Isolation of Methyl Troposulfenin from Phaeobacter inhibens

Isolation of Methyl Troposulfenin from Phaeobacter inhibens

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 th...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2019-05, Vol.82 (5), p.1387-1390
Hauptverfasser: Phippen, Christopher B. W, Jørgensen, Cecilie M, Bentzon-Tilia, Mikkel, Gotfredsen, Charlotte Held, Larsen, Thomas O, Gram, Lone, Sonnenschein, Eva C
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container_issue 5
container_start_page 1387
container_title Journal of natural products (Washington, D.C.)
container_volume 82
creator Phippen, Christopher B. W
Jørgensen, Cecilie M
Bentzon-Tilia, Mikkel
Gotfredsen, Charlotte Held
Larsen, Thomas O
Gram, Lone
Sonnenschein, Eva C
description 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.
doi_str_mv 10.1021/acs.jnatprod.8b01097
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title Isolation of Methyl Troposulfenin from Phaeobacter inhibens
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