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

Journal of Natural Products

Volumn 78, Issue 8, 2015, Pages 1937-1941

  Terada, Yuko ^a   Masuda, Hideki ^b   Watanabe, Tatsuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b Flavor System and Technology Laboratory   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLTHIOPROPYL ISOTHIOCYANIC ACID; 4 METHYLTHIOBUTYL ISOTHIOCYANIC ACID; 5 METHYLTHIOPENTYL ISOTHIOCYANIC ACID; 6 METHYLTHIOHEXYL ISOTHIOCYANIC ACID; 7 METHYLTHIOHEPTYL ISOTHIOCYANIC ACID; ALLYL ISOTHIOCYANATE; CALCIUM ION; ISOTHIOCYANIC ACID DERIVATIVE; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1; TRANSIENT RECEPTOR POTENTIAL CHANNEL M8; UNCLASSIFIED DRUG; TRANSIENT RECEPTOR POTENTIAL CHANNEL; TRPA1 PROTEIN, MOUSE; TRPV1 PROTEIN, HUMAN; VANILLOID RECEPTOR;

ARTICLE; CALCIUM TRANSPORT; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; HEK293 CELL LINE; HORSERADISH; HUMAN; HUMAN CELL; SINAPIS ALBA; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WASABI; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; MOUSE; MUSTARD;

ANIMALS; ARMORACIA; HUMANS; ISOTHIOCYANATES; MICE; MOLECULAR STRUCTURE; MUSTARD PLANT; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSIENT RECEPTOR POTENTIAL CHANNELS; TRPV CATION CHANNELS;

EID: 84940496462     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00272     Document Type: Article

References (34)

