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PubMed2003

The genetic basis of C-glycosyl flavone B-ring modification in maize (Zea mays L.) silks.

Resistance to corn earworm (CEW) (Helicoverpa zea Boddie) has been attributed to high concentrations of C-glycosyl flavones and chlorogenic acid in maize (Zea mays L.) silks. The most common C-glycosyl flavones isolated from maize silks are maysin, apimaysin, and methoxymaysin, which are distinguished by their B-ring substitutions. For a better understanding of the genetic mechanisms underlying the synthesis of these compounds, we conducted a quantitative trait locus (QTL) study with two populations: (Tx501 x NC7A)F2 and (Tx501 x Mp708)F2. For chlorogenic acid, maysin, and methoxymaysin concentration, the major QTL for both populations was located on chromosome 4 near umc1963. For apimaysin, the major QTL in both populations was located at the position of the pr1 locus on chromosome 5. The QTL alleles on chromosome 4 that increased the synthesis of methoxymaysin significantly decreased the synthesis of maysin and chlorogenic acid. This decrease in maysin concentration was four-fold greater than the increase in methoxymaysin. Our results indicate that the QTL on chromosome 4, responsible for the increase in methoxymaysin synthesis, alters the dynamics of both the phenylpropanoid and flavonoid pathways.

Alleles↗
PubMed2005

[Comparative study on internal quality of various Chrysanthemum morifolium].

OBJECTIVE: To study the quality and genetic diversity of Chrysanthemun morifolium, the chemical constituents of 20 medicinal chrysanthemum cultivars in China were compared. METHOD: Chemical constituents of the 20 cultivars were compared in three types of index: chlorogenic acid, flavonoid and volatile oil. RESULT: There are visible differences on the contents of chlorogenic acid, flavonoid and volatile oil between the cultivars. CONCLUSION: Each cultivar has its own internal quality, and it is affected by many factors. The chemical constituents of the cultivars showed the genetic diversity in medicinal chrysanthemums of China.

China↗
PubMed2005

Tungtungmadic acid, a novel antioxidant, from Salicornia herbacea.

Tungtungmadic acid (3-caffeoyl-4-dihydrocaffeoyl quinic acid) is a new chlorogenic acid derivative that was isolated from the Salicornia herbacea. The structure of tungtungmadic acid was determined using chemical and spectral analysis. The antioxidant activity of tungtungmadic acid was evaluated using various antioxidant assays, including free radical scavenging, lipid peroxidation and hydroxyl radical-induced DNA strand breaks assays. Tungtungmadic acid (IC50 = 5.1 microM and 9.3 microM) was found to have higher antioxidant activity in the DPPH scavenging assay as well as in the iron-induced liver microsomal lipid peroxidation system. In addition, the tungtungmadic acid was also effective in protecting the plasmid DNA against strand breakage induced by hydroxyl radicals.

Amaranthaceae↗
PubMed1972

The Binding of Indole-3-acetic Acid and 3-Methyleneoxindole to Plant Macromolecules.

Homogenates of pea (Pisum sativum L., var. Alaska) seedlings exposed to (14)C-indole-3-acetic acid or (14)C-3-methyleneoxindole, an oxidation product of indole-3-acetic acid, were extracted with phenol. In both cases 90% of the bound radioactivity was found associated with the protein fraction and 10% with the water-soluble, ethanol-insoluble fraction. The binding of radioactivity from (14)C-indole-3-acetic acid is greatly reduced by the addition of unlabeled 3-methyleneoxindole as well as by chlorogenic acid, an inhibitor of the oxidation of indole-3-acetic acid to 3-methyleneoxindole. Chlorogenic acid does not inhibit the binding of (14)C-3-methyleneoxindole. The labeled protein and water-soluble, ethanol-insoluble fractions of the phenol extract were treated with an excess of 2-mercaptoethanol. Independently of whether the seedlings had been exposed to (14)C-indole-3-acetic acid or (14)C-3-methyleneoxindole, the radioactivity was recovered from both fractions in the form of a 2-mercaptoethanol-3-methyleneoxindole adduct. These findings indicate that 3-methyleneoxindole is an intermediate in the binding of indole-3-acetic acid to macromolecules.

