title: Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade.
abstract: 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).
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Verena
authors.initials: V
authors.lastname: Thiel
authors.forename: Thorsten
authors.initials: T
authors.lastname: Brinkhoff
authors.forename: Jeroen S
authors.initials: JS
authors.lastname: Dickschat
authors.forename: Susanne
authors.initials: S
authors.lastname: Wickel
authors.forename: Jörg
authors.initials: J
authors.lastname: Grunenberg
authors.forename: Irene
authors.initials: I
authors.lastname: Wagner-Döbler
authors.forename: Meinhard
authors.initials: M
authors.lastname: Simon
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
mesh_terms: D015394:Molecular Structure; D041904:Roseobacter / Q000737:chemistry / Q000378:metabolism*; D013457:Sulfur Compounds / Q000032:analysis* / Q000378:metabolism; D014334:Tropolone / Q000031:analogs & derivatives* / Q000032:analysis* / Q000378:metabolism; D014835:Volatilization
chemical_list: D013457:Sulfur Compounds; D014334:Tropolone