Trans-coumaric Acid Research Articles

ANTIOXIDANT ACTIVITY AND PHENOLIC COMPOUNDS IN CACHICHÍN NUTS (Oecopetalum mexicanum Greenm. & C.H. Thomps.) EXPOSED TO DIFFERENT THERMAL TREATMENTS

The cachichín tree (Oecopetalum mexicanum Greenm. & C.H. Thomps.), present in the Sierra de Misantla, Veracruz, Mexico, produces fruits with bitter-tasting nuts, traditionally consumed as a healthy snack, boiled or toasted. These nuts have significant concentrations of lipids, proteins, fiber, and ash, although their antioxidant capacity and phenolic profile in response to different thermal treatments have not been explored. The objective of this study was to analyze the antioxidant activity and determine the concentrations of free and total phenolic compounds in the raw (T1) cachichín nuts and nuts subjected to different thermal treatments, including boiled (T2), commercial toast (T3), and controlled toast at laboratory level (T4). The nuts subjected to controlled toasting (T4) showed the highest mean in antioxidant activity (20.73 %), followed by commercial toasting (T3; 19.41 %) and raw nuts (T1; 15.38 %), while the boiled nuts (T2) showed the lowest values (9.68 %). Regarding free phenols, the highest concentration of catechin was found in raw nuts (T1), with 278.91 mg g-1 fresh biomass weight (FBW). Trans-ferulic acid was more abundant in the toasting treatments (7.09 ng g-1 FBW in T3 and 6.13 ng g-1 FBW in T4) compared to raw nuts (T1; 3.77 ng g-1 FBW). Trans-coumaric acid was higher with controlled toasting (T4; 2.67 ng g-1 FBW). In terms of total phenols, raw nuts (T1) showed the highest concentration of catechin (613.95 mg g-1 FBW), while chlorogenic acid was more abundant in commercial toasting (T3; 89.12 ng g-1 FBW). Total trans-ferulic acid was higher in boiled and toasted nuts (T2, T3, and T4), while trans-coumaric acid was highest in controlled toasting (T4) and lowest in boiled (T2). Cachichín nuts are concluded to contain phenolic compounds with beneficial functions, whose concentrations can be altered in response to the thermal treatments applied.

Anti-cancer Effect and Active Phytochemicals of Houttuynia cordata Thunb. against Human Breast Cancer Cells.

Houttuynia cordata Thunb (HCT) is a medicinal herb used in Southeast Asia. Aim of this work: This study aimed at investigating the cytotoxicity of this plant extract and fractions towards human breast cancer MDA-MB-231 and MCF-7 cells. HCT's phytoactive compounds are determined. Cell viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The mode of cell death was measured by staining with annexin V-FITC and propidium iodide (PI) employing flow cytometry technique. The oxidative stress was measured by using 2',7'-dihydrodichlorofluorescein diacetate (DCFH-DA) and dihydroethidium (DHE+) fluorescent probes and using a fluorescence microplate reader. HCT phytochemicals were characterized by high performance liquid chromatography (HPLC). The proliferation of MDA-MB-231 and MCF-7 cells was dramatically decreased by the crude extract and individual fraction of HCT. Ethyl acetate was the solvent fraction with the highest toxicity against MCF-7 cells, followed by dichloromethane, crude, and hexane fractions, respectively, whereas in MDA-MB231 cells, dichloromethane, crude, hexane, and ethyl acetate fractions each had the strongest impact, respectively. The methanol fraction had no effect on either cell line up to 200 μg/ml. The extract and fractions were less harmful to the NIH3T3 normal murine fibroblast cell line. The mode of both cell death was apoptosis evidenced by the increase of cell population stained with annexin V-FITC and PI. The fluorescence probes of both DCFH-DA and DHE in MDA-MB-231 cell line were enhanced. Phenolic acids included chlorogenic acid (CA), gallic acid (GA), transcoumaric acid (TCA), vanillic acid (VA), and syringic acid (SA), as well as flavonoids like quercetin and rutin, were identified as the active phytochemicals in the crude and fractions by using HPLC method. MDA-MB-231cells underwent apoptosis via oxidative stress when induced with HCT hexane fraction. Phenolic acids and flavonoids were identified in HCT's extract and fractions.

