Terpenoid glycosides

Pfander, P.; Stoll, H. R.

doi:10.1039/np9910800069

Cited by 24 publications

(10 citation statements)

References 11 publications

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“…The latter includes their role as energyrich metabolites and storage compounds, as structural components of a large number of natural products, and as cellular recognition and intercellular communication elements. A growing body of information indicates that the carbohydrates possess potent biological activities and that such oligosaccharides (0s) as well as compounds containing 0s partial structures are widespread in nature (Agrawal et al, 1985Agrawal and Bansal, 1989;Agrawal, 1992;Boros and Stermitz, 1990;Chopin and Dellamonica, 1988;Hiller, 1987;Kennedy and White, 1983;Mahato and Nandy, 1991;McNeil et al, 1979;Pfander and Stoll, 1991;Shibata, 1977;Srivastava and Kulshreshtha, 1989;Tschesche and Wulff, 1973).…”

Section: Introductionmentioning

confidence: 99%

Nuclear Magnetic Resonance Spectroscopic Approaches for the Determination of Interglycosidic Linkage and Sequence in Oligosaccharides

Agrawal

Pathak

1996

Phytochem. Anal.

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Section: Introductionmentioning

confidence: 99%

Nuclear Magnetic Resonance Spectroscopic Approaches for the Determination of Interglycosidic Linkage and Sequence in Oligosaccharides

Agrawal

Pathak

1996

Phytochem. Anal.

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“…This demonstrates how RMD values aid the grouping of metabolites based on common biosynthetic precursors, despite differences in molecular mass and absolute mass defect. Terpenoid glycosides represent a diverse class of phytochemicals that have been understudied due to the challenges in their identification and structure elucidation (Pfander and Stoll, 1991;Sahu and Achari, 2001). While some of these compounds display biological activity (Chang et al, 2002;da Silva et al, 2008), much remains to be learned about their synthesis and functionality in plants (Maier et al, 1995).…”

Section: Foundations Of Relative Mass Defect Filtering For Mining Plamentioning

confidence: 99%

“…Terpenoids exhibit remarkable structural diversity resulting from varied metabolic cyclizations, oxidations, rearrangements, and branching reactions (Chappell, 1995;Mizutani and Ohta, 2010) and from diversity in glycosylation (Dembitsky, 2006;Goodger and Woodrow, 2011). Such structural diversity challenges investigators to recognize novel terpenoids in a complex matrix (Pfander and Stoll, 1991;Fraga, 2012), because few features in the MS/MS spectra of nonvolatile terpenoids provide reliable keys for their annotation as terpenoids. As a result, nonvolatile terpenoids represent an underappreciated group of plant specialized metabolites.…”

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confidence: 99%

Relative Mass Defect Filtering of Mass Spectra: A Path to Discovery of Plant Specialized Metabolites

2015

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The rapid identification of novel plant metabolites and assignments of newly discovered substances to natural product classes present the main bottlenecks to defining plant specialized phenotypes. Although mass spectrometry provides powerful support for metabolite discovery by measuring molecular masses, ambiguities in elemental formulas often fail to reveal the biosynthetic origins of specialized metabolites detected using liquid chromatography-mass spectrometry. A promising approach for mining liquid chromatography-mass spectrometry metabolite profiling data for specific metabolite classes is achieved by calculating relative mass defects (RMDs) from molecular and fragment ions. This strategy enabled the rapid recognition of an extensive range of terpenoid metabolites in complex plant tissue extracts and is independent of retention time, abundance, and elemental formula. Using RMD filtering and tandem mass spectrometry data analysis, 24 novel elemental formulas corresponding to glycosylated sesquiterpenoid metabolites were identified in extracts of the wild tomato Solanum habrochaites LA1777 trichomes. Extensive isomerism was revealed by ultra-high-performance liquid chromatography, leading to evidence of more than 200 distinct sesquiterpenoid metabolites. RMD filtering led to the recognition of the presence of glycosides of two unusual sesquiterpenoid cores that bear limited similarity to known sesquiterpenes in the genus Solanum. In addition, RMD filtering is readily applied to existing metabolomics databases and correctly classified the annotated terpenoid metabolites in the public metabolome database for Catharanthus roseus.Plant metabolic networks generate amazing chemical diversity, but our understanding of the genetic factors responsible for plant chemistry remains primitive. The discovery and identification of metabolites has posed the greatest bottleneck in recent efforts to exploit metabolomics to address questions about the basis for biosynthetic diversity in the plant kingdom (Ji et al., 2009;Zhou et al., 2012). Since the specialized metabolism of nonmodel plants is taxonomically restricted, metabolite databases offer a poor representation of plant chemical diversity, and de novo recognition and discovery of metabolite chemistry is necessary. A common strategy for metabolite discovery has often started with the generation of tandem mass spectrometry (MS/MS) spectra, usually beginning with the most abundant metabolites, and uses characteristic fragment ions to assign metabolites to a particular class of compounds. Flavonoid identification from MS/MS spectra is often successful because most flavonoids yield MS/MS fragment ions characteristic of their flavonoid cores (Ma et al., 1997;Li et al., 2013). However, when MS/MS spectra fail to display classcharacteristic fragment ions, the recognition of a metabolite's structural class is less obvious.Specialized plant metabolites are often grouped as polyphenolic, terpenoid, alkaloid, polyketide, or fatty acid metabolites based upon the biosynthesis of their...

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“…643,644 Glycosylated terpenoids other than iridoids have also been isolated, but the large majority is mono-glycosylated, a structural feature that does not guarantee complete solubility in H 2 O. 640–646 Water-soluble iridoids have been isolated by various approaches, including 201 from the leaves of Premna japonica , 647 as well as picrorhizaoside A ( 202 ) from the rhizomes of Picrorhiza kurroa . 648 Known water-soluble glycosylated iridoids have been isolated using HPCCC, 649 HSCCC 650 and CPC.…”

Section: The Isolation Of Water-soluble Natural Productsmentioning

confidence: 99%

The isolation of water-soluble natural products – challenges, strategies and perspectives

et al. 2022

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Terpenoid glycosides

Cited by 24 publications

References 11 publications

Nuclear Magnetic Resonance Spectroscopic Approaches for the Determination of Interglycosidic Linkage and Sequence in Oligosaccharides

Nuclear Magnetic Resonance Spectroscopic Approaches for the Determination of Interglycosidic Linkage and Sequence in Oligosaccharides

Relative Mass Defect Filtering of Mass Spectra: A Path to Discovery of Plant Specialized Metabolites

The isolation of water-soluble natural products – challenges, strategies and perspectives

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