A Novel Type of Geosmin Biosynthesis in Myxobacteria
2005/05/26 by Jeroen S. Dickschat, Helge B. Bode, Taifo Mahmud +2 · 29 citations
Environmental Science · Medicine · Agricultural and Biological Sciences · #Microbial Community Ecology and Physiology #Microbial Natural Products and Biosynthesis #Biocrusts and Microbial Ecology
paper · doi:10.1021/jo050449g
Abstract
The biosynthesis of geosmin (1) and (1(10)E,5E)-germacradien-11-ol (2), two volatile terpenoid compounds emitted by the myxobacteria Myxococcus xanthus and Stigmatella aurantiaca, was investigated in feeding experiments with different labeled precursors. In these experiments, the volatiles released by the cell cultures grown on agar plates were collected with a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. [(2)H(10)]Leucine and [4,4,4,5,5,5-(2)H(6)]dimethylacrylate were fed to wild-type strains and bkd mutant strains, which are impaired in the degradation of leucine to isovaleryl-CoA. [(2)H(10)]Leucine was incorporated into 1 and 2 only by the wild-type strains via the biosynthetic pathway that involves leucine degradation and branching into the mevalonate pathway. Dimethylacrylyl-CoA (DMA-CoA) is an intermediate in the leucine degradation and in the recently discovered pathway from HMG-CoA to isovaleryl-CoA. The corresponding free acid, [4,4,4,5,5,5-(2)H(6)]dimethylacrylic acid, was incorporated into 1 and 2 only by the mutants impaired in leucine degradation. [4,4,6,6,6-(2)H(5)]Mevalonic acid lactone (12) was synthesized and fed to M. xanthus and S. aurantiaca wild-type strains and a double mutant strain of M. xanthus. This strain does not degrade leucine and is impaired in the reduction of 3-hydroxy-3-methylglutaryl-CoA to mevalonic acid. The mass spectral analysis of labeled 1 and 2 obtained in these feeding experiments led to a biosynthetic scheme to 1 with intermediate 2. This pathway differs from that observed in the liverwort Fossombronia pusilla and thus suggests microbial geosmin biosynthesis following a route different from that in liverworts. Our results are supported by a 1,2-hydride shift of the tertiary hydrogen atom at C-4a into the ring opposite to that in F. pusilla.
Cited by
- Identification of geosmin and 2-methylisoborneol in cyanobacteria and molecular detection methods for the producers of these compounds
- Bacterial terpene cyclases
- Biosynthesis, evolution and ecology of microbial terpenoids
- Bacterial terpenome
- Biochemical and ecological control of geosmin and 2-methylisoborneol in source waters. [europepmc]
- Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme. [europepmc]
- Identification of (8S,9S,10S)-8,10-dimethyl-1-octalin, a key intermediate in the biosynthesis of geosmin in bacteria. [europepmc]
- Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin. [europepmc]
- Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor. [europepmc]
- Isolation and characterization of the gene associated with geosmin production in cyanobacteria. [europepmc]
- Total synthesis and stereochemical assignment of (-)-ushikulide A. [europepmc]
- The AngFus3 Mitogen-Activated Protein Kinase Controls Hyphal Differentiation and Secondary Metabolism in Aspergillus niger. [europepmc]
- On the origin of 3-methylglutaconic acid in disorders of mitochondrial energy metabolism. [europepmc]
- Mechanistic investigations on six bacterial terpene cyclases. [europepmc]
- Volatiles from three genome sequenced fungi from the genus Aspergillus . [europepmc]
- A terpene synthase-cytochrome P450 cluster in Dictyostelium discoideum produces a novel trisnorsesquiterpene. [europepmc]
- Phylogenomic analyses and distribution of terpene synthases among Streptomyces . [europepmc]
- Depuration of geosmin- and 2-methylisoborneol-induced off-flavors in recirculating aquaculture system (RAS) farmed European whitefish Coregonus lavaretus . [europepmc]
- Microbial Production of the Off-Flavor Geosmin in Tilapia Production in Brazilian Water Reservoirs: Importance of Bacteria in the Intestine and Other Fish-Associated Environments. [europepmc]
- 2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene-Nucleoside. [europepmc]
- Chemical entrapment and killing of insects by bacteria. [europepmc]
- Bacterial terpenome. [europepmc]
- Assessment of Evolutionary Relationships for Prioritization of Myxobacteria for Natural Product Discovery. [europepmc]
- The Ubiquitous Soil Terpene Geosmin Acts as a Warning Chemical. [europepmc]
- Structures, Occurrences and Biosynthesis of 11,12,13-Tri- nor -Sesquiterpenes, an Intriguing Class of Bioactive Metabolites. [europepmc]
- Present Status, Limitations, and Prospects of Using Streptomyces Bacteria as a Potential Probiotic Agent in Aquaculture. [europepmc]
- Bivariate One Strain Many Compounds Designs Expand the Secondary Metabolite Production Space in Corallococcus coralloides . [europepmc]
- The microbial biosynthesis of noncanonical terpenoids. [europepmc]
- Geosmin, a Food- and Water-Deteriorating Sesquiterpenoid and Ambivalent Semiochemical, Activates Evolutionary Conserved Receptor OR11A1. [europepmc]
Related