High Chlorogenic Acid Content Research Articles

3-Hydroxy-6-Methylpyridine with Preventive Activity on Carbon Tetrachloride-Induced Liver Injury Is Produced During Roasting of Coffee Beans

Compounds which can be formed over the course of roasting coffee beans were investigated and isolated. One of these compounds was identified as 3-hydroxy-6-methylpyridine (3,6-Py). 3,6-Py and the coffee prepared from light-roasted coffee beans which contain this compound tended to suppress increases in plasma alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activities induced by carbon tetrachloride in mice, indicating that 3,6-Py formed during the roasting of coffee beans may be able to mitigate liver injury. The amounts of 3,6-Py were higher in French-roasted than light-roasted coffee beans of the Brazil Santos and Colombia Excelso varieties, suggesting that this compound might be produced under a more severe roasting condition. However, suppressive activity against liver injury was stronger in coffee from light-roasted than French-roasted beans. As the amounts of chlorogenic acid, which is known to have hepatoprotective activity, were higher in coffee from the light-roasted than French-roasted beans, stronger hepatoprotective activity in the coffee from light-roasted beans might be mainly concerned with its higher content of chlorogenic acid.

Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro

Chlorogenic acid and its related compounds are abundant plant polyphenols that have a diverse antiviral activity. In this study, HepG2.2.15 cells and duck hepatitis B virus infection model were used as in vitro and in vivo models to evaluate their anti-HBV activity. In the cell model, all the three compounds inhibited HBV-DNA replication as well as HBsAg production. Chlorogenic acid and caffeic acid also reduced serum DHBV level in DHBV-infected duckling model. Moreover, the anti-HBV activity of crude extracts of coffee beans, which have a high content of chlorogenic acid, was studied. Both the extracts of regular coffee and that of decaffeinated coffee showed inhibitory effect on HBV replication.

Quantification of phenolic acids and antioxidant activity in sweetpotato genotypes

Phenolic acid composition and antioxidant activity in roots of 14 commercially important sweetpotato genotypes were evaluated. Significant differences in total phenolics, individual phenolic acids, and antioxidant activity were found among the different sweetpotato genotypes. Total phenolic content, expressed in terms of chlorogenic acid equivalent, in different genotypes ranged from 1.4 to 4.7 mg g −1 dry weight (DW). Antioxidant activity was evaluated as Trolox equivalent, ranging from 1.3 to 4.6 mg g −1 DW. The highest total phenolic content and antioxidant activity were observed in a purple-fleshed genotype. Chlorogenic acid and 3,5-dicaffeoylquinic acid were the predominant phenolic acids, while caffeic acid was the least abundant in most genotypes. The highest content of chlorogenic acid (422.4 μg g −1 DW) was present in a white-fleshed cultivar ‘Quarter Million’ imported from Jamaica. However, a purple-fleshed genotype had the highest amounts of 3,5-dicaffeoylquinic (485.6 μg g −1 DW), 3,4-dicaffeoylquinic (125.6 μg g −1 DW), 4,5-dicaffeoylquinic (284.4 μg g −1 DW), and caffeic (20.5 μg g −1 DW) acids.

Enhancing phenylpropanoid secondary metabolites in Nicotiana tabacum and Salvia sclarea by overexpression of a rice myb4 transcription factor

Beside their crucial role in the plant's defence mechanisms, several compounds belonging to the plant phenylpropanoids have been demonstrated to be pharmacologically bioactive, as anti-oxidant, anti-inflammatory and anti-tumoral [1]. In this study, a metabolic engineering strategy was used to boost the synthesis of plant bioactive phenylpropanoids, by overexpression of the Osmyb4 transcription factor, isolated from rice [2], in N. tabacum plants and S. sclarea hairy roots. The heterologous TF was correctly expressed in both plants, confirming that the myb transcription factors are highly conserved in plant species. Several genes of the phenylpropanoid pathway were up-regulated in Osmyb4 overxpressing tobacco plants, including the PAL, 4CL1, 4CL2 and HQT genes, indicating that a specific branch of the phenylpropanoid pathway was activated by Osmyb4 TF. Accordingly to the level of expression of this set of genes, a higher content of chlorogenic acid (CGA) was synthesized in tobacco transgenic plants, as revealed by HPLC-DAD, LC-MSn and 1H-NMR analysis. Moreover, the overexpression of this TF in S. sclarea hairy roots caused a significant increase in the content of rosmarinic acid (RA), another biologically active phenylpropanoid [3]. Altogether these data indicate that Osmyb4, as a conserved positive regulator of the biosynthetic pathway of plant phenylpropanoids, is a useful molecular tool to genetically manipulate this pathway in crop and medicinal plants.

