Showing papers on "Cinnamic acid published in 1997"

Ester-Linked Phenolic Components of Carrot Cell Walls

Abstract: The cold alkali-labile cell wall phenolics of carrot storage roots have been examined by diode-array HPLC following sequential treatment of purified wall material with aqueous sodium hydroxide of increasing strength. In addition to 4-hydroxybenzoic acid and ferulic acid, which have previously been reported from this source, a range of other typical wall-bound phenolic aldehydes and cinnamic acid derivatives were also identified. An 8-O-4‘-linked dehydrodiferulic acid, which has recently also been identified as a major ferulic acid dimer in several monocots, was found to be present in readily measurable quantities, and other putative dimers were also noted. At least ca. 30% of the total ferulic acid existed in dimer form. Cell wall phenolics might have a role to play in influencing the physical properties of carrot tissue. Keywords: Carrot; cell wall; Daucus carota; dehydrodiferulic acid; phenolics

Blood Orange Juice Authentication Using Cinnamic Acid Derivatives. Variety Differentiations Associated with Flavanone Glycoside Content

Abstract: A phenyl propanoid glycoside, cinnamoyl-β-d-glucopyranoside (CIN), characteristic of blood oranges, was isolated by column and thin layer chromatographies The structure of this compound was established using 1H and 13C NMR spectral data and by analysis of its components upon hydrolysis Flavanone glycosides (FGs) [narirutin (NAT), hesperidin (HES), and didymin (DID)] and cinnamic derivatives [CIN and trans-cinnamic acid (TCA)] of four blood orange varieties (47 samples) were analyzed by HPLC Differences in the polyphenol profiles clearly showed variety differentiation Keywords: Fruit juice; Citrus sinensis; blood orange varieties; cinnamoyl-β-d-glucopyranoside; flavanone glycoside; NMR; liquid chromatography

Phenolic Antioxidants Prevent Peroxynitrite-Derived Collagen Modification in Vitro

Abstract: To investigate the prevention of protein modification by food components, effects of natural antioxidants on in vitro modification of collagen by peroxynitrite were examined using a polyclonal antibody specific to 3-nitrotyrosine. To perform the assay with many samples at a time, the inhibitory effects of antioxidants were evaluated using an enzyme-linked immunosorbent assay. Polyphenols such as caffeic acid, curcumin, and flavonoids showed strong inhibitory effects on the formation of 3-nitrotyrosine in peroxynitrite-modified collagen. The inhibitory effects of caffeic acid and its related compounds on nitration of Tyr were then further investigated. Both caffeic acid, ferulic acid, and p-coumaric acid inhibited the modification, whereas cinnamic acid did not. By the treatment of p-coumaric acid with peroxynitrite, nitrated p-coumaric acid was detected in the reaction mixture using a liquid chromatograph-mass spectrometer (LC-MS). These results suggest that some phenolic antioxidants may prevent tissue i...

Cinnamic acid derivative

Abstract: The invention provides a cinnamic acid derivative having a novel spacer introduced into cinnamic acid which is photodimerizable, a cinnamic acid-polysaccharide derivative photocurable with high sensitivity and efficiency obtainable by introducing the above cinnamic acid derivative into a host polysaccharide such as a glycosaminoglycan, and a photocrosslinked cinnamic acid-polysaccharide derivative obtainable by exposing the same cinnamic acid-polysaccharide derivative to ultraviolet light irradiation.

