Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes

Doran, Elena; Whittington, FM; Wood, J. D.; McGivan, J D

doi:10.1016/s0009-2797(02)00015-7

Cited by 132 publications

(126 citation statements)

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“…In porcine liver, CYP2E1 has an additional important role in catalysing the first step of skatole degradation and a defective hepatic skatole metabolism will lead to skatole accumulation in fat. Low skatole levels in fat have been associated with high levels of CYP2E1 in animals obtained from F4 wild pig crosses (but not in Swedish Yorkshire pigs) [13,43]. Skinner et al [41] have shown an association between a SNP in the promoter region of CYP2E1 gene and skatole deposition in a population of commercial pigs.…”

Section: Phase I Metabolismmentioning

confidence: 99%

“…No QTL for skatole has been characterized around the location of CYP2E1 (near 110 cM on SSC14 [41]), therefore it is unlikely that this mutation plays a major role in boar taint. However, a better understanding of the regulation of the expression of this gene might help to identify other candidate genes [13]. Tambyrajah et al [46] have exploited the recent sequencing of the 5' flanking region of the CYP2E1 gene to characterize factors regulating the CYP2E1 promoter activity.…”

Section: Phase I Metabolismmentioning

confidence: 99%

“…A first hypothesis to account for this observation is that male sex hormones increase skatole production [9]. However, a second hypothesis considering that androgens inhibit the catabolism of skatole has been more widely investigated [13]. Tambyrajah et al [46] have proposed that regulation mechanisms acting on the promoter of the CYP2E1 gene are very important to explain the variability of skatole level in fat.…”

Section: Relationship Between Androstenone and Skatole Levelsmentioning

confidence: 99%

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Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Robic

Larzul²,

Bonneau³

2007

Genet. Sel. Evol.

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-High levels of androstenone and skatole in fat tissues are considered the primary causes of boar taint, an unpleasant odour and flavour of the meat from non-castrated male pigs. The aim of this article is to review our current knowledge of the biology and genetic control of the accumulation of androstenone and skatole in fat tissue. Two QTL mapping studies have shown the complexity of the genetic control of these traits. During the last ten years, several authors have taken a more physiological approach to investigate the involvement of genes controlling the metabolism of androstenone and skatole. Although some authors have claimed the identification of candidate genes, it is more appropriate to talk about target genes. This suggests that genes affecting androstenone and skatole levels will have to be sought for among specific or non-specific transcription factors interacting with these target genes.androstenone / skatole / pig / boar taint / QTL

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Section: Phase I Metabolismmentioning

confidence: 99%

Section: Phase I Metabolismmentioning

confidence: 99%

Section: Relationship Between Androstenone and Skatole Levelsmentioning

confidence: 99%

See 1 more Smart Citation

Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Robic

Larzul²,

Bonneau³

2007

Genet. Sel. Evol.

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“…are regulated is via effects of testicular steroids on skatolemetabolizing enzymes CYP2E1 and CYP2A in the liver (Doran et al, 2002;Zamaratskaia et al, 2007). We have recently shown that CYP2E1 activities (measured as PNPH) were higher in female pigs at market live weight compared with those in entire male pigs at the same weight (Zamaratskaia et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

“…Kojima et al (2008) showed that administration of testosterone propionate to 1-month-old male and female pigs resulted in a significant decrease in the gene expression of CYP1A1 and CYP1A2 in the pigs of both sexes. Additionally, androstenone modified CYP2A6 protein expression and down-regulated the skatole-induced expression of CYP2E1 in primary cultured pig hepatocytes (Doran et al, 2002). Tambyrajah et al (2004) reported that androstenone decreases CYP2E1 promoter activity by inhibiting the binding of a transcription factor.…”

Section: Discussionmentioning

confidence: 99%

Modulation of porcine cytochrome P450 enzyme activities by surgical castration and immunocastration