Antioxidant Activity, Phenolic Composition, and Hormone Content of Wild Edible Vegetables

Wild edible plants have been used since antiquity as folk medicine and as preservatives in foods. This study aimed to determine the antioxidant activities, phenolic compounds, and hormone contents of 12 species of edible wild plants belonging to 9 families, which are consumed as vegetables by the local people at Ergan Mountain in Erzincan in Turkey. Polygonum cognatum and Malva neglecta were determined to have more antioxidant enzyme activity, more phenolic compounds, and higher hormone content than the other species. The highest catalase (CAT), peroxidase (POD), glutathione reductase (GR), glutathione-s-transferase (GST) values for P. cognatum were determined as 45.12, 94.83, 36.76, and 1218.35 EU g−1, respectively. The highest superoxide dismutase (SOD) and ascorbate peroxidase (AxPOD) content for M. neglecta were determined as 97.53 EU g−1 and 81.93 EU g−1, respectively. P. cognatum is the species in which the highest levels of the hormones indolacetic acid (IAA), gibberellic acid (GA), salicylic acid (SA), cytokinin, zeatin and jasmonic acid were detected. The highest levels of caftaric acid (CA), catechin (CAE), ferulic acid (FA), malvidin-3-o-glucoside (MG), myricetin (MYR), rutin (RT), trans-coumaric acid (TPCA), tyrosol (TY), and vanilic acid (VA) compounds were found in M. neglecta. It was determined that Falcaria vulgaris species had the highest levels of ferulic acid (FA) and quercetin (QUE) phenolics. The results show that edible wild vegetables consumed and studied by the people of the region are an important source of natural antioxidants. The possibilities of using these wild plants as functional foods should be investigated.

Seven compounds from Portulaca oleracea L. and their anticholinesterase activities

A novel lignan, identified as 4-(3,4-dihydroxyphenyl)-6,7-dimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one, named oleralignan A (1), together with six known compounds, loliolide (2), isololiolide (3), dehydrololiolide (4), daphnetin (5), esculetin (6), and trans-coumaric acid methyl ester (7) was obtained from Portulaca oleracea L., while compounds 3, 4, 6, and 7 were isolated from the plant for the first time. Their structures were elucidated using spectroscopic methods, including one- and two-dimensional NMR and high-resolution electrospray ionization time-of-flight mass spectrometry. In addition, the results of activity assay demonstrated that compounds 1-7 have anticholinesterase activities.

P-COUMARATES OF BETULA PENDULA (BETULACEAE) VEGETATIVE BUDS SESQUITERPENE ALCOHOLS

The composition of coumarates sesquiterpene alcohols of Betula pendula Roth. birch vegetative buds was determined. Fraction was isolated from buds extract by preparative liquid chromatography. The extract was isolated by sequential extraction of an alcoholic extract of the buds with methyl tert-butyl ether. The new sesquiterpene derivatives were first detected in the birch vegetative buds. The structure of 6-hydroxyisocaryophyllene [(1R,4Z,6R,9S)-8-methylene-11,11-dimethylbicyclo[7.2.0]undec-4-ene-6-ol] trans-p-coumarate isolated from the birch buds was determined by NMR spectroscopy. The physico-chemical characteristics and NMR data of 6-hydroxyisocaryophyllene p-coumarate and others coumarates are demonstrated. The gas chromatographic retention indices of all identified compounds were determined. Birch buds contain derivatives of trans-coumaric acid. The antimicrobial activity of sesquiterpene alcohols coumarates was evaluated. The antimicrobial activity of sesquiterpene alcohols coumarates in relation to the following microorganisms: Escherichia coli, Proteus mirabilis, Staphylococcus aureus, Staphylococcus pneumonia and Klebsiella pneumonia was evaluated. The fraction of sesquiterpene alcohols coumarates showed activity against Staphylococcus epidermidis.

Light-responsive multillamellar vesicles in coumaric acid/alkyldimethylamine oxide binary systems: Effects of surfactant and hydrotrope structures

