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Abstract: BACKGROUND: Consumers highly sensitive to androstenone María (AND) will probably reject meat from entire male pigs, which tends to have high levels of this hormone. To avoid this, the effect of different masking strategies (sprinkling with mixed spices or fennel, marinating and breading with garlic–parsley or curry) on the sensory parameters of pork loin chops obtained from entire animals with high levels of AND (1.0–2.9 mg kg−1 AND in fat) and castrated animals (<0.4 mg kg−1 AND in fat), both with low levels of skatole (<0.1 mg kg−1 skatole in fat) was investigated. RESULTS: The garlic–parsley breadcrumbs led to the highest reduction in the perception of AND compared with the other masking strategies used, and preserved the juiciness of the product. There was a negative correlation between AND and fat content. CONCLUSION: AND odor and flavor can be reduced in meat from entire male pigs by using suitable strategies, the best strategy being the garlic–parsley breadcrumbs. © 2017 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

One of the main issues related to entire male pigs is the occurrence of boar taint, an off-odour, which compromises meat consumability. In this study, odour thresholds (indole: 24–65 µg kg −1 , skatole: 44–89 µg kg −1 , androstenone: 121–342 µg kg −1 ) for the boar taint compounds were estimated in minced meat, dry fermented sausage and dry-cured ham. Afterwards, sensory evaluation of these products containing 10% tainted meat (minced meat and dry fermented sausage) or moderate boar taint compound levels (dry-cured ham) occurred. The beneficial effect of diluting tainted meat was demonstrated, as no significant difference in consumability was observed between gilts and 10% tainted meat by experts as well as consumers. Also dry-curing proved a promising technique for masking boar taint and preventing consumer dissatisfaction. The obtained results demonstrate the applicability of the estimated thresholds in meat as a tool for identifying masking and reducing strategies on the perception of boar taint. [ABSTRACT FROM AUTHOR]

The Claisen condensations of 3β-acetoxypregn-5-en-20-one ( 1 ) and 3β-acetoxypregna-5,16-diene ( 7 ) with dimethyl oxalate are known to lead to 3β-hydroxy-21-methoxalylpregn-5-en-20-one ( 2 ) and 3β-hydroxy-21-methoxalylpregna-5,16-dien-20-one ( 8 ), respectively. The reactions of 2 with p -substituted phenylhydrazines afford pyrazol-5-yl derivatives ( 5 ) as main, and 3-yl regioisomers ( 4 ) as minor products. The corresponding reactions of 16-ene analogue 8 afford only pyrazol-5-yl regioisomer 9 . Oppenauer oxidation of the pyrazolyl compounds yields the corresponding Δ 4 -3-ketosteroids. We investigated the antiandrogenic effects of new methoxycarbonylpyrazolyl compounds through determination of their in vitro inhibition of the activities of rat testicular C 17,20 -lyase, Δ 5 -3β-hydroxysteroid dehydrogenase (Δ 5 -3β-HSD) and 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3). A Δ 5 -3β-hydroxy compound in the D-ring-saturated androst-5-ene series bearing an unsubstituted phenyl group on the pyrazolyl heterocycle ( 5a ) proved to be a potent inhibitor of Δ 5 -3β-HSD. The 4-methoxyphenyl derivative ( 5e ) and the 3-oxo counterpart ( 6a ) of 5a also displayed substantial inhibition. The other tested compounds exerted only weak inhibitory action against the enzymes investigated. The newly synthetized compounds were evaluated in vitro by means of MTT assays for antiproliferative activity against Hela (cervical carcinoma), A431 (skin epidermoid carcinoma) and MCF7 (breast adenocarcinoma) cells. In all four groups (3β-hydroxy- and 3-ketosteroids with saturated or unsaturated ring D), the most potent analogs contain a 4-tolyl or 4-methoxyphenyl group. Compound 5d exhibited substantial antiproliferative action against the three cell lines investigated, whereas 9d inhibited the growth of Hela cells markedly. The most noteworthy inhibition was exerted by 6a against A431 cells. [ABSTRACT FROM AUTHOR]

Background Androstenone is one of the major compounds responsible for boar taint, a pronounced urinelike odor produced when cooking boar meat. Several studies have identified quantitative trait loci (QTL) for androstenone level on Sus scrofa chromosome (SSC) 6. For one of the candidate genes in the region SULT2A1, a difference in expression levels in the testis has been shown at the protein and RNA level. Results Haplotypes were predicted for the QTL region and their effects were estimated showing that haplotype 1 was consistently related with a lower level, and haplotype 2 with a higher level of androstenone. A recombinant haplotype allowed us to narrow down the QTL region from 3.75 Mbp to 1.94 Mbp. An RNA-seq analysis of the liver and testis revealed six genes that were differentially expressed between homozygotes of haplotypes 1 and 2. Genomic sequences of these differentially expressed genes were checked for variations within potential regulatory regions. We identified one variant located within a CpG island that could affect expression of SULT2A1 gene. An allele-specific expression analysis in the testis did not show differential expression between the alleles of SULT2A1 located on the different haplotypes in heterozygous animals. However a synonymous mutation C166T (SSC6: 49,117,861 bp in Sscrofa 10.2; C/T) was identified within the exon 2 of SULT2A1 for which the haplotype 2 only had the C allele which was higher expressed than the T allele, indicating haplotypeindependent allelic-imbalanced expression between the two alleles. A phylogenetic analysis for the 1.94 Mbp region revealed that haplotype 1, associated with low androstenone level, originated from Asia. Conclusions Differential expression could be observed for six genes by RNA-seq analysis. No difference in the ratio of C:T expression of SULT2A1 for the haplotypes was found by the allele-specific expression analysis, however, a difference in expression between the C over T allele was found for a variation within SULT2A1, showing that the difference in androstenone levels between the haplotypes is not caused by the SNP in exon 2. [ABSTRACT FROM AUTHOR]

Interest has developed into 7-hydroxylated derivatives of 3β-hydroxylated C19-steroids, such as dehydroepiandrosterone (DHEA) and epiandrosterone because of their effects on inflammation, immune response, and cell repair. These steroids are not currently available from commercial sources, and it is necessary to produce them for relevant studies. We report here the chemical and biochemical approaches that were used for their production. Simplified chemical approaches lead to the production of 7α-/7β-hydroxy-DHEA and 7β-hydroxy-epiandrosterone in gram quantities, which are made available to researchers. Biochemical approaches were used to produce isotope-labeled compounds. Thus, 2H-, 3H-, and 14C-labeled 7α-/7β-hydroxy-DHEA and 7β-hydroxy-epiandrosterone could be produced in quantities sufficient for use in investigations into their mode of action. [ABSTRACT FROM AUTHOR]