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At least 271 records · Page 15Linked to original sources
PubMed2006

UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid.

The physicochemical properties of 8,8-methylmethine catechin-malvidin 3-O-glucoside isomers, commonly referred to as catechin-ethyl-malvidin 3-O-glucoside, have been studied in aqueous solutions and compared with those of the parent anthocyanin (malvidin 3-O-glucoside). The hydration and acidity constants (pKh and pKa) of the catechin-ethyl-malvidin 3-O-glucoside pigments and malvidin 3-O-glucoside were determined by UV-visible spectroscopic measurements. The ethyl-linked catechin-malvidin 3-O-glucoside pigments present higher stability toward hydration than the parent anthocyanin. The high resistance of these ethyl-linked pigments toward the hydration is related to the self-association that offers optimal protection from the nucleophilic attack of water. Moreover, the ethyl link may confer to the molecule enough flexibility to undergo intramolecular interaction, further protecting it from hydration and bisulfite discoloration. In the wine pH range (3.2-4.0), due to the low pKa and high pKh values, the ethyl-linked pigments are present as colored forms (flavylium cation and quinonoid bases).

Anthocyanins↗
PubMed1998

Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds.

1. The effect of the phenolic compounds protocatechuic acid, chlorogenic acid, tannic acid, gallates and silybin on ethoxyresorufin O-dealkylase (CYP1A1), methoxyresorufin O-dealkylase (CYP1A2) and pentoxy-O-dealkylase (CYP2B) was examined in mouse liver microsomes from induced animals. 2. All compounds tested could inhibit cytochrome P450-mediated enzyme activities, but to different extents. Tannic acid was the most potent inhibitor, especially toward EROD activity with an IC50=2.6 microM. Synthetic dodecyl gallate was also relatively selective toward this enzyme activity with an IC50=120 microM. 3. Protocatechuic acid, chlorogenic and silybin were more selective towards PROD and MROD activities. Their relative inhibitory potency for PROD activity was as follows: chlorogenic acid > protocatechuic acid > silybin > dodecyl gallate > propyl gallate. Protocatechuic acid was a more effective inhibitor of MROD activity than chlorogenic acid, and propyl gallate more effective than dodecyl gallate. Thus, no clear structure-activity or selectivity relationship was observed. 4. Analysis of the kinetics of inhibition revealed that the inhibition in most cases was non-competitive in nature.

Animals↗
PubMed2004

[HPLC investigation of antioxidant components in Solidago herba].

Representatives of Solidago species have been used in European phytotheraphy for centuries as a component of urological and antiphlogistical remedies. Solidago canadensis L. (Asteraceae) contains a wide range of active ingredients, such as flavonoids, saponins, hydroxycinnamates and mineral elements, which are responsible for its characteristic anti-inflammatory, spasmolytic and diuretic properties. Quality control of collected Solidaginis herba were performed according to the instructions of the X. German Pharmacopoea, while different LC-MS technologies were applied to evaluate the exact phenoloid composition. Three flavonol aglycons (quercetin, kaempferol and isorhamnetin) connected to several sugar components (glucose, rhamnose, galactose and rutinose), caffeoylquinic acid and a caffeoyl-shikimic acid glycoside were identified in the samples. Quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-O-beta-galactoside (hyperoside), quercetin-3-O-beta-rhamnoside (quercitrin), quercetin-3-O-beta-rutinoside (rutin), kaempferol-3-O-beta-rhamnoside (afzelin), kaempferol-3-O-beta-rutinoside (nicotiflorin), caffeoil-quinic acid (chlorogenic acid) were identified in sample "A", while the presence of quercetin, quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-/6"-O-acetyl-/-beta-glucopiranoside, quercetin-3-O-beta-rutinoside (rutin), kaempferol, kaempferol-3-O-beta-glucoside (astragalin), kaempferol-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin, isorhamnetin-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin-3-O-beta-rutinoside (narcissin), caffeoil-quinic acid (chlorogenic acid), caffeoil-shikimic acid-glucoside (dattelic acid-glucoside) were confirmed in sample "B". According to the occurrence of acetyl-glycosides and the diversity of sugar component of flavonoid glycosides Solidaginis herba samples chemotaxonomically were classified into different varieties. Incidence of acetyl-glycosidic flavonoids and absence of flavonoid galactosides and rhamnosides in the sample "B" together give support for the taxonomic recognition of varietases Solidago canadensis L. var. canadensis and var. scabra. Sample "A" was identified as Solidago canadensis L. var. canadensis, while sample "B" has proved to be belong to variety Solidago canadensis L. var. scabra. Due to the same flavonoid aglycons and the large amounts of flavonol glycosides occurring in each drug, phytochemical characteristics of investigated samples proved to be very similar.

