Article | Published:

The Jekyll-and-Hyde chemistry of Phaeobacter gallaeciensis

Nature Chemistry volume 3, pages 331335 (2011) | Download Citation

Abstract

Emiliania huxleyi, an environmentally important marine microalga, has a bloom-and-bust lifestyle in which massive algal blooms appear and fade. Phaeobacter gallaeciensis belongs to the roseobacter clade of α-Proteobacteria, the populations of which wax and wane with that of E. huxleyi. Roseobacter are thought to promote algal growth by biosynthesizing and secreting antibiotics and growth stimulants (auxins). Here we show that P. gallaeciensis switches its secreted small molecule metabolism to the production of potent and selective algaecides, the roseobacticides, in response to p-coumaric acid, an algal lignin breakdown product that is symptomatic of aging algae. This switch converts P. gallaeciensis into an opportunistic pathogen of its algal host.

  • Compound C8H8O2

    2-Phenylacetic acid

  • Compound C8H4O3S2

    3-Oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid

  • Compound C8H4O3S2

    4-Hydroxy-8-thioxocyclohepta[c][1,2]oxathiol-3(8H)-one

  • Compound C9H8O3

    (E)-3-(4-Hydroxyphenyl)acrylic acid

  • Compound C13H13NO4

    (R,E)-3-(4-Hydroxyphenyl)-N-(2-oxotetrahydrofuran-3-yl)acrylamide

  • Compound C16H12O3S

    3-(p-Hydroxyphenyl)-7-thiomethyl-1-oxaazulan-2-one

  • Compound C16H12O2S

    3-Phenyl-7-thiomethyl-1-oxaazulan-2-one

  • Compound C15H12O2

    3-Phenyl-3,3a-dihydro-2H-cyclohepta[b]furan-2-one

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Acknowledgements

The authors thank Shao-Liang Zheng at the Center for Crystallographic Studies, Harvard University, for solving the crystal structure of roseobacticide A, and Yoko Saikawa and Brenda N. Goguen for helpful discussions. The authors also thank the Chisholm laboratory for use of and help with their flow cytometer, and J.B. Dacks for assistance with bioinformatic analyses. M.R.S. is a Novartis Fellow of the Life Sciences Research Foundation. R.J.C. is a Harvard Ziff Environmental Fellow. This work was supported by the Office of Naval Research (grant N000141010447) and the National Institutes of Health (grants GM58213 and GM82137, R.K.; grants CA24487 and GM086258, J.C.).

Author information

Author notes

    • Mohammad R. Seyedsayamdost
    •  & Rebecca J. Case

    These authors contributed equally to this work

Affiliations

  1. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA

    • Mohammad R. Seyedsayamdost
    •  & Jon Clardy
  2. Department of Microbiology and Molecular Genetics, Harvard Medical School, Boston, Massachusetts 02115, USA

    • Rebecca J. Case
    •  & Roberto Kolter

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Contributions

M.R.S., R.J.C, R.K. and J.C. designed the experiments and wrote the manuscript. M.R.S. performed roseobacticide isolation, structure elucidation and antibacterial assays. R.J.C. performed microscopy and flow cytometry for anti-algal activity assays.

Competing interests

The authors declare no competing financial interests.

Corresponding authors

Correspondence to Roberto Kolter or Jon Clardy.

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    Crystallographic data for compound 6

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DOI

https://doi.org/10.1038/nchem.1002

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