Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade
Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade
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DOI：
10.1039/b909133e
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发表时间：
2010-01-01
影响因子：
3.2
通讯作者：
Schulz, Stefan
中科院分区：
文献类型：
--
作者：
Thiel, Verena;Brinkhoff, Thorsten;Schulz, Stefan
玫瑰杆菌属细菌是丰富的海洋细菌，是全球硫循环的重要贡献者。对其两个成员Phaebacter Gallaeciensis和Ocean ibulbus indolifex产生的挥发物进行了分析，以探讨释放的化合物是否来自硫代谢，以及哪些生物合成途径参与了这些化合物的形成。这两种细菌产生不同的硫化物和硫代酯，包括新的天然化合物，如S-甲基苯乙硫酸酯(16)和甲烷磺酸丁酯(21)。用一种易于制备的铝/硫试剂通过一种新的方法从相应的烷基酸甲酯中合成了S-烷基酸甲酯，并与标准进行了比较，从而鉴定了它们。银杏棕榈杆菌也能够大量产生托洛酮(37)。通过不同的饲养实验对其生物合成进行了研究，结果表明，37是通过苯乙酸酯分解代谢的偏差而形成的。不稳定的托洛酮水合物42被鉴定为托洛酮生物合成的中间体，该中间体也与托洛酮(38)一起释放。
Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as S-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38).