Abstract
An S-methylated analogue of tropodithietic acid (TDA, 1), methyl troposulfenin (2), was isolated from the marine alphaproteobacterium Phaeobacter inhibens. The structure was elucidated by NMR and HRMS. Its inhibitory effect against the fish pathogen Vibrio anguillarum was 4-fold to 100-fold lower than that of the known antibacterial compound TDA. Methyl troposulfenin lacks the acidic proton of TDA, indicating that the methylation turns the potent antibacterial TDA into an inactive compound, and thereby, this analysis supports the proposed mode of action of TDA.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology*
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Fish Diseases / microbiology
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Methylation
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Microbial Sensitivity Tests
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Molecular Structure
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Rhodobacteraceae / chemistry*
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Sulfhydryl Compounds / isolation & purification*
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Sulfhydryl Compounds / pharmacology*
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Tropolone / analogs & derivatives*
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Tropolone / isolation & purification
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Tropolone / pharmacology
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Vibrio / drug effects
Substances
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Anti-Bacterial Agents
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Sulfhydryl Compounds
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troposulfenin
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Tropolone