Isolation of Methyl Troposulfenin from Phaeobacter inhibens

Christopher B. W. Phippen; Cecilie M. Jørgensen; Mikkel Bentzon-Tilia; Charlotte Held Gotfredsen; Thomas O. Larsen; Lone Gram; Eva C. Sonnenschein

doi:10.1021/acs.jnatprod.8b01097

Isolation of Methyl Troposulfenin from Phaeobacter inhibens

Christopher B. W. Phippen, Cecilie M. Jørgensen, Mikkel Bentzon-Tilia, Charlotte Held Gotfredsen, Thomas O. Larsen, Lone Gram, Eva C. Sonnenschein^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

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.

Original language	English
Journal	Journal of Natural Products
Volume	82
Issue number	5
Pages (from-to)	1387-1390
Number of pages	4
ISSN	0163-3864
DOIs	https://doi.org/10.1021/acs.jnatprod.8b01097
Publication status	Published - 2019

Cite this

Phippen, C. B. W., Jørgensen, C. M., Bentzon-Tilia, M., Gotfredsen, C. H., Larsen, T. O., Gram, L., & Sonnenschein, E. C. (2019). Isolation of Methyl Troposulfenin from Phaeobacter inhibens. Journal of Natural Products, 82(5), 1387-1390. https://doi.org/10.1021/acs.jnatprod.8b01097

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title = "Isolation of Methyl Troposulfenin from Phaeobacter inhibens",

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.",

author = "Phippen, {Christopher B. W.} and J{\o}rgensen, {Cecilie M.} and Mikkel Bentzon-Tilia and Gotfredsen, {Charlotte Held} and Larsen, {Thomas O.} and Lone Gram and Sonnenschein, {Eva C.}",

year = "2019",

doi = "10.1021/acs.jnatprod.8b01097",

language = "English",

volume = "82",

pages = "1387--1390",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "5",

}

Isolation of Methyl Troposulfenin from Phaeobacter inhibens. / Phippen, Christopher B. W.; Jørgensen, Cecilie M.; Bentzon-Tilia, Mikkel ; Gotfredsen, Charlotte Held ; Larsen, Thomas O.; Gram, Lone ; Sonnenschein, Eva C.

In: Journal of Natural Products, Vol. 82, No. 5, 2019, p. 1387-1390.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Isolation of Methyl Troposulfenin from Phaeobacter inhibens

AU - Phippen, Christopher B. W.

AU - Jørgensen, Cecilie M.

AU - Bentzon-Tilia, Mikkel

AU - Gotfredsen, Charlotte Held

AU - Larsen, Thomas O.

AU - Gram, Lone

AU - Sonnenschein, Eva C.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

U2 - 10.1021/acs.jnatprod.8b01097

DO - 10.1021/acs.jnatprod.8b01097

M3 - Journal article

C2 - 30978024

VL - 82

SP - 1387

EP - 1390

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 5

ER -

Access to Document

10.1021/acs.jnatprod.8b01097

Embargoed Document

Phippen MeTDA Stucture paper resubmission 190404
Accepted author manuscript, 536 KB
Embargo ends: 12/04/2020

Embargoed Document

Supporting information
Accepted author manuscript, 710 KB
Embargo ends: 12/04/2020