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1. (Article ID: 7156)
 
Barreto-Bergter E, Pinto MR, Rodrigues ML
Structural and Functional Aspects of Fungal Glycosphingolipids
Book: Studies in Natural Products Chemistry (2006) 1025-1056
 

During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

biosynthesis, structure, glycosphingolipids, fungi

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2. (Article ID: 8032)
 
Buré C, Cacas JL, Mongrand S, Schmitter JM
Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry
Analytical and Bioanalytical Chemistry 406(4) (2014) 995-1010
 

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.

mass spectrometry, Plants, sphingolipids, fungi, glycosyl inositol phosphoryl ceramide

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