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PubMed1983

Species variation in the metabolism of a substituted cinnamate ester anti-inflammatory pro-drug.

1. The metabolic fate of the substituted cinnamic acid ester, Ro 03-6037, has been examined in rat, mouse, baboon, dog, marmoset, rabbit and man. 2. All species are capable of reducing the cinnamate double bond, but the subsequent one-carbon fragment loss can be carried out only by rat, dog, rabbit and marmoset. 3. The inability of man, as well as baboon and mouse, to perform this terminal metabolic step, which results in formation of the active anti-inflammatory agent, renders the compound unsuitable as a drug for humans. 4. Reduction of the double bond is not carried out by gut flora. 5. An h.p.l.c. analytical method is described for estimation of the metabolites in biological fluids.

Animals↗

PubMed1991

Studies on the induction of cinnamic acid 4-hydroxylase in potato tuber.

The change in activity of cinnamic acid 4-hydroxylase (CA4H) in potato parenchyma tissue exposed to various conditions has been examined. Maximum induction of CA4H activity was obtained at 18 hr of incubation. Though CA4H induction can occur in dark, over 100% increase in enzyme activity was obtained on exposure of the tissue to light. Actinomycin D and cycloheximide inhibited the induction process. Mn2+, though known to cause an induction of CA4H in Jerusalem Artichoke, strongly inhibited potato CA4H induction. Dithiothreitol enhanced the CA4H activity due to either activation or protection of the enzyme. CA4H induction was significantly regulated at very low concentrations of trans-cinnamate and paracoumarate.

Cycloheximide↗

PubMed1985

Chloroperoxidase-catalyzed halogenation of trans-cinnamic acid and its derivatives.

Several 2,3-unsaturated carboxylic acids, such as trans-cinnamic acid and its derivatives, were found to be halogenated by chloroperoxidase of Caldariomyces fumago in the presence of hydrogen peroxide and either Cl- or Br-. Cinnamic acid, 4-hydroxycinnamic acid, 4-methoxycinnamic acid, and 3,4-dimethoxycinnamic acid were suitable substrates of chloroperoxidase, and were converted to 2-halo-3-hydroxycarboxylic acid, 2,3-dihydroxycarboxylic acid, decarboxylated halohydrin, or decarboxylated halocompound. However, 4-nitrocinnamic acid and 4-chlorocinnamic acid having electron-attracting groups did not serve as a substrate of the enzyme. The enzyme also did not act on acrylic acid, acrylamide, crotonic acid, fumaric acid, etc. From these data, the enzymatic reactions of chloroperoxidase, concerning the substrate specificity, stereoselectivity, and the reaction mechanism, are discussed on the basis of current knowledge regarding the reaction mechanism of the enzyme. Also they are compared with the chemical reactions of molecular halogen and hypohalous acid.

Carboxylic Acids↗

PubMed1996

[Analysis of cinnamic acid in storax and its original plant by HPLC].

The contents of free and hydrolytic cinnamic acid in storax and its original plant (Liquidambar orientalis) were determined by high performance liquid chromatography, and the chromatographic behaviors were studied. In styrax gummi, the contents of free and hydrolytic cinnamic acid were 7.03% and 25.26% respectively; and in its original plant, they were 0.3% evenly.

Chromatography, High Pressure Liquid↗

PubMed2004

Effect of 3,4-di(OH)-cinnamate synthetic derivative on plasma and hepatic cholesterol level and antioxidant enzyme activities in high cholesterol-fed rats.

The effect of 3,4-di(OH)-phenylpropionic acid (L-phenylalanine methyl ester) amide (SL-1063), a synthetic derivative of 3,4-di(OH)-cinnamate, on the cholesterol metabolism and antioxidant enzyme system was examined in rats. Diets that included either SL-1063 (0.046%, w/w) or lovastatin (0.02%, w/w) as a supplement, plus 1 g cholesterol/100 g diet were fed to rats ad libitum for 5 weeks. The total plasma cholesterol and triglyceride levels were significantly lowered by the SL-1063 supplement compared to the control group. Meanwhile, the levels of plasma HDL-cholesterol and ratio of HDL-cholesterol/total cholesterol (%) were significantly higher in the SL-1063 group than in the control group. However, the lovastatin supplement did not affect the plasma lipid level. The hepatic cholesterol level and 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase activity were significantly lowered in the lovastatin group compared to the SL-1063 group; however, the hepatic triglyceride level did not differ among the groups. The activity of hepatic acyl CoA: cholesterol acyltransferase (ACAT), the enzyme that catalyzes hepatic cholesterol esterification, was significantly lower in the lovastatin and SL-1063 groups than in the control group. Furthermore, the SL-1063 supplement elevated the excretion of fecal sterols. As regards the hepatic antioxidant enzyme system, the superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px), and glutathione reductase (GR) activities were all significantly higher in the SL-1063 group compared to the control group, whereas only the GR activity was significantly increased by the lovastatin supplement. No marked difference in the GSH levels and glucose-6-phosphate dehydrogenase (G6PD) activities was observed among the groups. The levels of plasma and hepatic thiobarbituric acid reactive substances (TBARS) were lowered by the SL-1063 supplement compared to the control group. Accordingly, the current results suggest that SL-1063, a synthetic derivative of 3,4-di(OH)-cinnamate, is effective in lowering the plasma lipids and improving the antioxidant enzyme system.

