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1.
The antiradical activity of caffeic acid (1), dihydrocaffeic acid (5), and their corresponding n-alkyl esters was evaluated by using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(*)) method. Dihydrocaffeic acid (5) was the most potent compound, having an antiradical effect higher than that of (+/-)-alpha-tocopherol, whereas caffeic acid (1) was less efficient. Esterification of the carboxyl group of dihydrocaffeic acid (5) had a dramatic effect on its antiradical potency, but similar effects were not observed for caffeic acid (1) derivatives. The n-alkyl esters of both phenolic series had similar potencies, and their antiradical activities were independent of the alkyl chain length. Dose-dependent scavenger effects were found in both series. Acid-base properties of the compounds, evaluated by using potentiometry and spectrophotometry, showed that the catechol moiety had pK(a2) and pK(a3) values of 9. 24-9.02 and 11.38-10.99 in the dihydrocaffeic series and 8.48-8.24 and 11.38-11.07 in the caffeic series, respectively. Antiradical activity and pK(a) values of the compounds were not related.  相似文献   

2.
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.  相似文献   

3.
Phenolic antioxidants from the leaves of Corchorus olitorius L.   总被引：3，自引：0，他引：3  
Six phenolic antioxidative compounds [5-caffeoylquinic acid (chlorogenic acid), 3,5-dicaffeoylquinic acid, quercetin 3-galactoside, quercetin 3-glucoside, quercetin 3-(6-malonylglucoside), and quercetin 3-(6-malonylgalactoside) (tentative)] were identified from the leaves of Corchorus olitorius L. (moroheiya) by NMR and FAB-MS. The contents of these phenolic compounds, ascorbic acid, and alpha-tocopherol in C. olitorius leaves were determined, and their antioxidative activities were measured using the radical generator-initiated peroxidation of linoleic acid. The results obtained showed that 5-caffeoylquinic acid was a predominant phenolic antioxidant in C. olitorius leaves.  相似文献   

4.
The in vitro biochemical stability of caffeic acid phenethyl ester in rat and human plasma was investigated and compared with the stability of other caffeic acid esters (chlorogenic acid and rosmarinic acid). The incubation of the compounds in rat plasma for up to 6 h showed that caffeic acid phenethyl ester, but not the other compounds, was hydrolyzed, whereas human plasma did not affect the stability of all the assayed compounds. The products in rat plasma were caffeic acid and an unknown compound, which was identified by mass spectrometry as caffeic acid ethyl ester, produced by transesterification in the presence of ethanol used as vehicle for standard compounds. Specific inhibitors of different plasma esterases allowed the identification of a carboxylesterase as the enzyme involved in the metabolism of caffeic acid phenethyl ester. The oral administration in rats of caffeic acid phenethyl ester in the presence of both ethanol and 2-(2-ethoxyethoxy)ethanol gave rise to a dramatic increase of caffeic acid, as well as low levels of caffeic acid phenethyl ester, caffeic acid ethyl ester, and caffeic acid 2-(2-ethoxyethoxy)ethyl ester, in urine collected within 24 h after treatment. These results suggest that caffeic acid phenethyl ester is hydrolyzed also in vivo to caffeic acid as the major metabolite and that its biological activities should be more properly assayed and compared with those of caffeic acid, its bioactive hydrolysis product. Moreover, alcohols should be carefully used in vivo as solvents for caffeic acid phenethyl ester, since they can give rise to new bioactive caffeic acid esters.  相似文献   

5.
High-performance liquid chromatography with diode array (LC-DAD) and electrospray ionization mass spectrometric detection (ESI-MS) was used to analyze phenolic compounds of two blackberry species ( Rubus glaucus Benth. and Rubus adenotrichus Schlech.) growing in South America. UV-visible spectrophotometry was a valuable tool for identifying the class of phenolic compound, whereas MS and MS ( n ) fragmentation data were useful for their structural characterization. Ellagitannins were the major compounds, with sanguiin H-6 and lambertianin C being the predominant ones. The anthocyanin composition as well as the presence or absence of kaempferol glycosides can be used to distinguish the Rubus species studied. Flavonol hexoside-malonates were identified in both berries. Hydroxycinnamic acids were minor compounds and found as ferulic, caffeic, and p-coumaric acid esters. Similar contents were obtained by analysis of soluble ellagitannins and ellagic acid glycosides as ellagic acid equivalents and by analysis of ellagic acid equivalents released after acid hydrolysis.  相似文献   

