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PubMed2007

Identification of free radical species derived from caffeic acid and related polyphenols.

Polyphenols are widely distributed in various fruits, vegetables and seasonings. It is well known that they have several physiological effects due to their antioxidative activities. Their activities depend on structural characteristics that favour the formation of their corresponding stable radicals. During the examination at which pH values, the polyphenol radicals are stabilized, we confirmed that polyphenol radicals were stabilized in NaHCO3/Na2CO3 buffer (pH 10) rather than in physiological pH region. Then, we measured electron spin resonance (ESR) spectra at pH 10 to examine the characteristics of free radical species derived from caffeic acid (CA) with an unsaturated side chain, dihydrocaffeic acid (DCA) with a saturated side chain, chlorogenic acid (ChA) and rosmarinic acid (RA). In analyzing the radical structures, ESR simulation, determinations of macroscopic and microscopic acid dissociation constants and molecular orbital (MO) calculation were performed. In CA, the monophenolate forms were assumed to participate in the formation of free radical species, while in DCA, the diphenol form and the monophenolate forms were presumed to contribute to the formation of free radical species. On the basis of the results, we propose the possible structures of the free radical species formed from polyphenols under alkaline conditions.

Caffeic Acids↗
PubMed1972

Sweet taste of water induced by artichoke (Cynara scolymus).

Exposure of the tongue to artichoke can make water taste sweet. Two major active components of artichoke are the salts of chlorogenic acid and cynarin. The sweetening of substances by temporarily modifying the tongue, rather than by adding a substance sweet in itself, may provide an alternative to currently used nonnutritive sweeteners.

Chlorogenic Acid↗
PubMed2004

[Studies on chemical constituents in dried buds of Lonicera confusa].

OBJECTIVE: To investigate the chemical constituents of the dried buds of Lonicera confusa. METHOD: Chromatography and spectral analysis were respectively used to isolate and identify the constituents. RESULT: Seven compounds were isolated from the dried buds of L. confusa, and identified as rutin, quercetin, luteilin-7-O-beta-D-galactoside, lonicerin, chlorogenic acid, beta-sitosterol and tetratriacontane. CONCLUSION: Rutin was isolated from the genus for the first time, and the others were isolated from the species for the first time.

Chlorogenic Acid↗
PubMed2004

Metabolic fingerprinting of wild type and transgenic tobacco plants by 1H NMR and multivariate analysis technique.

The metabolomic analysis of wild type and constitutive salicylic acid producing tobacco plants (CSA tobacco, Nicotiana tabacum 'Samsun' NN) plants overexpressing salicylate biosynthetic genes was carried out by 1H NMR spectrometry and multivariate analysis techniques. The principle component analysis (PCA) of the 1H NMR spectra showed a clear discrimination between those samples by PC1 and PC2. The discrimination of non-inoculated, TMV-virus inoculated, and systemic leaves or veins could also be obtained by PCA analysis. Major peaks in 1H NMR spectra contributing to the discrimination were assigned as those of chlorogenic acid, malic acid, and sugars. This method allows an efficient differentiation between wild type and transgenic plants without any pre-purification steps.

Chlorogenic Acid↗
PubMed1990

Inhibition by coffee of nitrosourea-mediated DNA damage in mice.

Oral administration of coffee at doses ranging from 150 mg to 1 g per kg body weight significantly decreased endogenously formed nitrosourea-mediated DNA damage in bone marrow as well as in colon epithelial cells in mice that had simultaneously received oral administration of methylurea and sodium nitrite. Since coffee (1 g/kg body weight) did not decrease DNA damage when administered orally together with performed methylnitrosourea, it was hypothesized that coffee inhibits nitrosation in the stomach of mice. The lowest effective level of coffee, when compared on the basis of body weight, corresponds to a human intake of about 5 cups of coffee. Both chlorogenic acid (150 mg/kg body weight) and premelanoidins (1 g/kg body weight), which occur as ingredients in, or are formed during roasting of, coffee, were shown to inhibit nitrosourea-induced DNA damage in mice.

Administration, Oral↗
PubMed2003

Superoxide radical scavenging activity of the major polyphenols in fresh plums.