Animals↗

PubMed1970

Formation of coenzyme a esters of cinnamic acids with an enzyme preparation from cell suspension cultures of parsley.

The formation of coenzyme A thiol esters of cinnamic, p-coumaric, p-methoxy cinnamic, and ferulic acids was catalyzed by enzyme preparations from cell suspension cultures of leaf petioles from parsley (Petroselinum hortense Hoffm.). Of these acids, p-coumaric acid served as the most efficient substrate. Enzyme activity is markedly increased upon illumination with white light in a manner very similar to that in which the activities of a number of enzymes involved in flavone biosynthesis are stimulated by light. This strongly suggests that the formation of p-coumaroyl coenzyme A is part of this biosynthetic pathway.

Journal Article↗

PubMed1993

Tissue distribution and excretion of 14C-labelled cinnamic aldehyde following single and multiple oral administration in male Fischer 344 rats.

14C-labelled cinnamic aldehyde (CNMA) was given as a single oral dose, or 24 hr after multiple oral administration of non-radioactive CNMA for 7 days at 24-hr intervals, to male Fischer 344 rats at dose levels of 5, 50 or 500 mg/kg body weight. Residues of radioactive CNMA were measured. After the single dose radioactivity was distributed primarily in the gastro-intestinal tract, the kidneys and the liver of the rats. The radiolabel was excreted mainly in the urine, and at 24 hr 85.1, 84.2 and 81.2% of the administered radiolabel was recovered in the urine at the 5, 50 and 500 mg/kg dose levels, respectively. Faecal excretion of radiolabel at 24 hr for the 5, 50 and 500 mg/kg doses was 5.1, 4.0 and 3.2% of the administered dose, respectively. At all dose levels, a small amount of the dose was distributed to the fat and was easily measured in animals killed 3 days after dosing at the 50 or 500 mg/kg dose levels. Following multiple oral administration, similar tissue distribution and excretion patterns of radiolabel were found at the three dose levels. After 24 hr the administered radiolabel was distributed mainly to the fat, liver and gastro-intestinal tract. At 24 hr, recoveries of the radiolabel in the urine were 80.4, 80.6 and 81.9% of the dose for the 5, 50 and 500 mg/kg dose levels, respectively. Faecal excretion of radiolabel after multiple dosing at 24 hr accounted for 6.3, 6.9 and 4.5% of the administered radioactivity at the 5, 50 and 500 mg/kg dose levels, respectively. The major metabolic pathway of CNMA for all single and the 5 and 50 mg/kg multiple dose levels in this species of rat was found to be degradation to benzoic acid through beta-oxidation and excretion in the urine mainly as hippuric acid, with much smaller amounts of benzoic and cinnamic acids. At the multiple dose level of 500 mg/kg, benzoic acid was the major urinary metabolite, indicating that in the Fischer 344 male rat at this relatively high oral dose level the detoxification of CNMA proceeds differently and an alternative metabolic pathway is proposed.

Acrolein↗

PubMed2002

Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: application to asymmetric synthesis of hydrodimers.

The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58 approximately 90% de). In all cases, small amounts (<10% yield) of meso hydrodimers were also formed. The electrolysis was performed conveniently using an undivided cell at a constant current. The transition states for the hydrocoupling were calculated with semiempirical methods. The all-trans cyclized hydrodimers were transformed to C(2)-symmetric dl-3,4-diaryladipic acids and trans-3,4-diarylcyclopentanones. The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, prepared from (1R)-(+)-camphor, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.

