Steroidal Glycoalkaloids: Isolation, Structure, Analysis, and Biosynthesis

Ghisalberti, Emilio L.

doi:10.1177/1934578x0600101007

Cited by 17 publications

(23 citation statements)

References 101 publications

(140 reference statements)

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“…For the Cluster 1 plants (S. melanocerasum, S. nigrum, and S. retroflexum), the primary glycoalkaloids present in all plants were 15, 17, 20, 28, and 46. In the Cluster 2 plants, three predominant compounds (16, 17, and 26) that belong to solanidine-type glycoalkaloids were present across all the species [19,34]. The clustering is consistent with the fact that S. nigrum, S. retroflexum, and S. melanocerasum belong to the Morelloid clade and have been shown to be genetically related based on morphological and molecular data [40,41].…”

Section: Glycoalkaloids Clustering In Solanum Plantssupporting

confidence: 69%

“…A pseudo-molecular ion of 414.33, corresponding to solanidine aglycone, was present in the MS spectra of 13 assigned glycoalkaloids. Solanidine, also known as solatubin or solanid-5-en-3-ol, contains an oxazaspirodecane ring system and is present in solamargine-and solasonine-type glycoalkaloids [19,34]. An aglycone with a molecular mass of 430.33 was present in four assigned glycoalkaloids.…”

Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

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

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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 Clustering In Solanum Plantssupporting

confidence: 69%

Section: Glycoalkaloids Assignmentmentioning

confidence: 99%

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

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Sell

Pillai

et al. 2022

Plants

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“…For instance, the triose of α-solanine consists of two six-carbon sugars, D-glucose and D-galactose and one five-carbon sugar L-rhamnose. On the other hand, the triose of α-chaconine consists of one six-carbon sugar D-glucose and two five-carbon sugar L-rhamnose (Ghisalberti, 2006). The fact that the two SGAs elicited a similar hatching response pattern, which varied with concentration suggest that the sugar type linked to the aglycone may influence J2 stimulation response.…”

Section: Discussionmentioning

confidence: 99%

Mediation of Potato–Potato Cyst Nematode, G. rostochiensis Interaction by Specific Root Exudate Compounds

et al. 2020

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Potato (Solanum tuberosum) is a widely consumed staple food crop worldwide whose production is threatened by potato cyst nematodes (PCN). To infect a host, PCN eggs first need to be stimulated to hatch by chemical components in the host root exudates, yet it remains unknown how most root exudate components influence PCN behavior. Here, we evaluated the influence of eight compounds identified by LC-QqQ-MS in the root exudate of potato on the hatching response of the PCN, Globodera rostochiensis at varying doses. The eight compounds included the amino acids tyrosine, tryptophan and phenylalanine; phytohormones zeatin and methyl dihydrojasmonate; steroidal glycoalkaloids α-solanine and α-chaconine and the steroidal alkaloid solanidine. We additionally tested two other Solanaceae steroidal alkaloids, solasodine and tomatidine, previously identified in the root exudates of tomato, an alternative host for PCN. In dose-response assays with the individual compounds, the known PCN hatching factors α-chaconine and α-solanine stimulated the highest number of eggs to hatch, ∼47 and ∼42%, respectively, whereas the steroidal alkaloids (aglycones), solanidine and solasodine and potato root exudate (PRE) were intermediate, 28% each and 21%, respectively, with tomatidine eliciting the lowest hatching response 13%. However, ∼60% of the hatched juveniles failed to emerge from the cyst, which was compoundand concentration-dependent. The amino acids, phytohormones and the negative control (1% DMSO in water), however, were generally non-stimulatory. The use of steroidal glycoalkaloids and their aglycones in the suicidal hatching of PCN offers promise as an environmentally sustainable approach to manage this pest.

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“…Glycosylated steroidal alkaloids are a large family of metabolites first reported in 1820, of which the prototypes were first identified in 1942 as solasonine ( 151 ) and solamargine. 499 An excellent and authoritative review including methods for isolation, identification and biosynthesis of these alkaloids discusses these topics in detail. 499 Importantly, glycosylated steroidal alkaloids are an alternative starting material for the synthesis of steroidal hormones, since the use of potato blossoms or of waste of potato starch production as a biological source is economically sustainable.…”

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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Steroidal Glycoalkaloids: Isolation, Structure, Analysis, and Biosynthesis

Cited by 17 publications

References 101 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

Mediation of Potato–Potato Cyst Nematode, G. rostochiensis Interaction by Specific Root Exudate Compounds

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

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