Metabolism Of Cinnamic Acid Research Articles

Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC).

Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC).

Metabolism of cinnamic acids by some Clostridiales and emendation of the descriptions of Clostridium aerotolerans, Clostridium celerecrescens and Clostridium xylanolyticum.

The ability of Clostridium aerotolerans DSM 5434T, Clostridium celerecrescens DSM 5628T, Clostridium methoxybenzovorans DSM 12182T, Clostridium stercorarium ATCC 35414T, Clostridium subterminale DSM 2636, Clostridium termitidis DSM 5398T, Clostridium thermolacticum DSM 2910T, Clostridium thermopalmarium DSM 5974T and Clostridium xylanolyticum DSM 6555T to metabolize cinnamic acid and various derivatives, with or without glucose supplementation, was examined. Only C aerotolerans DSM 5434T and C. xylanolyticum DSM 6555T, closely related species, transformed cinnamic acid to 3-phenylpropionic acid. Both species also reduced a wide range of cinnamic acid derivatives, including o-, m- and p-coumaric, o-, m- and p-methoxycinnamic, p-methylcinnamic, caffeic, ferulic, isoferulic and 3,4,5-trimethoxycinnamic acids to their corresponding 3-phenylpropionic acid derivatives. C. aerotolerans DSM 5434T, however, also decarboxylated p-coumaric acid into 4-vinylphenol, which was then reduced to 4-ethylphenol. C. celerecrescens was grouped with C. aerotolerans and C. xylanolyticum in subcluster XIVa of the Clostridiales. C. celerecrescens DSM 5628T only metabolized m- and p-methoxycinnamic and p-methylcinnamic acids to their corresponding 3-phenylpropionic acid derivatives, reducing the double bond in the C3 aliphatic side chain. Addition of glucose markedly increased the yield of the biotransformations by these three species. An emendation of the descriptions of C. aerotolerans, C. celerecrescens and C. xylanolyticum is proposed, based on these observations.

Effects of Safeners on the Oxidation of Multiple Substrates by Grain Sorghum Microsomes

Microsomes isolated from excised shoots of 3-day-old, dark-grown, grain sorghum [ Sorghum bicolor (L.) Moench. Funk G522DR, and DK 41Y] seedlings metabolized cinnamic acid, lauric acid, metolachlor, bentazon, and diazinon. but did not metabolize triasulfuron or primisulfuron. Pretreatment of G522DR seed with safeners (naphthalic anhydride, dichlormid, flurazole, BAS 145138, oxabetrinil, fluxofenim, and benoxacor) resulted in enhanced metabolism of lauric acid, bentazon, and diazinon. However, metabolism of cinnamic acid was not affected and that of metolachlor was depressed by safener treatments. Microsomes isolated from DK 41Y seedlings had higher endogenous levels of oxidative activity for lauric acid and bentazon than microsomes isolated from G522DR seedlings. Metabolism required NADPH and was affected by CO and other cytochrome P450 monooxygenase inhibitors (tetcyclacis, piperonyl butoxide, 1-aminobenzotriazole, SKF-525A, and tridiphane). The inhibitors differentially affected metabolism of the substrates. Only tetcyclacis strongly inhibited the metabolism of all substrates except cinnamic acid. Microsomal oxidations from both unsafened and safener-treated tissue responded similarly to the inhibitors. The differential inhibitory responses suggest that each substrate was probably metabolized by a different monooxygenase isoform.

The metabolism of cinnamic acid by healthy and phenylketonuric adults: a kinetic study.

The enzyme phenylalanine ammonia lyase taken orally has been found to reduce the rise in blood phenylalanine that normally occurs following a protein meal. Therefore the enzyme has a potential use in the management of the genetic disease phenylketonuria. The enzyme mediates the conversion of phenylalanine to cinnamic acid and its possible clinical future has necessitated a more detailed study of the product of its reaction. Cinnamic acid is a compound of low toxicity which is converted in the mammalian body primarily to hippuric acid. We have examined the kinetics of this process in a healthy male and in two patients with untreated phenylketonuria. In addition we have attempted to clarify the inconsistencies in earlier published work about the status of other, minor metabolites. Following an oral load of sodium (2H6) cinnamate there is an increase in urinary hippuric acid largely due to the excretion of (2H5) hippuric acid. In the subjects studied there was no major difference in the rate of elimination although the amount of cinnamic acid converted was less in those with phenylketonuria. This may reflect reduced first-pass absorption by the liver in untreated phenylketonuria enabling increased uptake to occur in other parts of the body.

Time-course tracer studies on the metabolism of cinnamic acid in Cestrum poeppigii

Time-course tracer studies were performed on the metabolism of trans-cinnamic acid-[3- 14C] and trans- p-coumaric acid-[2- 14C] in the

On the metabolism of cinnamic acid in Cestrum poepigii: identification of o-coumaric acid and an o-coumaroylquinic acid.

AbstractL'acide o-coumarique et un acide o-coumaroyl quinique sont des metabolites de l'acide cinnamique chez Cestrum poepigii.

Metabolism of cinnamic acid in plants: Chlorogenic acid formation

Rapid, efficient synthesis of chlorogenic acid from cinnamate was observed in leaves of plants of several genera. Use of labelled cinnamate, p-coumarate and caffeate showed two pathways were operative in this synthesis in tobacco. Trapping experiments indicated the major route to be: cinnamic acid → p-coumaric acid → p-coumaroylquinic acid → chlorogenic acid, and the secondary route cinnamic acid → p-coumaric acid → caffeic acid → chlorogenic acid. The metabolism of chlorogenic acid is discussed.

THE MICROBIAL METABOLISM OF CINNAMIC ACID.

A strain of Pseudomanas isolated from soil with cinnamic acid as a sole carbon source was found to be simultaneously adapted to the utilization of cinnamic acid and phenylpropionic acid. During growth on either of these compounds, o-hydroxyphenylpropionic acid and 2,3-dihydroxyphenylpropionic acid were produced in the culture medium. The organism, when grown on either cinnamic acid or phenylpropionic acid, was adapted to the utilization of m-hydroxyphenylpropionic acid and 2,3-dihydroxyphenylpropionic acid, but not to the utilization of o-hydroxyphenylpropionic acid. According to the principle of sequential induction introduced by Stanier, the initial steps in the metabolism of cinnamic acid appear to involve the intermediates phenylpropionic acid, m-hydroxyphenylpropionic acid, and 2,3-dihydroxyphenylpropionic acid.

Metabolism of Cinnamic Acid and Hydroxy-Cinnamic Acids by Lactobacillus pastorianus var. quinicus

PREVIOUS work has shown that caffeic acid, 3 : 4 dihydroxy-cinnamic acid is metabolized by Lactobacillus pastorianus var. quinicus 1,2 with the formation of dihydrocaffeic acid and ethyl catechol3. A pure culture of this organism was inoculated into a basal medium1 with the addition of 0.025 per cent cinnamic acid and 0.25 per cent fructose. After seven days' incubation at 25° C. under conditions of reduced oxygen tension, the cinnamic acid was completely metabolized. The end-product, an acid, was obtained as prismatic crystals, m.p. 47–48° C. in 85 per cent yield. A mixed melting-point with an authentic specimen of dihydrocinnamic acid showed no depression. Elementary analysis (Drs. Weiler and Strauss) gave C 71.85 per cent, H 6.84 per cent; C9H10O2 require requires C 72.0 per cent, H 6.7 per cent. The yield indicated that the organism had reduced cinnamic acid to dihydrocinnamic acid with little or no subsequent decarboxylation.