Title:Ascorbigen – Occurrence, Synthesis, and Analytics
Volume: 9
Issue: 4
Author(s): Martina Opietnik, Sharifah Nabihah Binti Syed Jaafar, Manuel Becker, Stefan Bohmdorfer, Andreas Hofinger and Thomas Rosenau
Affiliation:
Keywords:
Ascorbigen, glucobrassicin, cruciferous vegetables, ascorbic acid, indol derivatives, nuclear magnetic resonance pyrolysis-
GC/MS.
Abstract: Ascorbigen (2-C-(3-indolyl)-methyl-α-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.
