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Burkholderia thailandensis methylated hydroxy-alkylquinolines: biosynthesis and antimicrobial activity in co-cultures

Klaus, Jennifer R, Majerczyk, Charlott, Moon, Stéphanie, Eppler, Natalie A, Smith, Sierra, Tuma, Emily, Groleau, Marie-Christine, Asfahl, Kyle T, Smalley, Nicole E., Hayden, Hillary S, Piochon, Marianne, Ball, Patrick, Dandekar, Ajai A., Gauthier, Charles ORCID: https://orcid.org/0000-0002-2475-2050, Déziel, Éric ORCID: https://orcid.org/0000-0002-4609-0115 et Chandler, Joséphine R (2020). Burkholderia thailandensis methylated hydroxy-alkylquinolines: biosynthesis and antimicrobial activity in co-cultures Applied and Environmental Microbiology , vol. 86 , nº 24. p. 1-17. DOI: 10.1128/AEM.01452-20.

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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 co-culture 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"). Results confirm that BTH_II1576 is involved in generating N-oxide derivatives of HMAQs (HMAQ-NO). 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 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, mostly methylated 4-hydroxy-alkenylquinolines, a family of relatively unstudied metabolites similar to molecules also synthesized by Pseudomonas aeruginosa. Several of the methylated 4-hydroxy-alkenylquinolines have antimicrobial activity against other species. We show that Bacillus subtilis strain 168 is particularly susceptible to N-oxidated methyl-alkenylquinolines (HMAQ-NO). We confirmed 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-hydroxy-alkenylquinolines, which are unique to B. thailandensis. This study also has importance for understanding B. thailandensis secondary metabolites and has implications for potential therapeutic development.

Type de document: Article
Informations complémentaires: document e01452-20
Mots-clés libres: Burkholderia; cell-cell interaction; natural antimicrobial products; quinolones
Centre: Centre INRS-Institut Armand Frappier
Date de dépôt: 20 juill. 2021 04:02
Dernière modification: 15 févr. 2022 17:32
URI: https://espace.inrs.ca/id/eprint/11614

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