Journal Article↗

PubMed2003

Pd nanoparticles catalyzed stereospecific synthesis of beta-aryl cinnamic esters in ionic liquids.

Reaction of the catalyst 1 or Pd(OAc)(2) with tetrabutylammonium acetate, dissolved in tetrabutylammonium bromide, leads to a fast formation of Pd nanoparticles which efficiently catalyze the stereospecific reaction of cinnamates with aryl halides to give beta-aryl-substituted cinnamic esters. The role of tetrabutylammonium acetate is crucial in determining the formation of nanoparticles and stereospecificity of the C-C coupling process.

Journal Article↗

PubMed2007

Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage.

A water-soluble octahedral Pd nanocage acting as a reaction vessel templates the photodimerization of substituted trans-cinnamic acid methyl esters in water. Irradiation of the host-guest complexes of trans-cinnamic acid methyl esters with the Pd nanocage resulted in selective formation of a syn head-head dimer in addition to the corresponding cis isomer. These results suggest that the guest molecules are preoriented in a selective fashion with the hydrophilic ester group facing water and the hydrophobic aryl group tucked within the cavity of the host. Such an orientation occurs at the hydrophobic-hydrophilic interface between the nanocage exterior and interior. Weak intermolecular C-H-pi and pi-pi interactions between the host and the guest(s) are likely to be responsible for the lack of mobility of the reactant olefins during their short excited-state lifetime.

Journal Article↗

PubMed2005

Umbelactonyl cinnamate derivatives from Crypteronia paniculata that mediate DNA strand scission.

As part of an initiative to discover functional natural product analogues of bleomycin guided by the use of the COMPARE algorithm, a CH(2)Cl(2)-MeOH extract prepared from Crypteronia paniculata was found to exhibit relaxation of supercoiled pSP64 DNA in the presence of Cu(2+). Bioassay-guided fractionation employing a DNA strand scission assay resulted in the isolation of three novel DNA cleavage agents. Their structures were elucidated as umbelactonyl cinnamate derivatives 1-3 through their NMR and MS spectral data analyses. This is the first example of the isolation and structural characterization of naturally occurring umbelactonyl cinnamate derivatives. Compound 1 exhibited strong Cu(2+)-dependent relaxation of supercoiled pSP64 DNA, while compounds 2 and 3 had only weak DNA cleavage activity.

Algorithms↗

PubMed1976

Amine-catalyzed hydrolyses of cyclodextrin cinnamates.

Hydrolyses of beta-cyclodextrin cinnamate (betaCDC) and alpha-cyclodextrin cinnamate were catalyzed by amines such as 1,4-diazabicyclo(2.2.2)octane, triethylamine, quinuclidine, piperidine, diisobutylamine, and n-butylamine. The rate constant of hydrolyses of the betaCDC-amine complexes follows the order: 1,4-diazabicyclo(2.2.2)octane > n-butylamine > quinuclidine > piperidine > triethylamine >> diisobutylamine. The ratio of the catalytic rate constant for the betaCDC/1,4-diazabicyclo(2.2.2)octane complex to the spontaneous rate constant for betaCDC is about 6-fold and is almost independent of pH below pH 11.5; but, it then drastically increases with pH above pH 11.5, up to 57-fold at pH 13.6 which is much higher than previous attempts. The pH-rate constant profile and isotope effect with deuterium oxide solvent indicate that 1,4-diazabicyclo(2.2.2)octane, included in betaCDC, assists the catalytic nucleophilic attack by hydroxide ion toward the carbonyl carbon of betaCDC. Acceleration of deacylation of acyl-cyclodextrins, by amines, has made the cyclodextrin-catalyzed hydrolysis of esters an even better model of hydrolytic enzyme reactions than those developed previously.

Journal Article↗

PubMed1977

Localization of Cinnamic Acid 4-Monooxygenase and the Membrane-bound Enzyme System for Dhurrin Biosynthesis in Sorghum Seedlings.

The localization of three monooxygenase (hydroxylase) enzyme systems which occur in dark-grown seedlings of Sorghum bicolor has been studied. Cinnamic acid 4-hydroxylase (CAH) (trans-cinnamate 4-monooxygenase, EC 1.14.13.11), which has been increasingly utilized in plants as a marker for the endoplasmic reticulum, migrated with that fraction in continuous and discontinuous sucrose gradients. When 10 mm MgCl(2) was used to shift the density banding of the marker enzyme, NADPH cytochrome c reductase, from 1.12 to 1.17 g/cm(3), the CAH activity was displaced as well.The membrane-bound enzyme system involved in the biosynthesis of the cyanogenic glucoside dhurrin was also shown to be closely associated with the endoplasmic reticulum. This system contains hydroxylases capable of hydroxylating tyrosine to form N-hydroxytyrosine and hydroxylating p-hydroxyphenylacetonitrile to form p-hydroxy-(S)-mandelonitrile.

