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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)

NCBI PubMed ID: 9796423
Publication DOI: 10.1021/ac980365q
Journal NLM ID: 0370536
Correspondence: Van De Werken G <gerrit.van.de.werken

rivm.nl>
Institutions: Department of Molecular Spectroscopy, National Institute of Public Health and the Environment, Bilthoven, The Netherlands, Department for Vaccine Development, National Institute of Public Health and the Environment, Bilthoven, The Netherlands, Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht, The Netherlands

Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by γ-hydrogen rearrangements and successive retro- Diels-Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring- cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1-4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry.

Molecular Sequence Data, monosaccharides, deuterium, saponins, triterpenes, high pressure liquid chromatography, mass scpectometry

Structure type: oligomer
Location inside paper: Fig. 1, QS18
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_136044,IEDB_136105,IEDB_136907,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88

Methods: deacylation, HPLC, nanoESP IT MS

NCBI Taxonomy refs (TaxIDs): 23212
Show glycosyltransferases

There is only one chemically distinct structure:

CCC(C)C(CC(O)CC(=O)O[C@@H]1[C@H](O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O[C@@H]4OC[C@](O)(CO)[C@H]4O)[C@H]3O)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@H](OC(=O)[C@]23CCC(C)(C)C[C@@H]2C2=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@@](C)(C=O)C5CC[C@@]4(C)[C@]2(C)C[C@H]3O)O[C@@H]1C)OC(=O)CC(O)CC(O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O)C(C)CC

SVG MW SMILES 3D mol Ionize