The effect of polyphenols among different varieties of plums on superoxide radical scavenging activity (SRSA) was studied by an enzymatic method and their IC(50) values were determined. We found that the SRSA levels of the polyphenols were closely related to their chemical structures; cyanidin showed the lowest IC(50) among the polyphenols examined, and aglycones are more effective than their glycosides. BY 69-339 cultivar exhibited the lowest IC(50) among the eleven plum cultivars, which means the highest antioxidant activity in scavenging superoxide radicals, followed by French Damson, Cacaks Best, Beltsville Elite B70197, Empress, Castleton, Stanley, NY 6, NY 101, Mirabellier, and NY 9. IC(50) values showed a higher correlation with total flavonoids (r (2) = 0.8699) than total phenolics (r (2) = 0.8355), which indicated that flavonoids might contribute to the total SRSA more directly than other polyphenols. Anthocyanins in plums appeared to be the major contributors to the total SRSA, except for two yellow cultivars having no anthocyanins. Chlorogenic acid was the predominant phenolic acid, and it also exhibited SRSA significantly in the range of 1.0 to 94.9%. Quercetins were the major flavonols in plums. However, they showed relatively low contribution to the total SRSA.

Anthocyanins↗
PubMed2003

Activity-guided identification of a chemopreventive compound in coffee beverage using in vitro and in vivo techniques.

The aim of the present study was to apply an activity-guided screening procedure to coffee brew to identify a key chemopreventive compound by means of in vitro antioxidant tests as well as cell culture experiments and to prove the in vivo activity of that compound by an animal feeding experiment. Solvent fractionation, followed by multiple-step ultrafiltration, revealed that the polar coffee compounds with molecular weights below 1 kDa show the major inhibitory effect on the in vitro peroxidation of linoleic acid as well as the predominant chemopreventive enzyme modulating activity on the NADPH-cytochrome c reductase (CCR) and glutathione S-transferase (GST) in human intestinal Caco-2 cells. To identify the chemical structure of the most active antioxidants and chemopreventive compounds, the polar compounds were further separated by HPLC techniques, followed by the activity-guided screening of the individual HPLC fraction. These experiments demonstrated 5-chlorogenic acid to be the most powerful antioxidant in vitro, whereas, in contrast, chemopreventive effects on the GST activity were found for the N-methylpyridinium ion, the structure of which was elucidated by LC-MS and NMR experiments and confirmed by synthesis. The in vivo activities of coffee beverage and N-methylpyridinium ions were tested in a 15-day feeding experiment on rats. In the liver, feeding of 4.5% coffee beverage resulted in increases of GST and UDP-GT activities by 24 and 40% compared to animals fed the control diet (p > 0.05), respectively. Plasma total antioxidant capacity and plasma tocopherol were elevated in animals fed the coffee beverage and the N-methylpyridinium-containing diet. In summary, the results demonstrating a strong in vitro antioxidant activity for coffee were confirmed by the feeding study. Surprisingly, feeding of N-methylpyridinium also resulted in an increased total antioxidant capacity in the plasma. The data indicate that the mode of action demonstrated for N-methylpyridinium in biological systems is different from that in foods.

Animals↗
PubMed1977

[Studies on enzymic browning of potatoes (Solanum tuberosum). I. Phenoloxidases and phenolic compounds from different varieties (author's transl)].

31 samples of potato varieties with slow, medium and fast rates of browning were studies. Characteristic enzyme patterns were obtained from polyacrylamide gel electrophoresic of the phenoloxidases of varieties with different discolouration rates. The differences lie mainly in the intensities of the enzyme bands. The qualitative determinaiton of the phenols showed no significant differences. Tyrosine, chlorogenic acid and caffeic acid produce coloured oxidation products; the characteristic colour gradations of in vivo browning were only observed in the presence of tyrosine. It is concluded that the same reactions take place during the discolouration of all the varieties.

Catechol Oxidase↗
PubMed2002

Naringenin from cooked tomato paste is bioavailable in men.

Naringenin has been shown to exert antiestrogenic, cholesterol-lowering and antioxidant activities, as well as an indirect modulation on the metabolism of many xenobiotics. It is one of the most abundant polyphenols in tomato. Given the widespread consumption of tomato (Lycopersicum esculentum) and tomato-based products, this study was designed to determine whether plasma levels of naringenin were detectable in five men after consumption of a test meal containing 150 mg of cooked tomato paste. Naringenin intake with the test meal was 3.8 mg. Blood was drawn from fasting subjects and 2, 4, 6, 8 and 24 h after the meal. To compare the results with a control, the same meal without tomato paste (control meal) was administered to the same subjects 2 wk later. Analyses were performed using high-performance liquid chromatography coupled with a CoulArray electrochemical detector. The peak plasma concentration was 0.12 +/- 0.03 micro mol/L 2 h after the meal. Unconjugated naringenin was not detected. Naringenin was not detected in plasma at any time after consumption of the control meal. In addition to naringenin, we detected rutin and chlorogenic acid in tomato paste, but these polyphenols and their derivatives (quercetin and caffeic acid) were not detected in plasma at any time. To the best of our knowledge, this is the first study demonstrating naringenin bioavailability in humans after consumption of a meal containing cooked tomato paste.