Herein, we report a series of novel light-responsive multilamellar vesicles based on the surfactant/hydrotrope binary systems. The phase behaviors of alkyldimethylamine oxide (CmDMAO, m=10, 12, 14) and trans-coumaric acid (trans-CA) isomerides, including trans-ortho-coumaric acid (trans-OCA), trans-meta-coumaric acid (trans-MCA) and trans-para-coumaric acid (trans-PCA), show that the multilamellar vesicle (MLV) formation region is commonly presented in the trans-CA/CmDMAO systems except trans-PCA/C12DMAO. Moreover, the molecular structures of CmDMAO and trans-CA affect the multilamellar vesicle formation region significantly. Generally speaking, the bigger the m, the larger the MLV region. Various techniques such as rheology, polarized optical microscopy (POM), 1H NMR, 2H NMR, cryogen transmission electron microscopy (cryo-TEM) and freeze-fracture transmission electron microscopy (FF-TEM) are used to characterize the aggregate structures. The multilamellar vesicles can transform into a homogeneous and transparent micelle phase or a two-phase system in the trans-OCA/CmDMAO binary systems under UV light irradiation, which depends on the chain length of CmDMAO and the molar ratio of [trans-OCA]/[CmDMAO]. Specifically, the light-stimuli response of multilamellar vesicles in the trans-OCA/C12DMAO system is representatively studied in detail. UV–vis spectra and 1H NMR measurements illustrate that the light-induced trans-OCA to cis-OCA isomerization is essential during the transitions and the light-induced two-phase formation is attributed to the enrichment of surfactants, because the trans-cis isomerization can not only strengthen the hydrophilicity of cis-OCA but also increase the steric hindrance between cis-OCA and C12DMAO, and thereby altering the morphology of aggregate and the rheological response of bulk phase significantly.

Improved Photobactericidal Activity of Ultraviolet-A Light in Combination with Isomerizable p-Coumaric Acid Derivatives.

In order to improve the photobactericidal activity of ultraviolet-A (UV-A) mediated by reactive oxygen species (ROS), the present study focused on trans-coumaric acid (trans-CA), which is isomerized by UV-A. Generation of ROS was expected during the isomerization of trans-CA. Trans-CA derivatives, in which the carboxyl group was modified with a methyl, n-butyl or phenyl group, thereby changing the interaction with the cellular membrane by quenching the anionic properties of the carboxyl group and changing the UV adsorption properties, were used. The photobactericidal activities of trans-CA derivatives were evaluated by using UV-A light (wavelength 350 to 385 nm). The number of surviving Escherichia coli NBRC12713 was determined by colony-forming assay. Derivative 4c, which was esterified with a phenyl group, reduced survival by more than 5.0-log at a dose of 7.4 J/cm(2) and by 3.2-log at a dose of 4.9 J/cm(2). This synergistic activity may have been caused by the absorption of photon energy from UV-A, which is attributable to the UV spectrum of 4c. The photobactericidal activity was comparable to that of riboflavin, a known photo-activated agent. Isomerized molecules serve as a promising lead for improving the photobactericidal activity of UV-A by activating molecule-mediated ROS generation.

Cloning and characterization of a novel tyrosine ammonia lyase-encoding gene involved in bagremycins biosynthesis in Streptomyces sp.

Tyrosine ammonia lyase catalyzes the deamination of L: -tyrosine to trans-coumaric acid. A novel tyrosine ammonia lyase-encoding gene, bagA, was cloned and sequenced from bagremycins-producing strain Streptomyces sp. Tü 4128 whose protein product contains a Ala-Ser-Gly segment in the active site. The disruption of the bagA gene abolished trans-coumaric acid and bagremycins production. trans-coumaric acid restored the formation of bagremycin A in the mutant, but not bagremycin B. Thus, trans-coumaric acid is a precursor for biosynthesis of bagremycins and the bagA gene codes for tyrosine ammonia lyase to synthesize trans-coumaric acid. This is a novel bacterial tal gene reported in actinomycetes for the second time and for the first time in a Streptomyces sp.

Polarized Emission of Wholly Aromatic Bio-Based Copolyesters of a Liquid Crystalline Nature

A novel thermotropic liquid crystalline polymers poly{3-benzylidene amino-4-hydroxybenzoic acid (3,4-BAHBA)-co-trans-4-hydroxycinnamic acid (4HCA: trans-coumaric acid)} (Poly(3,4-BAHBA-co-4HCA)), was synthesized by the thermal polycondensation of 4HCA and 3,4-BAHBA, which was synthesized by a reaction of 3-amino-4-hydroxybenzoic acid (3,4-AHBA) with benzaldehyde. When the 4HCA compositions of Poly(3,4-BAHBA-co-4HCA)s were above 55 mol%, the copolymers showed a nematic, liquid crystalline phase. Differential scanning calorimetry (DSC) measurements of the copolymers showed a high glass transition temperature of more than 100 °C, sufficient for use in engineering plastics. Furthermore, the copolymers showed photoluminescence in an N-methylpyrrolidone (NMP) solution under ultraviolet (UV) light with a wavelength of 365 nm. Oriented film of Poly(3,4-BAHBA-co-4HCA) with a 4HCA composition of 75 mol% emitted polarized light, which was confirmed by fluorescent spectroscopy equipped with parallel and crossed polarizers.

