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Metabolites
2023 Jun 23;137:. doi: 10.3390/metabo13070783.
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A Mass Spectrometry Database for Sea Cucumber Triterpene Glycosides.
Popov RS
,
Ivanchina NV
,
Silchenko AS
,
Avilov SA
,
Kalinin VI
,
Malyarenko TV
,
Stonik VA
,
Dmitrenok PS
.
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Sea cucumber triterpene glycosides are a class of secondary metabolites that possess distinctive chemical structures and exhibit a variety of biological and pharmacological activities. The application of MS-based approaches for the study of triterpene glycosides allows rapid evaluation of the structural diversity of metabolites in complex mixtures. However, the identification of the detected triterpene glycosides can be challenging. The objective of this study is to establish the first spectral library containing the mass spectra of sea cucumber triterpene glycosides using ultraperformance liquid chromatography-quadrupole time-of-flight mass spectrometry. The library contains the electrospray ionization tandem mass spectra and retention times of 191 triterpene glycosides previously isolated from 15 sea cucumber species and one starfish at the Laboratory of the Chemistry of Marine Natural Products of the G.B. Elyakov Pacific Institute of Bioorganic Chemistry. In addition, the chromatographic behavior and some structure-related neutral losses in tandem MS are discussed. The obtained data will accelerate the accurate dereplication of known triterpene glycosides and the annotation of novel compounds, as we demonstrated by the processing of LC-MS/MS data of Eupentacta fraudatrix extract.
Figure 1. Structures of lanostane-type aglycons occurring in sea cucumber triterpene glycosides with 18(20)-lactone (a), 18(16)-lactone (b), and without a lactone cycle (c).
Figure 2. The MS/MS spectrum of the [M−H]− precursor ion of psolusoside C1.
Figure 3. The MS/MS spectrum of the [M−Na]− precursor ion of psolusoside E.
Figure 4. Molecular network of sea cucumber triterpene glycoside spectral library. Nodes were colored according to the number of sulfate groups in molecules.
Figure 5. Molecular networks of the profiled compounds detected in E. fraudatrix extract annotated by the sea cucumber triterpene glycoside library.
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