Journal Article↗

PubMed1999

Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivatives.

Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C-H.O intermolecular hydrogen bonds. In most cases the C atom of the C-H unit was a member of the aromatic ring. Intramolecular (olefinic) C-H.O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C-C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C-H.O hydrogen bonding. Here, the C atom of the C-H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The beta-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.

Journal Article↗

PubMed1975

Sensitivity to cinnamic aldehyde in a toothpaste. 2. Further studies.

The authors carried out further studies to assess the significance of the findings of patients sensitive to cinnamic aldehyde in a toothpaste. Selected groups of patients in whom sensitivity to this might have been overlooked were patch-tested. With the exception of three patients, two with cosmetic sensitivity and one with hand eczema, the results were negative. The frequency of use of the original toothpaste was assessed among patients attending the clinic and this was followed by a circular letter to general practitioners and dentists inviting referral of patients with oral symptoms. As a result, five further cases, four of whom gave positive patch test reactions to cinnamic aldehyde, were discovered. The authors emphasize the importance of attempting to obtain accurate information as quickly as possible when 'new' or hitherto unsuspected allergens are implicated.

Acrolein↗

PubMed1981

Production of l-Phenylalanine from trans-Cinnamic Acid with Rhodotorula glutinis Containing l-Phenylalanine Ammonia-Lyase Activity.

An enzymatic method using l-phenylalanine ammonia-lyase (EC 4.3.1.5) for the rapid conversion of trans-cinnamic acid to l-phenylalanine has been investigated. With Rhodotorula glutinis, enzyme activity as high as 0.3 U/ml of culture broth was obtained. The enzyme activity was kept stable for a relatively long time during cultivation by the addition of l-isoleucine. Optimization of the parameters of the conversion reaction resulted in accumulation of 18 mg of l-phenylalanine per ml of reaction mixture. The conversion yield from trans-cinnamic acid was about 70%. The method may provide a rapid and practical way to produce l-phenylalanine useful as an essential amino acid.

Journal Article↗

PubMed1994

Biological microemulsions: Part IV--Phase behaviour and dynamics of microemulsions prepared with vegetable oils mixed with aerosol-OT, cinnamic alcohol and water.

Microemulsification of vegetable oils (ricebran, saffola, soyabean, sesame, palm and linseed) with water using aerosol-OT and cinnamic alcohol as mixed amphiphiles was studied. The biological microemulsions formed covered on the average approximately 27% of single phase area in the triangular phase diagram. The multiphasic zone for saffola was studied in detail, two- and three-phase zones were identified with patches of thick gel. The effect of temperature on the multiphase formation in the range 29-55 degrees C was also studied. The formation of multiphase and their proportions found to depend on the type of oil. The biological microemulsions at reasonable water/AOT mole ratio showed moderate increase in conductance with temperature. The viscosity of the microemulsions was high. Of the studied systems (sesame, saffola and ricebran) the viscosity of the first two decreased with the rate of shear whereas that of ricebran increased. When cinnamic alcohol was used as the oil, the trend of viscosity was similar to that of sesame and saffola.

Dioctyl Sulfosuccinic Acid↗

PubMed1996

Cross-reactions in patch testing and photopatch testing with ketoprofen, thiaprophenic acid, and cinnamic aldehyde.

In the last 7 years, we have studied 123 patients with allergic reactions to topical arylpropionic anti-inflammatory drugs. We have investigated the rate of sensitization and the irritant potential of one of them, ketoprofen, and its cross-reactivity with such other derivatives as ibuproxam, ibuprofen, naproxen, fenoprofen, flurbiprofen, and thiaprofenic acid. Sensitization was single in most cases, and ketoprofen was the drug most often involved. The combination most frequently found was ketoprofen plus ibuproxam. The most frequent cross-reactions were to fragrance mix, especially cinnamic aldehyde and balsam of Peru, both contact and photocontact sensitizers. Because there is a ketonic group in the molecule of ketoprofen and cinnamic aldehyde and after conversion of thiaprofenic acid, this could be the trigger for this particular allergy and cross-reactivity.

Acrolein↗