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Genome Mining-Based Discovery of Fungal Macrolides Modified by glycosylphosphatidylinositol (GPI)–Ethanolamine Phosphate Transferase Homologues

  • Yohei Morishita
    Yohei Morishita
    Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan
  • Yu Aoki
    Yu Aoki
    Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan
    More by Yu Aoki
  • Mei Ito
    Mei Ito
    Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan
    More by Mei Ito
  • Daisuke Hagiwara
    Daisuke Hagiwara
    Department of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
    Microbiology Research Center for Sustainability (MiCS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
  • Kensho Torimaru
    Kensho Torimaru
    Department of Microbiology, Institute of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan
  • Daichi Morita
    Daichi Morita
    Department of Microbiology, Institute of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan
  • Teruo Kuroda
    Teruo Kuroda
    Department of Microbiology, Institute of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan
    More by Teruo Kuroda
  • Hanako Fukano
    Hanako Fukano
    Department of Mycobacteriology, Leprosy Research Center, National Institute of Infectious Diseases, 4-2-1 Aobacho, Higashimurayama-shi, Tokyo 189-0002, Japan
  • Yoshihiko Hoshino
    Yoshihiko Hoshino
    Department of Mycobacteriology, Leprosy Research Center, National Institute of Infectious Diseases, 4-2-1 Aobacho, Higashimurayama-shi, Tokyo 189-0002, Japan
  • Masato Suzuki
    Masato Suzuki
    Antimicrobial Resistance Research Center, National Institute of Infectious Diseases, 4-2-1 Aobacho, Higashimurayama-shi, Tokyo 189-0002, Japan
  • Tohru Taniguchi
    Tohru Taniguchi
    Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan
  • Keiji Mori
    Keiji Mori
    Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho, Koganei, Tokyo 184-8588, Japan
    More by Keiji Mori
  • , and 
  • Teigo Asai*
    Teigo Asai
    Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo 153-8902, Japan
    Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan
    *E-mail: [email protected]
    More by Teigo Asai
Cite this: Org. Lett. 2020, 22, 15, 5876–5879
Publication Date (Web):July 14, 2020
https://doi.org/10.1021/acs.orglett.0c01975
Copyright © 2020 American Chemical Society

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    Abstract

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    Through genome mining for fungal macrolide natural products, we discovered a characteristic family of putative macrolide biosynthetic gene clusters that contain a glycosylphosphatidylinositol–ethanolamine phosphate transferase (GPI-EPT) homologue. Through the heterologous expression of two clusters from Aspergillus kawachii and Colletotrichum incanum, new macrolides, including those with phosphoethanolamine or phosphocholine moieties, were formed. This study is the first demonstration of the tailoring steps catalyzed by GPI-EPT homologues in natural product biosynthesis, and it uncovers a new gene resource for phospholipid-resembling fungal macrolides.

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    Cited By

    This article is cited by 14 publications.

