The Hydroxylation of Skatole

Heacock, R. A.; Mahon, M. E.

doi:10.1139/y63-268

Cited by 6 publications

(3 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In some instances L-[U-benzene ring-14C ]tryptophan was obtained from DL-[U-benzene ring-14C]tryptophan by paper chromatography, using a solvent system of methanol-1-butanol-benzene-water (20: 10: 10: 1 vol/vol), modified by substituting 1-butanol for 1-pentanol (25). 5-Hydroxyskatole was chemically prepared from skatole (19).…”

Section: Methodsmentioning

confidence: 99%

“…Incorporation into IAA showed a reverse trend with 8.2% of the added radioactivity being associated with this metabolite at 6 h, increasing to a maximum of 12.1% at 12 h, then decreasing to 9.3 and 2.6% by 18 to 24 h. The aqueous fractions, containing the undegraded L [14C]tryptophan and other metabolites not extracted by methylene chloride, decreased from 7.8 to 1.4% over the 24-h incubation period. Total radioactivity found in the aqueous fraction and in the metabolites examined could only account for 16.2% of the added radioactivity at 6 h, 19 Influence of ruminal protozoa and bacteria on the formation of metabolites. Incubation of L-[U-benzene ring-4C Itryptophan with a crude preparation of ruminal protozoa for 24 h resulted in only 0.1% of the added radioactivity incorporated into skatole, 3% into indole, and 8% into IAA (Table 3).…”

Section: ]mentioning

confidence: 96%

See 1 more Smart Citation

Dissimilation of Tryptophan and Related Indolic Compounds by Ruminal Microorganisms In Vitro1

Yokoyama¹,

Carlson²

1974

Applied Microbiology

View full text Add to dashboard Cite

Intraruminal doses of L-tryptophan cause acute pulmonary edema and emphysema in cattle. The D and L isomers of tryptophan and 22 related indolic compounds were incubated with ruminal microorganisms in vitro. Incubation of L-[U-benzene ring-`C ]tryptophan with ruminal microorganisms for 24 h resulted in 39% of the added radioactivity being incorporated into skatole, 7% into indole, and 4% into indoleacetate (IAA). D-Tryptophan was not degraded to any of these metabolites. The major pathway of skatole formation from L-tryptophan appeared to be by the decarboxylation of IAA. Incubation of [2-14C ]IAA with ruminal microorganisms for 24 h resulted in 38% incorporation into skatole. L-[5-Hydroxy]tryptophan was degraded to 5-hydroxyskatole and 5-hydroxyindole, whereas 5-hydroxyindoleacetate was degraded to only 5-hydroxyskatole. Incubation of indolepyruvate, indolelactate, and indolealdehyde with ruminal microorganisms resulted in the formation of both skatole and indole. Under similar conditions, indoleacetaldehyde was converted to IAA and tryptophol. The addition of increasing concentrations of glucose (O to 110 mM) reduced the formation of both skatole and indole from L-tryptophan and resulted in the accumulation of IAA. Antibiotics reduced the degradation of L-tryptophan to skatole and indole, with kanamycin and neomycin particularly effective in reducing the decarboxylation of IAA to skatole. ' Scientific paper no. 4054, College of Agriculture Research Center, project 1893.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: ]mentioning

confidence: 96%

Dissimilation of Tryptophan and Related Indolic Compounds by Ruminal Microorganisms In Vitro1

Yokoyama¹,

Carlson²

1974

Applied Microbiology

View full text Add to dashboard Cite

show abstract

“…New paper-chromatographic methods have also been described for indoles (653,1477), nitroanthrimidines (270), quinoline-A7-oxides (1158), pyridylcarbinol-V-oxide and related compounds (1651), substituted trinitrobenzenes (303,304), cyanamide derivatives (1564), substituted cinnolines (571), aliphatic diamines (1150), and alkylammonium salts (536, 758).…”

Section: Carbohydratesmentioning

confidence: 99%