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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 15654124
Publication DOI: 10.1194/jlr.M400457-JLR200
Journal NLM ID: 0376606
Publisher: ASBMB
Correspondence: slevery

cisunix.unh.edu
Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602-7229, Center of Microbial and Plant Genetics, Katholieke Universiteit Leuven, B-3001 Heverlee-Leuven, Belgium

To defend themselves against fungal pathogens, plants produce numerous antifungal proteins and peptides, including defensins, some of which have been proposed to interact with fungal cell surface glycosphingolipid components. Although not known as a phytopathogen, the filamentous fungus Neurospora crassa possesses numerous genes similar to those required for plant pathogenesis identified in fungal pathogens (Galagan, J. E., et al. 2003. Nature 422: 859-868), and it has been used as a model for studying plant-phytopathogen interactions targeting fungal membrane components (Thevissen, K., et al. 2003. Peptides. 24: 1705 1712). For this study, neutral glycolipid components were extracted from wild-type and plant defensin-resistant mutant strains of N. crassa. The structures of purified components were elucidated by NMR spectroscopy and mass spectrometry. Neutral glycosphingolipids of both wild-type and mutant strains were characterized as beta-glucopyranosylceramides, but those of the mutants were found with structurally altered ceramides. Although the wild type expressed a preponderance of N-2'-hydroxy-(E)-Delta(3)-octadecenoate as the fatty-N-acyl component attached to the long-chain base (4E,8E)-9-methyl-4,8-sphingadienine, the mutant ceramides were found with mainly N-2'-hydroxyhexadecanoate instead. In addition, the mutant strains expressed highly increased levels of a sterol glucoside identified as ergosterol-beta-glucoside. The potential implications of these findings with respect to defensin resistance in the N. crassa mutants are discussed.

mass spectrometry, nuclear magnetic resonance spectroscopy, ceramide, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, glucoside, Aspergillus fumigatus, sphingolipid, cerebroside, ergosterol, sterol

Structure type: monomer
C₃₄H₅₆O₁₀
Location inside paper: p.766, scheme 3
Trivial name: ergosterol-β-D-glucopyranoside, ergosterol β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, sterylglycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, ion-exchange chromatography, extraction, HPTLC, ESI-QTOF-MS
Comments, role: Although the wild type expressed a preponderance of N-2'-hydroxy-(E)-delta3-octadecenoate as the fatty-N-acyl component attached to the long-chain base (4E,8E)-9-methyl-4,8-sphingadienine, mutant ceramides from a plant defensin-resistant strain were found with mainly N-2'-hydroxyhexadecanoate instead. In addition, the mutant strains expressed highly increased levels of a sterol glucoside identified as ergosterol-glucoside.

Related record ID(s): 41270, 41384
NCBI Taxonomy refs (TaxIDs): 5141
Reference(s) to other database(s): GenDB:KT240140
Show glycosyltransferases

NMR conditions: in vol 98%DMSO-d6 / vol 2%D2O at 308 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bDGlcp	101.38	73.87	77.19	70.55	77.09	61.53
	Subst	38.89	30.06	76.26	38.25	140.22	119.76	116.61	141.00	46.06	37.48	20.24	39.19	41.50	54.38	23.05	28.35	55.60	12.29	16.45	40.20	21.44	135.83	131.97	42.91	32.98	19.93	21.04	17.82


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28
3	bDGlcp	4.25	2.90	3.14	3.02	3.10	3.42-3.65
	Subst	1.25-1.83	1.45-1.88	3.58	2.16-2.52	-	5.53	5.34	-	1.92	-	1.56-1.64	1.25-2.00	-	1.87	1.31-1.64	1.27-1.71	1.27	0.57	0.88	2.02	1.19	5.21	5.23	1.86	1.47	0.82	0.82	0.89


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28
3	bDGlcp	101.38/4.25	73.87/2.90	77.19/3.14	70.55/3.02	77.09/3.10	61.53/3.42-3.65
	Subst	38.89/1.25-1.83	30.06/1.45-1.88	76.26/3.58	38.25/2.16-2.52		119.76/5.53	116.61/5.34		46.06/1.92		20.24/1.56-1.64	39.19/1.25-2.00		54.38/1.87	23.05/1.31-1.64	28.35/1.27-1.71	55.60/1.27	12.29/0.57	16.45/0.88	40.20/2.02	21.44/1.19	135.83/5.21	131.97/5.23	42.91/1.86	32.98/1.47	19.93/0.82	21.04/0.82	17.82/0.89

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28
3	bDGlcp	4.25	2.90	3.14	3.02	3.10	3.42 3.65
	Subst	1.25 1.83	1.45 1.88	3.58	2.16 2.52		5.53	5.34		1.92		1.56 1.64	1.25 2.00		1.87	1.31 1.64	1.27 1.71	1.27	0.57	0.88	2.02	1.19	5.21	5.23	1.86	1.47	0.82	0.82	0.89

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bDGlcp	101.38	73.87	77.19	70.55	77.09	61.53
	Subst	38.89	30.06	76.26	38.25	140.22	119.76	116.61	141.00	46.06	37.48	20.24	39.19	41.50	54.38	23.05	28.35	55.60	12.29	16.45	40.20	21.44	135.83	131.97	42.91	32.98	19.93	21.04	17.82

There is only one chemically distinct structure:

CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C

SVG MW SMILES 3D mol Ionize