6.
Phenolic acid profiles in some small berries   总被引：1，自引：0，他引：1  
The composition of phenolic acids in several small berries grown in Northeastern Poland, namely, low-bush blueberries, black mulberries, European juneberries, black currants, fruits of blue-berried honeysuckle, and blackberries, was determined by gas chromatography (GC) and mass spectrometry (MS). The total content of phenolic acids, identified by GC-MS, ranged from 2845.8 +/- 141.0 (black mulberries) to 5418.2 +/- 228.0 (blue-berried honeysuckle). Twenty phenolic acids were identified in the berries. Of these, hydroxycaffeic, m- and p-coumaric, and 3,4-dimethoxycinnamic acids were the major phenolic acids in blackberries and blueberries, m-coumaric acid was the major phenolic acid in blue-berried honeysuckle and black currant fruits, while salicylic, caffeic, and m- and p-coumaric acids were the predominant phenolic acids in European juneberries. Syringic and veratric acids were detected only in blueberries, while p-hydroxybenzoic and sinapic acids were present only in black currants and o-coumaric acid was present in blueberries and black mulberries. The phenolic acids liberated from esters and glycosidic bonds were the major fractions of phenolic acids in the berries.  相似文献   

7.
荣思川  师尚礼  孙灿灿 《土壤》2016,48(5):931-938
通过高效液相色谱(HPLC)法测定不同试验地间18个苜蓿(Medicago sativa L.)品种植株及根际土壤中主要酚酸和香豆素物质的含量,分析其在不同品种苜蓿植株中的分布特征及不同试验地间差异。经过ASE 350型加速溶剂萃取仪萃取苜蓿植株及根际土壤中酚酸类和香豆素物质,萃取液存放于2oC冰箱,并用0.45μm有机滤膜过滤后通过HPLC测定自毒物质含量。结果显示,18个苜蓿品种中香豆素、阿魏酸、绿原酸、咖啡酸的含量存在差异,其中香豆素、绿原酸含量显著高于阿魏酸、咖啡酸含量。各苜蓿品种间单一自毒物质含量差异显著(P0.05),香豆素、阿魏酸、绿原酸和咖啡酸的总含量差异明显。武威试验地酚酸和香豆素物质平均含量比会宁试验地低4.01%。研究表明:不同苜蓿品种间香豆素、阿魏酸、绿原酸、咖啡酸物质总含量差异显著;苜蓿植株中香豆素、阿魏酸、绿原酸、咖啡酸物质总含量与根际土壤中含量差异极显著。  相似文献   

8.
Hydroxycinnamic acids are antioxidant phenolic compounds which are widespread in plant foods, contribute significantly to total polyphenol intakes, and are absorbed by humans. The extent of their putative health benefit in vivo depends largely on their bioavailability. However, the mechanisms of absorption and metabolism of these phenolic compounds have not been described. In this study, we used the in vitro Caco-2 model of human small intestinal epithelium to investigate the metabolism of the major dietary hydroxycinnamates (ferulate, sinapate, p-coumarate, and caffeate) and of diferulates. The appearance of metabolites in the medium versus time was monitored, and the various conjugates and derivatives produced were identified by HPLC-DAD, LC/MS, and enzyme treatment with beta-glucuronidase or sulfatase. Enterocyte-like differentiated Caco-2 cells have extra- and intracellular esterases able to de-esterify hydroxycinnamate and diferulate esters. In addition, intracellular UDP-glucuronosyltransferases and sulfotransferases existing in Caco-2 cells are able to form the sulfate and the glucuronide conjugates of methyl ferulate, methyl sinapate, methyl caffeate, and methyl p-coumarate. However, only the sulfate conjugates of the free acids, ferulic acid, sinapic acid, and p-coumaric acid, were detected after 24 h. The O-methylated derivatives, ferulic and isoferulic acid, were the only metabolites detected following incubation of Caco-2 cells with caffeic acid. These results show that the in vitro model system differentiated Caco-2 cells have the capacity to metabolize dietary hydroxycinnamates, including various phase I (de-esterification) and phase II (glucuronidation, sulfation, and O-methylation) reactions, and suggests that the human small intestinal epithelium plays a role in the metabolism and bioavailability of these phenolic compounds.  相似文献   

