Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Caffeic Acids”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 973 records · Page 54Linked to original sources
PubMed1975

[On the phenolic acids of vegetables. III. Hydroxycinnamic acids and hydroxybenzoic acids of root vegetables (author's transl)].

In carrots, celeriac, scorzoneras, and horse radish caffeic acid, in small radishes p-coumaric acid, in beets ferulic acid and in radishes probably ferulic acid is dominating after hydrolysis. The contents of phenolic acids in the roots are much smaller than in the corresponding leaves. Carrots, small radishes, horse radish and partially scorzoneras show higher concentrations of phenolic acids in outer tissue layers. In contrary to hydroxycinnamic acid derivatives the contents of hydroxybenzoic acid derivatives (p-hydroxybenzoic, vanillic, salicylic and gentisic acid) mostly were small. Partially hydroxycoumarins (aesculetin and scopoletin) identified.

Caffeic Acids↗
PubMed1981

Reactions between phosphorylated thiamines and tannic acid as followed by difference spectroscopy.

Caffeic acid, catechin, chlorogenic acid, hydroquinone (also benzoquinone) and tannic acid were used to react with thiamine and the ultraviolet-visible difference spectra were recorded. The time-course of the thiamine-polyphenol interactions was studied by following the difference absorbance change with time. The rate of reaction as determined by difference spectroscopy was the same as that found by chemical assay. The spectroscopic method showed that thiamine, thiamine monophosphate and thiamine diphosphate reaction rate with tannic acid followed the order thiamine greater than thiamine monophosphate greater than thiamine diphosphate up to pH 7.4.

Flavonoids↗
PubMed2005

RP-HPLC analysis of the phenolic compounds of plant extracts. investigation of their antioxidant capacity and antimicrobial activity.

Extracts of aromatic plants of Greek origin were examined as potential sources of phenolic compounds. RP-HPLC with UV detection was employed for the identification and quantification of the phenolic antioxidants, present in methanolic extracts. The most abundant phenolic acids were ferulic acid (1.1-280 mg/100 g of dry sample) and caffeic acid (1.2-60 mg/100 g of dry sample). (+)-Catechin and quercetin were the most abundant flavonoids. Apigenin and luteolin were detected in high amounts in Menta pulegium and Thymus vulgaris, respectively. The antioxidant capacity was determined, in dried ground plants and in their methanol extracts, with the Rancimat test using sunflower oil as substrate. Both pulverized plants and extracts showed antioxidant capacity. Total phenolic content in the extracts was determined spectrometrically according to the Folin-Ciocalteu assay and ranged from 1 to 21 mg of gallic acid/100 g of dry sample. Antimicrobial activity of the extracts against selected microbes was also conducted in this study.

Anti-Bacterial Agents↗
PubMed2004

Antioxidant activity of phenolic and related compounds: a density functional theory study on the O-H bond dissociation enthalpy.

We report here on calculations at the hybrid DFT/HF (B3-LYP/6-31G(d, p)) level of the O-H bond dissociation enthalpy (O-H BDE) of phenylpropenoic acids (caffeic, ferulic, p-coumaric and cinnamic) and phenolic acids and related compounds (gallic, methylgallate, vanillic and gentisic) in order to gain insight into the understanding of structure-antioxidant activity relationships. The results were correlated and discussed mainly on the basis of experimental data in a companion work (Galato D, Giacomelli C, Ckless K, Susin MF, Vale RMR, Spinelli A. Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity. Redox Report 2001; 6: 243-250). The O-H BDE values showed remarkable dependence on the hydroxyl position in the benzene ring and the existence of additional interaction due to hydrogen bonding. For parent molecules, the experimental antioxidant activity (AA) order was properly obeyed only when intramolecular hydrogen bonding was present in the radicalized structures of o-dihydroxyl moieties. In structurally related compounds, excellent correlation with experimental data was in general observed (0.64 < rho < 0.99). However, it is shown that excellent correlation can also be obtained for this series of compounds considering p-radicalized structures which were not stabilized by intramolecular hydrogen bonding, but this had no physical meaning. These findings suggested that the antioxidant activity evaluation of phenolic and related compounds must take into consideration the characteristics of each particular compound.

Antioxidants↗
PubMed2002

[Studies on the phenylpropanoids from Eucommia ulmoides].