Journal Article↗
PubMed1999

Alterations of carbohydrate and lipid intermediary metabolism during inhibition of glucose-6-phosphatase in rats.

S 4048 (1-[2-(4-Chloro-phenyl)-cyclopropylmethoxy]-3, 4-dihydroxy-5-(3-imidazo[4, 5-b]pyridin-1-yl-3-phenyl-acryloyloxy)-cyclohexanecarboxylic acid), a derivative of chlorogenic acid, specifically inhibits the glucose-6-phosphate translocating component T1 of the glucose-6-phosphatase system. Its pharmacological effect was studied on carbohydrate and lipid parameters in rats. In starved and fed rats, S 4048 caused a dose-dependent reduction of blood glucose levels with a corresponding increase in hepatic and renal glycogen and glucose-6-phosphate. The major quantitative route of carbon flux in the liver during S 4048-induced inhibition of the glucose-6-phosphatase activity seemed to be glycogenesis. Plasma free fatty acids were increased secondarily due to the S 4048-induced hypoglycemia. Hepatic triglycerides were increased possibly due to increased re-esterification of the readily available free fatty acids. Glucose-6-phosphate translocase inhibitors may be useful for experimentally studying aspects of type 1 glycogen storage disease in laboratory animals as well as for the therapeutic modulation of inappropriately high rates of hepatic glucose production in type 2 diabetes.

Animals↗
PubMed1998

High-performance liquid chromatography with diode-array detection for the determination of phenolic compounds in peel and pulp from different apple varieties.

Quantitative analysis of phenolic compounds from four apple varieties (Golden and Red Delicious, Granny Smith and Green Reineta) using high-performance liquid chromatography with diode-array detection was carried out. For each variety, both peel and pulp were analysed. The identification of phenolic compounds was made by comparing their retention times and UV spectra with those of standards. The results revealed differences between pulp and peel in all cases studied. The highest levels of phenolic compounds were found in the peel. High levels of catechins and flavonol glycosides, especially rutin, were found in apple peels. Chlorogenic acid was the major peak in the pulp for all apple varieties studied except for Granny Smith. Significant quantitative differences between the apple varieties were also found, the Golden Delicious variety showing the lowest content of phenolic compounds and Green Reineta variety the highest. The recovery of phenolic compounds from both peel and pulp was measured in all apple varieties. The values ranged between 95 and 105%, indicating close to quantitative recovery for the method used.

Caffeic Acids↗
PubMed2002

On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.).

An on-line HPLC-DPPH screening method for phenolic antioxidants in apple methanol/water (80:20, v/v) extracts was applied. The determination of antioxidants was based on a decrease in absorbance at 515 nm after postcolumn reaction of HPLC-separated antioxidants with the 2,2'-diphenyl-1-picrylhydrazyl radicals (DPPH*). Each of the antioxidants separated by the HPLC column was observed as a negative peak corresponding to its antioxidative activity. The on-line method was applied for quantitative analysis of the antioxidants. A linear dependence of negative peak area on concentration of the reference antioxidants was observed. For validation of the on-line method the limit of detection, LOD (microg/mL), and the limit of quantification, LOQ (microg/mL), of the phenolic compounds were determined. Comparison of the UV and DPPH radical quenching chromatograms with authentic compounds identified catechin, chlorogenic acid, caffeic acid, epicatechin, and phloridzin in the apple cultivars (Lobo, Golden Delicious, and Boskoop), and the distribution of total antioxidant activity was calculated.

Antioxidants↗
PubMed1999

Novel antioxidant compounds from tart cherries (Prunus cerasus).

As indicated by an Fe(II)-induced liposome peroxidation bioassay, the EtOAc extract of tart cherries (Prunus cerasus) was found to have strong antioxidant activity. Purification of this extract afforded chlorogenic acid methyl ester (1) and three novel compounds, 2-hydroxy-3-(o-hydroxyphenyl) propanoic acid (2); 1-(3', 4'-dihydroxycinnamoyl)-cyclopenta-2,5-diol (3), and 1-(3', 4'-dihydroxycinnamoyl)-cyclopenta-2,3-diol (4), as determined by their spectral data. At a 20-microM concentration, the antioxidant activities of compounds 3 and 4 were comparable to the antioxidant activities of caffeic acid, whereas compound 1 showed activity similar to chlorogenic acid. Also, these compounds showed antioxidant activities similar to the commercial antioxidants tert-butylhydroquinone and butylated hydroxytoluene. However, compound 2 was not active when tested at a 100-microM concentration.

