Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard.
Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPA1. The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are not known except for a few compounds. To investigate the effect of carbon chain length and substituents of ITCs, the TRPA1-activiting ability of 16 ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency, the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small.
Graduate School of Nutritional and Environmental Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Yuko
Y
Terada
Maihama Research Center, Ogawa & Company, Ltd. , 15-7 Chidori, Urayasu-shi, Chiba 279-0032, Japan.
Hideki
H
Masuda
Graduate School of Nutritional and Environmental Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Tatsuo
T
Watanabe
D000818:Animals; D031215:Armoracia / Q000737:chemistry*; D006801:Humans; D017879:Isothiocyanates / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009149:Mustard Plant / Q000737:chemistry*; D013329:Structure-Activity Relationship; D000074025:TRPA1 Cation Channel; D050916:TRPV Cation Channels / Q000187:drug effects*; D050051:Transient Receptor Potential Channels / Q000187:drug effects*
D017879:Isothiocyanates; D000074025:TRPA1 Cation Channel; D050916:TRPV Cation Channels; C494482:TRPV1 protein, human; D050051:Transient Receptor Potential Channels; C475685:Trpa1 protein, mouse; C004471:allyl isothiocyanate