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Biosci Biotechnol Biochem ; 72(9): 2262-8, 2008 Sep.
Article in English | MEDLINE | ID: mdl-18776682

ABSTRACT

The photostability of (E)-2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan ((E)-TPMT), the main yellow pigment in salted radish, was studied. First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identified as Z-configurated TPMT, and isomerization from the Z- to the E-form was reversibly induced by Vis-light irradiation. The optimum wavelength for isomerization from the E- to the Z-form was 360-380 nm, and that for isomerization from the Z- to the E-form was 440-460 nm. The E/Z-ratios in the photostationary state under UV- and Vis-light irradiation conditions were approximately 0.95:1 and 26:1 respectively. The (Z)-isomer was more sensitive to light irradiation than the (E)-isomer in the quantum yield measurement. Yellowing was dependent on the ratio of the (Z)-isomer, because the b(*) and chroma value rose with increases in the (Z)-isomer by the colorimeters. Hence, it is possible that the formation of the (Z)-isomer contribute to the yellow color of takuan-zuke during long salting and fermentation.


Subject(s)
Pigments, Biological/chemistry , Raphanus/chemistry , Tryptophan/analogs & derivatives , Tryptophan/chemistry , Hydrogen-Ion Concentration , Isomerism , Light , Nuclear Magnetic Resonance, Biomolecular , Photochemistry , Pigments, Biological/isolation & purification , Plant Roots/chemistry , Sodium Chloride/chemistry , Spectrophotometry, Ultraviolet , Temperature , Thiones , Time Factors , Tryptophan/isolation & purification , Ultraviolet Rays
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