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PubMedDate not supplied

Protective effects of phenolic compounds on CCl4-induced toxicity in isolated rat hepatocytes.

The protective effects of a series of phenolic compounds, phenolic acids and flavonoids on the cytotoxicity of CCl4 in rat hepatocytes were studied. A number of flavones, 7,8-dihydroxy-flavone, luteolin and hypolaetin-8-glucoside, flavonols, morin, quercetin, robinetin and gossypin, phenolic acids, gallic, caffeic and chlorogenic acids, as well as the flavane (+)-catechin significantly inhibited alanine amine transferase (ALT) release. Catechol groups are determinant for the protective activity of flavonoids and cinnamic acid derivatives, as well as the resorcinol or pyrogallol moieties in the B ring of flavonoids. In benzoic acid derivatives a pyrogallol group is required. This feature is associated with the inhibition of ALT spontaneous release.

Animals↗
PubMedDate not supplied

[Qualitative determination of flavonoids and phenol-carboxylic acids of indigene Stachys species using HPLC method].

Indigene Stachys species have a high content in interesting compounds as iridoids, but also high quantities of flavonoids and phenol-carboxylic acids. These compounds present vasorelaxing effect on smooth vascular muscle interfering with metabolic degradation of nitric oxide pathways (inhibition of peroxynitrites formation) and by inhibition of phosphodiesterase. This work shows flavonoids spectrum of 3 Stachys species using HPLC methods. We identified quercetol, rutoside, miricetin and phenol-carboxylic acids (chlorogenic, caffeic and ferulic acids).

Carboxylic Acids↗
PubMed2005

[Phenolics from traditional Chinese medicine Sargentodoxa cuneata].

AIM: To study the chemical constituents of Sargentodoxa cuneata. METHODS: To isolate compounds with chromatography technology and to elucidate their structures by spectral analysis. RESULTS: Ten phenolics were isolated from Sargentodxa cuneata and their structures were determined as 1-O-(vanillic acid )-6-O-( 3", 5"-dimethoxy-galloyl)-beta-D-glycoside (I), (-)-epicatechin (II), phydroxyphenylethanol ferulate (III), chlorogenic acid (IV), methyl chlorogenate (V), apocynin (VI), vanillic acid (VII), protocatechuic acid (VIII), 3,4-dihydroxy-phenylethanol (IX), tyrosol (X). CONCLUSION: Compound I is new compound, compound III-VI and VIII-X were isolated from Sargentodoxa cuneata for the first time.

Acetophenones↗
PubMed1982

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid.

Ferulic, caffeic, chlorogenic, and ellagic acids, four naturally occurring plant phenols, inhibit the mutagenicity and cytotoxicity of (+/-)-7beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P 7,8-diol-9,10-epoxide-2), the only known ultimate carcinogenic metabolite of benzo[a]pyrene. The mutagenicity of 0.05 nmol of B[a]P 7,8-diol-9,10-epoxide-2 in strain TA100 of Salmonella typhimurium is inhibited 50% by incubation of the bacteria and the diol epoxide with 150 nmol of ferulic acid, 75 nmol of caffeic acid, 50 nmol of chlorogenic acid or, most strikingly, 1 nmol of ellagic acid in the 0.5-ml incubation mixture. A 3-nmol dose of ellagic acid inhibits mutation induction by 90%. Ellagic acid is also a potent antagonist of B[a]P 7,8-diol-9,10-epoxide-2 in Chinese hamster V79 cells. Mutations to 8-azaguanine resistance induced by 0.2 muM diol epoxide are reduced by 50% when tissue culture media also contains 2 muM ellagic acid. Similar to results obtained with the bacteria, ferulic, caffeic, and chlorogenic acids are approximately two orders of magnitude less active than ellagic acid in the mammalian cell assay. The antimutagenic effects of the plant phenols result from their direct interaction with B[a]P 7,8-diol-9,10-epoxide-2, because a concentration-dependent increase in the rate of diol epoxide disappearance in cell-free solutions of 1:9 dioxane/water, pH 7.0, is observed with all four phenols. In parallel with the mutagenicity studies, ellagic acid is 80-300 times more effective than the other phenols in accelerating the disappearance of B[a]P 7,8-diol-9,10-epoxide-2. Ellagic acid at 10 muM increases the disappearance of B[a]P 7,8-diol-9,10-epoxide-2 by approximately 20-fold relative to the spontaneous and hydronium ion-catalyzed hydrolysis of the diol epoxide at pH 7.0. Ellagic acid is a highly potent inhibitor of the mutagenic activity of bay-region diol epoxides of benzo[a]pyrene, dibenzo[a,h]pyrene, and dibenzo[a,i]pyrene, but higher concentrations of ellagic acid are needed to inhibit the mutagenic activity of the chemically less reactive bay-region diol epoxides of benz[a]anthracene, chrysene, and benzo[c]phenanthrene. These studies demonstrate that ellagic acid is a potent antagonist of the adverse biological effects of the ultimate carcinogenic metabolites of several polycyclic aromatic hydrocarbons and suggest that this naturally occurring plant phenol, normally ingested by humans, may inhibit the carcinogenicity of polycyclic aromatic hydrocarbons.

