Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451

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Photoisomerization of 2-[3-(2-Thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a Yellow Pigment in Salted Radish Roots
Hiroki MATSUOKA, Shuji HONZAWA, Asaka TAKAHASHI, Hiroko YOSHIKAWA, Emi WATANABE, Takeaki WATANABE, Yoshio OZAWA, Yoichi YAMADA, Takeshi IIZUKA, Yasushi UDA
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論文ID: 80092

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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.
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© 2008 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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