Structure–Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard

Abstract

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.

Identification and Characterization of Three Epithiospecifier Protein Isoforms in Brassica oleracea

“…While releasing glucose, a thiohydroximate-O-sulfate is formed, which can spontaneously degrade by a Lossenlike rearrangement to an isothiocyanate (ITC) or a nitrile (Rossiter et al, 2007). ITCs are the pungent principle found in mustard, wasabi, and radish (Terada et al, 2015), among others. Moreover, ITCs have antimicrobial, anti-inflammatory, and most frequently investigated, anticarcinogenic properties (Traka and Mithen, 2009;Veeranki et al, 2015).…”

Localized Excitation of Neural Activity via Rapid Magnetothermal Drug Release

“…This work makes use of nanoscale heating to excite neurons by triggering the release of a pharmacological agent, allyl isothiocyanate (AITC, a pungent component of wasabi), from the surfaces of MNPs targeted to membranes of neurons sensitized to the compound ( Figure a). To accomplish this, AITC molecules were bound to the surfaces of MNPs with thermally cleavable linkers activated by local AMF‐induced heating .…”

Anti-obesity Effects of Wasabi Leaf Extract on Rats Fed a High-fat Diet are Related to Upregulation of mRNA Expression of β3-adrenergic Receptors in Interscapular Brown Adipose Tissue

“…Isothiocyanates are known ligands of TRPA1 (Jordt et al, 2004;Terada et al, 2015;Uchida et al, 2012). TRPA1 activation results in sympathetic nerve stimulation.…”

“…These isothiocyanates have many physiological functions, including anti-microbial (Isshiki et al, 1992), anti-platelet (Morimitsu et al, 2000), anti-cancer, antioxidative (Morimitsu et al, 2000(Morimitsu et al, , 2002, anti-inflammatory (Uto et al, 2005), anti-diabetic (Fukuchi et al, 2004;Yoshida et al, 2011), and anti-allergic (Nagai and Okunishi, 2009;Yamada-Kato et al, 2012) activities. Furthermore, isothiocyanates are known ligands of transient receptor potential ankyrin 1 (TRPA1) (Jordt et al, 2004;Terada et al, 2015;Uchida et al, 2012).…”