Biosynthesis of Haloterpenoids in Red Algae via Microbial-like Type I Terpene SynthasesClick to copy article linkArticle link copied!
- Taylor S. SteeleTaylor S. SteeleScripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesDepartment of Chemistry and Biochemistry, University of California San Diego, La Jolla, California 92093, United StatesMore by Taylor S. Steele
- Immo Burkhardt*Immo Burkhardt*Email: [email protected]Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesMore by Immo Burkhardt
- Malia L. MooreMalia L. MooreScripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesThe Plant Molecular and Cellular Biology Laboratory, Salk Institute for Biological Studies, La Jolla, California 92037, United StatesMore by Malia L. Moore
- Tristan de RondTristan de RondScripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesSchool of Chemical Sciences, University of Auckland, Auckland 1142, New ZealandMore by Tristan de Rond
- Hannah K. BoneHannah K. BoneScripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesMore by Hannah K. Bone
- Kerrie BarryKerrie BarryLawrence Berkeley National Laboratory, JGI - DOE Joint Genome Institute, Berkeley, California 94720, United StatesMore by Kerrie Barry
- Victoria Mae BuntingVictoria Mae BuntingArizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United StatesMore by Victoria Mae Bunting
- Jane GrimwoodJane GrimwoodGenome Sequencing Center, HudsonAlpha Institute for Biotechnology, Huntsville, Alabama 35806, United StatesMore by Jane Grimwood
- Lori H. HandleyLori H. HandleyGenome Sequencing Center, HudsonAlpha Institute for Biotechnology, Huntsville, Alabama 35806, United StatesMore by Lori H. Handley
- Shanmugam RajasekarShanmugam RajasekarArizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United StatesMore by Shanmugam Rajasekar
- Jayson TalagJayson TalagArizona Genomics Institute, University of Arizona, Tucson, Arizona 85721, United StatesMore by Jayson Talag
- Todd P. MichaelTodd P. MichaelThe Plant Molecular and Cellular Biology Laboratory, Salk Institute for Biological Studies, La Jolla, California 92037, United StatesMore by Todd P. Michael
- Bradley S. Moore*Bradley S. Moore*Email: [email protected]Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, United StatesSkaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, United StatesMore by Bradley S. Moore
Abstract

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.
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