Antioxidants↗
PubMed2006

Regulation of secondary metabolism by the carbon-nitrogen status in tobacco: nitrate inhibits large sectors of phenylpropanoid metabolism.

Interactions between nitrogen and carbon metabolism modulate many aspects of the metabolism, physiology and development of plants. This paper investigates the contribution of nitrate and nitrogen metabolism to the regulation of phenylpropanoid and nicotine synthesis. Wild-type tobacco was grown on 12 or 0.2 mm nitrate and compared with a nitrate reductase-deficient mutant [Nia30(145)] growing on 12 mm nitrate. Nitrate-deficient wild-type plants accumulate high levels of a range of phenylpropanoids including chlorogenic acid, contain high levels of rutin, are highly lignified, but contain less nicotine than nitrogen-replete wild-type tobacco. Nia30(145) resembles nitrate-deficient wild-type plants with respect to the levels of amino acids, but accumulates large amounts of nitrate. The levels of phenylpropanoids, rutin and lignin resemble those in nitrogen-replete wild-type plants, whereas the level of nicotine resembles that in nitrate-deficient wild-type plants. Expression arrays and real time RT-PCR revealed that a set of genes required for phenylpropanoid metabolism including PAL, 4CL and HQT are induced in nitrogen-deficient wild-type plants but not in Nia30(145). It is concluded that nitrogen deficiency leads to a marked shift from the nitrogen-containing alkaloid nicotine to carbon-rich phenylpropanoids. The stimulation of phenylpropanoid metabolism is triggered by changes of nitrate, rather than downstream nitrogen metabolites, and is mediated by induction of a set of enzymes in the early steps of the phenylpropanoid biosynthetic pathway.

Amino Acids↗
PubMed2006

Inhibitory effect of phenolic acids on the proliferation of 3T3-L1 preadipocytes in relation to their antioxidant activity.

Obesity is an important topic in the world of public health and preventive medicine. Inhibition of preadipocyte proliferation plays an important role in the mechanisms of proposed antiobesity. In this in vitro study, the inhibitory effect of phenolic acids on 3T3-L1 preadipocytes was evaluated, and a relationship analysis was then conducted. The results showed that the addition of phenolic acids to the growth medium decreased the cell population growth of 3T3-L1 preadipocytes. The IC50 values of chlorogenic acid, gallic acid, o-coumaric acid and m-coumaric acid on 3T3-L1 preadipocytes were 72.3, 43.3, 48.2, and 49.2 microM, respectively. A relationship analysis indicated that there is a significant linear correlation between the influence of phenolic acids on cell population growth and their antioxidant activity (r = 0.77, p < 0.01). The cell cycle assay indicated that the treatment of 3T3-L1 preadipocytes with chlorogenic acid, o-coumaric acid, and m-coumaric acid caused cell cycle arrest in the G1 phase. Gallic acid did not affect the cell cycle profile; however, it increased the number of apoptotic cells (sub-G1 phase) in a time- and dose-dependent manner. Annexin V-fluorescein isothiocyanate (FITC)-propidium iodide (PI) apoptosis flow cytometric assay showed that gallic acid increased the number of early apoptotic (annexin V-FITC+/PI-) and late apoptotic cells (annexin V-FITC+/PI+) but not necrotic cells (annexin V-FITC-/PI+). The treatment of cells with gallic acid caused the loss of mitochondrial membrane potential (delta psi(m)). These results indicate that the inhibition of preadipocyte population growth by some phenolic acids might have further implication in in vivo antiobesity effects.

3T3-L1 Cells↗
PubMed1995

Selective extraction of quercetrin in vegetable drugs and urine by off-line coupling of boronic acid affinity chromatography and high-performance liquid chromatography.

Quercetrin, quercetin and chlorogenic acid were measured in urine or in drugs by combination of boronic acid affinity chromatography and HPLC. Simple reversed-phase HPLC with UV detection was used to determine quercetrin in five different Solidago virgaurea drugs. For determination of quercetrin in human urine immobilized boronic acid was applied for sample pretreatment. this procedure leads to a determination limit of 0.01 micrograms/ml with a recovery rate of 95.3%. The first results using this method for quercetrin pharmacokinetics are presented.

