Glycogen Synthase Kinase-3β Inhibition of 6-(Methylsulfinyl)hexyl Isothiocyanate Derived from Wasabi (Wasabia japonica Matsum)

Jun YOSHIDA; Satomi NOMURA; Naoyuki NISHIZAWA; Yoshiaki ITO; Ken-ichi KIMURA

doi:10.1271/bbb.100507

Food & Nutrition Science Notes

Glycogen Synthase Kinase-3β Inhibition of 6-(Methylsulfinyl)hexyl Isothiocyanate Derived from Wasabi (Wasabia japonica Matsum)

Jun YOSHIDA, Satomi NOMURA, Naoyuki NISHIZAWA, Yoshiaki ITO, Ken-ichi KIMURA

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Keywords: wasabi, Wasabia japonica Matsum, methylsulfinyl isothiocyanate, GSK-3β

JOURNAL FREE ACCESS

2011 Volume 75 Issue 1 Pages 136-139

DOI https://doi.org/10.1271/bbb.100507

View "Advance Publication" version (January 7, 2011).

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Abstract

A new biological activity of 6-(methylsulfinyl)hexyl isothiocyanate derived from Wasabia japonica was discovered as an inhibitor of glycogen synthase kinase-3β. The most potent isothiocyanate, 9-(methylsulfinyl)hexyl isothiocyanate, inhibited glycogen synthase kinase-3β at a K_i value of 10.5 μM and showed ATP competitive inhibition. The structure-activity relationship revealed an inhibitory potency of methylsulfinyl isothiocyanate dependent on the alkyl chain length and the sulfoxide, sulfone, and/or the isothiocyanate moiety.

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