methyl-caffeate and caffeic-acid

The transient disruption of membranes for the passive permeation of ions or small molecules is a complex process relevant to understanding physiological processes and biotechnology applications. Phenolic compounds are widely studied for their antioxidant and antimicrobial properties, and some of these activities are based on the interactions of the phenolic compound with membranes. Ions are ubiquitous in cells and are known to alter the structure of phospholipid bilayers. Yet, ion-lipid interactions are usually ignored when studying the membrane-altering properties of phenolic compounds. This study aims to assess the role of Ca

Topics: Antioxidants; Caffeic Acids; Chelating Agents; Esters; Hydroxybenzoates; Ions; Lipid Bilayers; Phospholipids

To explore the in-vitro and in-vivo antimalarial potential of caffeic acid and derivatives.. Two common phenolic acids (caffeic acid and chlorogenic acid) were evaluated for in-vitro and in-vivo antiplasmodial activity in comparison with some semi-synthetic derivatives that were synthesized. An in-vitro assay based on plasmodial lactate dehydrogenase activity, and the classical in-vivo 5-day suppressive test from Peters on an artemisinin-resistant Plasmodium berghei strain was used. Parasitic stage sensitivity to ethyl caffeate was determined in this work.. Our study provides evidence for an antimalarial potential of caffeic acid derivatives which are common in several medicinal plants traditionally used against malaria. It also demonstrates the possibility to use such derivatives in the treatment of malaria.

Topics: Animals; Antimalarials; Caffeic Acids; Chlorogenic Acid; Inhibitory Concentration 50; Mice; Parasitic Sensitivity Tests; Plasmodium berghei

The relationships between the hydrophilic-lipophilic balance (HLB) of antioxidants (AOs) and their distributions and efficiencies in emulsions are not fully understood. Recent reports indicate that, for series of homologous antioxidants of different hydrophobicity, the variation of their efficiency with the HLB of the AO increases with the alkyl chain length up to a maximum (C. We determined the distributions of a series of caffeic acid derivatives in intact soybean emulsions by employing a specifically designed chemical probe located in the interfacial region of the emulsion. We also determined the AO efficiencies in the very same emulsions. We demonstrate that the variation of the percentage of AO in the interfacial region of soybean oil-in-water emulsions with the AO HLB parallels that of their antioxidant efficiency.. The results provide physical evidence that the variations in the efficiency of homologous series of antioxidants in emulsions are the result of differences in their distribution. The results confirm that, with other things being equal, there is a direct relationship between the percentage of AO in the interfacial region of the emulsions and their efficiency, providing a natural explanation, based on molecular properties, of the cut-off effect. © 2016 Society of Chemical Industry.

Topics: Antioxidants; Caffeic Acids; Diazonium Compounds; Emulsions; Fat Emulsions, Intravenous; Hydrophobic and Hydrophilic Interactions; Indicators and Reagents; Kinetics; Models, Chemical; Molecular Structure; Molecular Weight; Soybean Oil; Surface-Active Agents

To investigate the chemical constituents from Xanthium mongolicum.. The constituents were isolated and purified by silicagel,Sephadex LH-20 column chromatography. Their structures were identified on the basis of spectral data and physiochemical characteristics.. Ten compounds were isolated and identified as hexadecanoic acid( 1), methyl 3, 4-dihydroxybenzoate ( 2), protocatechuic aldehyde( 3), caffeic acid methyl ester( 4), vanillic acid( 5), 4-hydroxybenzoic acid( 6), caffeic acid ethyl ester( 7), chlorogenic acid( 8), caffeic acid( 9), 3, 4-di-O-caffeoylquinic acid( 10).. Compounds 1 ~ 5,7 and 10 are isolated from this plant for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Hydroxybenzoates; Parabens; Quinic Acid; Vanillic Acid; Xanthium

The aim of this study was to evaluate the caffeic acid (1) and ester derivatives (2-10) against Candida albicans biofilm and to investigate whether these compounds are able to inhibit the biofilm formation or destroy pre-formed biofilm. Caffeic acid ester 7, cinnamic acid ester 8 and 3,4-dihydroxybenzoic acid ester 10 are more active than fluconazole, used as reference drug, both on biofilm in formation with MIC50 values of 32, 32 and 16μg/mL, respectively, and in the early stage of biofilm formation (4h) with MIC50 values of 64, 32 and 64μg/mL, respectively. These esters result also more active than fluconazole on mature biofilm (24h), especially 8 and 10 with MIC50 values of 64μg/mL.

Topics: Antifungal Agents; Biofilms; Caffeic Acids; Candida albicans; Cell Line, Tumor; Cell Survival; Humans; Microbial Sensitivity Tests

Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 μM range, potencies that were up to five-fold greater than that of CAPE (33.7±4.0 μM). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8±0.3 and 2.4±0.8 μM, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 μM. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR.

Topics: Antineoplastic Agents; Caffeic Acids; Cell Line, Tumor; Cell Proliferation; Cell Survival; Cinnamates; Humans; Male; Prostate-Specific Antigen; Prostatic Neoplasms; Receptors, Androgen; Structure-Activity Relationship

In this study, a new method was developed to prepare enantiopure caffeic acid amides by enzyme-catalyzed asymmetric aminolysis reaction. Methoxymethyl chloride (MOMCl) was first introduced as a protective and esterified reagent to obtain the MOM-protected caffeic acid MOM ester 1d. Aminolysis reaction occurred between 1d and (R, S)-α-phenylethylamine in the presence of an immobilized lipase (Novozym 435) from Candida antarctica. Compared with the methyl-protected caffeic acid methyl ester 1c, 1d as substrate improved the lipase-catalyzed reaction rate by 5.5-fold. After Novozym 435-catalyzed aminolysis reaction was established, we evaluated the effects of synthesis parameters on the catalytic activity and enantioselectivity of Novozym 435. A reaction conversion rate of 25.5% and an E value of >100 were achieved under the following optimum conditions: reaction solvent, anhydrous isooctane; reaction temperature, 70°C; reaction time, 24h; ester-to-amine substrate molar ratio, 1:40; and enzyme additive amount, 40 mg. Kinetic and thermodynamic analyses were conducted to determine the main factors affecting enantiomeric discrimination. Novozym 435 still showed 80% of its initial activity after recycling five times. Highly optically pure caffeic acid amides with an enantiomeric excess of 98.5% were finally obtained by HCl deprotection. The established enzyme-catalyzed asymmetric aminolysis method in this study might be used to prepare other caffeic acid amides.