1. McGregor, D. I.; Mullin, W. J.; Fenwick, G. R. J. Assoc. Off. Ana. Chem. 1983, 66, 825-849
2. Masuda, H.; Harada, Y.; Tanaka, K.; Nakajima, M.; Tabeta, H. Characteric Odorants of Wasabi (Wasabia japonica matum), Japanese Horseradish, in Comparison with Those of Horseradish (Armoacia rusticana). In ACS Symposium Series 637; Takeoka, G. R.; Teranishi, R.; Williams, P. J.; Kobayashi, A., Eds.; American Chemical Society: Washington, DC, 2009; Chapter 6, pp 67-78.
3. Sultana, T.; Savage, G. P. J. Food Agric. Environ. 2003, 1, 117-121
4. Etoh, H.; Nishimura, A.; Takasawa, R.; Yagi, A.; Saito, K.; Sakata, K.; Kishima, I.; Ina, K. Agric. Biol. Chem. 1990, 54, 1587-1589 10.1271/bbb1961.54.1587
5. Hasegawa, Y.; Ugai, Y.; Murata, M. Wasabi hakubutsushi, Kinnzirushi group sougyou 75 syuunenn kinennshi. Kinjirushi Co. Ltd.: Nagoya, Japan, 2004.
6. Shankaranarayana, M. L.; Nagalakshmi, S.; Raghavan, B.; Natarajan, C. P. Agric. Biol. Chem. 1971, 35, 959-961 10.1271/bbb1961.35.959
7. Jordt, S. E.; Bautista, D. M.; Chuang, H. H.; McKemy, D. D.; Zygmunt, P. M.; Hogestatt, E. D.; Meng, I. D.; Julius, D. Nature 2004, 427, 260-265 10.1038/nature02282
8. Story, G. M.; Peier, A. M.; Reeve, A. J.; Eid, S. R.; Mosbacher, J.; Hricik, T. R.; Earley, T. J.; Hergarden, A. C.; Andersson, D. A.; Hwang, S. W.; McIntyre, P.; Jegla, T.; Bevan, S.; Patapoutian, A. Cell 2003, 112, 819-829 10.1016/S0092-8674(03)00158-2
9. Caspani, O.; Heppenstall, P. A. J. Gen. Physiol. 2009, 133, 245-249 10.1085/jgp.200810136
10. Chen, J.; Kang, D.; Xu, J.; Lake, M.; Hogan, J. O.; Sun, C.; Walter, K.; Yao, B.; Kim, D. Nat. Commun. 2013, 4, 2501 10.1038/ncomms3501
11. Bandell, M.; Story, G. M.; Hwang, S. W.; Viswanath, V.; Eid, S. R.; Petrus, M. J.; Earley, T. J.; Patapoutian, A. Neuron 2004, 41, 849-857 10.1016/S0896-6273(04)00150-3
12. Macpherson, L. J.; Geierstanger, B. H.; Viswanath, V.; Bandell, M.; Eid, S. R.; Hwang, S.; Patapoutian, A. Curr. Biol. 2005, 15, 929-934 10.1016/j.cub.2005.04.018
13. Okumura, Y.; Narukawa, M.; Iwasaki, Y.; Ishikawa, A.; Matsuda, H.; Yoshikawa, M.; Watanabe, T. Biosci., Biotechnol., Biochem. 2010, 74, 1068-1072 10.1271/bbb.90964
14. Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Dewachter, I.; van Leuven, F.; Vennekens, R.; De Ridder, D.; Nilius, B.; Voets, T.; Talavera, K. Curr. Biol. 2011, 21, 316-321 10.1016/j.cub.2011.01.031
15. Uchida, K.; Miura, Y.; Nagai, M.; Tominaga, M. Chem. Senses 2012, 37, 809-818 10.1093/chemse/bjs065
16. Mandadi, S.; Roufogalis, B. D. Curr. Neuropharmacol. 2008, 6, 21-38 10.2174/157015908783769680
17. Hinman, A.; Chuang, H. H.; Bautista, D. M.; Julius, D. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 19564-19568 10.1073/pnas.0609598103
18. Macpherson, L. J.; Dubin, A. E.; Evans, M. J.; Marr, F.; Schultz, P. G.; Cravatt, B. F.; Patapoutian, A. Nature 2007, 445, 541-545 10.1038/nature05544
19. Fujita, F.; Uchida, K.; Moriyama, T.; Shima, A.; Shibasaki, K.; Inada, H.; Sokabe, T.; Tominaga, M. J. Clin. Invest. 2008, 118, 4049-4057 10.1172/JCI35957
20. Caterina, M. J.; Schumacher, M. A.; Tominaga, M.; Rosen, T. A.; Levine, J. D.; Julius, D. Nature 1997, 389, 816-824 10.1038/39807
21. McNamara, F. N.; Randall, A.; Gunthorpe, M. J. Br. J. Pharmacol. 2005, 144, 781-790 10.1038/sj.bjp.0706040
22. Iwasaki, Y.; Tanabe, M.; Kobata, K.; Watanabe, T. Biosci., Biotechnol., Biochem. 2008, 72, 2608-2614 10.1271/bbb.80289
23. Okumura, Y.; Narukawa, M.; Watanabe, T. Biosci., Biotechnol., Biochem. 2010, 74, 1545-1549 10.1271/bbb.100117
24. Iwasaki, Y.; Tamura, Y.; Inayoshi, K.; Narukawa, M.; Kobata, K.; Chiba, H.; Muraki, E.; Tsunoda, N.; Watanabe, T. Biosci., Biotechnol., Biochem. 2011, 75, 904-909 10.1271/bbb.100850
25. Iwai, K.; Yazawa, A.; Watanabe, T. Proc. Jpn. Acad., Ser. B 2003, 79B, 207-212 10.2183/pjab.79B.207
26. Iwasaki, Y.; Morita, A.; Iwasawa, T.; Kobata, K.; Sekiwa, Y.; Morimitsu, Y.; Kubota, K.; Watanabe, T. Nutr. Neurosci. 2006, 9, 169-178 10.1080/10284150600955164
27. Iwasaki, Y.; Tanabe, M.; Kayama, Y.; Abe, M.; Kashio, M.; Koizumi, K.; Okumura, Y.; Morimitsu, Y.; Tominaga, M.; Ozawa, Y.; Watanabe, T. Life Sci. 2009, 85, 60-69 10.1016/j.lfs.2009.04.017
28. Kobata, K.; Todo, T.; Yazawa, S.; Iwai, K.; Watanabe, T. J. Agric. Food Chem. 1998, 46, 1695-1697 10.1021/jf980135c
29. Iwasaki, Y.; Saito, O.; Tanabe, M.; Inayoshi, K.; Kobata, K.; Uno, S.; Morita, A.; Watanabe, T. Lipids 2008, 43, 471-483 10.1007/s11745-008-3182-5
30. Ohnuki, K.; Niwa, S.; Maeda, S.; Inoue, N.; Yazawa, S.; Fushiki, T. Biosci., Biotechnol., Biochem. 2001, 65, 2033-2036 10.1271/bbb.65.2033
31. Masuda, H.; Tsuda, T.; et al., Preparation of alkenyl iosthiocyanates as wasabi-like flavorants. JP 02221255, Sep 4, 1990.
32. Manabe, H.; Hiraoka, K.; et al., Preparation of (alkylthio) alkyl isothiocyanates. JP 05339229, Dec 21, 1993.
33. Harada, Y.; Masuda, H.; et al., Preparation of ω-alkylthioalkyl isothiocyanates as food flavoring materials. JP 07215931, Aug 15, 1995.
34. Terada, Y.; Horie, S.; Takayama, H.; Uchida, K.; Tominaga, M.; Watanabe, T. J. Nat. Prod. 2014, 77, 285-297 10.1021/np400885u