5-Caffeoylquinic Acid and Caffeic Acid Down-Regulate the Oxidative Stress- and TNF-α-Induced Secretion of Interleukin-8 from Caco-2 Cells

Although chlorogenic acid (CHA) easily reaches a millimolar level in the gastrointestinal tract because of its high concentration in coffee and fruits, its effects on intestinal epithelial cells have been little reported. We investigated in this study the down-regulative effects of 5-caffeoylquinic acid (CQA), the predominant isomer of CHA, on the H(2)O(2-) or TNF-alpha-induced secretion of interleukin (IL)-8, a central pro-inflammatory chemokine involved in the pathogenesis of inflammatory bowel diseases, in human intestinal epithelial Caco-2 cells. After the cells had been pre- and simultaneously treated with CQA, the oversecretion of IL-8 and overexpression of its mRNA induced by H(2)O(2) were significantly suppressed in a dose-dependent manner in the range of 0.25-2.00 mmol/L. We further found that a metabolite of CQA, caffeic acid (CA), but not quinic acid, significantly inhibited the H(2)O(2)-induced IL-8 secretion and its mRNA expression in the same dose-dependent manner. Both CQA and CA suppressed the TNF-alpha-induced IL-8 secretion as well. Caffeic acid at 2.00 mmol/l was able to absolutely block the H(2)O(2)- or TNF-alpha-induced oversecretion of IL-8 in Caco-2 cells. However, CQA and CA did not suppress the TNF-alpha-induced increase in the IL-8 mRNA expression, indicating that the suppressive mechanisms are different between TNF-alpha-induced and H(2)O(2)-induced IL-8 production models. These results suggest that the habit of drinking coffee and/or eating fruits with a high CHA content may be beneficial to humans in preventing the genesis of inflammatory bowel diseases.

Effect of Style of Cut and Storage on Phenolic Composition and Antioxidant Activity of Fresh-cut Sweetpotatoes

Three different style fresh-cut (shredded, French fry, and sliced) sweetpotatoes [Ipomoea batatas (L.) Lam.] were stored at 0 and 5 °C for 4 and 8 days. At specified storage intervals, the fresh-cut sweetpotatoes were analyzed for total phenolics, individual phenolic acids, and antioxidant activity. Sweetpotato tissue analyzed immediately after cutting was considered the control. Storage at 5 °C resulted in an increase in total phenolics in all types of fresh-cut sweetpotatoes, except in shredded tissue analyzed after 4 days of storage. However, at 0 °C, only sliced tissue accumulated higher total phenolics than the control. In general, antioxidant activity in all fresh-cut sweetpotatoes held at 5 °C was higher than in the control. No significant increase in antioxidant activity was observed in shredded sweetpotatoes stored at 0 °C. Chlorogenic acid followed by 3,5-dicaffeoylquinic acid were the predominant phenolic acids present in fresh-cut sweetpotatoes. The highest content of chlorogenic acid (539.9 μg·g−1 dry weight) in sliced tissue stored for 8 days at 5 °C was ≈6-fold higher than in the control (88.3 μg·g−1 dry weight). No significant development of tissue browning, off-odors, or off-flavors were observed after 8 days of storage and the products were considered to be marketable.

Content levels of various fruit metabolites in the ‘Conference’ pear response to branch bending

The response of ‘Conference’ pear subjected to branch bending in the content levels of various metabolites in its fruit was investigated. The fruits in commercial maturity were sampled in 2004 and 2005 from branches bent in the late summer of 2003 (the summer treatment), from branches bent in the late spring of 2004 (the spring treatment) and from control branches. The content levels of carbohydrates, organic acids and phenolic compounds were compared among treatments in two successive years. The fruit revealed various responses in content levels of metabolites. In the first year after bending, no significant differences were found in the content of each carbohydrate, but in 2005 by far the highest content level of glucose and fructose and the lowest content level of sucrose were found in fruits from the control. The control fruit showed significantly higher content levels of malic acid and lower content levels of some phenolics (chlorogenic and vanillic acid) in the first year after bending, but in the next year the opposite reaction occurred—the control fruit had the lowest content level of malic acid and the highest content level of epicatechin, quercetin-3- d-galactoside and quercetin-3-β- d-glucoside. The comparison of the two bending treatments alone in 2004 showed that the summer treatment often produced a slightly higher value of each phenolic in comparison to the spring treatment. However, in 2005 the significantly highest content of chlorogenic acid was in fruit from the spring treatment. Sorbitol, as well as citric acid, catechin and sinapic acid showed no clear tendency among treatments, neither in 2004 nor in 2005. It is suggested that these variations of ‘Conference’ fruit subjected to different bending treatments could not be the result of bending alone, but that they could be indirectly affected by other physiological responses of the fruit tree. However, it seemed that variations are affected by the time of bending and by the year-to-year, and such responses can be attributed to the ‘Conference’ genotype only.

The influence of the operation conditions and the extraction techniques on the yield, kinetics and the composition of ethanol extracts of Hieracium pilosella L.