Elicitor-induced changes of phenylalanine ammonia-lyase activity in barley cell suspension cultures

Abstract: Suspension-cultured barley cells responded to treatments with crude yeast extract and purified glucan preparation by rapidly and transiently (4 h postelicitation) inducing L-phenylalanine ammonia-lyase activity. Similarly, treatment of cell cultures with chitosan resulted in increased phenylalanine ammonia-lyase activity 2–4 h after elicitation, whereas a mycelium preparation of a fungal pathogen, Bipolaris sorokiniana, and purified chitin caused a more delayed induction of phenylalanine ammonia-lyase (8 h postelicitation). The most abundant of the plant cell wall degrading enzymes produced by Bipolaris sorokiniana, β-1,4-xylanase, had only a weak elicitor activity in barley cells suggesting that fungal cell wall components rather than the hydrolytic enzymes secreted by the fungus function as recognizable components that cause barley cells to induce defences. Treatment of the elicited cells with a phenylalanine ammonia-lyase inhibitor, α-aminooxy-β-phenylpropionic acid, resulted in the superinduction of the enzyme indicating the blocking of the feedback regulation mechanisms, whereas in the presence of 1 mM trans-cinnamic acid the elicitor-induction of phenylalanine ammonia-lyase was completely inhibited. Elicitor treatments increased the accumulation of wall-bound phenolics as evidenced by phloroglucinol-HCl staining and thioglycolic acid methods. However, α-aminooxy-β-phenylpropionic acid applied in combination with the elicitor did not prevent the accumulation of phenolics in barley cell walls. This suggested that phenylalanine ammonia-lyase might not play an important role in the synthesis wall-bound phenolic compounds in barley. However, cinnamic acid, whether applied alone or together with the elicitor, increased the amount of wall-bound phenolics in suspension-cultured barley cells.

Analytical study of free and ester bound benzoic and cinnamic acids of gum benzoin resins by GC-MS and HPLC-frit FAB-MS.

Abstract: Sumatra benzoin resins originating from two species of Styrax were studied using modern analytical techniques. Analysis of these types of resins usually involves several steps including alkaline hydrolysis, derivatization of the polar groups and chromatography. Two different resins, and three different qualities from each resin, were investigated using a fast analytical method which omits the hydrolysis step and makes it possible to identify all of the individual components of the resin in one gas-chromatography–mass spectrometry measurement. Resins from both Styrax benzoin Dryand and S. paralleloneurum Perk contain free cinnamic and benzoic acids and their corresponding esters with p-coumaryl and coniferyl alcohols, although in different relative amounts. Pinoresinol and some higher molecular weight esters of cinnamic and benzoic acids were also found. The structure of these compounds was verified by high performance liquid chromatography–continuous flow fast atom bombardment mass spectrometry. For quantitation, gas chromatography with flame ionization detection was performed. Molecular response factors of the identified compounds were calculated as correction factors of the peak areas. © 1997 by John Wiley & Sons, Ltd.

Cinnamic acid derivatives

Abstract: The present invention relates to a class of compounds represented by the Formula I ##STR1## or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the α v β 3 integrin.

Structopendant unsaturated cellulose esters via acylation in homogeneous lithium chloride/N,N‐dimethylacetamide solutions

Abstract: Novel acylation reactions of cellulose were accomplished with a series of unsaturated carboxylic acids or their respective anhydrides including crotonic acid (CRA), methacrylic acid (MAA), vinyl acetic acid (VAA), fumaric acid monoethyl ester (FAME), and cinnamic acid (CINA) in lithium chloride (LiCl)/dimethylacetamide (DMAc) homogeneous solutions. The acylation reactions were conducted at room temperature using dicyclohexylcarbodiimide (DCC) as a condensation agent and 4-dialkylaminopyridine (4-[N,N-dimethylamino-] or 4-pyrrolidino-pyridine, DMAP or PP) as a catalyst. A reaction mechanism is proposed based on experimental evidence. The acylated cellulose derivatives obtained from CRA, MAA, or their anhydrides exhibit poor solubility in organic solvents. Side reactions, e.g., the Michael addition, likely occur at the high temperatures required for reaction of these acyl groups. However, acylation of cellulose with VAA, FAME, and CINA is facile with derivatives readily soluble in DMSO. The structures of these derivatized celluloses were characterized with FTIR and 1 H-NMR spectroscopy and degrees of substitution were calculated.

Design of fluorescent substrates and potent inhibitors of CYP73As, P450s that catalyze 4-hydroxylation of cinnamic acid in higher plants.