Animals↗
PubMed2002

Effects of anthocyanins and other phenolic compounds on the production of tumor necrosis factor alpha in LPS/IFN-gamma-activated RAW 264.7 macrophages.

Flavonoids have been reported to demonstrate their benefits in lowering oxidative stress and beneficial effects on cardiovascular and chronic inflammatory diseases. Common phenolic compounds, including phenolic acids, flavonols, isoflavones, and anthocyanins, present in fruits, vegetables, and grains were investigated for their effects on the production of tumor necrosis factor alpha (TNF-alpha) in LPS/IFN-gamma-activated RAW 264.7 macrophages. Gallic acid and (+)-catechin showed small but significant effects, whereas chlorogenic acid had no effect on TNF-alpha production. The flavonol quercetin inhibited TNF-alpha production, but kaempferol and myricetin induced the secretion of TNF-alpha. The isoflavone genistein was an inhibitor of TNF-alpha, whereas daidzein induced TNF-alpha production. Glycosylation of genistein changed its inhibitory effects to TNF-alpha induction, and glycosylation of daidzein had no effect on its activity. Anthocyanidins/anthocyanins and anthocyanin-rich extracts induced TNF-alpha production and acted as modulators of the immune response in activated macrophages. This is the first study to report the effects of anthocyanins and berry extracts on TNF-alpha production.

Animals↗
PubMed2001

[Protective effects of organic acids on human vascular endothelial cells].

OBJECTIVES: In order to examine if organic acids (OA), a kind of natural food components, will prevent from atherosclerosis formation, the effects of four OA, namely chlorogenic acid (CHA), ascorbic acid (AA), citric acid (CA), and malic acid (MA) on human vascular endothelial cells were studied. METHODS: Primary human umbilical vein endothelial cells (EC) were cultured, and the changes of cell morphology, cell growth, lactate dehydrogenase (LDH) released from cells were measured when EC was incubated with oxidized low density lipoprotein (oxLDL) in the presence or not of four OA added at three different conditions, i.e. before 4 hours oxLDL added, at the same time as oxLDL added, and after 3 hours oxLDL added, as well as at the indicated doses (10, 20 or 40 mg/L). RESULTS: The EC survival rate of the oxLDL control group was lower (P < 0.01) and LDH release rate was higher (P < 0.01) than those of normal control group. CHA, AA, CA and MA protected EC from damage caused by oxLDL when they were added before and/or at the same time of oxLDL, but the same beneficial effects of these four OA added after oxLDL were not observed. The EC survival rates of CHA + oxLDL and AA + oxLDL groups in three doses were higher (P < 0.05) and the LDH release rates were lower (P < 0.05) in a dose-effect manner when compared with those of oxLDL control group, respectively. Similar results were found in the CA + oxLDL and MA + oxLDL of the high dose groups. CONCLUSION: Four tested OA could effectively prevent EC from damage induced by oxLDL. CHA and AA had the strongest effects, the next was CA, followed by MA.