Adult↗
PubMed2003

Efficacy of different Cynara scolymus preparations on liver complaints.

Cynara scolymus leaves extracts have long been used in folk medicine for their choleretic and hepatoprotective activities, that are often related to the cynarin content. These therapeutic properties are also attributed to mono- and di-caffeoylquinic acids and since commercial C. scolymus preparations can differ for their activities, we studied four extracts to evaluate, if present, a relationship between the hepatobiliary properties of the different preparations and their content in phenolics. The antioxidant activity of the commercial preparations examined was also considered in an in vitro system. The results showed that the extract with the highest content in phenolic derivatives (GAE) exerted the major effect on bile flow and liver protection. Also the results of the antioxidant capacity (BR) of the different preparations are in good agreement with the results obtained in vivo. On the contrary, administering rats with doses of chlorogenic acid, equivalent to those present in this extract, we did not observe any choleretic or protective action. An histopathological analysis of liver sections confirmed the biochemical results. Perhaps caffeoyl derivatives have a role in the therapeutic properties of C. scolymus extracts, as reported in literature for "in vitro" studies, but when administered alone, they are not so effective in exerting this action.

Alanine Transaminase↗
PubMed2000

Triterpene saponins in the defensive secretion of a chrysomelid beetle, Platyphora ligata.

The secretion of the defensive glands of adults of the chrysomelid beetle Platyphora ligata from Panama has been shown to contain, besides chlorogenic acid (1) and a mixture of phosphatidylcholines, two new oleanane triterpene saponins, named ligatosides A and B. Their structures were established as 3-O-beta-D-glucuronopyranosyl-16alpha,23-dihydroxyoleanol ic acid-28-O-2-(3,4-dimethoxybenzoyl)-beta-D-glucopyranoside (2) and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-16a lpha, 23-dihydroxyoleanolic acid-28-O-2-(3, 4-dimethoxybenzoyl)-beta-D-glucopyranoside (3), respectively, by a combination of extensive 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. This is the first report of triterpene saponins in the defensive secretion of an insect.

Animals↗
PubMed2000

Chemopreventive effects of coffee bean and rice constituents on colorectal carcinogenesis.

Polyphenolic compound chlorogenic acid (CGA) known to be much contained in coffee beans was found to have a regressive effect on induced aberrant crypt foci (ACF) as well as on development of ACF in azoxymethane (AOM)-induced colorectal carcinogenesis in rats. Rice germ and gamma-aminobutyric acid-enriched defatted rice germ inhibited AOM-induced ACF formation and colorectal carcinogenesis in rats. Ferulic acid (FA) also known to be contained in coffee beans and rice prevented AOM-induced ACF formation and intestinal carcinogenesis in rats. Both of food factors, coffee and rice may be of benefit to prevention of human colorectal cancers.

Animals↗
PubMed1996

Enzymatic oxidation products of allelochemicals as a basis for resistance against insects: effects on the corn leafhopper Dalbulus maidis.

Oxidation products of com allelochemicals generated by peroxidases or tyrosinases were tested in 10% sucrose solutions for effects on the corn leafhopper Dalbulus maidis. Some reduction in feeding was noted with hydrogen peroxide (a cofactor for peroxidase). Significant reduction in feeding was noted with chlorogenic acid, ferulic acid, p-coumaric acid, and 6-methoxybenzoxazolinone (MBOA), but not rutin at 400 ppm in solution. Oxidation products of these compounds all caused significantly less feeding by the leafhoppers compared to the original compound. Oxidation products generated by peroxidase from ferulic acid and 6-methoxybenzoxazolinone caused significant mortality to the leafhoppers within 5 days. Thus, provided conditions are such that oxidizing enzymes and allelochemicals can interact due to damage by insects, resistance may be significantly enhanced by the oxidized products as opposed to the effects of the allelochemicals alone.

Analysis of Variance↗
PubMed2001

Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems.

In liver endoplasmic reticulum the intralumenal glucose-6-phosphatase activity requires the operation of a glucose 6-phosphate transporter (G6PT1). Mutations in the gene encoding G6PT1 cause glycogen storage disease type 1b, which is characterized by a loss of glucose-6-phosphatase activity and impaired glucose homoeostasis. We describe a novel glucose 6-phosphate (G6P) transport activity in microsomes from human fibroblasts and HeLa cells. This transport activity is unrelated to G6PT1 since: (i) it was similar in microsomes of skin fibroblasts from glycogen storage disease type 1b patients homozygous for mutations of the G6PT1 gene, and in microsomes from human control subjects; (ii) it was insensitive to the G6PT1 inhibitor chlorogenic acid; and (iii) it was equally active towards G6P and glucose 1-phosphate, whereas G6PT1 is highly selective for G6P. Taken together, our results provide evidence for the presence of multiple transporters for G6P (and other hexose phosphoesters) in the endoplasmic reticulum.

