.
Opitz, S., et al., 2011. Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae). ChemBioChem, 12(8), p 1252-1257.
S. Opitz, et al., “Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae)”, ChemBioChem, vol. 12, 2011, pp. 1252-1257.
Opitz, S., Mix, A., Winde, I.B., Müller, C.: Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae). ChemBioChem. 12, 1252-1257 (2011).
Opitz, Sebastian, Mix, Andreas, Winde, Inis B., and Müller, Caroline. “Desulfation Followed by Sulfation: Metabolism of Benzylglucosinolate in *Athalia rosae* (Hymenoptera: Tenthredinidae)”. ChemBioChem 12.8 (2011): 1252-1257.

9 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Identification of sawflies and horntails (Hymenoptera, 'Symphyta') through DNA barcodes: successes and caveats.
Schmidt S, Taeger A, Morinière J, Liston A, Blank SM, Kramp K, Kraus M, Schmidt O, Heibo E, Prous M, Nyman T, Malm T, Stahlhut J., Mol Ecol Resour 17(4), 2017
PMID: 27768250
Glucosinolate Desulfation by the Phloem-Feeding Insect Bemisia tabaci.
Malka O, Shekhov A, Reichelt M, Gershenzon J, Vassão DG, Morin S., J Chem Ecol 42(3), 2016
PMID: 26961756
Uncovering different parameters influencing florivory in a specialist herbivore
ABDALSAMEE MK, MÜLLER C., Ecol Entomol 40(3), 2015
PMID: IND601326117
Taste detection of the non-volatile isothiocyanate moringin results in deterrence to glucosinolate-adapted insect larvae.
Müller C, van Loon J, Ruschioni S, De Nicola GR, Olsen CE, Iori R, Agerbirk N., Phytochemistry 118(), 2015
PMID: 26318325
Phyllotreta striolata flea beetles use host plant defense compounds to create their own glucosinolate-myrosinase system.
Beran F, Pauchet Y, Kunert G, Reichelt M, Wielsch N, Vogel H, Reinecke A, Svatoš A, Mewis I, Schmid D, Ramasamy S, Ulrichs C, Hansson BS, Gershenzon J, Heckel DG., Proc Natl Acad Sci U S A 111(20), 2014
PMID: 24799680
Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia.
Opitz SE, Boevé JL, Nagy ZT, Sonet G, Koch F, Müller C., PLoS One 7(4), 2012
PMID: 22485146
Genes involved in the evolution of herbivory by a leaf-mining, Drosophilid fly.
Whiteman NK, Gloss AD, Sackton TB, Groen SC, Humphrey PT, Lapoint RT, Sønderby IE, Halkier BA, Kocks C, Ausubel FM, Pierce NE., Genome Biol Evol 4(9), 2012
PMID: 22813779

40 References

Daten bereitgestellt von Europe PubMed Central.

METABOLISM OF NICOTINE BY TOBACCO-FEEDING INSECTS.
SELF LS, GUTHRIE FE, HODGSON E., Nature 204(), 1964
PMID: 14212440
The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids.
Lindigkeit R, Biller A, Buch M, Schiebel HM, Boppre M, Hartmann T., Eur. J. Biochem. 245(3), 1997
PMID: 9182998

Dowd, Insect Biochem. 13(), 1983

Brattsten, 1992
The enzymic and chemically induced decomposition of glucosinolates.
Bones AM, Rossiter JT., Phytochemistry 67(11), 2006
PMID: 16624350

Müller, Phytochem. Rev. 8(), 2009
Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant.
Bridges M, Jones AM, Bones AM, Hodgson C, Cole R, Bartlet E, Wallsgrove R, Karapapa VK, Watts N, Rossiter JT., Proc. Biol. Sci. 269(1487), 2002
PMID: 11798435
Sequestration of glucosinolates by harlequin bug Murgantia histrionica.
Aliabadi A, Renwick JA, Whitman DW., J. Chem. Ecol. 28(9), 2002
PMID: 12449503
Disarming the mustard oil bomb.
Ratzka A, Vogel H, Kliebenstein DJ, Mitchell-Olds T, Kroymann J., Proc. Natl. Acad. Sci. U.S.A. 99(17), 2002
PMID: 12161563
Successful herbivore attack due to metabolic diversion of a plant chemical defense.
Wittstock U, Agerbirk N, Stauber EJ, Olsen CE, Hippler M, Mitchell-Olds T, Gershenzon J, Vogel H., Proc. Natl. Acad. Sci. U.S.A. 101(14), 2004
PMID: 15051878
Glycine conjugates in a lepidopteran insect herbivore--the metabolism of benzylglucosinolate in the cabbage white butterfly, Pieris rapae.
Vergara F, Svatos A, Schneider B, Reichelt M, Gershenzon J, Wittstock U., Chembiochem 7(12), 2006
PMID: 17086559

Vergara, ChemBioChem 8(), 2007
Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae.
Muller C, Agerbirk N, Olsen CE, Boeve JL, Schaffner U, Brakefield PM., J. Chem. Ecol. 27(12), 2001
PMID: 11789955
Uptake and turn-over of glucosinolates sequestered in the sawfly Athalia rosae.
Muller C, Wittstock U., Insect Biochem. Mol. Biol. 35(10), 2005
PMID: 16102424
Sulphotransferases and phosphotransferases in insects.
Yang RS, Wilkinson CF., Comp. Biochem. Physiol., B 46(4), 1973
PMID: 4271668

Agerbirk, Biochem. Syst. Ecol. 34(), 2006
Selective transport systems mediate sequestration of plant glucosides in leaf beetles: a molecular basis for adaptation and evolution.
Kuhn J, Pettersson EM, Feld BK, Burse A, Termonia A, Pasteels JM, Boland W., Proc. Natl. Acad. Sci. U.S.A. 101(38), 2004
PMID: 15365181
A versatile transport network for sequestering and excreting plant glycosides in leaf beetles provides an evolutionary flexible defense strategy.
Discher S, Burse A, Tolzin-Banasch K, Heinemann SH, Pasteels JM, Boland W., Chembiochem 10(13), 2009
PMID: 19623597

Pasteels, Annu. Rev. Entomol. 28(), 1983

Gfeller, J. Mass Spectrom. 30(), 1995

Brückmann, Chemoecology 10(), 2000
Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants.
Narberhaus I, Theuring C, Hartmann T, Dobler S., J. Comp. Physiol. B, Biochem. Syst. Environ. Physiol. 173(6), 2003
PMID: 12802610

Chen, Phytochem. Anal. 11(), 2000

Thies, Fat Sci. Technol. 90(), 1988

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 21506231
PubMed | Europe PMC

Suchen in

Google Scholar