Girard derivatization for LC-MS/MS profiling of endogenous ecdysteroids in Drosophila

Lavrynenko, Oksana; Nedielkov, Ruslan; Möller, Heiko M.; Shevchenko, Andrej

Girard derivatization for LC-MS/MS profiling of endogenous ecdysteroids in Drosophila

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Date

2013

Authors

Lavrynenko, Oksana

Nedielkov, Ruslan

Möller, Heiko M.

Shevchenko, Andrej

Publication type

Journal article

Published in

The Journal of Lipid Research ; 54 (2013), 8. - pp. 2265-2272. - ISSN 0022-2275. - eISSN 1539-7262

Abstract

Ecdysteroids are potent developmental regulators that control molting, reproduction, and stress response in arthropods. In developing larvae, picogram quantities of individual ecdysteroids and their conjugated forms are present along with milligrams of structural and energy storage lipids. To enhance the specificity and sensitivity of ecdysteroid detection, we targeted the 6-ketone group, which is common to all ecdysteroids, with Girard reagents. Unlike other ketosteroids, during the reaction, Girard hydrazones of ecdysteroids eliminated the C14-hydroxyl group, creating an additional C14-C15 double bond. Dehydrated hydrazones of endogenous ecdysteroids were detected by LC-MS/MS in the multiple reaction monitoring (MRM) mode using two mass transitions: one relied upon neutral loss of a quaternary amine from the Girard T moiety; another complementary transition followed neutral loss of the hydrocarbon chain upon C20-C27 cleavage. We further demonstrated that a combination of Girard derivatization and LC-MS/MS enabled unequivocal detection of three major endogenous hormones at the picogram level in an extract from a single Drosophila pupa.

Subject (DDC)

540 Chemistry

Keywords

Ecdysone,Drosophila melanogaster,Girard reagent

Cite This

ISO 690

LAVRYNENKO, Oksana, Ruslan NEDIELKOV, Heiko M. MÖLLER, Andrej SHEVCHENKO, 2013. Girard derivatization for LC-MS/MS profiling of endogenous ecdysteroids in Drosophila. In: The Journal of Lipid Research. 54(8), pp. 2265-2272. ISSN 0022-2275. eISSN 1539-7262. Available under: doi: 10.1194/jlr.D035949

BibTex

@article{Lavrynenko2013-08Girar-27878,
  year={2013},
  doi={10.1194/jlr.D035949},
  title={Girard derivatization for LC-MS/MS profiling of endogenous ecdysteroids in Drosophila},
  number={8},
  volume={54},
  issn={0022-2275},
  journal={The Journal of Lipid Research},
  pages={2265--2272},
  author={Lavrynenko, Oksana and Nedielkov, Ruslan and Möller, Heiko M. and Shevchenko, Andrej}
}

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