Antioxidants↗
PubMed2001

Metabolism of phenolic compounds during loquat fruit development.

Phenolic compounds in loquat fruit were identified as 5-caffeoylquinic acid (chlorogenic acid), neochlorogenic acid, hydroxybenzoic acid, 5-p-feruloylquinic acid, protocatechuic acid, 4-caffeoylquinic acid, epicatechin, o-coumaric acid, ferulic acid, and p-coumaric acid. Neochlorogenic acid was found to be dominant in the early stages of loquat fruit development. Both the concentrations and types of phenolic compounds were high in young fruit but then decreased steadily during growth. However, the concentration of chlorogenic acid increased during ripening and became predominant in ripe fruit. The large rise in chlorogenic acid concentration appears to be a characteristic of loquat fruit ripening. In all of the cultivars tested, the types of phenolic compounds were similar but the total phenolic content varied from 81.8 to 173.8 mg/100 g of fresh pulp. In the biosynthetic pathway of chlorogenic acid, the enzyme activities of phenylalanine ammonia-lyase (PAL), 4-coumarate:CoA ligase (CL), and hydroxycinnamoyl CoA:quinate hydroxycinnamoyl transferase (CQT) were high at the early stage of growth, diminished to low levels approximately 3 weeks prior to harvest, but then rose to a peak at 1 week before harvest. The changes of these enzyme activities seemed to be associated with variations in chlorogenic acid concentration during development, maturation, and ripening of loquat fruit.

Chlorogenic Acid↗
PubMed2002

Absorption of phenolic acids in humans after coffee consumption.

Despite extensive literature describing the biological effects of polyphenols, little is known about their absorption from diet, one major unresolved point consisting of the absorption of the bound forms of polyphenols. In this view, in the present work we studied the absorption in humans of phenolic acids from coffee, a common beverage particularly rich in bound phenolic acids, such as caffeic acid, ferulic acid, and p-coumaric acid. Coffee brew was analyzed for free and total (free + bound) phenolic acids. Chlorogenic acid (5'-caffeoylquinic acid), a bound form of caffeic acid, was present in coffee at high levels, while free phenolic acids were undetectable. After alkaline hydrolysis, which released bound phenolic acids, ferulic acid, p-coumaric acid, and high levels of caffeic acid were detected. Plasma samples were collected before and 1 and 2 h after coffee administration and analyzed for free and total phenolic acid content. Two different procedures were applied to release bound phenolic acids in plasma: beta-glucuronidase treatment and alkaline hydrolysis. Coffee administration resulted in increased total plasma caffeic acid concentration, with an absorption peak at 1 h. Caffeic acid was the only phenolic acid found in plasma samples after coffee administration, while chlorogenic acid was undetectable. Most of caffeic acid was present in plasma in bound form, mainly in the glucuronate/sulfate forms. Due to the absence of free caffeic acid in coffee, plasma caffeic acid is likely to be derived from hydrolysis of chlorogenic acid in the gastrointestinal tract.

Absorption↗
PubMed2003

Antioxidant constituents of almond [Prunus dulcis (Mill.) D.A. Webb] hulls.

Almond hulls (Nonpareil variety) were extracted with methanol and analyzed by reversed phase HPLC with diode array detection. The extract contained 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid (cryptochlorogenic acid), and 3-O-caffeoylquinic acid (neochlorogenic acid) in the ratio 79.5:14.8:5.7. The chlorogenic acid concentration of almond hulls was 42.52 +/- 4.50 mg/100 g of fresh weight (n = 4; moisture content = 11.39%). Extracts were tested for their ability to inhibit the oxidation of methyl linoleate at 40 degrees C. At an equivalent concentration (10 microg/1 g of methyl linoleate) almond hull extracts had higher antioxidant activity than alpha-tocopherol. At higher concentrations (50 microg/1 g of methyl linoleate) almond hull extracts showed increased antioxidant activity that was similar to chlorogenic acid and morin [2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one] standards (at the same concentrations). These data indicate that almond hulls are a potential source of these dietary antioxidants. The sterols (3beta,22E)-stigmasta-5,22-dien-3-ol (stigmasterol) and (3beta)-stigmast-5-en-3-ol (beta-sitosterol) (18.9 mg and 16.0 mg/100 g of almond hull, respectively) were identified by GC-MS of the silylated almond hull extract.