9.
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.  相似文献   

10.
In this paper is considered a new computerized approach to the determination of concentrations of phenolic compounds (caffeic acid and catechol). An integrated artificial neural network (ANN)/laccase biosensor is designed. The data collected (current signals) from amperometric detection of the laccase biosensor were transferred into an ANN trained computer for modeling and prediction of output. Such an integrated ANN/laccase biosensor system is capable of the prediction of caffeic acid and catechol concentrations of olive oil mill wastewater, based on the created models and patterns, without any previous knowledge of this phenomenon. The predicted results using the ANN were compared with the amperometric detection of phenolic compounds obtained at a laccase biosensor in olive oil wastewater of the 2004-2005 harvest season. The difference between the real and the predicted values was <0.5%. biosensor; olive oil mill wastewater; chemical analysis; phenolic compounds.  相似文献   

11.
The behavior of antioxidants in emulsions is influenced by several factors such as pH and emulsifier type. This study aimed to evaluate the interaction between selected food emulsifiers, phenolic compounds, iron, and pH and their effect on the oxidative stability of n-3 polyunsaturated lipids in a 10% oil-in-water emulsion. The emulsifiers tested were Tween 80 and Citrem, and the phenolic compounds were naringenin, rutin, caffeic acid, and coumaric acid. Lipid oxidation was evaluated at all levels, that is, formation of radicals (ESR), hydroperoxides (PV), and secondary volatile oxidation products. When iron was present, the pH was crucial for the formation of lipid oxidation products. At pH 3 some phenolic compounds, especially caffeic acid, reduced Fe(3+) to Fe(2+), and Fe(2+) increased lipid oxidation at this pH compared to pH 6. Among the evaluated phenols, caffeic acid had the most significant effects, as caffeic acid was found to be prooxidative irrespective of pH, emulsifier type, and presence of iron, although the degrees of lipid oxidation were different at the different experimental conditions. The other evaluated phenols were prooxidative at pH 3 in Citrem-stabilized emulsions and had no significant effect at pH 6 in Citrem- or Tween-stabilized emulsions on the basis of the formation of volatiles. The results indicated that phenol-iron complexes/nanoparticles were formed at pH 6.  相似文献   

12.
To check the influence of the conservation procedure in the chemical composition of chanterelle mushroom, phenolic compounds and organic acids of samples preserved under four different conditions (drying, freezing, conservation in olive oil and in vinegar) were determined. Phenolics and organic acids were analyzed by HPLC-DAD and HPLC-UV, respectively. The results showed that chanterelle is characterized by the presence of six phenolic compounds (3-, 4-, and 5-O-caffeoylquinic acid, caffeic acid, p-coumaric acid, and rutin) and five organic acids (citric, ascorbic, malic, shikimic, and fumaric acids). Samples preserved in olive oil also exhibited hydroxytyrosol, tyrosol, luteolin, and apigenin, whereas conservation in vinegar led to the detection of hydroxytyrosol, tyrosol, and tartaric acid in the analyzed samples. The conservation procedures to which chanterelle samples were subjected seem to affect the qualitative and quantitative phenolics and organic acids profiles.  相似文献   