Antiporters↗
PubMedDate not supplied

Formation of mutagens in cooked foods. V. The mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef.

Cooking beef patties results in the formation of mutagens detectable by Salmonella typhimurium TA98 with metabolic activation. Decreased mutagenic activity results when frying beef with added soy protein concentrates (SPC). The reduction in mutagenicity takes place during the cooking process. Whereas fried beef hamburgers show high mutagenic activity, by comparison, similarly fried soy-hamburgers have much less mutagenic activity. Volumetric effects are responsible partly for the reduction on mutagenicity by SPC. Naturally occurring antioxidants in SPC, such as chlorogenic acid, also play a role. Also, a commonly used antioxidant, butylated hydroxyanisole (BHA), has been found effective in reducing the mutagenicity of fried beef. Thus, the addition of SPC or BHA in beef patties may provide a practical way of reducing mutagen formation during frying of beef.

Animals↗
PubMed2000

Energy dissipation and radical scavenging by the plant phenylpropanoid pathway.

Environmental stresses such as high light, low temperatures, pathogen infection and nutrient deficiency can lead to increased production of free radicals and other oxidative species in plants. A growing body of evidence suggests that plants respond to these biotic and abiotic stress factors by increasing their capacity to scavenge reactive oxygen species. Efforts to understand this acclimatory process have focused on the components of the 'classical' antioxidant system, i.e. superoxide dismutase, ascorbate peroxidase, catalase, monodehydroascorbate reductase, glutathione reductase and the low molecular weight antioxidants ascorbate and glutathione. However, relatively few studies have explored the role of secondary metabolic pathways in plant response to oxidative stress. A case in point is the phenylpropanoid pathway which is responsible for the synthesis of a diverse array of phenolic metabolites such as flavonoids, tannins, hydroxycinnamate esters and the structural polymer lignin. These compounds are often induced by stress and serve specific roles in plant protection, i.e. pathogen defence, ultraviolet screening, antiherbivory, or structural components of the cell wall. This review will highlight a novel antioxidant function for the taxonomically widespread phenylpropanoid metabolite chlorogenic acid (CGA; 5-O-caffeoylquinic acid) and assess its possible role in abiotic stress tolerance. The relationship between CGA biosynthesis and photosynthetic carbon metabolism will also be discussed. Based on the properties of this model phenolic metabolite, we propose that under stress conditions phenylpropanoid biosynthesis may represent an alternative pathway for photochemical energy dissipation that has the added benefit of enhancing the antioxidant capacity of the cell.

Antioxidants↗
PubMed2006

[Effects of water stress on the growth of Lonicera japonica and quality of honeysuckle].

OBJECTIVE: Effects of water stress on the growth of Lonicera japonica and quality of honeysuckle were studied. METHODS: Different extent water stress treatment imposed to potted plants before the first florescence of honeysuckle, and the growth and related physiological indexes of Lonicera japonica were determined. RESULTS: Shoot grow slowly as well as the increases of specific weight of leaf and the decrease of the yield of honeysuckle under water stress. The contents of chlorophyl in the leaves treated water stress all increased, and the content of soluble suger had a rising stream. The content of soluble protein in leaves of plant imposed by minor stress treatment was obviously higher than that of CK and severe stress treatment. As the stress was hard, the content of proline in leaves increased significantly. With water stress severing, the content of chlorogenic acid in the flower bud decreased very significantly than CK. CONCLUSION: Water condition was a important factor affected the growth and development of shoots, leaves and flower buds as well as the quality of honeysuckle. In the cultivation of Loniccra japonica, irrigation timing and certain irrigation condition was necessary.

Chlorogenic Acid↗
PubMed2002

[Phenological analysis upon yield and quality of Flos Lonicerae].

Yield and quality of Flos Lonicerae varied in different phenological phase. Yield in the first flowering season was the highest. Yield in the last three flowering season decreased one by one. The dry weight of one thousand flower buds and chlorogenic acid content in the first flowering season were the highest during a year, then was the fourth, the second and the third were both the lower. The difference of above was related to such biologic factors as days of flower bud differentiation, types of flower branch, leaf area, chlorophyll content, and also to such climatic factors as air temperature, hours of sunshine and precipitation.

Chlorogenic Acid↗