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The second Phytophthora mating hormone defines interspecies biosynthetic crosstalk

Nature Chemical Biology volume 7, pages 591–593 (2011)Cite this article

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Abstract

The heterothallic species of the agricultural pest Phytophthora use mating hormones α1 and α2 to regulate their sexual reproduction. Here we describe the absolute stereostructure of the second mating hormone α2 as defined by spectroscopic analysis and total synthesis. We have uncovered not only the interspecies universality of α hormones but also the pathway by which α2 is biosynthesized from phytol by A2–mating type strains and metabolized to α1 by A1 strains.

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Figure 1: Production and stereochemical determination of α2.
Figure 2: Biosynthetic pathway of α hormones.

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Acknowledgements

We thank K. Kawakita for P. infestans strains and W.H. Ko for valuable suggestions. This work was supported by Grants-in-Aid for Scientific Research from Japan Society for the Promotion of Science (22248012, 21710239 and 18380073). S.D.M. is a recipient of a Japanese Ministry of Education, Culture, Sports, Science and Technology (MEXT) scholarship (080028).

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Authors and Affiliations

  1. Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya, Japan

    Makoto Ojika, Shylaja D Molli, Harumi Kanazawa, Haimeng Mao, Ryo Murata, Tomoyo Asano, Jianhua Qi & Youji Sakagami

  2. Department of Fermentation Science, Faculty of Applied Bioscience, Tokyo University of Agriculture, Tokyo, Japan

    Arata Yajima, Kou Toda & Tomoo Nukada

  3. College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China

    Jianhua Qi

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  1. Makoto Ojika
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  2. Shylaja D Molli
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  4. Arata Yajima
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  5. Kou Toda
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  6. Tomoo Nukada
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  7. Haimeng Mao
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  8. Ryo Murata
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  10. Jianhua Qi
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Contributions

M.O. designed the project and wrote the manuscript; S.D.M. isolated 2, tested hormone response and prepared the manuscript; H.K. isolated 2; A.Y., K.T. and T.N. performed chemical syntheses; H.M. did isotope-labeled experiments; R.M. contributed to LC/MS analysis; T.A. contributed to bioassay; J.Q. isolated 1; and Y.S. designed the project.

Corresponding author

Correspondence to Makoto Ojika.

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The authors declare no competing financial interests.

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Ojika, M., Molli, S., Kanazawa, H. et al. The second Phytophthora mating hormone defines interspecies biosynthetic crosstalk. Nat Chem Biol 7, 591–593 (2011). https://doi.org/10.1038/nchembio.617

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