Comparison of thin-layer chromatography and overpressured layer chromatographic techniques for the separation of ascorbigen and 1′-methylascorbigen

Kátay, Gy.; Mincsovics, Emil; Szókán, Gy.; Tyihák, E.

doi:10.1016/s0021-9673(96)00860-6

Cited by 24 publications

(12 citation statements)

References 17 publications

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“…In more acidic medium, the ring closure is retarded, and in more alkaline media the lactone is opened. (1), isolation of small amounts of socalled ascorbigen B has been reported repeatedly in earlier accounts [2][3][4][5][6][7][8][9]. (2) in cruciferous vegetables depends on the pH of the reaction medium [20].…”

Section: Discussionmentioning

confidence: 99%

“…It has been the subject of analytical and pharmacological investigations since the early 1950s, but was initially described only as a component of rather complex mixtures [1][2][3][4][5][6][7][8][9]. It has been the subject of analytical and pharmacological investigations since the early 1950s, but was initially described only as a component of rather complex mixtures [1][2][3][4][5][6][7][8][9].…”

Section: Discussionmentioning

confidence: 99%

“…Ascorbigen (1) is usually isolated from some fresh, stored, or fermented cruciferous vegetables [6]. Also a low-yield synthesis with gramine instead of 3-indolyl-carbinol (3) as the indole precursor in the presence of pyridine was established [25].…”

Section: Synthesis Of Ascorbigenmentioning

confidence: 99%

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Ascorbigen – Occurrence, Synthesis, and Analytics

Opietnik¹,

Jaafar²,

Becker³

et al. 2012

MROC

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Ascorbigen (2-C-(3-indolyl)-methyl--L-xylo-hex-3-ulofuranosono-1,4-lactone, 1) is a breakdown product of glucobrassicins found in cruciferous vegetables, such as cabbage, cauliflower, Brussel sprouts, or broccoli, formed by direct C-alkylation of ascorbic acid (vitamin C) by (3-indolyl)-methyl intermediates under physiological conditions. It is a labile compound, and direct synthesis approaches are hampered by the oxidative instability of the indol moiety and ring transformations of the ascorbyl part. The latter have also impeded ascorbigen analytics for decades, and only recently different ascorbigens have been shown to represent mixtures of compounds rather than individual ascorbigen-type compounds. Following a review of pertinent literature, timely aspects of ascorbigen chemistry, including the most recent synthesis approaches and in-depth characterization of the compound, are presented.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Ascorbigen – Occurrence, Synthesis, and Analytics

Opietnik¹,

Jaafar²,

Becker³

et al. 2012

MROC

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“…Analytical OPLC was performed on 0.2 mm thick, 200 × 200 mm TLC silica gel 60 F 254 (Merck, Darmstadt, Germany) chromatoplates sealed on four edges (Kátay et al, 1997).…”

Section: Experimental Materialsmentioning

confidence: 99%

“…Kátay et al (1997) demonstrated the superiority of overpressured layer chromatography (OPLC) to conventional thin-layer chromatography (TLC) for separation of AG and MeAG, and its suitability for analysis of plant extracts (Kátay et al, 1998(Kátay et al, , 2002. OPLC, which combines numerous advantages of TLC (e.g.…”

Section: Introductionmentioning

confidence: 99%

Potential role of formaldehyde in the mechanism of action of ascorbigens on the basis of BioArena studies

Kátay

Ott

Kátay

et al. 2008

Biomedical Chromatography

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The effect of ascorbigen and 1'-methylascorbigen as a model compound pair was studied on the phytopathogenic bacterium Pseudomonas savastanoi pv. phaseolicola in the BioArena experimental system after overpressured layer chromatography. Results showed a characteristic, strong antibacterial effect of 1'-methylascorbigen and weak effect of ascorbigen present on the adsorbent layer as chromatographic spot. Addition of formaldehyde capture compounds (L-arginine, glutathione, dimedone) partially or totally reduced the antibacterial effect of 1'-methylascorbigen and ascorbigen. On adding Cu(II) ions--which mobilize and coordinate formaldehyde--to the culture medium, the antibacterial effect of both compounds became stronger. It is supposed that the weak antibacterial effect of ascorbigen may have originated from the 1'-methylascorbigen formed in situ on the adsorbent layer by partial enzymatic methylation of ascorbigen.

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Critical evaluation of experimental conditions influencing the surface-enhanced Raman spectroscopic (SERS) detection of substances separated by layer liquid chromatographic techniques

et al. 2000

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SummarySurface-enhanced Raman spectra (SERS) of p-dimethylaminobenzylidenerhodanine have been recorded on silica gel 60 F254 and Si60 F254 Raman TLC plates. Spectra were enhanced by use of a silver sol prepared according to the modified Lee-Meisel procedure. The standard deviations of the intensities and the band ratios for the seven most intense peaks were calculated for 30 parallel measurements. Although the Raman plate gives more reproducible results, several experimental difficulties are encountered in the development of chromatograms. SERS detection ofascorbigen and 1 '-methylascorbigen was performed after chromatography on silica gel 60 F254 TLC and HPTLC plates and on Si60 F254 Raman TLC plates. Traditional development was used for the silica gel 60 F254 TLC plates and Si60 F254 Raman plates, and the personal OPLC technique for the silica gel 60 F254 HPTLC plates. It was found that the SERS spectrum gave information about the indole ring only. Because bonding of the analyte to the stationary phase results in a change in molecular conformation-in contrast with the behaviour of rhodanine-the type of the plate used and the development procedure employed can significantly influence the quality of the SERS spectrum.

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Comparison of thin-layer chromatography and overpressured layer chromatographic techniques for the separation of ascorbigen and 1′-methylascorbigen

Cited by 24 publications

References 17 publications

Ascorbigen – Occurrence, Synthesis, and Analytics

Ascorbigen – Occurrence, Synthesis, and Analytics

Potential role of formaldehyde in the mechanism of action of ascorbigens on the basis of BioArena studies

Critical evaluation of experimental conditions influencing the surface-enhanced Raman spectroscopic (SERS) detection of substances separated by layer liquid chromatographic techniques

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