A novel sesquiterpenoid from the leaves of Cinnamomum subavenium

A novel sesquiterpenoid, subamol ((3-methoxy-5H-9,10-dihydroxybenzo[3,4]cyclohepta[1,2-f])inden-7-yl)methanol)) (1), along with six compounds, including one ionone: (+)-abscisic acid (2); and five benzenoids: syringaldehyde (3), trans-coumaric acid (4), cis-coumaric acid (5), vanillic acid (6), and p-hydroxybenzoic acid (7), were isolated from the leaves of Cinnamomum subavenium Miq (Lauraceae). These compounds were identified and characterized by physical and spectral evidence.

Polyprenol from the Whole Plants of Leucaena leucocephala

Ficaprenol-11 (polyprenol) (1), squalene (2), lupeol (3), ?-sitostenone (4), trans-coumaric acid (5), cis-coumaric acid (6) pheophytin-a (7), pheophorbide a methyl ester (8), methyl-132-hydroxy-(132-S)- pheophorbide-b (9) and aristo-phyll-C (10) were isolated from the whole plants of Leucaena leucocephala (Leguminosae). Among them, 1 and 2 was found for the first time from this species. The structure of these compounds were characterized and identified by spectra analyses.

Enhanced effects of lithocholic acid incorporation into liquid-crystalline biopolymer poly(coumaric acid) on structural ordering and cell adhesion

A novel thermotropic liquid-crystalline biocopolymer, poly{ trans-4-hydroxycinnamic acid (4HCA: trans-coumaric acid)- co-lithocholic acid (LCA)}, was synthesized by a thermal polycondensation of 4HCA and LCA. When the LCA composition of P(4HCA- co-LCA) was 0, 5, 7, 23, 27, and 45 mol%, the copolymers showed a nematic liquid-crystalline phase. The melting point of the copolymers was 120–250 °C depending on the LCA composition, and showed a maximum at 7 mol%. Wide angle X-ray diffraction (WAXD) analyses showed a typical diffraction pattern of a hexagonal arrangement for 0, 7, 23, and 27 mol% LCA composition, which were cooled from a nematic melt. The other polymers showed no distinct diffraction. In particular, the copolymer of 7 mol% LCA composition showed four distinct diffractions corresponding to spacings with a reciprocal ratio of 1, √3, 2, and √7, indicating the highest structural ordering of all copolymers prepared here. The results of the cell adhesion and static contact angle tests suggest that the 7 mol% LCA composition copolymer had the highest hydrophobicity and cell adhesion ability, which was easily controlled by altering in feed. We conclude that the structural ordering may have a significant correlation with cell adhesion activity.

Identification of six phenylpropanoids from garlic skin as major antioxidants.

The extract of garlic skins (peels) showed strong antioxidant activity, and some responsible constituents were isolated and identified. Garlic (Allium sativum L.) has been used as an herbal medicine, but there is no report on the health benefits of the skin or peel. In this study, the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity of garlic skin extract was evaluated. Using chromatographic techniques, the active constituents were isolated and subsequently identified. Analyses by high-performance liquid chromatography coupled with a photodiode array detector (HPLC-PDA) suggested that these compounds were phenylpropanoids, which had a characteristic absorbance at 300-320 nm. Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance analyses allowed the chemical structures of the isolated constituents to be postulated. The proposed compounds were subsequently synthesized and compared with the constituents in the extract using HPLC-PDA and LC-MS. N-trans-Coumaroyloctopamine, N-trans-feruloyloctopamine, guaiacylglycerol-beta-ferulic acid ether, and guaiacylglycerol-beta-caffeic acid ether were identified as were trans-coumaric acid and trans-ferulic acid. Also, the antioxidant activities of these compounds were determined.

Oxidative cross-linking of corn bran hemicellulose: formation of ferulic acid dehydrodimers

