Isolation of Methyl Troposulfenin from Phaeobacter inhibens | Zendy

Christopher B. W. Phippen | Zendy; Cecilie M. Jørgensen | Zendy; Mikkel BentzonTilia | Zendy; Charlotte H. Gotfredsen | Zendy; Thomas O. Larsen | Zendy; Lone Gram | Zendy; Eva C. Sonnenschein | Zendy

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Isolation of Methyl Troposulfenin from Phaeobacter inhibens

Author(s) -

Christopher B. W. Phippen,

Cecilie M. Jørgensen,

Mikkel BentzonTilia,

Charlotte H. Gotfredsen,

Thomas O. Larsen,

Lone Gram,

Eva C. Sonnenschein

Publication year - 2019

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.8b01097

Subject(s) - vibrio anguillarum , stereochemistry , chemistry , pathogen , vibrionaceae , marine bacteriophage , methylation , vibrio , antibacterial agent , bacteria , fish <actinopterygii> , mode of action , microbiology and biotechnology , biology , biochemistry , gene , fishery , genetics

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.

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