Abstract: CYP73As are the major functional cytochromes P450 in higher plants. Several of them have been shown to catalyze the 4-hydroxylation of cinnamic acid, the first oxidative step in the synthesis of lignin, flavonoids, coumarins, and other phenylpropanoids. The coding sequence for CYP73A1, the enzyme from Helianthus tuberosus, has been isolated and expressed in yeast. Previous studies indicate that the yeast-expressed enzyme is capable of metabolizing cinnamic acid and several small, planar molecules but with low efficiency. Using this we further examined how CYP73A1 could bind and metabolize a set of possible alternate substrates. We show here that naphthalenes, quinolines, and indoles substituted with an aldehyde, a carboxylic, or a sulfonic acid group make good ligands and substrates for CYP73A1. The best ligands are hydroxynaphthoic acids, which show higher affinity than cinnamate. Naphthalene, 2-naphthol, and molecules with two-carbon side chains, such as natural and synthetic auxins, are not substrates of this enzyme. Methyl-2-naphthoate and 2-hydroxy-1-naphthoic acid are strong ligands of CYP73A1 but are not metabolized. Uncoupling and low spin conversion induced by these compounds suggest that their positioning in the heme pocket is inadequate for catalysis. These compounds can act as potent inhibitors of the second step of the phenylpropanoid pathway, the first described so far. The molecule which most closely mimics cinnamic acid, 2-naphthoic acid, is metabolized with a catalytic turnover and efficiency similar to those measured with the physiological substrate. Using this compound we designed a fluorometric assay to measure the catalytic activity of CYP73As. This assay was then used to monitor the CYP73As activity in microsomes from transgenic yeast and several plant species.

Free and glucosylated phenolics, phenol β-glucosyltransferase activity and membrane permeability in cucumber roots affected by derivatives of cinnamic and benzoic acids

Abstract: Seven-day-old seedlings of cucumber (Cucumis sativus L.) cv. Wisconsin were treated with 0.01, 0.1 and 0.5 mM solutions of derivatives of cinnamic acid (ferulic and p-coumaric acids) and benzoic acid (p-hydroxybenzoic and vanillic acids) as stress factors. In cucumber roots phenolics (free and glucosylated), phenol β-glucosyltransferase (E.C. 2.4.1.35) activity as well as membrane permeability were examined. The most intensive glucosylation took place in the first hour of stress duration in roots treated with 0.01 mM ferulic and p-coumaric acids and with 0.01 and 0.1 mM p-hydroxybenzoic and vanillic acids. At these concentrations a high phenol β-glucosyltransferase activity was found. The deterioration of capacity for phenolic glucosylation as well as the decrease of the phenol β-glucosyltransferase was observed at the higher concentrations. It was associated with increased membrane permeability.

Lipase-catalyzed Synthesis of Arbutin Cinnamate in an Organic Solvent and Application of Transesterification to Stabilize Plant Pigments

Abstract: Arbutin cinnamate was synthesized from arbutin (4-hydroxy-phenyl β-D-glucopyranoside) and vinyl cinnamate by regioselective transesterification with a bacterial lipase in acetonitrile. The product was identified by NMR and FAB-MS analyses. These spectra showed that one ester bond was formed between the primary alcohol moiety of the D-glucose of arbutin and the carboxyl residue of cinnamic acid. Furthermore, plant pigments such as isoquercitrin (quercetin 3-O-β-D-glucopyranoside) and callistephin (pelargonidin 3-O-β-D-glucopyranoside) were also converted to their corresponding cinnamate esters in the same manner.

Chemical characterization and spectroscopic analysis of the solubilization products from wheat straw produced by Streptomyces strains grown in solid-state fermentation.

