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Genetics and Molecular Biology | Spotlight

Burkholderia thailandensis Methylated Hydroxyalkylquinolines: Biosynthesis and Antimicrobial Activity in Cocultures

Jennifer R. Klaus, Charlotte Majerczyk, Stephanie Moon, Natalie A. Eppler, Sierra Smith, Emily Tuma, Marie-Christine Groleau, Kyle L. Asfahl, Nicole E. Smalley, Hillary S. Hayden, Marianne Piochon, Patrick Ball, Ajai A. Dandekar, Charles Gauthier, Eric Déziel, Josephine R. Chandler
Isaac Cann, Editor
Jennifer R. Klaus
aDepartment of Molecular Biosciences, University of Kansas, Lawrence Kansas, USA
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Charlotte Majerczyk
bDepartment of Biology, Oregon State University—Cascades, Bend, Oregon, USA
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Stephanie Moon
bDepartment of Biology, Oregon State University—Cascades, Bend, Oregon, USA
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Natalie A. Eppler
aDepartment of Molecular Biosciences, University of Kansas, Lawrence Kansas, USA
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Sierra Smith
bDepartment of Biology, Oregon State University—Cascades, Bend, Oregon, USA
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Emily Tuma
bDepartment of Biology, Oregon State University—Cascades, Bend, Oregon, USA
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Marie-Christine Groleau
cCentre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Laval (Québec), Canada
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Kyle L. Asfahl
dDepartment of Microbiology, University of Washington, Seattle Washington, USA
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Nicole E. Smalley
dDepartment of Microbiology, University of Washington, Seattle Washington, USA
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Hillary S. Hayden
dDepartment of Microbiology, University of Washington, Seattle Washington, USA
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Marianne Piochon
cCentre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Laval (Québec), Canada
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Patrick Ball
bDepartment of Biology, Oregon State University—Cascades, Bend, Oregon, USA
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Ajai A. Dandekar
dDepartment of Microbiology, University of Washington, Seattle Washington, USA
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Charles Gauthier
cCentre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Laval (Québec), Canada
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Eric Déziel
cCentre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Laval (Québec), Canada
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Josephine R. Chandler
aDepartment of Molecular Biosciences, University of Kansas, Lawrence Kansas, USA
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Isaac Cann
University of Illinois at Urbana—Champaign
Roles: Editor
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DOI: 10.1128/AEM.01452-20
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ABSTRACT

The bacterium Burkholderia thailandensis produces an arsenal of secondary metabolites that have diverse structures and roles in the ecology of this soil-dwelling bacterium. In coculture experiments, B. thailandensis strain E264 secretes an antimicrobial that nearly eliminates another soil bacterium, Bacillus subtilis strain 168. To identify the antimicrobial, we used a transposon mutagenesis approach. This screen identified antimicrobial-defective mutants with insertions in the hmqA, hmqC, and hmqF genes involved in biosynthesis of a family of 2-alkyl-4(1H)-quinolones called 4-hydroxy-3-methyl-2-alkenylquinolines (HMAQs), which are closely related to the Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs). Insertions also occurred in the previously uncharacterized gene BTH_II1576 (“hmqL”). The results confirm that BTH_II1576 is involved in generating N-oxide derivatives of HMAQs (HMAQ-NOs). Synthetic HMAQ-NO is active against B. subtilis 168, showing ∼50-fold more activity than HMAQ. Both the methyl group and the length of the carbon side chain account for the high activity of HMAQ-NO. The results provide new information on the biosynthesis and activities of HMAQs and reveal new insight into how these molecules might be important for the ecology of B. thailandensis.

IMPORTANCE The soil bacterium Burkholderia thailandensis produces 2-alkyl-4(1H)-quinolones that are mostly methylated 4-hydroxyalkenylquinolines, a family of relatively unstudied metabolites similar to molecules also synthesized by Pseudomonas aeruginosa. Several of the methylated 4-hydroxyalkenylquinolines have antimicrobial activity against other species. We show that Bacillus subtilis strain 168 is particularly susceptible to N-oxidated methylalkenylquinolines (HMAQ-NOs). We confirmed that HMAQ-NO biosynthesis requires the previously unstudied protein HmqL. These results provide new information about the biology of 2-alkyl-4(1H)-quinolones, particularly the methylated 4-hydroxyalkenylquinolines, which are unique to B. thailandensis. This study also has importance for understanding B. thailandensis secondary metabolites and has implications for potential therapeutic development.

FOOTNOTES

    • Received 18 June 2020.
    • Accepted 15 September 2020.
    • Accepted manuscript posted online 2 October 2020.
  • Supplemental material is available online only.

  • Copyright © 2020 American Society for Microbiology.

All Rights Reserved.

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Burkholderia thailandensis Methylated Hydroxyalkylquinolines: Biosynthesis and Antimicrobial Activity in Cocultures
Jennifer R. Klaus, Charlotte Majerczyk, Stephanie Moon, Natalie A. Eppler, Sierra Smith, Emily Tuma, Marie-Christine Groleau, Kyle L. Asfahl, Nicole E. Smalley, Hillary S. Hayden, Marianne Piochon, Patrick Ball, Ajai A. Dandekar, Charles Gauthier, Eric Déziel, Josephine R. Chandler
Applied and Environmental Microbiology Nov 2020, 86 (24) e01452-20; DOI: 10.1128/AEM.01452-20

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Burkholderia thailandensis Methylated Hydroxyalkylquinolines: Biosynthesis and Antimicrobial Activity in Cocultures
Jennifer R. Klaus, Charlotte Majerczyk, Stephanie Moon, Natalie A. Eppler, Sierra Smith, Emily Tuma, Marie-Christine Groleau, Kyle L. Asfahl, Nicole E. Smalley, Hillary S. Hayden, Marianne Piochon, Patrick Ball, Ajai A. Dandekar, Charles Gauthier, Eric Déziel, Josephine R. Chandler
Applied and Environmental Microbiology Nov 2020, 86 (24) e01452-20; DOI: 10.1128/AEM.01452-20
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KEYWORDS

Burkholderia
cell-cell interaction
natural antimicrobial products
quinolones

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