Topics: Amides; Biocatalysis; Caffeic Acids; Enzymes, Immobilized; Fungal Proteins; Ions; Kinetics; Lipase; Solvents; Temperature

The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure-activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates. Phenylsulfonylfuroxan nitrates of FA, especially compounds 8b-8d, exhibited more potent activities in anticancer.

Topics: Antineoplastic Agents; Caffeic Acids; Cell Line, Tumor; Cell Proliferation; Coumaric Acids; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HeLa Cells; High-Throughput Screening Assays; Humans; Molecular Structure; Stereoisomerism; Structure-Activity Relationship

In our previous paper, we reported that rosmarinic acid (1) of Argusia argentea could neutralize snake venom induced hemorrhagic action. Rosmarinic acid (1) consists of two phenylpropanoids: caffeic acid (2) and 3-(3,4-dihydroxyphenyl)lactic acid (3). In this study, we investigated the structural requirements necessary for inhibition of snake venom activity through the use of compounds, which are structurally related to rosmarinic acid (1). By examining anti-hemorrhagic activity of cinnamic acid analogs against Protobothrops flavoviridis (Habu) venom, it was revealed that the presence of the E-enoic acid moiety (-CH=CH-COOH) was critical. Furthermore, among the compound tested, it was concluded that rosmarinic acid (1) (IC(50) 0.15 μM) was the most potent inhibitor against the venom.

Topics: Animals; Antivenins; Caffeic Acids; Cinnamates; Crotalid Venoms; Depsides; Hemorrhage; Humans; Male; Mice; Rosmarinic Acid; Snakes; Structure-Activity Relationship

Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID(50) value of 15.1 (11.9-19.1)micromol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.

Topics: Analgesics; Animals; Caffeic Acids; Mice; Molecular Structure; Pain; Structure-Activity Relationship

As a part of a research project on the elucidation of the chain-breaking antioxidation mechanism of natural phenols in food components, caffeic acid, a polyphenolic acid widely distributed in edible plants, was investigated. The identification and time course analysis of the antioxidation reaction products from methyl caffeate were carried out in the ethyl linoleate oxidation system. The antioxidation reaction produced a quinone derivative of methyl caffeate as an antioxidation product during the initial stage, which was identified by (13)C NMR. The quinone, however, was not the final product, and a further reaction occurred to produce several new peroxides. The isolation and structure determination of the peroxides revealed that they had tricyclic structures, which consisted of ethyl linoleate, methyl caffeate, and molecular oxygen. On the basis of the formation pathway of these products, an antioxidation reaction mechanism of methyl caffeate, including the redox reaction of the caffeate and Diels-Alder reaction of the produced peroxides, was proposed.

Topics: Antioxidants; Caffeic Acids; Kinetics; Lipid Peroxidation; Magnetic Resonance Spectroscopy; Oxidation-Reduction; Plants, Edible; Quinones

The anti-inflammatory effects of caffeic acid (CA), caffeic acid methyl ester (CM) and di-O-acetylcaffeic acid (DAC) were investigated in rats using the carrageenin-induced edema model and the antinociceptive effects of these compounds were also assessed in mice by means of the acetic acid-induced abdominal constriction test and hot plate test. CM (10mg/kg, p.o.) showed the most potent anti-inflammatory and antinociceptive effects in these animal models. To investigate the mechanism of the anti-inflammatory action, we examined the effects of these compounds on the lipopolysaccharide (LPS)-induced NO and PGE2 responses in the murine macrophage cell line, RAW 264.7. Our data indicate that CM is the most potent inhibitor of NO and PGE2 production and it also significantly decreased tumor necrosis factor-alpha (TNF-alpha) release. Consistent with these observations, the protein and mRNA expression levels of iNOS and COX-2 were found to be inhibited by CM in a dose-dependent manner. Furthermore, CM inhibited the nuclear factor-kappaB (NF-kappaB) activation induced by LPS, which was associated with the prevention of the degradation of the inhibitor kappaB, and subsequently with decreased p65 protein levels in the nucleus. Taken together, our data indicate that the anti-inflammatory properties of CM might result from the inhibition of iNOS, COX-2 and TNF-alpha expression through the down-regulation of NF-kappaB binding activity.

Topics: Active Transport, Cell Nucleus; Animals; Anti-Inflammatory Agents; Caffeic Acids; Carrier Proteins; Cells, Cultured; Cyclooxygenase 2; Esters; I-kappa B Proteins; Lipopolysaccharides; Male; Mice; Mice, Inbred ICR; Neoplasm Proteins; NF-kappa B; NF-KappaB Inhibitor alpha; Nitric Oxide; Nitric Oxide Synthase; Nitric Oxide Synthase Type II; Nucleocytoplasmic Transport Proteins; Prostaglandin-Endoperoxide Synthases; Prostaglandins E; Rats; Rats, Sprague-Dawley; RNA, Messenger; Transcription Factor RelA; Tumor Necrosis Factor-alpha