Optimization of Hidden Target Screening for Solanum sisymbriifolium Glycoalkaloids

Popova, Inna E.; Morra, Matthew J.

doi:10.1007/s10337-020-03989-7

Cited by 2 publications

(3 citation statements)

References 33 publications

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“…Root, leaf, and stem extracts from seven Solanum species were assessed using time-offlight MS analysis for exact molecular mass assessment, and a characteristic neutral loss pattern analysis of typical sugar moieties (pentose, deoxyhexose, and hexose) for glycoalkaloid assignment [16]. A total of 51 compounds that were assigned as glycoalkaloids were shared among all Solanum plants and accounted for 97-99% of the peak area in the total ion chromatograms (Table 1).…”

Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

“…For the remaining assigned glycoalkaloids, the fragmentation pattern in the lower mass ranges was not strong enough to accurately identify the aglycone. Based on the neutral loss analysis (Table 1), 20 and 10 assigned glycoalkaloids were determined to contain a triose and teraose sugar moiety, respectively [16,35]. While the specific sugars and their linkage to the aglycone molecule cannot be accurately assigned, based on the consequent neutral loss mass, mono-, di-, tri-, and tetrameric sugar forms that could be obtained by combining pentose, hexose, and deoxyhexose were suggested (Table 1) [35].…”

Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

“…HPLC TOF MS chromatograms were processed in MassHunter B.08.00 Agilent Profinder software (Agilent Technologies Inc, Santa Clara, CA, USA). The assignment of glycoalkaloids was performed based on neutral loss analysis using fragmentation and isotopic patterns for each compound [16,35]. Neutral loss corresponding to mono-, di-, tri-, and tetrameric sugar moieties that could be obtained by combining pentose, hexose, and deoxyhexose units were considered to be with the error of less than 3 ppm.…”

Section: Hplc Tof Ms Analysis Of Glycoalkaloidsmentioning

confidence: 99%

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High-Performance Liquid Chromatography–Mass Spectrometry Analysis of Glycoalkaloids from Underexploited Solanum Species and Their Acetylcholinesterase Inhibition Activity

Popova

Sell

Pillai

et al. 2022

Plants

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Solanum glycoalkaloids are gaining increased scientific attention due to their bioactive potential in the defense of plants against pests and pathogens. The comprehensive glycoalkaloid profiling from the leaves, stems, and roots of seven underexploited Solanum species (S. caripense, S. melanocerasum, S. muricatum, S. nigrum, S. quitoense, S. retroflexum, and S. sisymbriifolium) was conducted using high-performance liquid chromatography–time-of-flight mass spectrometry. A total of 51 glycoalkaloids were shared among the studied Solanum species, with concentrations ranging from 7 to 5.63 × 105 ng g−1. Based on the glycoalkaloid composition, plants were separated into two clusters, Cluster 1 (S. melanocerasum, S. nigrum, and S. retroflexum) and Cluster 2 (S. caripense, S. muricatum, S. quitoense, and S. sisymbriifolium). The inhibition activity of glycoalkaloid extracts on acetylcholinesterase showed a half-maximal inhibitory concentration (IC50), ranging from 0.4 (S. nigrum stems) to 344.9 µg mL−1 (S. sisymbriifolium leaves), that was not directly correlated to the total glycoalkaloid contents. This suggests that the composition of glycoalkaloids in the plant extract, rather than the total concentration, is a driver of biological activity. The study provides a framework for the bioprospecting of underexploited Solanum species for exploring bioactive glycoalkaloids and other compounds with potential pesticidal activities for the development of green bioformulation. This is the first comprehensive report on the glycoalkaloid profiles of S. retroflexum.

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Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

Section: Hplc Tof Ms Analysis Of Glycoalkaloidsmentioning

confidence: 99%

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High-Performance Liquid Chromatography–Mass Spectrometry Analysis of Glycoalkaloids from Underexploited Solanum Species and Their Acetylcholinesterase Inhibition Activity

Popova

Sell

Pillai

et al. 2022

Plants

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Molecular Networks as Strategy for Dereplication of Steroidal Alkaloids of Herbarium Samples of Solanum jabrense Agra and M. Nee, an Endemic and Unexplored Species

Lima e Silva,

de Medeiros Brito,

Agra

et al. 2024

Chemistry & Biodiversity

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Solanum jabrense is an endemic species from Brazil, distributed in the phytogeographic domains of the Caatinga and Atlantic Forest, in the states of Northeast. Solanum L. species have great economic importance not only because they are used in human food, but also because they present several secondary metabolites, especially glycosylated steroidal alkaloids, giving them medicinal properties. Recently, dry herbarium specimens have been used to identify metabolites of interest preserved even after years of storage, using a simple and fast method of extraction and analysis by liquid chromatography coupled to mass spectrometry. Dereplication techniques aided by molecular networks were used to analyze the chemical composition from samples of S. jabrense herbarium specimens, and to identify chemical markers and bioactive molecules with potential medicinal use. From the LC‐MS/MS dataset of the crude extracts and a standard (solasodine), a molecular network was generated that resulted in the dereplication of 19 spirosolane‐type alkaminas. Our results suggest that dereplication using fragments of dried Solanum specimens is a quick tool to identify potential conserved metabolites, being useful not only for chemotaxonomy and metabolomic but also for the discovery of new molecules in natural products.

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Optimization of Hidden Target Screening for Solanum sisymbriifolium Glycoalkaloids

Cited by 2 publications

References 33 publications

High-Performance Liquid Chromatography–Mass Spectrometry Analysis of Glycoalkaloids from Underexploited Solanum Species and Their Acetylcholinesterase Inhibition Activity

High-Performance Liquid Chromatography–Mass Spectrometry Analysis of Glycoalkaloids from Underexploited Solanum Species and Their Acetylcholinesterase Inhibition Activity

Molecular Networks as Strategy for Dereplication of Steroidal Alkaloids of Herbarium Samples of Solanum jabrense Agra and M. Nee, an Endemic and Unexplored Species

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