Isolation, Identification, and Decomposition of Antibacterial Dialkylresorcinols from a Chinese Pseudomonas aurantiaca Strain

A chemical investigation of a Chinese Pseudomonas aurantiaca strain has yielded a new benzoquinone (4) and furanone (5), in addition to the known dialkylresorcinols 1 and 2. Extensive decomposition studies on the major metabolite 1 produced an additional furanone derivative (6), a hydroxyquinone (7)...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-02, Vol.83 (2), p.194-201
Main Authors: Shi, Yue, Zaleta-Pinet, Diana A, Clark, Benjamin R
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Asian Continental Ancestry Group
Humans
Magnetic Resonance Spectroscopy
Molecular Structure
Pseudomonas - chemistry
Resorcinols - isolation & purification
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Summary:A chemical investigation of a Chinese Pseudomonas aurantiaca strain has yielded a new benzoquinone (4) and furanone (5), in addition to the known dialkylresorcinols 1 and 2. Extensive decomposition studies on the major metabolite 1 produced an additional furanone derivative (6), a hydroxyquinone (7), and two unusual resorcinol and hydroxyquinone dimers (8 and 9). Structures were elucidated by nuclear magnetic resonance spectroscopy in combination with tandem mass spectrometry analysis. These studies illustrate the potential of artifacts as a source of additional chemical diversity. Compounds 1 and 2 showed moderate antibacterial activity against a panel of Gram-positive pathogens, while the antibacterial activities of the artifacts (4–9) were reduced.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b00315