Zamaratskaia

Žlábek

Chen

et al. 2009

Animal

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The present study aimed to evaluate some cytochrome P450 metabolic enzyme activities in hepatic microsomes prepared from entire male pigs (uncastrated pigs), surgically castrated pigs and pigs immunized against gonadotropin-releasing hormone (immunocastrated pigs). The activities of the following enzymes were measured: ethoxyresorufin O-deethylase (EROD, CYP1A1/ 1A2), methoxyresorufin O-deethylase (MROD, CYP1A2), pentoxyresorufin O-depentylase (PROD, CYP2B), coumarin hydroxylase (COH, CYP2A) and p-nitrophenol hydroxylase (PNPH, CYP2A/2E1). The total cytochrome P450 contents were not affected by either surgical or immunocastration. Hepatic microsomal activities for EROD, PROD, COH and PNPH were lower in entire male pigs compared with surgically castrated and immunocastrated pigs ( P , 0.05). Surgically and immunocastrated male pigs were similar with respect to EROD, MROD, PROD and COH activities ( P . 0.05), whereas surgically castrated pigs exhibited lower PNPH activity compared with immunocastrated pigs ( P 5 0.029). The effect of different concentrations of testicular steroidstestosterone, 17b-estradiol, free estrone and androstenone -on enzyme activities was evaluated by in vitro microsomal study. Testosterone at the concentration of 8 pmol/ml inhibited EROD activities and estradiol-17b at the concentration of 1.8 pmol/ml inhibited PROD activities in hepatic microsomes from surgically castrated pigs. The highest concentration of androstenone (7520 pmol/ml) inhibited COH activities, whereas a 42-fold lower concentration of androstenone (180 pmol/ml) stimulated COH activities in surgically castrated pigs. Both free estrone (3.5 pmol/ml) and androstenone (55 pmol/ml) inhibited EROD activities in microsomes from entire male pigs. Stimulation of COH activities by the highest dose of free estrone (18 pmol/ml) was recorded in microsomes from entire male pigs. However, these effects of steroids were not concentration-dependent and the maximum extent did not exceed 615% variation compared with the controls. There was no inhibition of PNPH activities in the hepatic microsomes from either entire or castrated pigs. In conclusion, we showed that EROD, PROD, COH and PNPH activities were lower in entire male pigs compared with those in surgically and immunocastrated pigs. Direct inhibition by the testicular steroids -testosterone, 17b-estradiol, free estrone and androstenone -was not the primary cause of the reduced enzyme activities.Keywords: castration, cytochrome P450, porcine liver microsomes, steroids ImplicationsThe present study evaluated some cytochrome P450 enzyme activities in liver microsomes from uncastrated male pigs, surgically castrated pigs and pigs immunized against gonadotropin-releasing hormone (immunocastrated pigs). We found that CYP1A1, CYP2A, CYP2B and CYP2E1 activities were lower in uncastrated male pigs compared with surgically castrated and immunocastrated pigs. These findings strengthen the hypothesis of testicular steroid involvement in cytochrome P450 enzyme regulation. The differences in the ac...

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Synthesis of deuterium‐labeled d₃‐androstenone and d₃‐skatole for boar taint analysis

Fischer

Elsinghorst

Wüst

2011

Labelled Comp Radiopharmac

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The steroidal pig pheromone androstenone (5α-androst-16-en-3-one) as well as the indole derivate skatole are known to be the major compounds contributing to boar taint. The preparation of 2 H-labeled internal standards of androstenone and skatole for stable isotope dilution assay-gas chromatography-mass spectrometry analysis of pig back fat samples is presented. The synthesis of d 3 -androstenone is highlighted by a palladium catalyzed deuteration of a Δ5,6-double bond of a hydrophobic steroid in a polar, D 2 O-containing solvent mixture. Moreover, the utilization of D 2 O as a deuterium source with in situ formation of D 2 by means of Mg 0 was found to be a very feasible and convenient alternative with respect to costs and technical effort.

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Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes

Cited by 132 publications

References 27 publications

Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Modulation of porcine cytochrome P450 enzyme activities by surgical castration and immunocastration

Synthesis of deuterium‐labeled d₃‐androstenone and d₃‐skatole for boar taint analysis

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Cytochrome P450IIE1 (CYP2E1) is induced by skatole and this induction is blocked by androstenone in isolated pig hepatocytes

Cited by 132 publications

References 27 publications

Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Genetic and metabolic aspects of androstenone and skatole deposition in pig adipose tissue: A review(Open Access publication)

Modulation of porcine cytochrome P450 enzyme activities by surgical castration and immunocastration

Synthesis of deuterium‐labeled d3‐androstenone and d3‐skatole for boar taint analysis

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Synthesis of deuterium‐labeled d₃‐androstenone and d₃‐skatole for boar taint analysis