Development of an Enzymatic Method To Quantify Methyl Ketones from Bacterial Origin

Fadda, Silvina; Lebert, A.; Talon, Régine

doi:10.1021/jf011298v

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…The procedure employs a thermostable NADPH-dependent alcohol dehydrogenase (ADH) (EC 1.1.1.2) [16]. This enzyme reduces the methyl ketone to its secondary alcohol and the rate of NADPH oxidation is directly related to the ketone content [17]. The enzymic reduction of 2-pentanone was monitored continuously with a Shimadzu UV-Visible 160A spectrophotometer.…”

Section: Enzymic Methods To Quantify Methyl Ketonesmentioning

confidence: 99%

Decarboxylase activity involved in methyl ketone production by Staphylococcus carnosus 833, a strain used in sausage fermentation

Fadda

2002

FEMS Microbiology Letters

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Staphylococcus carnosus strain 833, inoculated into sausage, increased the levels of methyl ketones which contributed to the cured aroma. These ketones were predicted to arise from incomplete L-oxidation followed by a decarboxylation. To check this hypothesis, we measured the L-decarboxylase activity in resting cells of S. carnosus grown in complex or in synthetic medium, using as substrate a L-ketoacid, which can be an intermediate of the L-oxidation pathway. This activity was present throughout the growth period. The enzyme appeared to be constitutive because no induction was observed. High aeration, a pH of 5 and the presence of nitrate promoted the production of methyl ketones. ß

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Section: Enzymic Methods To Quantify Methyl Ketonesmentioning

confidence: 99%

Decarboxylase activity involved in methyl ketone production by Staphylococcus carnosus 833, a strain used in sausage fermentation

Fadda

2002

FEMS Microbiology Letters

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“…Concerning S. carnosus , Engelvin et al [3] have reported the existence of a β‐oxidative pathway and the liberation of intermediates from a β‐oxidation cycle. Recently, we have reported a β‐decarboxylase activity in resting cells of S. carnosus using a β‐ketoacid as substrate [4,5]. These results show that S. carnosus , as do fungi, may produce ketones via this pathway.…”

Section: Introductionmentioning

confidence: 68%

“…The reduction of ketones by the ADH was monitored spectrophotometrically with a Shimadzu ultraviolet (UV)‐visible 160A spectrophotometer in kinetic mode [4]. The reaction mixture, in Tris–HCl buffer (100 mM, pH 7.8) and made up to a final volume of 1 ml, contained the following reagents: 200 μl of sample, 50 μl of β‐NADPH (4 mM), 21 μl of ADH solution (0.94 U ml −1 ).…”

Section: Methodsmentioning

confidence: 99%

Preliminary characterization of Î²-decarboxylase activities inStaphylococcus carnosus833, a strain used in sausage fermentation

Fadda¹,

Leroy-Sétrin²,

Talon³

2003

FEMS Microbiology Letters

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In sausage, Staphylococcus carnosus increases the levels of methyl ketones which could arise from incomplete L-oxidation of fatty acids followed by a decarboxylation. The objective of this work was to characterize the L-decarboxylase activities in cell-free extract. By using different substrates, at least two kinds of L-decarboxylase activities were shown: an acetoacetate-like and an oxaloacetate-like. The first one leads to the production of ketones from ethylbutyryl acetate or acetoacetic acid. The activity was optimal at pH 6.0, stimulated by pyridoxal phosphate but ethylenediamine tetraacetic acid (EDTA), NaCl, iodoacetate and curing additives were inhibitory. The second decarboxylase activity leads to the production of pyruvic acid from oxaloacetic acid. This activity was optimal at pH 5.0 and stimulated by divalent ions and biotin.

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“…In bacteria, methylketones, such as 2-heptanone, 2-butanone, 2-petanone, and 3-methyl-1-butanone, are detected in the volatile organic compounds (VOCs) of Lactobacillus casei (Gallegos et al, 2017). Staphylococcus carnosus produces 2-pentanone and a highly autolytic strain of Lactobacillus helveticus is reported to enhance the levels of methylketones during cheese ripening (Fadda et al, 2002; Hannon et al, 2006). In fungi, both 2-heptanone and 2-petanone are detected from a range of species, from unicellular yeast to filamentous fungi (Sunesson et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of the Nematode Attractant 2-Heptanone and Its Co-evolution Between the Pathogenic Bacterium Bacillus nematocida and Non-pathogenic Bacterium Bacillus subtilis

Zhu

et al. 2019

Front. Microbiol.

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Methylketones are broadly distributed in nature and perform a variety of functions. Most microorganisms are thought to produce methylketone by abortive β-oxidation of fatty acid catalytic metabolism. However, two methylketone synthetase genes in wild tomatoes are reported to synthesize methylketone using intermediates of the fatty acids biosynthetic pathway. In our previous study on Trojan horse-like interactions between the bacterium Bacillus nematocida B16 and its host worm, the chemical 2-heptanone was found to be an important attractant for the hosts. So here we used this model to investigate the genes involved in synthesizing 2-heptanone in microorganisms. We identified a novel methylketone synthase gene yneP in B. nematocida B16 and found enhancement of de novo fatty acid synthesis during 2-heptanone production. Interestingly, a homolog of yneP’ existed in the non-pathogenic species Bacillus subtilis 168, a close relative of B. nematocida B16 that was unable to lure worms, but GC-MS assay showed no 2-heptanone production. However, overexpression of yneP’ from B. subtilis in both heterologous and homologous systems demonstrated that it was not a pseudogene. The transcriptional analysis between those two genes had few differences under the same conditions. It was further shown that the failure to detect 2-heptanone in B. subtilis 168 was at least partly due to its conversion into 6-methyl-2-heptanone by methylation. Our study revealed methylketone biosynthesis of Bacillus species, and provided a co-evolution paradigm of second metabolites during the interactions between pathogenic/non-pathogenic bacteria and host.

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Development of an Enzymatic Method To Quantify Methyl Ketones from Bacterial Origin

Cited by 9 publications

References 26 publications

Decarboxylase activity involved in methyl ketone production by Staphylococcus carnosus 833, a strain used in sausage fermentation

Decarboxylase activity involved in methyl ketone production by Staphylococcus carnosus 833, a strain used in sausage fermentation

Preliminary characterization of Î²-decarboxylase activities inStaphylococcus carnosus833, a strain used in sausage fermentation

Biosynthesis of the Nematode Attractant 2-Heptanone and Its Co-evolution Between the Pathogenic Bacterium Bacillus nematocida and Non-pathogenic Bacterium Bacillus subtilis

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