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Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry

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Abstract

Although glycosyl inositol phosphoryl ceramides (GIPCs) represent the most abundant class of sphingolipids in plants, they still remain poorly characterized in terms of structure and biodiversity. More than 50 years after their discovery, little is known about their subcellular distribution and their exact roles in membrane structure and biological functions. This review is focused on extraction and characterization methods of GIPCs occurring in plants and fungi. Global methods for characterizing ceramide moieties of GIPCs revealed the structures of long-chain bases (LCBs) and fatty acids (FAs): LCBs are dominated by tri-hydroxylated molecules such as monounsaturated and saturated phytosphingosine (t18:1 and t18:0, respectively) in plants and mainly phytosphingosine (t18:0 and t20:0) in fungi; FA are generally 14–26 carbon atoms long in plants and 16–26 carbon atoms long in fungi, these chains being often hydroxylated in position 2. Mass spectrometry plays a pivotal role in the assessment of GIPC diversity and the characterization of their structures. Indeed, it allowed to determine that the core structure of GIPC polar heads in plants is Hex(R1)-HexA-IPC, with R1 being a hydroxyl, an amine, or a N-acetylamine group, whereas the core structure in fungi is Man-IPC. Notably, information gained from tandem mass spectrometry spectra was most useful to describe the huge variety of structures encountered in plants and fungi and reveal GIPCs with yet uncharacterized polar head structures, such as hexose–inositol phosphoceramide in Chondracanthus acicularis and (hexuronic acid)4–inositol phosphoceramide and hexose–(hexuronic acid)3–inositol phosphoceramide in Ulva lactuca.

Example of GIPC with its three building blocks (fatty acid, FA; long chain base, LCB; polar head) where R1 could be a hydroxyl, an amine or a N-acetylamine group

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Abbreviations

CID:

Collision-induced dissociation

DHA:

2,6-dihydroxy-acetophenone

ESI:

Electrospray ionization

FA:

Fatty acid

FAME:

Fatty acid methyl ester

Gal:

Galactose

GIPC:

Glycosyl inositol phosphoryl ceramide

GlcA:

Glucuronic acid

GlcN:

Glucosamine

GlcNAc:

N-acetyl glucosamine

Hex:

Hexose

IPC:

Inositol phosphoryl ceramide

IT:

Ion trap

LCB:

Long-chain base

MALDI:

Matrix-assisted laser desorption ionization

Man:

Mannose

MRM:

Multiple reaction monitoring

MS/MS:

Tandem mass spectrometry

NAc:

N-acetyl

Q:

Quadrupole

TIC:

Total ion current

ToF:

Time of flight

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Acknowledgments

The work was supported by the French Agence Nationale pour la Recherche (contract no. NT09_517917 PANACEA).

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Author notes

  1. Jean-Luc Cacas

    Present address: UMR1347 Agroécologie, INRA/Université de Bourgogne/Agrosup, Pôle Interactions Plante-Microorganisme, ERL CNRS 6300, 17 Rue Sully, 21000, Dijon, France

Authors and Affiliations

  1. Université de Bordeaux, Chimie Biologie des Membranes et Nanoobjets CBMN-UMR 5248 Centre de Génomique Fonctionnelle, Université Bordeaux Segalen, 146, rue Léo Saignat, 33076, Bordeaux Cedex, France

    Corinne Buré & Jean-Marie Schmitter

  2. Université de Bordeaux, Laboratoire de Biogenèse Membranaire, UMR 5200 CNRS-Université Bordeaux Segalen, 71, avenue Edouard Bourlaux, 33883, Villenave-d’Ornon Cedex, France

    Jean-Luc Cacas & Sébastien Mongrand

Authors
  1. Corinne Buré
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  2. Jean-Luc Cacas
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  3. Sébastien Mongrand
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  4. Jean-Marie Schmitter
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Corresponding author

Correspondence to Corinne Buré.

Additional information

Published in the special issue Analytical Science in France with guest editors Christian Rolando and Philippe Garrigues.

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Buré, C., Cacas, JL., Mongrand, S. et al. Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry. Anal Bioanal Chem 406, 995–1010 (2014). https://doi.org/10.1007/s00216-013-7130-8

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  • DOI: https://doi.org/10.1007/s00216-013-7130-8

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