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Biosynthesis of Haloterpenoids in Red Algae via Microbial-like Type I Terpene Synthases
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    Biosynthesis of Haloterpenoids in Red Algae via Microbial-like Type I Terpene Synthases
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    • Taylor S. Steele
      Taylor S. Steele
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
      Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, California 92093, United States
    • Immo Burkhardt*
      Immo Burkhardt
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
      *Email: [email protected]
    • Malia L. Moore
      Malia L. Moore
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
      The Plant Molecular and Cellular Biology Laboratory, Salk Institute for Biological Studies, La Jolla, California 92037, United States
    • Tristan de Rond
      Tristan de Rond
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
      School of Chemical Sciences, University of Auckland, Auckland 1142, New Zealand
    • Hannah K. Bone
      Hannah K. Bone
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
    • Kerrie Barry
      Kerrie Barry
      Lawrence Berkeley National Laboratory, JGI - DOE Joint Genome Institute, Berkeley, California 94720, United States
      More by Kerrie Barry
    • Victoria Mae Bunting
      Victoria Mae Bunting
      Arizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United States
    • Jane Grimwood
      Jane Grimwood
      Genome Sequencing Center, HudsonAlpha Institute for Biotechnology, Huntsville, Alabama 35806, United States
    • Lori H. Handley
      Lori H. Handley
      Genome Sequencing Center, HudsonAlpha Institute for Biotechnology, Huntsville, Alabama 35806, United States
    • Shanmugam Rajasekar
      Shanmugam Rajasekar
      Arizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United States
    • Jayson Talag
      Jayson Talag
      Arizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United States
      More by Jayson Talag
    • Todd P. Michael
      Todd P. Michael
      The Plant Molecular and Cellular Biology Laboratory, Salk Institute for Biological Studies, La Jolla, California 92037, United States
    • Bradley S. Moore*
      Bradley S. Moore
      Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United States
      Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, United States
      *Email: [email protected]
    Other Access OptionsSupporting Information (1)

    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2024, 19, 1, 185–192
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    https://doi.org/10.1021/acschembio.3c00627
    Published December 11, 2023
    Copyright © 2023 American Chemical Society

    Abstract

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    Red algae or seaweeds produce highly distinctive halogenated terpenoid compounds, including the pentabromochlorinated monoterpene halomon that was once heralded as a promising anticancer agent. The first dedicated step in the biosynthesis of these natural product molecules is expected to be catalyzed by terpene synthase (TS) enzymes. Recent work has demonstrated an emerging class of type I TSs in red algal terpene biosynthesis. However, only one such enzyme from a notoriously haloterpenoid-producing red alga (Laurencia pacifica) has been functionally characterized and the product structure is not related to halogenated terpenoids. Herein, we report 10 new type I TSs from the red algae Portieria hornemannii, Plocamium pacificum, L. pacifica, and Laurencia subopposita that produce a diversity of halogenated mono- and sesquiterpenes. We used a combination of genome sequencing, terpenoid metabolomics, in vitro biochemistry, and bioinformatics to establish red algal TSs in all four species, including those associated with the selective production of key halogenated terpene precursors myrcene, trans-β-ocimene, and germacrene D-4-ol. These results expand on a small but growing number of characterized red algal TSs and offer insight into the biosynthesis of iconic halogenated algal compounds that are not without precedence elsewhere in biology.

    Copyright © 2023 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acschembio.3c00627.

    • General methods and materials of sequencing; biochemical validation; and structure elucidation experiments; as well as supporting figures and GC-MS analysis (PDF)

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    Cited By

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    Citation Statements
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    This article is cited by 6 publications.

    1. Huibin Wang, Yi Yang, Ikuro Abe. Modifications of Prenyl Side Chains in Natural Product Biosynthesis. Angewandte Chemie International Edition 2024, 63 (52) https://doi.org/10.1002/anie.202415279
    2. Huibin Wang, Yi Yang, Ikuro Abe. Modifications of Prenyl Side Chains in Natural Product Biosynthesis. Angewandte Chemie 2024, 136 (52) https://doi.org/10.1002/ange.202415279
    3. Kensuke Kaneko, Miyu Shinke, Takashi Kamada, Tatsufumi Okino, Ayumi Yamamoto. Evaluation of the cytotoxicity, genotoxicity, and antifungal activities of race-index compounds from the red alga Laurencia nipponica. Journal of Applied Phycology 2024, 36 (6) , 3795-3808. https://doi.org/10.1007/s10811-024-03327-6
    4. Yukimasa Yamagishi, Takashi Kamada, Takahiro Ishii, Hiroshi Matsuura, Norio Kikuchi, Tsuyoshi Abe, Minoru Suzuki. Morphological and Chemical Diversity within Japanese Laurencia Complex (Rhodomelaceae, Ceramiales, Rhodophyta). Chemistry & Biodiversity 2024, 21 (10) https://doi.org/10.1002/cbdv.202400833
    5. Robert A. Hill, Andrew Sutherland. Hot off the Press. Natural Product Reports 2024, 41 (4) , 520-524. https://doi.org/10.1039/D4NP90015D
    6. Jackson T. Baumgartner, Lia I. Lozano Salazar, Lukas A. Varga, Gabriel H. Lefebre, Shaun M.K. McKinnie. Vanadium haloperoxidases as noncanonical terpene synthases. 2024, 447-475. https://doi.org/10.1016/bs.mie.2024.03.024

    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2024, 19, 1, 185–192
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acschembio.3c00627
    Published December 11, 2023
    Copyright © 2023 American Chemical Society

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