Arteriosclerosis↗
PubMed2004

A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.

A new compound, 5-O-(4'-[beta-d-glucopyranosyl]-trans-feruloyl)quinic acid (GPFQ, 10), is reported from the medicinal plant goldenseal (Hydrastis canadensis). A new HPLC method is described and used to show that GPFQ is a potential marker for goldenseal roots (1.0% w/w) and rhizomes (2.3%). GPFQ was found at much lower levels in stems (<0.1%) and could not be detected in leaves. Neochlorogenic acid (9), which has not previously been reported from goldenseal, and chlorogenic acid (6) reached their highest levels in leaves (0.9% 9 and 0.5% 6). The main alkaloids, hydrastine (1) and berberine (2), were highest in rhizomes (2.8% 1 and 4.6% 2), but palmatine (5) was not found in genuine goldenseal.

Algorithms↗
PubMed1969

o-Quinones formed in plant extracts. Their reactions with amino acids and peptides.

1. The reactions of amino acids and peptides with the o-quinones produced by the enzymic oxidation of chlorogenic acid and caffeic acid have been studied manometrically and spectrophotometrically. 2. Amino acids, except lysine and cysteine, react primarily through their alpha-amino groups to give red or brown products. These reactions, which compete with the polymerization of the quinones, are followed by secondary reactions that may absorb oxygen and give products with other colours. 3. The in-amino group of lysine reacts with the o-quinones in a similar way. The thiol group of cysteine reacts with the quinones, without absorbing oxygen, giving colourless products. 4. Peptides containing cysteine react with the o-quinones through their thiol group. 5. Other peptides, such as glycyl-leucine and leucylglycine, react primarily through their alpha-amino group and the overall reaction resembles that of the N-terminal amino acid except that it is quicker. 6. With some peptides, the secondary reactions differ from those that occur between the o-quinones and the N-terminal amino acids. The colours produced from carnosine resemble those produced from histidine rather than those from beta-alanine, and the reactions of prolylalanine with o-quinones are more complex than those of proline.

Amino Acids↗
PubMed1995

Reduction of ferrylmyoglobin by dietary phenolic acid derivatives of cinnamic acid.

The reaction of dietary phenolic acid derivatives of cinnamic acid with high valence states of horse myoglobin was studied. When metmyoglobin was oxidized by hydrogen peroxide (H2O2) in the presence of the phenolic acids, ferrylmyoglobin was reduced to metmyoglobin. However, addition of the phenolic acids to a ferrylmyoglobin solution resulted in a modified metmyoglobin spectrum characterized mainly by a blue shift of the 631 nm peak and a new isosbestic point at 613 nm suggesting an irreversible modification of the hemeprotein. The efficiency and the kinetic profile of ferrylmyoglobin reduction were dependent on both the concentration and the structure of the phenolic acid. Electron-donating substituent groups in the phenol ring increased the efficiency of ferrylmyoglobin reduction whereas electron-withdrawing groups decreased it. The phenolic acids exhibiting a catechol structure were the most efficient in reducing ferrylmyoglobin. Caffeic and chlorogenic acids react faster than trolox, and caffeic acid faster than ascorbate. During the electron-transfer reactions, the phenolic acids were oxidized to quinoid forms and, in some cases, to polymer products as indicated by comparison of the ultraviolet (UV) spectra obtained in the presence of metmyoglobin/H2O2 with those recorded after oxidation of phenolic acids by horseradish peroxidase/H2O2 and catechol oxidase. The results suggest that dietary phenolic derivatives of cinnamic acid may counteract deleterious oxidations initiated by ferrylmyoglobin.

Animals↗
PubMed2002

Antiviral activity of Plantago major extracts and related compounds in vitro.

