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Isothiocyanates from Wasabia japonica activate transient receptor potential ankyrin 1 channel.
Chem Senses. 2012 Nov; 37(9):809-18.CS

Abstract

6-(Methylsulfinyl)hexyl isothiocyanate (6-MSITC) and 6-(methylthio)hexyl isothiocyanate (6-MTITC) have low pungency and are responsible for the fresh flavor of wasabi (Wasabia japonica [Miq] Matsumura). In this study, we found that these two isothiocyanates activate transient receptor potential ankyrin 1 (TRPA1), and 6-MSITC activates transient receptor potential vanilloid 1 (TRPV1), but not other transient receptor potential channels expressed in sensory neurons. Both 6-MSITC and 6-MTITCinduced intracellular Ca(2+) increases in human embryonic kidney-derived 293 cells expressing mouse TRPA1 (mTRPA1) as measured by Ca(2+) imaging. In whole-cell patch-clamp recordings, 6-MSITC and 6-MTITC dose-dependently activated both mTRPA1 (EC(50) = 147±26 µM for 6-MSITC and 30±3 µM for 6-MTITC) and human TRPA1 (hTRPA1; EC(50) = 39±4 µM for 6-MSITC and 34±3 µM for 6-MTITC). In addition, TRPA1 N-terminal cysteines, which are reported to be important for channel activation by electrophilic ligands, were involved in 6-MSITC- and 6-MTITC-evoked TRPA1 activation. These isothiocyanates also activated endogenous TRPA1 expressed in mouse dorsal root ganglion neurons and intraplantar injection of 10-30 mM 6-MSITC-evoked pain-related behaviors in mice. These results indicate the following: 1) 6-MSITC and 6-MTITC activate both mTRPA1 and hTRPA1; 2) 6-MSITC activates mTRPV1; and 3) the pharmacological functions of these isothiocyanates could be derived from TRPA1 activation.

Authors+Show Affiliations

Division of Cell Signaling, Okazaki Institute for Integrative Bioscience (National Institute for Physiological Sciences), National Institutes of Natural Sciences, Okazaki, Aichi 444-8787, Japan. kuchida@nips.ac.jpNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22869685

Citation

Uchida, Kunitoshi, et al. "Isothiocyanates From Wasabia Japonica Activate Transient Receptor Potential Ankyrin 1 Channel." Chemical Senses, vol. 37, no. 9, 2012, pp. 809-18.
Uchida K, Miura Y, Nagai M, et al. Isothiocyanates from Wasabia japonica activate transient receptor potential ankyrin 1 channel. Chem Senses. 2012;37(9):809-18.
Uchida, K., Miura, Y., Nagai, M., & Tominaga, M. (2012). Isothiocyanates from Wasabia japonica activate transient receptor potential ankyrin 1 channel. Chemical Senses, 37(9), 809-18. https://doi.org/10.1093/chemse/bjs065
Uchida K, et al. Isothiocyanates From Wasabia Japonica Activate Transient Receptor Potential Ankyrin 1 Channel. Chem Senses. 2012;37(9):809-18. PubMed PMID: 22869685.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isothiocyanates from Wasabia japonica activate transient receptor potential ankyrin 1 channel. AU - Uchida,Kunitoshi, AU - Miura,Yosuke, AU - Nagai,Masashi, AU - Tominaga,Makoto, Y1 - 2012/08/06/ PY - 2012/8/8/entrez PY - 2012/8/8/pubmed PY - 2013/3/15/medline SP - 809 EP - 18 JF - Chemical senses JO - Chem Senses VL - 37 IS - 9 N2 - 6-(Methylsulfinyl)hexyl isothiocyanate (6-MSITC) and 6-(methylthio)hexyl isothiocyanate (6-MTITC) have low pungency and are responsible for the fresh flavor of wasabi (Wasabia japonica [Miq] Matsumura). In this study, we found that these two isothiocyanates activate transient receptor potential ankyrin 1 (TRPA1), and 6-MSITC activates transient receptor potential vanilloid 1 (TRPV1), but not other transient receptor potential channels expressed in sensory neurons. Both 6-MSITC and 6-MTITCinduced intracellular Ca(2+) increases in human embryonic kidney-derived 293 cells expressing mouse TRPA1 (mTRPA1) as measured by Ca(2+) imaging. In whole-cell patch-clamp recordings, 6-MSITC and 6-MTITC dose-dependently activated both mTRPA1 (EC(50) = 147±26 µM for 6-MSITC and 30±3 µM for 6-MTITC) and human TRPA1 (hTRPA1; EC(50) = 39±4 µM for 6-MSITC and 34±3 µM for 6-MTITC). In addition, TRPA1 N-terminal cysteines, which are reported to be important for channel activation by electrophilic ligands, were involved in 6-MSITC- and 6-MTITC-evoked TRPA1 activation. These isothiocyanates also activated endogenous TRPA1 expressed in mouse dorsal root ganglion neurons and intraplantar injection of 10-30 mM 6-MSITC-evoked pain-related behaviors in mice. These results indicate the following: 1) 6-MSITC and 6-MTITC activate both mTRPA1 and hTRPA1; 2) 6-MSITC activates mTRPV1; and 3) the pharmacological functions of these isothiocyanates could be derived from TRPA1 activation. SN - 1464-3553 UR - https://www.unboundmedicine.com/medline/citation/22869685/Isothiocyanates_from_Wasabia_japonica_activate_transient_receptor_potential_ankyrin_1_channel_ L2 - https://academic.oup.com/chemse/article-lookup/doi/10.1093/chemse/bjs065 DB - PRIME DP - Unbound Medicine ER -