Utility of coupled-HSQC experiments in the intact structural elucidation of three complex saponins from Blighia sapida

[Display omitted] ► Non-destructive structure elucidation of complex saponins by NMR. ► Utility of 1H coupled HSQC NMR spectra for sugar identification in strongly coupled systems. ► NMR and MS characterization of saponins from Blighia sapida (ackee). The structures of three complex saponins from th...

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Bibliographic Details
Published in:Carbohydrate research 2011-05, Vol.346 (6), p.759-768
Main Authors: Mazzola, Eugene P., Parkinson, Ainsley, Kennelly, Edward J., Coxon, Bruce, Einbond, Linda S., Freedberg, Darón I.
Format: Article
Language:English
Subjects:
Ackee
Blighia - chemistry
Blighia sapida
carbon
Coupled-HSQC
Magnetic Resonance Spectroscopy
Molecular Structure
monosaccharides
nuclear magnetic resonance spectroscopy
pods
Saponins
Saponins - analysis
Saponins - chemistry
stable isotopes
Triterpene glycosides
Triterpenes - analysis
Triterpenes - chemistry
triterpenoids
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Summary:[Display omitted] ► Non-destructive structure elucidation of complex saponins by NMR. ► Utility of 1H coupled HSQC NMR spectra for sugar identification in strongly coupled systems. ► NMR and MS characterization of saponins from Blighia sapida (ackee). The structures of three complex saponins from the fruit pods of Blighia sapida have been elucidated and their 1H and 13C NMR spectra assigned employing a variety of one- and two-dimensional NMR techniques without degradative chemistry. The saponins have either four or six monosaccharide units linked to a triterpene aglycone. High-resolution, proton-coupled-HSQC spectra were important for determining both the identities of the intact monosaccharide units and coupling constants in strongly coupled proton spin systems. These NMR experiments will prove crucial as the complexity of saponin structures reaches the limit that can be determined solely by NMR.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.02.019