Volatile Organic Compounds from Arctic Bacteria of the <i>Cytophaga‐Flavobacterium‐Bacteroides</i> Group: A Retrobiosynthetic Approach in Chemotaxonomic Investigations

Dickschat, Jeroen S.; Helmke, Elisabeth; Schulz, Stefan

doi:10.1002/cbdv.200590014

Cited by 56 publications

(87 citation statements)

References 46 publications

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“…Some liverworts produce "unusual" (ϩ)-␤-caryophyllene (34,35). In bacteria, marine arctic strains of the Cytophaga-Flavobacterium-Bacteroides group produce ␤-caryophyllene, although the absolute configuration has not been determined (36). At least 17 ␤-caryophyllene synthase genes have been cloned from different plants, and the recombinant enzymes have been characterized (2,(37)(38)(39)(40)(41).…”

Section: Discussionmentioning

confidence: 99%

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

Nakano

Horinouchi²,

Ohnishi

2011

Journal of Biological Chemistry

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Most terpenoids have been isolated from plants and fungi and only a few from bacteria. However, an increasing number of genome sequences indicate that bacteria possess a variety of terpenoid cyclase genes. We characterized a sesquiterpene cyclase gene (SGR2079, named gcoA) found in Streptomyces griseus. When expressed in Streptomyces lividans, gcoA directed production of a sesquiterpene, isolated and determined to be (؉)-caryolan-1-ol using spectroscopic analyses. (؉)-Caryolan-1-ol was also detected in the crude cell lysate of wild-type S. griseus but not in a gcoA knockout mutant, indicating that GcoA is a genuine (؉)-caryolan-1-ol synthase. Enzymatic properties were characterized using N-terminally histidine-tagged GcoA, produced in Escherichia coli. As expected, incubation of the recombinant GcoA protein with farnesyl diphosphate yielded (؉)-caryolan-1-ol. However, a small amount of another sesquiterpene was also detected. This was identified as the bicyclic sesquiterpene hydrocarbon (؉)-␤-caryophyllene by comparison with an authentic sample using GC-MS. Incorporation of a deuterium atom into the C-9 methylene of (؉)-caryolan-1-ol in an in vitro GcoA reaction in deuterium oxide indicated that (؉)-caryolan-1-ol was synthesized by a proton attack on the C-8/C-9 double bond of (؉)-␤-caryophyllene. Several ␤-caryophyllene synthases have been identified from plants, but these cannot synthesize caryolan-1-ol. Although caryolan-1-ol has been isolated previously from several plants, the enzyme responsible for its biosynthesis has not been identified previously. GcoA is thus the first known caryolan-1-ol synthase. Isolation of caryolan-1-ol from microorganisms is unprecedented.Terpenoids are the largest family of natural products, including over 24,000 known compounds. They have various biological functions and act as flavorings, pigments, antibiotics, hormones, and antitumor agents. Most terpenoids have been isolated from plants and fungi and only a few from bacteria. All terpenoids are derived from the C 5 precursors isopentenyl diphosphate and dimethylallyl diphosphate. The successive condensation of isopentenyl diphosphate and dimethylallyl diphosphate gives rise to linear isoprenyl diphosphate precursors of various chain lengths, such as geranyl diphosphate (C 10 ), farnesyl diphosphate (FPP, 2 C 15 ), and geranylgeranyl diphosphate (C 20 ). These linear substrates are generally cyclized by terpenoid cyclases to produce the parent skeletons of monoterpenes (C 10 ), sesquiterpenes (C 15 ), diterpenes (C 20 ), and other homologs. Terpenoid cyclases are therefore the first key enzymes in pathways leading to the diverse range of terpenoids. A large number of terpenoid cyclases have been reported from eukaryotes, and these have been studied extensively (1, 2). In contrast, at present there are only a small number of reports of bacterial terpenoid cyclases. Most of the bacterial terpenoid cyclases reported are sesquiterpene cyclases (SCs). Bacterial SCs show no significant amino acid sequence identity with eukaryotic S...