OBJECTIVE: To study the chemical constituents from the leaves of Eucommia ulmoides. METHOD: The constituents were isolated by chromatography method and the structures were identified on the basis of spectral analysis. RESULT: Six compounds, ursolic acid(1), beta-sitosterol(2), p-coumaric(3), caffeic acid ethyl ester(4), chlorogenic acid(5) and syringin(6) were obtained. CONCLUSION: Compound 3, 4, 5 were obtained from the plant for the first time.

Caffeic Acids↗
PubMed2005

Inhibitory effect of the Agrobacterium rhizogenes rolC gene on rabdosiin and rosmarinic acid production in Eritrichium sericeum and Lithospermum erythrorhizon transformed cell cultures.

Rabdosiin and related caffeic acid metabolites have been proposed as active pharmacological agents demonstrating potent anti-HIV and antiallergic activities. We transformed Eritrichium sericeum and Lithospermum erythrorhizon seedlings by the rolC gene, which has been recently described as an activator of plant secondary metabolism. Surprisingly, the rolC-transformed cell cultures of both plants yielded two- to threefold less levels of rabdosiin and rosmarinic acid (RA) than respective control cultures. This result establishes an interesting precedent when the secondary metabolites are differently regulated by a single gene. We show that the rolC gene affects production of rabdosiin and RA irrespective of the methyl jasmonate (MeJA)-mediated and the Ca(2+)-dependent NADPH oxidase pathways. Cantharidin, an inhibitor of serine/threonine phosphatases, partly diminishes the rolC-gene inhibitory effect that indicates involvement of the rolC-gene-mediated signal in plant regulatory controls, mediated by protein phosphatases. We also show that the control MeJA-stimulated E. sericeum root culture produces (-)-rabdosiin up to 3.41% dry weight, representing the highest level of this substance for plant cell cultures reported so far.

Boraginaceae↗
PubMed2004

Biosynthesis of fukinolic acid isolated from Petasites japonicus.

The biosynthesis of fukinolic acid, which had been isolated from the Japanese fuki vegetable, Petasites japonicus, was investigated by feeding selected (13)C-labeled compounds to axenic cultures of P. japonicus. [1,2-(13)C(2)] sodium acetate and [1-(13)C] L-tyrosine were incorporated into the fukiic acid sub group, while [3-(13)C] L-phenylalanine was incorporated into the caffeic acid moiety.

Caffeic Acids↗
PubMed2002

Effect of acute ingestion of fresh and stored lettuce (Lactuca sativa) on plasma total antioxidant capacity and antioxidant levels in human subjects.

The present study investigated whether storage under modified-atmosphere packaging (MAP) affected the antioxidant properties of fresh lettuce (Lactuca sativa). Eleven healthy volunteers (six men, five women) consumed 250 g fresh lettuce, and blood was sampled before (0 h) and 2, 3 and 6 h after consumption. The protocol was repeated 3 d later with the same lettuce stored at 5 degrees C under MAP conditions (O2-N2 (5:95, v/v)). Results showed that after ingestion of fresh lettuce, plasma total radical-trapping antioxidant potential (TRAP), measured as area under the curve, was significantly higher (1.3 (sem 0.3) mmol/l per 6 h; P<0.05) than the value obtained with MAP-stored lettuce (0.1 (sem 0.2) mmol/l per 6 h). Plasma TRAP, quercetin and p-coumaric acid were significantly different from baseline values (P<or=0.05) 2 and 3 h after fresh lettuce ingestion. Caffeic acid increased significantly at 3 h (P<0.05). Plasma beta-carotene levels increased significantly at 6 h (P<0.05). Vitamin C concentrations (mg/l) rose from 10.9 (sem 2.0) to 12.7 (sem 3.0) (P<0.001), 12.7 (sem 2.0) (P<0.01) and 12.9 (sem 3.0) (P<0.05) at 0, 2, 3 and 6 h respectively. No changes were observed after ingestion of MAP-stored lettuce for all the measured markers. Our present results showed that ingestion of MAP-stored lettuce does not modify plasma redox status in healthy subjects. Further research is needed to develop post-harvesting techniques able to preserve the bioactive molecule content of plant food.

Adult↗
PubMed2002

Essential fatty acids and phenolic acids from extracts and leachates of southern cattail (Typha domingensis P.).

