Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum

被引：27

作者：

Pauly, Julia ^{[1
]}

Spiteller, Dieter ^{[2
]}

Linz, Jeanine ^{[3
]}

Jacobs, Jonathan ^{[4
]}

Allen, Caitilyn ^{[4
]}

Nett, Markus ^{[5
]}

Hoffmeister, Dirk ^{[1
]}

机构：

[1] Univ Jena, Dept Pharmaceut Biol, Hans Knoll Inst, D-07745 Jena, Germany

[2] Univ Konstanz, Dept Chem Ecol Chem Biol, D-78457 Constance, Germany

[3] Max Planck Inst Chem Ecol, Dept Evolutionary Neuroethol, D-07745 Jena, Germany

[4] Univ Wisconsin, Dept Plant Pathol, Madison, WI 53706 USA

[5] Leibniz Inst Nat Prod Res & Infect Biol eV, Hans Knoll Inst, D-07745 Jena, Germany

来源：

CHEMBIOCHEM | 2013年 / 14卷 / 16期

关键词：

biosynthesis; natural products; ralfuranones; Ralstonia solanacearum; thioethers; BIOSYNTHESIS; VIRULENCE; METABOLISM; TOMATO; GENES; METHIONINE; BACTERIA; PHCA;

D O I：

10.1002/cbic.201300364

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Ralfuranones are aryl-substituted furanone secondary metabolites of the Gram-negative plant pathogen Ralstonia solanacearum. New sulfur-containing ralfuranone derivatives were identified, including the methyl thioether-containing ralfuranone D. Isotopic labeling in vivo, as well as headspace analyses of volatiles from R. solanacearum liquid cultures, established a mechanism for the transfer of an intact methylthio group from L-methionine or -keto--methylthiobutyric acid. The methylthio acceptor molecule ralfuranone I, a previously postulated biosynthetic intermediate in ralfuranone biosynthesis, was isolated and characterized by NMR. The highly reactive Michael acceptor system of this intermediate readily reacts with various thiols, including glutathione.

引用

页码：2169 / 2178

页数：10

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