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Chemical Senses 2004 29(9):815-822; doi:10.1093/chemse/bjh247
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Chemical Senses Vol. 29 No. 9 © Oxford University Press 2004; all rights reserved

An Odorant Derivative as an Antagonist for an Olfactory Receptor

Yuki Oka1, Akio Nakamura2, Hidenori Watanabe3 and Kazushige Touhara1

1 Department of Integrated Biosciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan, 2 Technical Research Center, T. Hasegawa Co., Ltd, 335 Kariyado, Nakahara-ku, Kawasaki 211-0022, Japan and 3 Department of Applied Biological Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan

Correspondence to be sent to: Kazushige Touhara, Department of Integrated Biosciences, Rm201, The University of Tokyo, Kashiwa, Chiba 277-8562 Japan. e-mail: touhara{at}k.u-tokyo.ac.jp

Different odorants are recognized by different combinations of G protein-coupled olfactory receptors, and thereby, odor identity is determined by a combinatorial receptor code for each odorant. We recently demonstrated that odorants appeared to compete for receptor sites to act as an agonist or an antagonist. Therefore, in natural circumstances where we always perceive a mixture of various odorants, olfactory receptor antagonism between odorants may result in a receptor code for the mixture that cannot be predicted from the codes for its individual components. Here we show that stored isoeugenol has an antagonistic effect on a mouse olfactory receptor, mOR-EG. However, freshly purified isoeugenol did not have an inhibitory effect. Instead, an isoeugenol derivative produced during storage turned out to be a potent competitive antagonist of mOR-EG. Structural analysis revealed that this derivative is an oxidatively dimerized isoeugenol that naturally occurs by oxidative reaction. The current study indicates that as odorants age, they decompose or react with other odorants, which in turn affects responsiveness of an olfactory receptor(s).

Key words: antagonist, isoeugenol, odorant, olfactory receptor


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