We have been able to isolate several phytotoxic compounds from aqueous extracts and leachates of cattails (Typha domingensis) using activated charcoal as an absorbant, followed by successive extraction with organic solvents, analysis by GC/MS, and structural elucidation by NMR spectroscopy when possible. The phytotoxins were identified as essential fatty acids (linoleic acid and alpha-linolenic acid) and phenolic compounds of known phytotoxic activity (caffeic acid from the aqueous extracts; caffeic, p-coumaric, and gallic acid from the leachates). Both extracts and the phytotoxins in the extracts have the potential of inhibiting the growth and chlorophyll production of several ecologically relevant species.

Fatty Acids, Essential↗
PubMed1975

[Cinnamic acid 4-hydroxylase and 0-methyltransferase activities in leaves of hypersensitive tobacco plants infected by tobacco mosaic virus].

Tobacco leaves of Nicotiana tabacum L., variety Samsun NN, show a low cinnamic acid-4-hydroxylase activity and a rather high O-methyltransferase activity. Caffeic acid, the substrate of the latter enzyme, is methylated specifically in the meta position. In TMV-infected leaves a strong increase in the activities of phenylalanine ammonia-lyase and of these two enzymes occurs at the time of appearance and development of the necrotic reaction.

Caffeic Acids↗
PubMed2006

[Studies on phenolic compounds from Polygonum aviculane].

OBJECTIVE: To study the chemical constituents from the aerial parts of Polygomun aviculane. METHOD: The chemical constituents were isolated by silica gel column chromatography and preparative silica thin layer chromatography, and their structures were elucidated on the basis of physico-chemical evidences and spectroscopic analysis (IR, MS, 1H and 13C-NMR). RESULT: Seven phenolic compounds were identified as rosmarinic acid (1), gallic acid (2), gentisic acid 5-O-(6'-O-galloyl)-beta-D-glucopyranoside (3), caffeic acid (4), p-coumaric acid (5), ethyl caffeate (6) and acteoside (7), respectively. CONCLUSION: Compounds 1, 3, 6 and 7 were isolated from this plant for the first time. These results provided theoretical evidences for the further bioactive investigation on this plant.

Caffeic Acids↗
PubMed2004

Boron deficiency causes accumulation of chlorogenic acid and caffeoyl polyamine conjugates in tobacco leaves.

The effects of boron (B) deficiency on carbohydrate concentrations and the pattern of phenolic compounds were studied in leaves of tobacco plants (Nicotiana tabacum L.). Plants grown under B deficiency showed a notable increase in leaf carbohydrates and total phenolic compounds when compared to controls. The qualitative composition of phenolics was analyzed by HPLC-mass spectrometry. The level of caffeate conjugates (i.e., chlorogenic acid) increased in B-deficient plants. In addition, the accumulation of two caffeic acid amides (N-caffeoylputrescine and putative dicaffeoylspermidine) was observed.

Boron↗
PubMed2002

Daphnetin methylation by a novel O-methyltransferase is associated with cold acclimation and photosystem II excitation pressure in rye.

In plants, O-methylation of phenolic compounds plays an important role in such processes as lignin synthesis, flower pigmentation, chemical defense, and signaling. However, apart from phenylpropanoids and flavonoids, very few enzymes involved in coumarin biosynthesis have been identified. We report here the molecular and biochemical characterization of a gene encoding a novel O-methyltransferase that catalyzes the methylation of 7,8-dihydroxycoumarin, daphnetin. The recombinant protein displayed an exclusive methylation of position 8 of daphnetin. The identity of the methylated product was unambiguously identified as 7-hydroxy-8-methoxycoumarin by co-chromatography on cellulose TLC and coelution from high performance liquid chromatography, with authentic synthetic samples, as well as by UV, mass spectroscopy, (1)H NMR spectral analysis, and NOE correlation signals of the relevant protons. Northern blot analysis and enzyme activity assays revealed that the transcript and corresponding enzyme activity are up-regulated by both low temperature and photosystem II excitation pressure. Using various phenylpropanoid and flavonoid substrates, we demonstrate that cold acclimation of rye leaves increases O-methyltransferase activity not only for daphnetin but also for the lignin precursors, caffeic acid, and 5-hydroxyferulic acid. The significance of this novel enzyme and daphnetin O-methylation is discussed in relation to its putative role in modulating cold acclimation and photosystem II excitation pressure.