The aim of this study was to investigate the nature and extent of ferulate dehydrodimer cross-links formed during peroxide and peroxidase-catalysed gelation of an arabinoxylan ferulate polysaccharide from American Corn Bran ( Zea mays L.). Alkali-soluble phenolics from the arabinoxylan (AXF) and its gel (AXFG), were identified and quantified by HPLC. AXF was rich in trans-ferulic acid and contained small quantities of 8-0-4′-diferulic acid ((Z)-β-(4-(( E)-2-carboxyvinyl)-2-methoxyphenoxy)-4-hydroxy-3-methoxycinnamic acid; 8-0-4′-DiFA); 8,5′-diferulic acid benzofuran form ( trans-5-(( E)-2-carboxyvinyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid; 8,5′-DiFA benzofuran form); and 5,5′-diferulic acid (( E, E)-4,4′-dihydroxy-5,5′-dimethoxy-3′-bicinnamic acid; 5,5′-DiFA) in addition to vanillin and trans-coumaric acid. Gel formation resulted in a considerable increase in the levels of 8-0-4′-DiFA, 8,5′-DiFA benzofuran form and the appearance of significant quantities of 8,8′-diferulic acid open form (4,4′-dihydroxy-3,3′-dimethoxy-β, β′-bicinnamic acid; 8,8′-DiFA); 8,5′-diferulic acid open form (( E, E)-4,4′ dihydroxy-3,5′-dimethoxy-β,3′-bicinnamic acid; 8,5′-DiFA) and 8,8′-diferulic acid aryltetralin form ( trans-7-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-1,2-dihydronaphthalene-2.3-dicarboxylic acid; 8,8′-DiFA aryl form). The results confirm that peroxidase/peroxide-induced gelation results from oxidative cross-linking of ferulic acid moieties.

Antimutagenicity of Tochu tea (an aqueous extract of Eucommia ulmoides leaves): : 1. The clastogen-suppressing effects of Tochu tea in CHO cells and mice

The suppressing effect of crude extracts of Tochu tea, an aqueous extract of Eucommia ulmoides leaves and a popular beverage in Japan, on the induction of chromosome aberrations in CHO cells and mice was studied. When CHO cells were treated with Tochu tea crude extract after MMC treatment, the frequency of chromosome aberrations was reduced. Out of 17 Tochu tea components, 5 irridoids (geniposidic acid, geniposide, asperulosidic acid, deacetyl asperulosidic acid, and asperuloside) and 3 phenols (pyrogallol, protocatechuic acid, and p- trans-coumaric acid) were found to have anticlastogenic activity. Since the anticlastogenic irridoids had an α-unsaturated carbonyl group, this structure was considered to play an important role in the anticlastogenicity. The anticlastogenic effect of Tochu tea extracts was examined in mice using a micronucleus assay. When mice received 1.0 ml 4% Tochu tea extract by oral gavage 6 h before intraperitoneal injection of MMC, a decrease in the frequency of micronuclei was observed. This decrease was not due to a delay in the maturation of micronucleated reticulocytes.

Phenylketonuria: a new method for the simultaneous determination of plasma phenylalanine and tyrosine.

This quantitative spectrophotometric method is based on the conversion of phenylalanine and tyrosine by phenylalanine ammonia-lyase to trans-cinnamic acid and trans-coumaric acid, respectively. Neither deproteinization nor prior incubation of the sample is required, and the entire procedure can be performed in 20 minutes. The method is sensitive to 1-micromolar concentrations of the two compounds, and only 20 microliters of plasma or serum is required to determine both phenylalanine and tyrosine simultaneously. These amino acids were determined between molar ratios (phenylalanine to tyrosine) of 0.1 to 40 in the serum or plasma of healthy individuals and plasma of phenylketonuric patients.

Phenylalanine ammonia-lyase. Induction and purification from yeast and clearance in mammals.

Yeast phenylalanine ammonia-lyase (EC 4.3.1.5) catalyzes the deamination of L-phenylalanine to form trans-cinnamic acid and tyrosine to trans-coumaric acid. Maximal enzyme activity in Rhodotorula glutinis (2 units/g, wet weight, of yeast) was induced in late-log phase (12 to 14 hours) of growth in a culture medium containing 1.0% malt extract, 0.1% yeast extract, and 0.1% L-phenylalanine. A highly purified enzyme was obtained by fractionation with ammonium sulfate and sodium citrate followed by chromatography on DEAE-cellulose and Sephadex G-200. The active preparation yielded a major component on three different polyacrylamide gel electrophoretic systems. Antisera to phenylalanine ammonia-lyase was raised in rabbits and detected by double immunodiffusion. The antigen-antibody complex was enzymatically active in vitro. The biological half-life of the enzyme was approximately 21 hours in several mammalian species (mice without and with BW10232 adenocarcinoma and B16 melanoma, rats, and monkeys) after a single injection; however, upon repeated administration, phenylalanine ammonia-lyase had a much shorter biological half-life. The onset of rapid clearance occurred earlier in tumor-bearing than in nontumor-bearing mice indicating a direct or indirect influence by the tumor on the biological half-life of phenylalanine ammonia-lyase.