The optimal operational extraction conditions (50 % v/v ethanol, solvomodule l:15 m/v, temperature: the solvent boiling temperature) were determined by investigating the influence of the ethanol concentration (30 - 95 % v/v), solvomodule (1:10 - 1:25 m/v) and the temperature of the maceration extraction on the yield and kinetics of total extraction matter, chlorogenic acid, umbelliferone and apigenin-7-O-glucoside from Hieracium pilosella L. Based on the results of Soxhlet and Tillepape extraction kinetics, the investigations of the total extraction matter and the components under the optimal maceration operation conditions it was found that the highest yield of the extraction matter from the dry plant material (43.0 g/100 g of the dry plant material, i.e. 97.7% of the extractive matter content in the plant material), chlorogenic acid (20.30 g/100 g of dry plant material, i.e. 94 % of the chlorogenic acid content in the plant material), umbelliferone (0.30 g/100 g of the dry plant material, i.e. 96.7% of umbelliferone content in the plant material, and apigenin-7-O-glucoside (0.24 g/100 g of the dry plant material, i.e. 96 % of the apigenin-7-O-glucoside content in the plant material) was obtained by using a Soxhlet extraction method. The contents of chlorogenic acid, umbelliferone and apigenin-7-O-glucoside in the extracts were determined by HPLC method. Chlorogenic acid is the component with the highest share in all the extracts. (It was found) The high content of chlorogenic acid in the investigated plant material (21.60 %) and the high level of its extraction from the plant material (75-94**%) were found under the defined optimal maceration conditions, Soxhlet and Tillepape extraction.

(184) Phenolic Composition and Antioxidant Activity of Sweetpotato Cultivars Marketed in the European Union

Phenolic compounds and antioxidant activity were quantified in the principal sweetpotato cultivars marketed in the European Union. Total phenolic content, individual phenolic acids, and antioxidant activity in each cultivar were determined using Folin-Denis reagent, reversed-phase HPLC, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods, respectively. Significant differences in phenolic composition and antioxidant activity were found between cultivars. A Jamaican-grown, white-fleshed cultivar had the highest total phenolic content [4.11 mg·g-1 chlorogenic acid (dry tissue weight)], while the highest antioxidant activity [3.60 mg·g-1 Trolox (dry tissue weight)] was observed in the orange-fleshed California-grown cultivar Diane. Chlorogenic acid and 3,5-dicaffeoylquinic acid were the predominant phenolic acids, while caffeic acid was the least abundant in most cultivars. The highest content of chlorogenic acid (0.42 mg·g-1 dry tissue weight); 3,5-dicaffeoylquinic acid (0.43 mg·g-1 dry tissue weight); and 3,4-dicaffeoylquinic acid (0.25 mg·g-1 dry tissue weight) was present in the white-fleshed Jamaican cultivar. The orange-fleshed cultivars Diane and Beauregard had the highest content of caffeic acid (0.13 mg·g-1 dry tissue weight) and 4,5-dicaffeoylquinic acid (0.32 mg·g-1 dry tissue weight), respectively.

CHARACTERIZATION OF FIVE SUNFLOWER VARIETIES CULTIVATED IN BRAZIL

Neste trabalho foram determinados os principais índices de qualidade do óleo de cinco variedades de girassol. Amostras das sementes integrais e descascadas foram analisadas quanto à sua composição centesimal e submetidas a processo de extração com éter de petróleo para quantificação e caracterização do óleo. A cor verde escura observada na água, após classificação das amêndoas trituradas, indica que o ácido clorogênico é parcialmente removido durante a etapa de flotação em meio aquoso. Observou-se considerável diferença entre os índices de acidez dos óleos obtidos a partir de sementes integrais e descascadas devido, provavelmente, ao maior teor de ácido clorogênico nas sementes integrais. Os óleos obtidos a partir das sementes descascadas apresentaram melhores índices de qualidade que aqueles obtidos a partir da semente com casca. Dentre as cinco variedades analisadas apenas a M737 apresenta restrições para aplicação industrial sem pré-tratamento para remoção das cascas, devido à alta acidez no óleo obtido a partir da semente integral. Esta variedade apresentou intensa cor verde-escuro na casca o que compromete o uso da torta, tanto para consumo humano como para ração. Os índices de qualidade do óleo das demais variedades diferem pouco entre si. Óleo com elevado teor de ácidos graxos monoinsaturados foi obtido a partir das variedades M737 e DK180, respectivamente 42 e 40%. A variedade E-122–V2000, geneticamente melhorada pela Embrapa, foi a que apresentou melhores características para processamento industrial dada sua maior proporção de amêndoa (61%) e alto teor de óleo na amêndoa (47,83%) e poderia ser indicada não fosse sua menor produtividade, 1208 Kg/ha de acordo com dados fornecidos pela Embrapa-Soja.

Rapid Spectrophotometric Method for Determination of Chlorogenic Acid in Leaf Tobacco

Abstract A simple, rapid, quantitative procedure has been devised to measure chlorogenic acid in a 75% aqueous ethanolic extract of ground tobacco. The absorbance of the extract at 330 mμ is directly proportional to the concentration of chlorogenic acid, provided a suitable background line is drawn to correct for interfering nonpolyphenolic substances. Analysis of a series of eight bright tobacco samples has shown large variations among leaves from different stalk positions, with a very definite trend toward higher chlorogenic acid content nearer the top of the stalk. The chlorogenic acid content of burley tobaccos appears to be extremely low. The precision of replicate analyses has been found to be ± 3%, relative, for virtually all samples analyzed. Many vary less than 1% between duplicate determinations.