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Genome Mining Discovery of Protegenins A–D, Bacterial Polyynes Involved in the Antioomycete and Biocontrol Activities of Pseudomonas protegens

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    Genome Mining Discovery of Protegenins A–D, Bacterial Polyynes Involved in the Antioomycete and Biocontrol Activities of Pseudomonas protegens
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    • Kazuya Murata
      Kazuya Murata
      Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
      More by Kazuya Murata
    • Mayuna Suenaga
      Mayuna Suenaga
      Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
      More by Mayuna Suenaga
    • Kenji Kai*
      Kenji Kai
      Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
      *Email: [email protected]
      More by Kenji Kai
      Orcidhttps://orcid.org/0000-0002-4036-9959
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2022, 17, 12, 3313–3320
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    https://doi.org/10.1021/acschembio.1c00276
    Published May 21, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    Some bacteria uniquely produce “bacterial polyynes”, which possess a conjugated C≡C bond starting with a terminal alkyne, and use them as chemical weapons against hosts and competitors. Pseudomonas protegens Cab57, a biocontrol agent against plant pathogens, has an orphan biosynthetic gene cluster for bacterial polyynes (named protegenins). In this study, the isolation, structure elucidation, and biological characterization of protegenins A–D are reported. The structures of protegenins A–D determined by spectroscopic and chemical techniques were octadecanoic acid derivatives possessing an ene–tetrayne, ene–triyne–ene, or ene–triyne moiety. The protegenins exhibited weak to strong antioomycete activity against Pythium ultimum OPU774. The deletion of proA, a protegenin biosynthetic gene, resulted in the reduction of the antioomycete activity of P. protegens. The Gac/Rsm system, a quorum sensing-like system of Pseudomonas bacteria, regulated the production of protegenins. The production profile of protegenins was dependent on the culturing conditions, suggesting a control mechanism for protegenin production selectivity. P. protegens suppressed the damping-off of cucumber seedlings caused by P. ultimum, and this protective effect was reduced in the proA-deletion mutant. Altogether, protegenins are a new class of bacterial polyynes which contribute to the antioomycete and plant-protective effects of P. protegens.

    Copyright © 2021 American Chemical Society

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    This article is cited by 24 publications.

    1. Daiki Kawahara, Kenji Kai. Disproof of the Structures and Biosynthesis of Ergoynes, Gs-Polyyne–l-Ergothioneine Cycloadducts from Gynuella sunshinyii YC6258. The Journal of Organic Chemistry 2024, 89 (8) , 5715-5725. https://doi.org/10.1021/acs.joc.4c00243
    2. Mayuna Suenaga, Naoka Katayama, Kokoro Kitamura, Kenji Kai. Structures and Biosynthesis of Caryoynencins, Unstable Bacterial Polyynes from Pseudomonas protegens Recombinant Expressing the cayG Gene. The Journal of Organic Chemistry 2023, 88 (23) , 16280-16291. https://doi.org/10.1021/acs.joc.3c01789
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    4. Daniel Back, Brenda T. Shaffer, Joyce E. Loper, Benjamin Philmus. Untargeted Identification of Alkyne-Containing Natural Products Using Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reactions Coupled to LC-MS/MS. Journal of Natural Products 2022, 85 (1) , 105-114. https://doi.org/10.1021/acs.jnatprod.1c00798
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    6. Mingpeng Wang, Lei Chen, Zhaojie Zhang, Qinhong Wang. Recent advances in genome mining and synthetic biology for discovery and biosynthesis of natural products. Critical Reviews in Biotechnology 2025, 45 (1) , 236-256. https://doi.org/10.1080/07388551.2024.2383754
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    10. Carmen E. Stoenoiu, Mihai V. Putz, Lorentz Jäntschi. Is triple crossed C 28 cyclic polyyne cluster a stable conformation?. Fullerenes, Nanotubes and Carbon Nanostructures 2024, 32 (1) , 55-67. https://doi.org/10.1080/1536383X.2023.2261573
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    13. Gordon Webster, Alex J. Mullins, Yoana D. Petrova, Eshwar Mahenthiralingam. Polyyne-producing Burkholderia suppress Globisporangium ultimum damping-off disease of Pisum sativum (pea). Frontiers in Microbiology 2023, 14 https://doi.org/10.3389/fmicb.2023.1240206
    14. Vartika Mathur, Dana Ulanova. Microbial Metabolites Beneficial to Plant Hosts Across Ecosystems. Microbial Ecology 2023, 86 (1) , 25-48. https://doi.org/10.1007/s00248-022-02073-x
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    18. Kenji Kai. Multidimensional chemical communication among microorganisms. Japanese Journal of Pesticide Science 2022, 47 (2) , 99-103. https://doi.org/10.1584/jpestics.W22-29
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    22. Antonio Del Rio Flores, Colin C. Barber, Maanasa Narayanamoorthy, Di Gu, Yuanbo Shen, Wenjun Zhang. Biosynthesis of Isonitrile- and Alkyne-Containing Natural Products. Annual Review of Chemical and Biomolecular Engineering 2022, 13 (1) , 1-24. https://doi.org/10.1146/annurev-chembioeng-092120-025140
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2022, 17, 12, 3313–3320
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acschembio.1c00276
    Published May 21, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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