The Metabolism of [1-14C] Phenylalanine, [3-14C] Cinnamic Acid and [2-14C] Ferulic Acid in the Rat

Teuchy, H.; Sumere, C. F. Van

doi:10.3109/13813457109085341

Cited by 31 publications

(21 citation statements)

References 45 publications

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“…Previous in vivo studies have shown that free dietary FA is rapidly absorbed in the upper parts of the intestine and conjugated mainly in the liver either into its phase II metabolites, mainly sulfonate or glucuronide conjugates and further excreted in urine [22]. A small proportion of ingested free FA may also be metabolized through beta-oxidation in liver to form vanillic acid, or through phase I metabolism into dihydroferulic acid and different forms of dihydroxybenzoic acids [20,24,25]. Notably, the cluster 1 was particularly rich in glycine conjugated metabolites.…”

Section: Resultsmentioning

confidence: 99%

Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice

et al. 2014

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BackgroundPhenolic acids are covalently bound to the arabinoxylan fibre matrix of wheat aleurone layer. In order to be bioavailable they need to be released by endogenous or bacterial enzymes and absorbed within the intestinal lumen. The intestinal microbiota can metabolize phenolic acids and other food-born phytochemicals. However, the effect of structure of the cereal bran or aleurone layer on these processes is not comprehensively studied.MethodsThe structure of aleurone layer was modified either by dry-grinding or by enzymatic treatments with xylanase alone or in combination with feruloyl esterase. Diet induced obese C57BL6/J mice were fed with high-fat diets containing either pure ferulic acid, or one of the four differentially treated aleurone preparations for 8 weeks. The diets were designed to be isocaloric and to have similar macronutrient composition. The urinary metabolite profiles were investigated using non-targeted LC-qTOF-MS-metabolomics approach.ResultsThe different dietary groups were clearly separated in the principal component analysis. Enzymatic processing of aleurone caused increased excretion of ferulic acid sulfate and glycine conjugates reflecting the increase in unbound form of readily soluble ferulic acid in the diet. The urinary metabolite profile of the diet groups containing native and cryo-ground aleurone was more intense with metabolites derived from microbial processing including hippuric acid, hydroxyl- and dihydroxyphenylpropionic acids. Furthermore, aleurone induced specific fingerprint on the urinary metabolite profile seen as excretion of benzoxazinoid metabolites, several small dicarboyxlic acids, and various small nitrogen containing compounds.ConclusionsThe structural modifications on wheat aleurone fraction resulted in altered metabolism of aleurone derived phenolic acids and other phytochemicals excreted in urine of diet-induced obese mice.

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Section: Resultsmentioning

confidence: 99%

Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice

et al. 2014

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“…The metabolizing process by microflora includes reduction, demethylation, and dehydroxylation to transform FA into m-hydroxyphenylpropionic acid (Chesson et al 1999;Scheline 1968;Scheline and Midtvedt 1970). Furthermore, a small portion of FA may be metabolized through boxidation in the liver which accounts for the urinary metabolites of FA, such as dihydroferulic acid, vanillic acid and vanilloylglycine in rats (Teuchy and Van Sumere 1971;Chesson et al 1999;Zhao and Moghadasian 2008).…”

Section: Metabolism Of Famentioning

confidence: 99%

“…Similarly, the urinary excretion of free FA tends to increase with larger oral doses (Chang et al 1993;Zhao et al 2003b). High oral doses or intraperitoneal injections may increase the secretion of FA via bile, which can reach the colon and be metabolized by intestinal microflora (Teuchy and Van Sumere 1971). The metabolizing process by microflora includes reduction, demethylation, and dehydroxylation to transform FA into m-hydroxyphenylpropionic acid (Chesson et al 1999;Scheline 1968;Scheline and Midtvedt 1970).…”

Section: Metabolism Of Famentioning

confidence: 99%

Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies

2009

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Hydroxycinnamates including p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, and their esterified/etherified conjugates such as chlorogenic acids are abundant in cereals, coffee, fruit and vegetables. Studies have shown their potential in the prevention of chronic diseases such as cardiovascular disease and cancer. The impact of these dietary hydroxycinnamates on health depends on their bioavailability. In this article, in vivo and in vitro studies pertaining to bioavailability of hydroxycinnamates are reviewed and discussed. The chemical structures, existing forms, and/or doses of hydroxycinnamates may affect their metabolic fate. Limited studies suggest that the relative bioavailability of hydroxycinnamates may be in the following order: chlorogenic acid \ rosmarinic acid \ caffeic acid \ ferulic acid \ p-coumaric acid. Bound hydroxycinnamates generally have lower bioavailability than their monomer counterparts. Further pharmacokinetic and phamacodynamic studies are required to characterize the metabolism of hydroxycinnamates and their potential health impact in humans.

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“…Vanillic acid was also excreted (Teuchy & Van Sumere, 1971). The conversion of ferulic acid to vanillic acid by rat liver homogenates has also been reported (Dirscherl & Brisse, 1966).…”

Section: Iii34 Candidate Substancesmentioning

confidence: 91%

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester der

2005

EFSA Journal

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The present Flavouring Group Evaluation deals with eight aryl-substituted saturated and unsaturated primary alcohol, aldehyde, carboxylic acid and ester derivatives.Due to the presence and the position of double bonds, three of the eight flavouring substances can exist as geometrical isomers. In each of these cases, no indication of the preponderance of either of the possible isomers in the commercial flavouring material has been given.The eight flavouring substances are classified into structural class I.Five of the eight flavouring substances in the present group have been reported to occur naturally in a wide range of food items.In its evaluation, the Scientific Panel as a default used the Maximised Survey-derived Daily Intakes (MSDIs) approach to estimate the per capita intakes of the flavouring substances in Europe. However, when the Scientific Panel examined the information provided by the European flavouring industry on the use levels in various foods, it appeared obvious that the MSDI approach in a number of cases would grossly underestimate the intake by regular consumers of products flavoured at the use level reported by the industry, especially in those cases where the annual production values were reported to be small. In consequence, the Scientific Panel had reservations about the data on use and use levels provided and the intake estimates obtained by the MSDI approach.In the absence of more precise information that would enable the Scientific Panel to make a more realistic estimate of the intakes of the flavouring substances, the Scientific Panel has decided also to perform an estimate of the daily intakes per person using a modified Theoretical Added Maximum Daily Intake (mTAMDI) approach based on the normal use levels reported by industry. In those cases where the mTAMDI approach indicated that the intake of a flavouring substance might exceed its corresponding threshold of concern, the Scientific Panel decided not to carry out a formal Flavouring Evaluation Group 15Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22The EFSA Journal (2005) 247 2 safety assessment using the Procedure. In these cases the Scientific Panel requires more precise data on use and use levels.According to the default MSDI approach, the eight flavouring substances in this group have intakes in Europe from 0.012 to 0.37 microgram/capita/day which are below the threshold of concern value for structural class I (1800 microgram/person/day) substances.All eight candidate substances in this flavouring group may be expected to be metabolised to innocuous products.The available genotoxicity data are not sufficient to evaluate the genotoxicity adequately, however, the data available on mutagenic and clastogenic activity of both candidate and supporting substances as well as the chemical structures of the candidate substances do not give reason for concern with respect to genotoxicity of the eight candidate substances in this flavouring group evaluation.It is noted that ...

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The Metabolism of [1-¹⁴C] Phenylalanine, [3-¹⁴C] Cinnamic Acid and [2-¹⁴C] Ferulic Acid in the Rat

Cited by 31 publications

References 45 publications

Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice

Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice

Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester der

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