Gas chromatographic determination and mass spectrometric confirmation of traces of indole and 3-methylindole (skatole) in pig back fat

Peleran, J.C.; Bories, Georges

doi:10.1016/s0021-9673(01)81350-9

Cited by 22 publications

(12 citation statements)

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“…One of the more malodorous compounds identified in swine manure odor is skatole (3-methylindole). Skatole has also been implicated as an off-flavor component of pig meat (referred to as "boar taint") (4,6,17,19) and as a contributing factor in acute bovine pulmonary edema and emphysema (15,23,27).Although the production of skatole has been attributed to the bacterial degradation of the amino acid tryptophan, the pathway by which skatole is produced from tryptophan has not been elucidated. The primary metabolite of tryptophan fermentation is indole (26,27), and skatole is produced from tryptophan and indoleacetic acid (IAA) by pig fecal slurries (13).…”

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Catabolic Pathway for the Production of Skatole and Indoleacetic Acid by the Acetogen Clostridium drakei , Clostridium scatologenes , and Swine Manure

Whitehead

Price

Drake

et al. 2008

Appl Environ Microbiol

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Skatole (3-methylindole) is a malodorous chemical in stored swine manure and is implicated as a component of foul-tasting pork. Definitive evidence for the skatole pathway is lacking. Deuterium-labeled substrates were employed to resolve this pathway in the acetogenic bacterium Clostridium drakei and Clostridium scatologenes and to determine if a similar pathway is used by microorganisms present in stored swine manure. Indoleacetic acid (IAA) was synthesized from tryptophan by both bacteria, and skatole was synthesized from both IAA and tryptophan. Microorganisms in swine manure produced skatole and other oxidation products from tryptophan, but IAA yielded only skatole. A catabolic mechanism for the synthesis of skatole is proposed.Storage of swine manure is associated with the generation of a number of malodorous compounds (18,22,30), and the production of odor associated with concentrated livestock facilities creates a nuisance and has resulted in considerable conflicts between producers and rural neighbors. These odors are produced as a result of anaerobic degradation of materials present in manure and include sulfides, organic acids, ammonia, phenols, amines, and other volatile compounds (30). One of the more malodorous compounds identified in swine manure odor is skatole (3-methylindole). Skatole has also been implicated as an off-flavor component of pig meat (referred to as "boar taint") (4,6,17,19) and as a contributing factor in acute bovine pulmonary edema and emphysema (15,23,27).Although the production of skatole has been attributed to the bacterial degradation of the amino acid tryptophan, the pathway by which skatole is produced from tryptophan has not been elucidated. The primary metabolite of tryptophan fermentation is indole (26,27), and skatole is produced from tryptophan and indoleacetic acid (IAA) by pig fecal slurries (13). However, very few bacterial isolates have been shown to produce skatole. A Lactobacillus species from the rumen has been reported to produce skatole from IAA but not directly from tryptophan (28,29). Clostridium scatologenes and the acetogen Clostridium drakei (originally isolated as C. scatologenes SL1) (14, 16) have also been reported to produce skatole (13, 14) and were selected for resolving the skatole catabolic pathway by using deuterium-labeled substrates and a combination of gas chromatography-mass spectrometry (GC-MS) and matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI-TOF MS).Bacterial strains, cultivation conditions, and swine manure. C. drakei SL1 DSM 12750 and C. scatologenes ATCC 25775 were utilized in this study. Preparation of media and inoculations were performed under anaerobic conditions using the method of Hungate as modified by Bryant (2). The basic medium for culturing C. drakei and C. scatologenes contained macrominerals, microminerals, buffers, reducing agents, and other components in routine growth medium (RGM) (9) and was supplemented with 1% (wt/vol) tryptone and either 1% (wt/vol) tryptophan or 1% (wt/vol) IAA...

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Catabolic Pathway for the Production of Skatole and Indoleacetic Acid by the Acetogen Clostridium drakei , Clostridium scatologenes , and Swine Manure

Whitehead

Price

Drake

et al. 2008

Appl Environ Microbiol

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“…Skatole has been quantified from pig backfat by gas chromatography (GC), [53,54] high-performance liquid chromatography (HPLC), [55] and spectrophotometry methods. [8,56] HPLC was used to quantify indole and skatole in swine gut contents, [57] and to quantify skatole in various animal feces.…”

Section: Introductionmentioning

confidence: 99%

Effect of nitroethane and nitroethanol on the production of indole and 3-methylindole (skatole) from bacteria in swine feces by gas chromatography

Beier

Anderson

Krueger

et al. 2009

Journal of Environmental Science and Health, Part B

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Indole and 3-methylindole (skatole) are odor pollutants in livestock waste, and skatole is a major component of boar taint. Skatole causes pulmonary edema and emphysema in ruminants and causes damage to lung Clara cells in animals and humans. A gas chromatographic method that originally used a nitrogen-phosphorus detector to increase sensitivity was modified resulting in an improved flame ionization detection response for indole and skatole of 236% and 207%, respectively. The improved method eliminates the large amount of indole decomposition in the injector. A 10 micro g mL(-1) spike of indole and skatole in water and swine fecal slurries resulted in recovery of 78.5% and 96% in water and 76.1% and 85.8% in fecal slurries, respectively. The effect of the addition of nitroethane and nitroethanol at 21.8 mM in swine fecal slurries was studied on the microbial production of indole and skatole. Nitroethane and nitroethanol decreased the production of skatole in swine fecal slurries at 24 h. The nitroethane effect on l-tryptophan-supplemented fecal slurries after 6 and 24 h incubation resulted in a decrease of 69.0% (P = 0.02) and 23.5% skatole production, respectively, and a decrease of 14.9% indole at 6 h, but an increase in indole production of 81.1% at 24 h.

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“…Packed column chromatography gave good resolution for macro quantities of the analytes, as in the case of gut contents, but when scaled down to sub-microgram kg-' fat levels there was poor separation from interfering compounds. This problem has been overcome by some workers by using fused silica glass capillary columns (Hoshika and Murayama 1983;Peleran and Bories 1985;Garcia-Regueiro et a1 1986a). Others have used spectrophotometric methods based on Chernoff's modification of the Ehrlich reaction of indoles with p-dimethylamine-benzaldehyde (Myers 1950;Cant and Walker 1980;Mortensen and Sorensen 1984).…”

Section: Introductionmentioning

confidence: 99%

Method for the determination of indole and skatole in pig fat

Porter¹,

Hawe²,

Walker³

1989

J Sci Food Agric

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Gas chromatographic determination and mass spectrometric confirmation of traces of indole and 3-methylindole (skatole) in pig back fat

Cited by 22 publications

References 5 publications

Catabolic Pathway for the Production of Skatole and Indoleacetic Acid by the Acetogen Clostridium drakei , Clostridium scatologenes , and Swine Manure

Catabolic Pathway for the Production of Skatole and Indoleacetic Acid by the Acetogen Clostridium drakei , Clostridium scatologenes , and Swine Manure

Effect of nitroethane and nitroethanol on the production of indole and 3-methylindole (skatole) from bacteria in swine feces by gas chromatography

Method for the determination of indole and skatole in pig fat

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