Antioxidants↗
PubMed1996

Determination of some pharmacologically active phenolic acids in juices by high-performance liquid chromatography.

Several phenolic acids, e.g. caffeic acid, chlorogenic acid, ferulic acid, gallic acid and ellagic acid, which occur naturally, are inhibitors of carcinogenesis. In this paper we present a new method for the simultaneous determination of all of these compounds, except ellagic acid, in juices by reversed-phase high-performance liquid chromatography (HPLC) using ultraviolet detection and involving isocratic elution, and we have devised an HPLC method for the determination of ellagic acid in juices. The experimental results showed that cherry juice contains a high concentration of chlorogenic acid and the content of bound gallic acid in black and green grape juices is high compared to that of other phenolic acids.

Beverages↗
PubMed1998

[Chemical constituents of Taraxacum sinicum Kitag].

Five compounds were separated from Taraxacum sinicum by means of solvent extraction and rechromatography on silical gel. Their structures were established as caffeic acid, ferulic acid, chlorogenic acid, luteolin and diosmetin by spectral analysis and chemical evidence. All the compounds were isolated from this plant for the first time. Chlorogenic acid and diosmetin have not been discovered from Taraxacum genus previously.

Asteraceae↗
PubMed2003

The effect of plant phenolics on the formation of 7,12-dimethylbenz[a]anthracene-DNA adducts and TPA-stimulated polymorphonuclear neutrophils chemiluminescence in vitro.

Phenolics, common plant constituents, form up an important part of human diet and are considered potential chemopreventive agents. In the present study, structurally diverse phenolics, such as tannic acid, protocatechuic acid, chlorogenic acid and resveratrol, were investigated for their inhibitory effects on covalent binding of 7,12-dimethylbenz[a]anthracene (DMBA) to DNA in vitro and the suppression of oxidative burst in 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated human polymorphonuclear neutrophils (PMNs). 32P-postlabeling analysis of DNA incubated with DMBA in the presence of 3-methylcholanthrene (3-MC)-induced microsomes produced three major adducts derived from anti-, syn- and anti-dihydrodiol epoxides through reactions with dGuo and dAdo, respectively. Phenolic compounds at the concentration of 150 microM reduced the levels of all DMBA-DNA adducts by 55-98%. The most dramatic effect was observed in case of tannic acid, which completely inhibited the formation of DMBA-dAdo adducts. Chlorogenic acid was the least effective inhibitor of DMBA-DNA adducts formation particularly syn-DMBADE-dAdo (20%). Human neutrophils showed a significant dose-related decrease of TPA-induced chemiluminescence after pretreatment with phenolic compounds. The most effective inhibitors were tannic acid and resveratrol with IC(50)=5.19 and 5.76 microM, respectively. These results suggest that the suppression of reactive oxygen species (ROS) and carcinogen-DNA adducts formation may be important for anticarcinogenic activity of the examined phenolics.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed2005

Plant phenolics behave as radical scavengers in the context of insect (Manduca sexta) hemolymph and midgut fluid.

To evaluate the prooxidant versus antioxidant properties of plant phenolics toward leaf-feeding caterpillars, quenching of the stable ABTS radical by five phenolics was measured in two physiological contexts: hemolymph and midgut fluid. Addition of tannic acid, chlorogenic acid, quercetin, or catechin to Manduca sexta (L.) gut fluid increased its total antioxidant capacity by 12-45%, with tannic acid and quercetin being the most powerful in this regard. The antioxidant contribution of the phenolics increased with longer (30-60 min) incubation time in gut fluid. Chlorogenic acid and caffeic acid exhibited the weakest antioxidant activity in gut fluid. The total antioxidant capacity of hemolymph is considerably less than that of gut fluid, and in hemolymph chlorogenic and caffeic acids sometimes acted as mild prooxidants, particularly after longer incubation periods (30-60 min), although this trend was not statistically significant. Tannic acid, catechin, and quercetin behaved as antioxidants in hemolymph. These results suggest that many phenolics have radical scavenging activity in the digestive tract, but some may have more detrimental effects after absorption into the hemolymph compartment.

Animals↗