Identification of the components of aldoses in a tautomeric equilibrium mixture as their trimethylsilyl ethers by capillary gas chromatography

Páez, Martha; Martı́nez-Castro, I.; Sanz, J.; Olano, Agustı́n; Garcı́a-Raso, Ángel; Saura‐Calixto, Fulgencio

doi:10.1007/bf02310417

Cited by 26 publications

(7 citation statements)

References 9 publications

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“…[21] It can be explained by the fact that enol formation depends directly on the ratio of open and cyclic monosaccharides species concentrations in solution. The concentration of open form in fructose solution is higher than that in glucose solution, [29,30] that probably explains the greater reactivity of the first monose. Values of pK a and rate constants of ionized enols formation quantitatively explain that Frc -is produced faster and at lower pH values than Glc -(vide supra).…”

Section: Reaction Of Cbi(ii) With Glucose and Fructosementioning

confidence: 99%

Reactions of Cobinamide with Glucose and Fructose

Dereven’kov¹,

Salnikov²,

Shpagilev³

et al. 2012

MHC

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Section: Reaction Of Cbi(ii) With Glucose and Fructosementioning

confidence: 99%

Reactions of Cobinamide with Glucose and Fructose

Dereven’kov¹,

Salnikov²,

Shpagilev³

et al. 2012

MHC

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“…The hydrolysate of 3 was trimethylsilylated and then subjected to GC-MS. d -Xylose, d -ribose, and l -arabinose, which are common pentoses in natural products, were also trimethylsilylated and analyzed by GC-MS. The chromatograms of the trimethylsilylated (TMS) derivatives of the pentoses showed four peaks, which were indicative of the α-pyranose, β-pyranose, α-furanose, and β-furanose forms of the compounds [ 14 ]. The TMS derivative of the hydrolysate of 3 showed four peaks with t R s that coincided with those of xylose.…”

Section: Resultsmentioning

confidence: 99%

Xylosylated Detoxification of the Rice Flavonoid Phytoalexin Sakuranetin by the Rice Sheath Blight Fungus Rhizoctonia solani

2018

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Sakuranetin (1) is a rice flavanone-type phytoalexin. We have already reported that the metabolites from the detoxification of 1 by Pyricularia oryzae are naringenin (2) and sternbin. In this study, we investigated whether the rice sheath blight fungus Rhizoctonia solani, another major rice pathogen, can detoxify 1. The extract of R. solani suspension culture containing 1 was analyzed by LC-MS to identify the metabolites of 1. Three putative metabolites of 1 were detected in the extract from the R. solani suspension culture 12 h after the addition of 1, and they were identified as 2, sakuranetin-4′-O-β-d-xylopyranoside (3), and naringenin-7-O-β-d-xylopyranoside (4) by NMR, LC-MS/MS, and GC-MS analyses. The accumulation of 2, 3, and 4 reached their maximum levels 9–12 h after the addition of 1, whereas the content of 1 decreased to almost zero within 9 h. The antifungal activities of 3 and 4 against R. solani were negligible, and 2 showed weaker antifungal activity than 1. We concluded that 2, 3, and 4 are metabolites from the detoxification of 1 by R. solani. Xylosylation is a rare and efficient detoxification method for phytoalexins.

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“…Gas chromatography was successfully used for the identification of various pentoses and hexoses, e. g. allofuranose ( b31 ), allopyranose, glucofuranose ( b32 ), glucopyranose, mannofuranose, and mannopyranose after silylation ,. However, each aldose showed 4 peaks in the GC chromatogram that were attributed to the α and β‐ configurations of the furanose and pyranose forms of the respective carbohydrate . This makes the GC/MS analysis of these mixtures rather difficult when they are obtained by extraction using methanol.…”

Section: Resultsmentioning

confidence: 99%

White Birch Trunk Extracts as a Source of Organic Compounds

2017

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Extracts of white birch (Betula pendula) may be a useful source of aromatics, polyols, and fatty acids. Ultra performance liquid chromatography/electrospray ionization‐quadrupole time‐of‐flight mass spectrometry (UPLC/ESI(−)‐QTOFMS) and gas chromatography/electron impact‐quadrupole mass spectrometry (GC/EI‐QMS) were applied to analyze the soluble fractions obtained after the sequential extraction of the bark and interior wood of a white birch trunk using methanol and the ionic liquid 1‐butyl‐3‐methylimidazolium chloride. Methanolic extracts of both the bark and interior wood contained diarylheptanoids and polyols. By contrast, fatty acids were found only in the methanolic extracts of interior wood. Additional diarylheptanoids, 3‐O‐caffeoyl‐betulin, and smaller phenolic compounds were extracted with the ionic liquid. Surprisingly, the ionic liquid extracts included additional compounds, which may be have formed in a reaction of the ionic liquid. The use of the bark resulted in more soluble material. Thus, this bark may be preferred as a renewable resource for organic materials.

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Identification of the components of aldoses in a tautomeric equilibrium mixture as their trimethylsilyl ethers by capillary gas chromatography

Cited by 26 publications

References 9 publications

Reactions of Cobinamide with Glucose and Fructose

Reactions of Cobinamide with Glucose and Fructose

Xylosylated Detoxification of the Rice Flavonoid Phytoalexin Sakuranetin by the Rice Sheath Blight Fungus Rhizoctonia solani

White Birch Trunk Extracts as a Source of Organic Compounds

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