Plantago major L., a popular traditional Chinese medicine, has long been used for treating various diseases varying from cold to viral hepatitis. The aim of present study was to examine the antiviral activity of aqueous extract and pure compounds of P. major. Studies were conducted on a series of viruses, namely herpesviruses (HSV-1, HSV-2) and adenoviruses (ADV-3, ADV-8, ADV-11). The antiviral activity of EC50 was defined as the concentration achieved 50% cyto-protection against virus infection and the selectivity index (SI) was determined by the ratio of CC50 (concentration of 50% cellular cytotoxicity) to EC50. Results showed that aqueous extract of P. major possessed only a slight anti-herpes virus activity. In contrast, certain pure compounds belonging to the five different classes of chemicals found in extracts of this plant exhibited potent antiviral activity. Among them, caffeic acid exhibited the strongest activity against HSV-1 (EC50=15.3 microg/ml, SI=671), HSV-2 (EC50=87.3 microg/ml, SI=118) and ADV-3 (EC50=14.2 microg/ml, SI=727), whereas chlorogenic acid possessed the strongest anti-ADV-11 (EC50=13.3 microg/ml, SI=301) activity. The present study concludes that pure compounds of P. major, which possess antiviral activities are mainly derived from the phenolic compounds, especially caffeic acid. Its mode of action against HSV-2 and ADV-3 was found to be at multiplication stages (postinfection of HSV-1: 0-12 h; ADV-3: 0-2 h), and with SI values greater than 400, suggesting the potential use of this compound for treatment of the infection by these two viruses.

Adenoviridae↗
PubMed2006

Free radical scavenging and cytoprotective activities of phenolic antioxidants.

The free radical scavenging activities of three flavonoids (quercetin, rutin and catechin) and four hydroxycinnamic acids (caffeic, ferulic, sinapic, and chlorogenic acids) were evaluated using both oxygen radical absorbance capacity (ORAC) and lipid peroxidation inhibition capacity (LPIC) assays. The cytoprotective effects of these compounds were also measured by the degree of protection against H(2)O(2)-induced damage of human Jurkat cells. All compounds exhibited protection against H(2)O(2)-mediated cytotoxicity in a dose-dependent manner. The concentrations required to result in a 50% reduction in cell death (EC(50) value) were calculated from their dose-response curves. These ranged from 0.15-2.65 microM. Overall, the four hydroxycinnamic acids tested were less effective than the three flavonoids, and of all compounds tested, quercetin offered the strongest protection against H(2)O(2)-induced cell death. A comparison of the results showed that the ability to inhibit peroxidation of lipids in a liposomal system (LPIC) correlated well with the cytoprotective activities (EC(50)), but not with the ability to protect an aqueous fluorescent substrate in the ORAC assays. The results suggest that the behavior of antioxidants in a liposomal membrane is to some extent similar to the mechanism involved in the protection of living cells from oxidative damage.

Antioxidants↗
PubMed2006

Antioxidant flavonol glycosides from Schinus molle.

Chromatographic separation of aqueous MeOH extract of the leaves of Schinus molle L. has yielded two new acylated quercetin glycosides, named isoquercitrin 6''-O-p-hydroxybenzoate (12) and 2''-O-alpha-L-rhamnopyranosyl-hyperin 6''-O-gallate (13), together with 12 known polyphenolic metabolites for the first time from this species, namely gallic acid (1), methyl gallate (2), chlorogenic acid (3), 2''-alpha-L-rhamnopyranosyl-hyperin (4), quercetin 3-O-beta-D-neohesperidoside (5), miquelianin (6), quercetin 3-O-beta-D-galacturonopyranoside (7), isoquercitrin (8), hyperin (9), isoquercitrin 6''-gallate (10), hyperin 6''-O-gallate (11) and (+)-catechin (14). Their structures were established on the basis of chromatographic properties, chemical, spectroscopic (UV, 1H, 13C NMR) and ESI-MS (positive and negative modes) analyses. Compounds 4-9 and 11 exhibited moderate to strong radical scavenging properties on lipid peroxidation, hydroxyl radical and superoxide anion generations with the highest activities shown by 6 and 7 in comparison with that of quercetin as a positive control in vitro.

Anacardiaceae↗
PubMed2002

Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.