Boronic Acids↗
PubMed2004

Content of free phenolic compounds in cultivars of potatoes harvested in Tenerife (Canary Islands).

Determination of free phenolic compounds in potato samples was optimized using a high-performance liquid chromatographic (HPLC) method with on-line diode array detection. This method was applied to samples of four cultivars of potatoes harvested in Tenerife (Canary Islands). The free phenolic compounds found in the potato samples were (+)-catechin, chlorogenic acid, caffeic acid, p-coumaric acid, and ferulic acid. Potato samples belonging to Colorada cultivar, ssp. andigena, had mean concentrations of total phenolic compounds and chlorogenic acid higher than those found for Kerr's Pink and Cara cultivars, ssp. tuberosum, and for Negra cultivar, S. x chaucha. In contrast, p-coumaric acid was not detected in any potato samples of the Colorada cultivar. Traditional potatoes presented a higher mean concentration of ferulic acid than recently imported potatoes. A significant and negative correlation was established between (+)-catechin and p-coumaric acid. A considerable contribution to the daily intake of flavonoids was observed with the actual consumption of potatoes.

Atlantic Islands↗
PubMed2002

[Comparative study on internal quality of four cultivars of Chrysanthemum morifolium].

OBJECTIVE: To study the genetic diversity of C. morifolium on the chemical constituents. METHOD: Chemical constituents of four cultivars cultivated with the same conditions were compared in three types of index: chlorogenic acid, flavonoid and volatile oil. RESULT AND CONCLUSION: With different cultivars and processing methods, the contents of chlorogenic acid, flavonoid and volatile oil extracted from C. morifolium vary great extent.

Chlorogenic Acid↗
PubMed2003

Distribution of hydroxycinnamic acid conjugates in fruit of commercial eggplant (Solanum melongena L.) cultivars.

There is gathering evidence that antioxidant phytonutrients in fruits and vegetables have health-promoting effects. Eggplant fruit have a high content of antioxidant phenolic compounds. We evaluated the main class of eggplant phenolics, hydroxycinnamic acid conjugates, in the fruit of seven commercial cultivars. Fourteen conjugates were quantified and identified by high-performance liquid chromatography, ES(-)-MS, and (1)H NMR data. Significant differences in their content and composition were evident among cultivars and in tissue from stem, middle, and blossom end segments. Chlorogenic acid (5-O-caffeoylquinic acid) was the predominant compound, and its 3-O-, 4-O-, and 5-O-cis isomers were also present. The 10 other phenolics fell into four groups, including 3,5- and 4,5-dicaffeoylquinic acid isomers, four amide conjugates, two unknown caffeic acid conjugates, and 3-O-acetyl esters of 5-O- and 4-O-caffeoylquinic acid. Dicaffeoylquinic and 3-O-acetyl chlorogenic acids were most variable among the cultivars. Dicaffeoyquinic acids were most abundant in the blossom end, whereas 3-O-acetyl esters were highest in the midsection.

Chlorogenic Acid↗
PubMed2006

Quantification of the polyphenols and triterpene acids in chinese hawthorn fruit by high-performance liquid chromatography.

The levels of seven polyphenols (epicatechin, procyanidin B2, procyanidin B5, procyanidin C1, hyperoside, isoquercitrin, and chlorogenic acid) and two triterpene acids (oleanolic acid and ursolic acid) in the matured fruits of Chinese hawthorn (Crataegus pinnatifida Bge. var. major N.E.Br.) were determined by high-performance liquid chromatography methods. The average contents of those constituents in 37 representative cultivars were 1405, 1505, 339, 684, 56, 41, 234, 952, and 147 microg/g fresh weight (FW), respectively. A significant inverse correlation between the procyanidin contents and the latitude of the geographical origin of the cultivars was observed (r = 0.3851, P < 0.02). Correlation analysis of the levels of the nine compounds in the 37 cultivars yielded a strong correlation (P < 0.001) between the individual levels of the four procyanidins and the sum of the procyanidins level (r = 0.7413-0.9898) and between the flavonoids and the chlorogenic acid (r = 0.5383-0.9212). The changes in level of the nine compounds in the hawthorn fruit were evaluated during maturation using the Hebei Dajinxing cultivar. Sixty-one days after blossom, the polyphenol level reached the highest point and the sum of the contents was 1.36 g/100 g FW.