13.
Cydonia oblonga Miller leaves phenolic compounds were analyzed by reversed-phase HPLC/DAD and HPLC/UV. Qualitative and quantitative analysis of phenolics were carried out in a total of 36 samples of quince leaves from three different geographical origins of Northern (Bragan?a and Carrazeda de Ansi?es) and Central Portugal (Covilh?) and three collection months (June, August, and October of 2006). These leaves presented a common phenolic profile composed by nine compounds: 3- O-, 4- O- and 5- O-caffeoylquinic acids, 3,5- O-dicaffeoylquinic acid, quercetin-3- O-galactoside, quercetin-3- O-rutinoside, kaempferol-3- O-glycoside, kaempferol-3- O-glucoside, and kaempferol-3- O-rutinoside. 5- O-caffeoylquinic acid was the major phenolic compound (36.2%), followed by quercetin 3- O-rutinoside (21.1%). Quince leaves are characterized by higher relative contents of kaempferol derivatives than fruits (pulps, peels, and seeds), especially in what concerns kaempferol-3- O-rutinoside (12.5%). C. oblonga leaves total phenolic content was very high, varying from 4.9 to 16.5 g/kg dry matter (mean value of 10.3 g/kg dry matter), indicating that these leaves can be used as a good and cheap source of bioactive constituents. Significantly differences were observed in 3- O-caffeoylquinic and 3,5- O-dicaffeoylquinic acids contents, according to geographical provenance and harvesting month, suggesting a possible use of these compounds as geographical origin and/or maturity markers.  相似文献   

14.
Aroma compounds in Chinese "Wuliangye" liquor were identified by gas chromatography-olfactometry (GC-O) after fractionation. A total of 132 odorants were detected by GC-O in Wuliangye liquor on DB-wax and DB-5 columns. Of these, 126 aromas were identified by GC-mass spectrometry (MS). Aroma extract dilution analysis (AEDA) was further employed to identify the most important aroma compounds in "Wuliangye" and "Jiannanchun" liquors. The results showed that esters could be the most important class, especially ethyl esters. Various alcohols, aldehydes, acetals, alkylpyrazines, furan derivatives, lactones, and sulfur-containing and phenolic compounds were also found to be important. On the basis of flavor dilution (FD) values, the most important aroma compounds in Wuliangye and Jiannanchun liquors could be ethyl butanoate, ethyl pentanoate, ethyl hexanoate, ethyl octanoate, butyl hexanoate, ethyl 3-methylbutanoate, hexanoic acid, and 1,1-diethoxy-3-methylbutane (FD > or = 1024). These compounds contributed to fruity, floral, and apple- and pineapple-like aromas with the exception of hexanoic acid, which imparts a sweaty note. Several pyrazines, including 2,5-dimethyl-3-ethylpyrazine, 2-ethyl-6-methylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, and 3,5-dimethyl-2-pentylpyrazine, were identified in these two liquors. Although further quantitative analysis is required, it seems that most of these pyrazine compounds had higher FD values in Wuliangye than in Jiannanchun liquor, thus imparting stronger nutty, baked, and roasted notes in Wuliangye liquor.  相似文献   

15.
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.  相似文献   

16.
Research was initiated to measure antioxidant activity of extracts from oat (Avena sativa L.) groats and hulls and the concentrations of phenolic substances that may contribute to antioxidant activity. Antioxidant activity of ethanolic extracts of four cultivars was evaluated by an in vitro assay that measures the inhibition of coupled autoxidation of linoleic acid and β-carotene. Total phenolic content was determined using Folin and Ciocalteau's phenol reagent and was expressed as gallic acid equivalents. Phenolic compounds were separated by reversed-phase HPLC and detected at 290 nm. Peaks were identified by comparing retention times and spectra with known standards and verified with internal standards. Groats had significantly higher antioxidant activity than hulls. For two cultivars, total phenolic content was similar in groats and hulls, whereas one cultivar had higher and another lower total phenolic content in groats than hulls. Ten phenolic compounds were separated and identified in extracts, and one flavan-3-ol and three avenanthramides were tentatively identified. The concentrations of many of these compounds differed among cultivars and between fractions. In general, caffeic acid and the avenanthramides were predominantly found in groats, whereas many of the other phenolics were present in greater concentrations in hulls.  相似文献   

17.
Antioxidant properties of ferulic acid and its related compounds   总被引：13，自引：0，他引：13  
Antioxidant activity of 24 ferulic acid related compounds together with 6 gallic acid related compounds was evaluated using several different physical systems as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order caffeic acid > sinapic acid > ferulic acid > ferulic acid esters > p-coumaric acid. In bulk methyl linoleate, test hydroxycinnamic acids and ferulic acid esters showed antioxidant activity in parallel with their radical scavenging activity. In an ethanol-buffer solution of linoleic acid, the activity of test compounds was not always associated with their radical scavenging activity. Ferulic acid was most effective among the tested phenolic acids. Esterification of ferulic acid resulted in increasing activity. The activity of alkyl ferulates was somewhat influenced by the chain length of alcohol moiety. When the inhibitory effects of alkyl ferulates against oxidation of liposome induced by AAPH were tested, hexyl, octyl, and 2-ethyl-1-hexyl ferulates were more active than the other alkyl ferulates. Furthermore, lauryl gallate is most effective among the tested alkyl gallates. These results indicated that not only the radical scavenging activity of antioxidants, but also their affinity with lipid substrates, might be important factors in their activity.  相似文献   