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Section: Discussionmentioning

confidence: 99%

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

Nakano

Horinouchi²,

Ohnishi

2011

Journal of Biological Chemistry

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“…From retention index calculations the presence of an wÀ1 methyl branch was suggested (FG(2-one) = 200). [4] Furthermore, the corresponding methyl carbinol was also present, eluting slightly later than the methyl ketone (FG(2-ol) = 210) [4] . Its mass spectrum showed a strong fragment ion at m/z = 45, whereas the molecular ion was not detected.…”

Section: Identification Of Fatty Acid Derivativesmentioning

confidence: 98%

“…In recent studies we have reported on the profiles of volatiles released by different bacteria such as the myxobacteria Chondromyces crocatus and Myxococcus xanthus, [1,2] bacteria of the Roseobacter clade, [3] Flavobacteriaceae, [4] and Streptomyces sp. [5] by use of a modified closed-loop stripping apparatus (CLSA).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis and Identification of Volatiles Released by the Myxobacterium Stigmatella aurantiaca

et al. 2005

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The volatiles released by agar plate cultures of two strains of the myxobacterium Stigmatella aurantiaca (strains Sg a15 and DW4/3-1) were collected in a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Large numbers of substances from different compound classes (ketones, esters, lactones, terpenes, and sulfur and nitrogen compounds) were identified; several of them are reported from natural sources for the first time. The volatiles 2-methyltridecan-4-one (17), its isomer 3-methyltridecan-4-one (20), and the higher homologue 2-methyltetradecan-4-one (18) were identified in the extracts of both strains and were synthesized. In addition, strain Sg a15 produced 2,12-dimethyltridecan-4-one (19), 2-methyltridec-2-en-4-one (23), and a series of phenyl ketones, among them 1-phenyldecan-1-one (14) and 9-methyl-1-phenyldecan-1-one (16), whereas strain DW4/3-1 emitted traces of 10-methylundecan-2-one (21). The biosynthesis of 14 and 16 was examined in feeding experiments with deuterated precursors carried out on agar plate cultures. The leucine-derived starter unit isovalerate was shown to be incorporated into 16, as was phenylalanine-derived benzoic acid into both 14 and 16. The results point to formation both of the phenyl ketones and of the structurally related aliphatic ketones through an unusual head-to-head coupling between a starter unit such as benzoyl-CoA and a fatty acyl-CoA, followed by decarboxylation.

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“…For example, members of the Cytophaga-FlavobacteriumBacteroides group that use valine, and others that use isoleucine for ketone biosynthesis, emit different ketones that serve as fatty acid precursor substances. These volatile intermediate products may be lost without any purpose (Dickschat et al 2005a). Similarly, it is possible that other intermediate products especially metabolites of low molecular weight (e.g., isopropanol, isoprene, furan, etc.)…”

Section: Microorganisms and Voc Productionmentioning

confidence: 99%

Volatile organic compounds (VOCs) in soils

2010

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Soils may act as sources or sinks of volatile organic compounds (VOCs). Many of the formed VOCs are produced by microorganisms, and it would be a challenge to investigate soil microbial communities by studying their VOC profile. Such "volatilomics" would have the advantage of avoiding extraction steps that are often a limit in genomic or proteomic approaches. Abundant literature on microbially produced VOCs is available, and in particular novel detection methods allow additional insight. The aim of this paper was to give an overview on the current knowledge of microbial VOC emissions from soils.

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Volatile Organic Compounds from Arctic Bacteria of the Cytophaga‐Flavobacterium‐Bacteroides Group: A Retrobiosynthetic Approach in Chemotaxonomic Investigations

Cited by 56 publications

References 46 publications

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

Biosynthesis and Identification of Volatiles Released by the Myxobacterium Stigmatella aurantiaca

Volatile organic compounds (VOCs) in soils

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