    1. Yuto Homma, Akihiro Sugawara, Yohei Morishita, Kento Tsukada, Taro Ozaki, Teigo Asai. Discovery of a Cyclic Depsipeptide from Chaetomium mollipilium by the Genome Mining Approach. Organic Letters 2022, 24 (19) , 3504-3509. https://doi.org/10.1021/acs.orglett.2c01172
    2. Yohei Morishita, Kento Tsukada, Kazuma Murakami, Kazuhiro Irie, Teigo Asai. Synthetic Biology-Based Discovery of Diterpenoid Pyrones from the Genome of Eupenicillium shearii. Journal of Natural Products 2022, 85 (2) , 384-390. https://doi.org/10.1021/acs.jnatprod.1c00973
    3. De-Wei Gao, Cooper S. Jamieson, Gaoqian Wang, Yan Yan, Jiahai Zhou, K. N. Houk, Yi Tang. A Polyketide Cyclase That Forms Medium-Ring Lactones. Journal of the American Chemical Society 2021, 143 (1) , 80-84. https://doi.org/10.1021/jacs.0c11226
    4. Yue Shi, Taro Ozaki, Akihiro Sugawara, Yohei Morishita, Yu Pei Tan, Roger G. Shivas, Rohan A. Davis, Teigo Asai. A new 3,6-dialkyl-α-pyrone produced by the heterologous expression of a PKS-NRPS hybrid enzyme derived from a Pestalotiopsis endophyte. Tetrahedron Letters 2024, 134 , 154865. https://doi.org/10.1016/j.tetlet.2023.154865
    5. Teigo Asai. Synthetic Biology-Based Natural Product Discovery. 2023, 3-16. https://doi.org/10.1007/978-981-99-1714-3_1
    6. Atsushi Minami. A New Trend in Biosynthetic Studies of Natural Products: The Bridge Between the Amino Acid Sequence Data and the Chemical Structure. 2023, 123-145. https://doi.org/10.1007/978-981-99-1714-3_7
    7. José Rivera-Chávez, Corina-Diana Ceapă, Mario Figueroa. Biological Dark Matter Exploration using Data Mining for the Discovery of Antimicrobial Natural Products. Planta Medica 2022, 88 (09/10) , 702-720. https://doi.org/10.1055/a-1795-0562
    8. Teigo Asai. Discovery of Diverse Natural Products from Undeveloped Fungal Gene Resource by Using Epigenetic Regulation. YAKUGAKU ZASSHI 2022, 142 (5) , 439-446. https://doi.org/10.1248/yakushi.21-00218
    9. Elizabeth Skellam. Biosynthesis of fungal polyketides by collaborating and trans -acting enzymes. Natural Product Reports 2022, 39 (4) , 754-783. https://doi.org/10.1039/D1NP00056J
    10. Bruno Perlatti, Nan Lan, Meichun Xiang, Cody E Earp, Joseph E Spraker, Colin J B Harvey, Connie B Nichols, J Andrew Alspaugh, James B Gloer, Gerald F Bills. Anti-cryptococcal activity of preussolides A and B, phosphoethanolamine-substituted 24-membered macrolides, and leptosin C from coprophilous isolates of Preussia typharum. Journal of Industrial Microbiology and Biotechnology 2021, 48 (9-10) https://doi.org/10.1093/jimb/kuab022
    11. Yali Kong, Wei Ye, Taomei Liu, Hongxin Liu, Zhaoming Liu, Wei-Min Zhang. The important role of P450 monooxygenase for the biosynthesis of new benzophenones from Cytospora rhizophorae. Applied Microbiology and Biotechnology 2021, 105 (24) , 9219-9230. https://doi.org/10.1007/s00253-021-11648-6
    12. Junya Takino, Akari Kotani, Taro Ozaki, Wenquan Peng, Jie Yu, Yian Guo, Susumu Mochizuki, Kazuya Akimitsu, Masaru Hashimoto, Tao Ye, Atsushi Minami, Hideaki Oikawa. Biochemistry‐Guided Prediction of the Absolute Configuration of Fungal Reduced Polyketides. Angewandte Chemie 2021, 133 (43) , 23591-23599. https://doi.org/10.1002/ange.202110658
    13. Junya Takino, Akari Kotani, Taro Ozaki, Wenquan Peng, Jie Yu, Yian Guo, Susumu Mochizuki, Kazuya Akimitsu, Masaru Hashimoto, Tao Ye, Atsushi Minami, Hideaki Oikawa. Biochemistry‐Guided Prediction of the Absolute Configuration of Fungal Reduced Polyketides. Angewandte Chemie International Edition 2021, 60 (43) , 23403-23411. https://doi.org/10.1002/anie.202110658
    14. Robert A. Hill, Andrew Sutherland. Hot off the Press. Natural Product Reports 2020, 37 (10) , 1294-1299. https://doi.org/10.1039/D0NP90037K

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