Amino Acid Sequence↗
PubMed2006

Polyphenol composition and antioxidant activity of Kei-apple (Dovyalis caffra) juice.

The polyphenolic and ascorbate (ASC) components as well as the antioxidant capacity of Kei-apple (Dovyalis caffra) juice were analyzed and compared to three other fruit juices. The Kei-apple juice had significantly the highest total polyphenolic concentrations (1013 mg gallic acid equivalent/L), and solid phase (C(18)) fractionation identified the majority of these polyphenols to be phenolic acids. The Kei-apple juice also had significantly the highest ASC concentrations (658 mg/L), which showed exceptional heat stability with very little conversion to dehydroascorbate (DHA). Antioxidant capacities of both the unfractionated fruit juices and their solid phase-extracted fractions, as determined by oxygen radical absorbance capacity and ferric reducing antioxidant power analyses, correlated well to the polyphenol concentrations. Gas chromatography-mass spectrometry analyses showed caffeic acid as the most abundant polyphenol present (128.7 mg/L) in the Kei-apple juice; it contributed to 63% of the total antioxidant capacity (of all of the individual compounds identified). Other notable polyphenols identified in higher concentrations included p-coumaric acid, p-hydroxyphenylacetic acid, and protocatechuic acid. Our results therefore support the putative high antioxidant value linked to this fruit and better define this potential in terms of the major antioxidants that exist in the Kei-apple.

Antioxidants↗
PubMed2004

Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli.

Flavonoids are important plant-specific secondary metabolites synthesized from 4-coumaroyl coenzyme A (CoA), derived from the general phenylpropanoid pathway, and three malonyl-CoAs. The synthesis involves a plant type III polyketide synthase, chalcone synthase. We report the cloning and coexpression in Escherichia coli of phenylalanine ammonia lyase, cinnamate-4-hydroxylase, 4-coumarate:CoA ligase, and chalcone synthase from the model plant Arabidopsis thaliana. Simultaneous expression of all four genes resulted in a blockage after the first enzymatic step caused by the presence of nonfunctional cinnamate-4-hydroxylase. To overcome this problem we fed exogenous 4-coumaric acid to induced cultures. We observed high-level production of the flavanone naringenin as a result. We were also able to produce phloretin by feeding cultures with 3-(4-hydroxyphenyl)propionic acid. Feeding with ferulic or caffeic acid did not yield the corresponding flavanones. We have also cloned and partially characterized a new tyrosine ammonia lyase from Rhodobacter sphaeroides. Tyrosine ammonia lyase was substituted for phenylalanine ammonia lyase and cinnamate-4-hydroxylase in our E. coli clones and three different growth media were tested. After 48 h induction, high-level production (20.8 mg L(-1)) of naringenin in metabolically engineered E. coli was observed for the first time.

Arabidopsis↗
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↗
PubMed2004

Application of preparative high-speed counter-current chromatography for separation of chlorogenic acid from Flos Lonicerae.

Chlorogenic acid, an ester formed between caffeic acid and quinic acid, is a major phenolic compound in the traditional Chinese medicinal herb Flos Lonicerae. The separation and purification of chlorogenic acid from the crude extract of Flos Lonicerae was achieved by high-speed counter-current chromatography (HSCCC). A high acid, highly polar two-phase solvent system containing n-butanol-acetic acid-water (4:1:5) was run on a preparative scale. The upper phase was used as the mobile phase in the head to tail elution mode. A 300-mg quantity of the crude extract containing 5.97% chlorogenic acid was loaded on a 342-ml HSCCC column. Double separations were performed with the same solvent system yielding 16.9 mg chlorogenic acid at 94.8% purity with approximately 90% recovery.

Chlorogenic Acid↗
PubMed2006

Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae.

Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiranthus cheiri L. These pigments were determined to be cyanidin 3-O-[2-O-((acyl-II)-(beta-d-xylopyranosyl))-6-O-(acyl-I)-beta-d-glucopyranoside]-5-O-[6-O-(acyl-III)-beta-d-glucopyranoside], in which the acyl-I group is represented by glucosyl-p-coumaric acid, p-coumaric acid and ferulic acid, acyl-II by caffeic acid and ferulic acid, and acyl-III by malonic acid, respectively. The distribution and biosynthesis of acylated cyanidin 3-sambubioside-5-glucosides are discussed according to the variations of acylation and glucosylation at their 3-sambubiose residues.

Acylation↗