18.
The antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl. (Hsian-tsao) was investigated. Hsian-tsao was extracted with various solvents, and the results showed that the fraction treated with acidic ethyl acetate (pH 2) possessed large amounts of phenolic compounds and a strong antioxidant activity on peroxidation of linoleic acid. The antioxidant activity (inhibition of peroxidation, IP%) of the acidic ethyl acetate of Hsian-tsao extract at 50 microg/mL (98.9%) was stronger than those of 50 microg/mL alpha-tocopherol (78%) and BHA at 10 microg/mL (90%). When fractionated with Amberlite XAD-7 gel chromatography, the acidic ethyl acetate fraction of Hsian-tsao extract was separated into four subfractions (A-D). Subfraction B, with high yield and strong antioxidant activity, was further isolated and purified and then identified as containing protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, and syringic acid by means of UV, EI-MS, and (1)H and (13)C NMR. The antioxidant capability of isolated compounds was also determined using the thiocyanate system and the erythrocyte ghost system. The results indicate that the phenolic acids could be important antioxidant components in Hsian-tsao, among which caffeic acid with the highest antioxidant activity and the greatest content is most important.  相似文献   

19.
Sweetpotato leaves (Ipomoea batatas L.) contain a high content of polyphenolics that consist of caffeic acid, chlorogenic acid, 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, and 3,4,5-tri-O-caffeoylquinic acid. We investigated the suppression of the proliferation of selected human cancer cells by phenolic compounds isolated from sweetpotato leaf. The human cancer cells used in this research included a stomach cancer (Kato III), a colon cancer (DLD-1), and a promyelocytic leukemia cell (HL-60). Caffeic acid and di- and tricaffeoylquinic acids dose-dependently depressed cancer cell proliferation, and the difference in sensitivity between caffeoylquinic acid derivatives and each kind of cancer cell was observed. Specifically, 3,4,5-tri-O-caffeoylquinic acid effectively depressed the growth of three kinds of cancer cells, and caffeic acid had an exceptionally higher effect against HL-60 cells than other di- and tricaffeoylquinic acids. In attempting to clarify the mechanism of growth suppression with the addition of the apoptotic inhibitor N-ethylmaleimide, we observed that the nuclear granulation in 3,4,5-tri-O-caffeoylquinic acid-treated HL-60 cells suggested apoptosis induction. This effect was confirmed by DNA fragmentation, an increase of caspase-3 activity, and expression of c-Jun. Growth suppression of HL-60 cells by 3,4,5-tri-O-caffeoylquinic acid was determined to be the result of apoptotic death of the cells. These results indicate that 3,4,5-tri-O-caffeoylquinic acid may have potential for cancer prevention.  相似文献   

20.
Inhibitory effects of plant phenols on the activity of selected enzymes   总被引：3，自引：0，他引：3  
Selected enzymes (alpha-amylase, trypsin, and lysozyme) were allowed to react with some simple phenolic and related compounds (caffeic acid, chlorogenic acid, ferulic acid, gallic acid, m-, o-, and p-dihydroxybenzenes, quinic acid, and p-benzoquinone). The derivatized enzymes obtained were characterized in terms of their activity. In vitro experiments showed that the enzymatic activity of the derivatives was adversely affected. This enzyme inhibition depended on the reactivity of the phenolic and related substances tested as well as on the kind of substrate applied. The decrease in the activity was accompanied by a reduction in the amount of free amino and thiol groups, as well as tryptophan residues, which resulted from the covalent attachment of the phenolic and related compounds to these reactive nucleophilic sites in the enzymes. The enzyme inhibition correlates well with the blocking of the mentioned amino acid side chains.  相似文献   

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