2-Aminoacetophenone — A hepatic skatole metabolite as a potential contributor to boar taint

Fischer, Jochen; Gerlach, Christoph; Meier-Dinkel, Lisa; Elsinghorst, Paul W.; Boeker, Peter; Schmarr, Hans-Georg; Wüst, Matthias

doi:10.1016/j.foodres.2014.02.045

Cited by 22 publications

(21 citation statements)

References 30 publications

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“…S2) is very similar to that of 2‐aminoacetophenone, and this compound is likely a derivative of 2‐aminoacetophenone (the closest NIST2017 library match was the structurally related 2‐acetylformanilide, but this identification was not clearly supported by the available Kovats retention index). 2‐Aminoacetophenone is derived from skatole in porcine liver (Fischer et al , 2014), and these compounds may similarly be derived from skatole in W. elatior . An alternative possibility is that these compounds are products of ultraviolet (UV) photooxidation of skatole, which has been shown to yield 2‐aminoacetophenone (and 2‐acetylformanilide; Evans, 1977; Kumar et al , 1998).…”

Section: Discussionmentioning

confidence: 99%

Dung mimicry: the function of volatile emissions and corolla patterning in fly‐pollinated Wurmbea flowers

et al. 2020

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Summary It has been suggested that flowers of some angiosperms mimic vertebrate faeces (dung) in order to exploit insect pollinators that utilize faeces as a source of food and/or oviposition sites. We investigated a potential case of mimicry in Wurmbea elatior (Colchicaceae), a lily that exhibits a faecal odour and pattern of dark spots on the corolla. We found that W. elatior is pollinated by a broad assemblage of coprophagous flies and is dependent on pollinator visits for seed production. The flowers emit volatiles that are characteristic of vertebrate faeces, and three of these compounds – skatole, indole, and an unidentified compound – elicited electrophysiological antennal responses from flies. Artificial flowers laced with indole and skatole or skatole alone attracted the same assemblage of flies as was recorded on flowers of W. elatior. Spotted artificial flowers attracted twice as many flies as did those lacking spots. Experimental addition of indole and skatole to flowers of Wurmbea kraussii, a congener with unscented flowers pollinated by hoverflies, induced a shift to an insect visitor assemblage dominated by coprophagous flies. This study clarifies the roles of volatile emissions (particularly skatole) and visual signals in floral dung mimicry.

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Section: Discussionmentioning

confidence: 99%

Dung mimicry: the function of volatile emissions and corolla patterning in fly‐pollinated Wurmbea flowers

et al. 2020

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“…Several other molecules have been suggested in the literature as responsible for boar taint. These include indole, 4-phenyl but-3-en-2one, styrene, 1,4-dichlorobenzene, 2-aminoacetophenone, 5-α-androst-16-en-3-α-ol, and 5-α-androst-16-en-3-β-ol [2,34,52,53]. However, these molecules were not observed in the SCAN data, and no targeted approach (such as the use of the SIM mode) was used to attempt to detect them.…”

Section: Understanding the Differences Between The Voc Profiles Generatedmentioning

confidence: 99%

Comprehensive SPME-GC-MS Analysis of VOC Profiles Obtained Following High-Temperature Heating of Pork Back Fat with Varying Boar Taint Intensities

Burgeon

Markey

Debliquy

et al. 2021

Foods

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Boar taint detection is a major concern for the pork industry. Currently, this taint is mainly detected through a sensory evaluation. However, little is known about the entire volatile organic compounds (VOCs) profile perceived by the assessor. Additionally, many research groups are working on the development of new rapid and reliable detection methods, which include the VOCs sensor-based methods. The latter are susceptible to sensor poisoning by interfering molecules produced during high-temperature heating of fat. Analyzing the VOC profiles obtained by solid phase microextraction gas chromatography–mass spectrometry (SPME-GC-MS) after incubation at 150 and 180 °C helps in the comprehension of the environment in which boar taint is perceived. Many similarities were observed between these temperatures; both profiles were rich in carboxylic acids and aldehydes. Through a principal component analysis (PCA) and analyses of variance (ANOVAs), differences were highlighted. Aldehydes such as (E,E)-nona-2,4-dienal exhibited higher concentrations at 150 °C, while heating at 180 °C resulted in significantly higher concentrations in fatty acids, several amide derivatives, and squalene. These differences stress the need for standardized parameters for sensory evaluation. Lastly, skatole and androstenone, the main compounds involved in boar taint, were perceived in the headspace at these temperatures but remained low (below 1 ppm). Higher temperature should be investigated to increase headspace concentrations provided that rigorous analyses of total VOC profiles are performed.

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“…The two main compounds responsible for boar taint are androstenone (5α-androst-16-ene-3-one) [ 14 ] and skatole (3-methylindole) [ 15 , 16 ] even though several other compounds have also been indicated to be involved, like androstenols [ 17 ], indols [ 18 ] and 4-phenyl-3-buten-2-one [ 19 ], as reviewed by Zamaratskaia and Squires [ 20 ]. Lately, 2-aminoacetophenone was also suggested to contribute to boar taint [ 21 ]. The detection of boar taint is important because boar taint can negatively affect consumers’ acceptability [ 12 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Feasibility of on/at Line Methods to Determine Boar Taint and Boar Taint Compounds: An Overview

Font-i-Furnols

Martín-Bernal

Aluwé

et al. 2020

Animals

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Classification of carcasses at the slaughter line allows an optimisation of its processing and differentiated payment to producers. Boar taint is a quality characteristic that is evaluated in some slaughter plants. This odour and flavour is mostly present in entire males and perceived generally by sensitive consumers as unpleasant. In the present work, the methodologies currently used in slaughter plants for boar taint classification (colorimetric method and sensory quality control-human nose) and the methodologies that have the potential to be implemented on/at the slaughter line (mass spectrometry, Raman and biosensors) have been summarized. Their main characteristics are presented and an analysis of strengths, weaknesses, opportunities and threats (SWOT) has been carried out. From this, we can conclude that, apart from human nose, the technology that arises as very promising and available on the market, and that will probably become a substitute for the colorimetric method, is the tandem between the laser diode thermal desorption ion source and the mass spectrometry (LDTD-MS/MS) with automation of the sampling and sample pre-treatment, because it is able to work at the slaughter line, is fast and robust, and measures both androstenone and skatole.

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2-Aminoacetophenone — A hepatic skatole metabolite as a potential contributor to boar taint

Cited by 22 publications

References 30 publications

Dung mimicry: the function of volatile emissions and corolla patterning in fly‐pollinated Wurmbea flowers

Dung mimicry: the function of volatile emissions and corolla patterning in fly‐pollinated Wurmbea flowers

Comprehensive SPME-GC-MS Analysis of VOC Profiles Obtained Following High-Temperature Heating of Pork Back Fat with Varying Boar Taint Intensities

Feasibility of on/at Line Methods to Determine Boar Taint and Boar Taint Compounds: An Overview

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