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An unsaturated aliphatic alcohol as a natural ligand for a mouse odorant receptor

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Abstract

We report the identification of a physiological receptor-volatile pair in the mouse olfactory system. By activity-guided fractionation of exocrine gland extracts and subsequent chemical analysis, (Z)-5-tetradecen-1-ol was identified as a natural ligand for a mouse odorant receptor. (Z)-5-tetradecen-1-ol is excreted into male mouse urine under androgen control and enhances urine attractiveness to female mice. This report is to our knowledge the first to describe natural product–based deorphanization of an odorant receptor.

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Figure 1: Responses of Olfr288-expressing oocytes to exocrine gland extracts.
Figure 2: Purification and identification of ligand for Olfr288 in PPG extract.
Figure 3: Z5-14:OH is a PPG-derived male urinary volatile that enhances urine attractiveness to female mice.

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Acknowledgements

This work was supported in part by a Grant-in-Aid for Scientific Research (S) from the Ministry of Education, Culture, Sports, Science and Technology Japan (grant 24227003), a Grant-in-Aid for Scientific Research on Priority Areas from the Japan Society for the Promotion of Science (JSPS) (grant 18077001) and a research grant from the Astellas Foundation for Research on Metabolic Disorders to K.T. K.Y. was supported by a Grant-in-Aid for JSPS fellows. We thank T. Ando for Z8-14:OH (Tokyo University of Agriculture and Technology), and T. Kikusui and T. Hattori for advice on behavioral experiments.

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Authors and Affiliations

  1. Department of Applied Biological Chemistry, The University of Tokyo, Tokyo, Japan

    Keiichi Yoshikawa, Hiroaki Nakagawa, Naoki Mori, Hidenori Watanabe & Kazushige Touhara

Authors
  1. Keiichi Yoshikawa
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  2. Hiroaki Nakagawa
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  3. Naoki Mori
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  4. Hidenori Watanabe
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  5. Kazushige Touhara
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Contributions

K.Y. performed experiments; H.N. identified δ-undecalactone as a synthetic ligand for Olfr288; N.M. generated the reagents; K.Y and K.T. designed the research, analyzed data and wrote the manuscript; H.W. and K.T. supervised the work.

Corresponding author

Correspondence to Kazushige Touhara.

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The authors declare no competing financial interests.

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Yoshikawa, K., Nakagawa, H., Mori, N. et al. An unsaturated aliphatic alcohol as a natural ligand for a mouse odorant receptor. Nat Chem Biol 9, 160–162 (2013). https://doi.org/10.1038/nchembio.1164

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