Discovery and metabolic origin of 4,4ʹ-dihydroxy-3,3ʹ,5,5ʹ-tetrachlorobenzophenone from a Burkholderia oklahomensis clinical isolate

Dashti, Yousef, Clarkson, Guy J., Mahenthiralingam, Eshwar ORCID: https://orcid.org/0000-0001-9014-3790 and Challis, Gregory L. 2026. Discovery and metabolic origin of 4,4ʹ-dihydroxy-3,3ʹ,5,5ʹ-tetrachlorobenzophenone from a Burkholderia oklahomensis clinical isolate. Pure and Applied Chemistry 10.1515/pac-2025-0623

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Abstract

Burkholderia oklahomensis LMG 23618T is a B. pseudomallei-like bacterium originally isolated in 1973 from a wound infection caused by a farming accident in Oklahoma. Metabolic profiling of an organic extract from cultures of B. oklahomensis LMG 23618T using UHPLC-ESI-Q-ToF-MS led to identification of three known metabolites, betulinan A, yersiniabactin and ulbactin B, in addition to a novel polychlorinated compound. Mass-directed purification enabled isolation of the novel specialized metabolite, which was shown by X-ray crystallography and NMR spectroscopic analysis to be 4,4ʹ-dihydroxy-3,3ʹ,5,5ʹ-tetrachlorobenzophenone. Feeding experiments with stable isotope-labelled precursors established that the carbon skeleton of this unusual metabolite derives from two molecules of tyrosine. This led us to propose a plausible biosynthetic pathway via decarboxylative condensation of 3, 5-dichloro-4-hydroxybenzoic acid with its coenzyme A thioester derivative. The absolute configuration of ulbactin B was also established as 4ʹR, 3ʺS, 7ʺS, 8ʺR using X-ray crystallography and NMR spectroscopy.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Biosciences
Publisher:	De Gruyter
ISSN:	1365-3075
Date of First Compliant Deposit:	2 February 2026
Date of Acceptance:	5 January 2026
Last Modified:	02 Feb 2026 10:17
URI:	https://orca.cardiff.ac.uk/id/eprint/184297

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