Abstract: The effects of two extraction procedures on the yield and properties of APPL (acid-precipitable polymeric lignin, or solubilized lignocellulose) produced by four streptomycetes during growth in solid-state fermentation were examined. When APPL was extracted with NaOH (0.1 M) rather than distilled water, yields increased threefold, with Streptomyces chattanoogensis exhibiting maximum solubilization levels [163 mg product (g straw)-1]. Alterations in the characteristics of APPL obtained during extraction with NaOH were detected using cross-polarization and magic-angle spinning (CPMAS) 13C NMR and IR spectroscopy and by GC-MS analysis after CuO oxidation, with the most significant changes detected in the cinnamic acid and lignin moieties. When APPL was extracted with NaOH, ester links between hemicellulose and lignin and between hemicellulose and cinnamic acid were cleaved, resulting in a decrease in the alkyl and carbonyl groups attached to lignin, enabling greater solubilization. Yields of APPL extracted with water were lower, but spectral characterization of this APPL suggested a possible role for actinomycete peroxidases and phenolic acid esterases in lignin solubilization. For industrial solubilization of lignocellulose, a possible role for the application of streptomycetes, or their enzymes, in alkali extraction is suggested as a means of increasing solubilization levels.

Isolation and Characterization of Cinnamic Acid with Antimicrobial Activity from Needle of Pinus densiflora

Abstract: The ethyl acetate (EtOAc) extracts from needles of Pinus densiflora were showed antimicrobial activities against bacteria, yeast and fungi. The antimicrobial active substance of EtOAc extracts were successively purified with solvent fractionation, silica gel adsorption column chromatography and Sephadex LH-20 column chromatography. The purified active substance was isolated as crystals and identified as benzoic acid by . The amount of benzoic acid was 0.608 mg per gram of fresh needle of Pinus densiflora.

Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

Abstract: A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an α-truxillate-type cyclobutane pho...

Accumulation of ferulic acid in cell cultures of Ajuga pyramidalis metallica crispa

Abstract: Cell cultures of Ajuga pyramidalis Metallica Crispa accumulate ferulic acid, a potent antioxidant cinnamic acid. Most of the ferulic acid was found in a soluble form in the cultures. Maximum accumulation of ferulic acid was found in highly pigmented cultures (138 mg/100 g of fresh weight). The leaves from greenhouse-grown plants had lower levels of ferulic acid (24 mg/100 g of fresh weight) compared to the cultures. A close relationship was observed between anthocyanin and ferulic acid accumulation in the cultures. Supplementation with gibberellic acid, a specific anthocyanin inhibitor, at 10, 100, and 1000 μM reduced the levels of both anthocyanins and ferulic acid in the cultures. Keywords: Ajuga pyramidalis; cell culture; ferulic acid

Modulation of tumour necrosis factor‐α‐induced cytotoxicity by polyphenols

Abstract: The effects of several aromatic compounds on tumour necrosis factor-α (TNF)-induced cytotoxicity in murine fibroblast L929 cells were studied. Those phenolics which bear the O -dihydroxy aromatic structure (catechols), i.e. caffeic acid, catechol, 3,4-dihydroxybenzoic acid, dopamine and noradrenaline effectively inhibited TNF-induced cytotoxicity in a concentration dependent manner. Related compounds (cinnamic acid, 3,4-dimethoxycinnamic acid, 2,4-dihydroxybenzoic acid, ferulic acid, 3-hydroxy-4-methoxybenzoic acid and p -hydroxybenzoic acid) which lack the catecholic functional group failed to protect cells from TNF cytotoxicity. All concentrations of catechols which effectively inhibited the TNF-induced cytotoxicity were also protective as a post treatment, suggesting an effect at some step(s) in the TNF-signal transduction pathway following receptor activation. © 1997 John Wiley & Sons, Ltd.