Chlorogenic Acid↗
PubMed2001

Structural damage to proteins caused by free radicals: asessment, protection by antioxidants, and influence of protein binding.

Oxidative damage to proteins results in biological dysfunctions such as perturbed activity in enzymes, transport proteins, and receptors. Here, we investigated structural damage to proteins induced by free radicals. Structural alterations to lysozyme, human serum albumin (HSA) and beta-lactoglobulin A were monitored by capillary zone electrophoresis. Four well-known antioxidants (quercetin, melatonin, Trolox, and chlorogenic acid) were examined for their ability to inhibit protein damage and to bind to these proteins. Melatonin and chlorogenic acid, which did not bind to any of the three proteins under study, showed scavenging and protective activities well correlated with the amount of free radicals generated. Trolox, which bound only to HSA, was a better protector of HSA than of the two other proteins, indicating that its antioxidant capacity is increased by a shielding effect. Finally, quercetin was a good antioxidant in protecting lysozyme and beta-lactoglobulin A, but its binding to HSA resulted in a pro-oxidant effect that accelerated HSA fragmentation. These results demonstrate that binding of an antioxidant to a protein may potentiate protection or damage depending on the properties of the antioxidant.

Amidines↗
PubMedDate not supplied

Combination effect of lignin F and natural products.

We investigated the effect of lignin F, isolated from the alkaline extract of the cone of Pinus parviflora Sieb. et Zucc, on the cytotoxic activity and radical intensity (measured by ESR spectroscopy) of various natural products. Lignin F slightly inhibited the proliferation of human oral tumor cell lines (human squamous cell carcinoma HSC-2, human salivary gland tumor HSG), but not that of human gingival fibroblast HGF, suggesting its tumor specific cytotoxic action. Lignin F enhanced the cytotoxic activity of vitamin K2, vitamin K3, sodium ascorbate (vitamin C), epigallocatechin gallate (EGCG) (a major component of green tea), gallic acid (structural unit of tannin), chlorogenic acid, and 6 tea extracts (Japanese green tea, Japanese barley tea, black tea, Chinese green tea, Chinese Jasmin tea, Chinese Oolong tea), to various extents. On the other hand, lignin inhibited the cytotoxic activity of curcumin and dopamine. ESR spectroscopy demonstrated that combination of lignin and vitamin K3, EGCG or gallic acid synergistically augmented the radical intensity. Lignin F enhanced the bactericidal activity of EGCG against E. coli. These data suggest the beneficial effect of the combination of lignin F and natural products.

Antineoplastic Agents, Phytogenic↗
PubMed2005

Screening of raw coffee for thiol binding site precursors using "in bean" model roasting experiments.

The purpose of the following study was to investigate the influence of coffee roasting on the thiol-binding activity of coffee beverages, and to investigate the potential of various green bean compounds as precursors of thiol-binding sites by using promising "in bean" model roast experiments. Headspace gas chromatographic analysis on coffee brews incubated in the presence of the roasty-sulfury smelling 2-furfurylthiol for 20 min at 30 degrees C in septum-closed vessels revealed that the amounts of "free" thiol decreased drastically with increasing the roasting degree of the beans used for preparation of the brews. A half-maximal binding capacity (BC(50)) of 183 mg of 2-furfurylthiol per liter of standard coffee beverage was determined for a roasted coffee (CTN value of 67), thus demonstrating that enormous amounts of the odor-active thiol are "bound" by the coffee. Furthermore, biomimetic "in bean" precursor experiments have been performed in order to elucidate the precursor for the thiol-binding sites in the raw coffee bean. These experiments opened the possibility of studying coffee model reactions under quasi-natural roasting conditions and undoubtedly identified chlorogenic acids as well as thermal degradation products caffeic acid and quinic acid as important precursors for low-molecular-weight thiol-binding sites. In particular, when roasted in the presence of transition metal ions, chlorogenic acids and even more caffeic acid showed thiol-binding activity which was comparable to the activity measured for the authentic coffee brew.

Binding Sites↗