PURPOSE: Recent preclinical assays using animal models have shown that naturally-occurring and synthetic chemicals such as auraptene (AUR), nobiletin (NOB), hesperidin (HE), diosmin (DIO), indole-3-carbinol (I3C), 1'-acetoxychavicol acetate (ACA), 2,5-di-O-acetyl-D-1,4-glucaro-6,3-dilactone (ACE), D-glucuronic acid gamma-lactone (GL), chlorogenic acid (CGA), protocatechuic acid (PA), and sinigrin (SIN) are possible preventive agents against the development of cancer. However, the mode of action of such preventive agents remains to be elucidated. The current study, therefore, was conducted to analyze whether these agents induce apoptosis and/or inhibit DNA synthesis in human colorectal cancer cell lines. METHODS: We performed an 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium assay to evaluate the modifying effects of the chemicals on cell viability as the first screening. Then, induction of apoptosis was detected by means of a DNA fragmentation assay, a quantitative enzyme immunoassay, and morphological analysis using 4-diamidino-2-phenylindole staining. In addition, the modulating effects of the compounds on DNA synthesis of the cells with fixed doses of the compounds were analyzed by scoring the 5-bromo-2'-deoxyuridine labeling index. RESULTS: AUR, NOB, I3C, ACA, and ACE had apoptosis-inducing effects in a concentration- and time-dependent manner, some of which were followed by a reduction in replicating DNA synthesis. CGA, PA, SIN, GL, DIO, and HE had little modulating effect on cell viability, apoptosis, and DNA synthesis in this cell system. CONCLUSIONS: Our results suggest that AUR, I3C, ACA, NOB, and ACE might exert tumor-preventive action through apoptosis- and/or cell proliferation-dependent mechanisms and, on the other hand, CGA, PA, SIN, HE, DIO, and GL might be apoptosis- and cell proliferation-independent. These assays provided an initial tool for further mechanical studies of tumor-preventive agents and future applications to mechanism-based chemopreventive studies.

Anticarcinogenic Agents↗
PubMed1995

Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants.

In this study the antioxidant activities of the hydroxycinnamic acids, chlorogenic, caffeic, ferulic and p-coumaric, have been investigated in peroxidising lipid systems mediated by metmyoglobin. The results show that the order of effectiveness in increasing the resistance of LDL to peroxidation, in protecting LDL cholesterol from oxidation and preventing the oxidative modification of the LDL apoprotein B100 is caffeic = chlorogenic > ferulic > p-coumaric acid. Assessment of the rates of reaction of the hydroxycinnamates with ferrylmyoglobin, a product of the reductive decomposition of lipid hydroperoxides, reveals that the compounds are more effective as peroxyl radical scavengers than reductants of ferryl myoglobin in peroxidising LDL systems mediated by haem proteins.

Antioxidants↗
PubMed2004

Cytoprotective effects of heme oxygenase-1 induction by 3-O-caffeoyl-1-methylquinic acid.

The novel antioxidant 3-O-caffeoyl-one-methylquinic acid (MCGA3) is a methyl chlorogenic acid derivative isolated from bamboo leaves. MCGA3 scavenges reactive oxygen species (ROS) and inhibits lipid peroxidation and xanthine oxidase in vitro. In this study, we evaluated the cytoprotective effect of MCGA3, which occurs via heme oxygenase-1 (HO-1) induction in bovine vascular endothelial cells exposed to tert-butylhydroperoxide (tBHP). Cells treated with 1 mM tBHP (6-18 h) generated substantial ROS and concomitantly lost most intracellular lactate dehydrogenase (LDH), which then caused necrotic cell death. Of the several MCGA antioxidants and structurally related phenolic acids examined in this study, MCGA3 (0.01-0.15 mM) was found to completely block this necrosis and generation of ROS by tBHP. Surprisingly, MCGA3 by itself was found to be a potent inducer of HO-1. We observed the time- and dose-dependent induction of HO-1 mRNA and protein, which was closely associated with decreased intracellular ROS and necrosis against tBHP. Deesterified or Al-chelated MCGA3 or co-treatment with MCGA3 and actinomycin D abolished HO-1 induction and the antinecrotic effect of MCGA3. Zinc protoporphyrin IX and cycloheximide attenuated the cytoprotection afforded by MCGA3, but did not reduce HO-1 mRNA. Interestingly, N-acetylcysteine (1 mM) enhanced the HO-1 induction of MCGA3, but N-acetylcysteine itself did not induce HO-1. These results suggested that not only ortho-dihydroxyl groups but also aromatic ester and methoxyl ester moieties are necessary for full HO-1 induction and cytoprotection against toxic tBHP-derived ROS. Ferritin mRNA was also upregulated during all HO-1 induction by MCGA3, which might decrease iron and lower ROS levels. Consequently, the combined action of HO-1 and ferritin may protect cells from toxic tBHP-mediated necrosis.