Beautifully whitening agent and beautifully whitening

Abstract: PROBLEM TO BE SOLVED: To obtain a beautifully whitening agent capable of being easily dissolved or dispersed in water, oils or other media and free from a specific smell by including cinnamic acid (derivative) and cyclodextrin. SOLUTION: This beautifully whitening agent contains (A) cinnamic acid (derivative) and (B) cyclodextrin(CD) in an amount of 1-10 moles per mole of the component A preferably in the form of their clathrate compound. The cinnamic acid derivative of component A is preferably a p-methoxycinnamic acid ester, caffeic acid, etc. The component B is preferably α, β and γ-CDs produced in the presence of a CD-producing enzyme produced from a microorganism and maltosylated α, β and γ-CDs. The components A and B are preferably contained in amounts of 0.01-20 wt.% and 0.1-15 wt.%, respectively, in the beautifully whitening agent. COPYRIGHT: (C)1998,JPO

Synthesis of substituted cinnamoyl-tyramine derivatives and their platelet anti-aggregatory activities

Abstract: Substituted cinnamoyl-tyramine derivatives were synthesized by DCC-coupling of substituted cinnamic acid with tyramine or tyramine methyl-1-ether to evaluate PAF-receptor binding antagonistic activities and inhibitory activities on PAF-induced platelet aggregation with interest on structure-activity relations. The results show that 3,4-dimethoxy-cinnamoyl tyramine-amide or its methyl ether have significant PAF-receptor binding antagonistic activity and platelet anti-aggregatory activities.

Comparison of Antioxidative Activity of Phenolic Compounds in Boreava orientalis and Their Related Compound

Abstract: Examination was made by the effects of antioxidative activity of phenolic compounds isolated from Boreava orientalis fruit (Cruciferae) and related compounds on free radical-oxidation of methyl linolate in solution. Based on methyl linolate hydroperoxide production using 2, 2'-azobis (2, 4-dimethyl valeronitrile) (AMVN) as the radical initiator. Dihydroxybenzoic acids and phenylpropanoids, particularly cinnamic acid derivatives, were shown to be strong antioxidatnts.

Study on the antioxidant activity of cholesteryl esters of some phenolic acids by chemiluminescence

Abstract: Four cholesteryl esters of cinnamic acid derivatives, cholesteryl 2″-hydroxycinnamate, cholesteryl 3″-hydroxycinnamate, cholesteryl 4″-hydroxy-cinnamate and cholesteryl 3″,4″-dihydroxycinnamate, as well as cholestanyl 2″-hydroxycinnamate, which can be used as potential inhibitors of lipids oxidation, have been investigated for their radical scavenging efficiency by a chemiluminescence method. The rate constants of inhibition( k 1nH ) were determined in a model reaction of an initiated oxidation of tetraline at 353 K. The chemiluminescent results show that the four cholesteryl esters are efficient radical acceptors, and that among them, cholesteryl 3″,4″-dihydroxycinnamate is a particularly efficient radical scavenger with an inhibition rate constant of 1.8 × 10 5 dm 3 mol 1 s −1 .

Cinnamic acid derivatives

Abstract: (57) Abstract: The present invention provides a compound of formula I Compound or a pharmaceutically acceptable salt thereof of the class represented by the pharmaceutical compositions comprising a compound of formula I, and alpha

Production of phenolic acid saccharide ester

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound useful as a tumor necrosis factor production inhibitor having an antiinflammatory action, etc., by reacting a phenolic acid alcohol ester with a saccharide in the presence of an enzyme capable of cleavable the ester bond in a solvent. SOLUTION: A phenolic acid alcohol ester in which the phenolic acid- corresponding site of the phenolic acid alcohol ester is ferulic acid residue, p-coumaric acid residue, caffeic acid residue, sinapinic acid residue or cinnamic acid residue (e.g. trichloroethyl ferulate) is reacted with a saccharide such as an acidic saccharide, a neutral saccharide, an aminosaccharide or an oligo saccharide or polysaccharide containing these monosaccharides as constituting saccharides in the presence of an enzyme capable of cleaving the ester bond (e.g. lipase) in a solvent (e.g. pyridine) to obtain the objective phenolic acid saccharide ester useful as a tumor necrosis factor production inhibitor having an antiinflammatory action, etc.