Acetylcysteine↗
PubMed2004

Effect of different washing procedures on phenolic metabolism of shredded, packaged iceberg lettuce during storage.

Different washing treatments applying chlorinated, ozonated, and tap water were examined for their effect on the phenolic metabolism of minimally processed iceberg lettuce (Lactuca sativa L.) during storage in consumer-sized bags at 4 degrees C for up to 9 days. To eliminate problems associated with raw material inhomogeneity, processing was conducted on a pilot-plant scale under operating conditions of industrial practice. Inherent product heterogeneity caused by diverse lettuce leaf tissues was compensated for by pooling large-sized samples, and frequent sampling ensured significant data about the activities of phenylalanine ammonia-lyase (PAL), polyphenol oxidase (PPO), and peroxidase (POD), as well as the contents of caffeic acid derivatives over storage time. In the homogeneous lettuce samples, specific responses caused by different washing procedures were detectable. PAL activity in the samples increased for up to 5-8 days of storage. Compared to tap and ozonated water, the use of chlorinated water (100-200 mg/L free chlorine) for washing trimmed heads or shredded lettuce significantly reduced PAL activity and the concomitant rise of 3,5-di-O-caffeoylquinic acid (isochlorogenic acid isomer) concentrations. The phenolic acids O-caffeoyltartaric (caftaric acid), di-O-caffeoyltartaric (chicoric acid), 5-O-caffeoylquinic (chlorogenic acid isomer), and O-caffeoylmalic were less influenced by different washing treatments. Individual contents either were constant or decreased during storage. Additionally, the novel finding of a further caffeic acid isomer, tentatively identified as meso-di-O-caffeoyltartaric acid, is reported. PPO and POD activities were less affected by different washing treatments and thus were less suitable physiological indicators of stress reactions triggered by alternative processing.

Caffeic Acids↗
PubMed2004

Comparison of anthocyanin pigment and other phenolic compounds of Vaccinium membranaceum and Vaccinium ovatum native to the Pacific Northwest of North America.

Two huckleberry species, Vaccinium membranaceum and Vaccinium ovatum, native to Pacific Northwestern North America, were evaluated for their total, and individual, anthocyanin and polyphenolic compositions. Vaccinium ovatum had greater total anthocyanin (ACY), total phenolics (TP), oxygen radical absorbing capacity (ORAC), and ferric reducing antioxidant potential (FRAP) than did V. membranaceum. The pH and degrees Brix were also higher in V. ovatum. Berry extracts from each species were separated into three different fractions--anthocyanin, polyphenolic, and sugar/acid-by solid-phase extraction. The anthocyanin fractions of each species had the highest amount of ACY, TP, and antioxidant activity. Each species contained 15 anthocyanins (galactoside, glucoside, and arabinoside of delphinidin, cyanidin, petunidin, peonidin, and malvidin) but in different proportions. Their anthocyanin profiles were similar by high-performance liquid chromatography with photodiode array detection (LC-DAD) and high-performance liquid chromatography with photodiode array and mass spectrometry detections (LC-DAD-MS). Each species had a different polyphenolic profile. The polyphenolics of both species were mainly composed of cinnamic acid derivatives and flavonol glycosides. The major polyphenolic compound in V. membranaceum was neochlorogenic acid, and in V. ovatum, chlorogenic acid.

Anthocyanins↗