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PubMed2003

Antimicrobial activity of some Hypericum species.

The crude methanolic extracts of six species of Hypericum [H. caprifoliatum Cham. & Schlecht., H. carinatum Griseb., H. connatum Lam., H. ternum A. St. Hil., H. myrianthum Cham. & Schlecht. and H. polyanthemum Klotzsch ex Reichardt] growing in southern Brazil were analyzed for antimicrobial activity against several microorganisms (bacteria and fungi). The most active plant was H. caprifoliatum, which showed activity against Staphylococcus aureus. Only H. polyanthemum and H. ternum extracts were active against Bacillus subtilis. None of the crude methanolic extracts showed activity against S. epidermidis, Escherichia coli or Saccharomyces cerevisiae. Extracts from these species were evaluated chemically and tannin, flavonoid and phenolic acids were the prominent compounds. The plants contained quercitrin, hyperoside (except H. connatum) and, less frequently, isoquercitrin and chlorogenic acid. In contrast to H. perforatum, which has high concentrations of rutin, these species do not produce this flavonoid or it appears as traces. The tannin concentration varied between 5.1 and 16.7% in H. myrianthum and H. ternum, respectively.

Anti-Infective Agents↗
PubMed2006

Quantitative determination of phenolic compounds in artichoke-based dietary supplements and pharmaceuticals by high-performance liquid chromatography.

Dietary supplements are among the most rapidly growing products in the food and personal care market with an estimated worldwide volume exceeding $60 billion. The main problem associated with dietary supplements is their legal classification. Being neither food nor medicine, they often inhabit a gray area between the two, which makes legal regulatory extremely difficult. Thus, a coexistence of products processed from the same botanical source on the same market as dietary supplement or pharmaceutical is possible. In the present study, various artichoke-based dietary supplements were investigated for their phenolic profile and compared to artichoke phytopharmaceuticals. Quantification of individual hydroxycinnamic acids and flavonoids was carried out by external calibration. For the first time, determination of several apigenin derivatives was included. Chlorogenic acid represented the major constituent in all samples investigated with the exception of juice derived from fresh flower heads, which exhibited a higher cynarin content. Furthermore, a distinction between products made from artichoke leaves or flower heads was possible. The results obtained revealed great diversity of pharmaceuticals and dietary supplements, highlighting the need of standardized quality requirements.

Chromatography, High Pressure Liquid↗
PubMed1999

Polyphenol profiles of French cider apple varieties (Malus domestica sp.).

The cortex of 14 French apple varieties (12 cider and 2 juice varieties), one English cider variety, and one dessert apple (i.e., Golden Delicious) were studied for their polyphenol composition. Total polyphenols were assayed by the Folin-Ciocalteu method, and the precise polyphenolic composition (monomeric catechins, proanthocyanidins, hydroxycinnamic acids, and dihydrochalcones) was obtained by HPLC following thiolysis. ESI-MS and ESI-MS/MS analyses showed that chlorogenic acid and p-coumaroylquinic acid were methylated under the conditions of thiolysis. Depending on the variety, the global polyphenol concentration varied from 1 to 7 g per kilogram of fresh cortex. Cider varieties globally showed a higher polyphenol concentration than the dessert apple Golden Delicious, bitter varieties being the more concentrated. The proportion of the polyphenol classes varied greatly from one cultivar to another. For all varieties, procyanidins were always the predominant class. They were mainly constituted of (-)-epicatechin units with a small proportion of (+)-catechin as a terminal unit. The average degree of polymerization ranged between 4.2 and 7.5 depending upon the variety with an exception for the sharp varieties Guillevic and Avrolles which showed significant concentrations of procyanidins with DPn of 40 and 50, respectively.

Beverages↗
PubMed1996

Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models.

The water extract of propolis (PWE) showed a strong hepatoprotective activity against CCl4-toxicity in rats and D-galactosamine (GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. The PWE also showed a significant hepatoprotective activity against CCl4-induced liver cell injury in cultured rat hepatocytes. The in vitro hepatoprotective activity guided fractionation and chemical analysis led to the isolation of four dicaffeoyl quinic acid derivatives from the PWE. The structure of these isolates was determined to be methyl 3,4-di-O-caffeoyl quinate (1), 3,4-di-O-caffeoyl quinic acid (2), methyl 4,5-di-O-caffeoyl quinate (3), and 3,5-di-O-caffeoyl quinic acid (4) by spectroscopic methods. These compounds were more potent hepatoprotective agents than glycyrrhizin at a concentration of 10 micrograms/ml and 1 was the most potent among the four compounds in the cultured hepatocytes. Quinic acid (5) alone did not show hepatoprotective effects in cultured rat hepatocytes against CCl4-toxicity. On the other hand, chlorogenic acid (6) or caffeic acid alone was found to be less potent than the dicaffeoyl quinic acid derivatives.

Animals↗
PubMed1976

[Effect of prolonged glucidic starvation on the contents of starch and tannins of Blechnum brasiliense L. gametophytes].

Some Blechnum brasiliense gametophytes have been maintained in darkness, in a purely mineral medium, for the purpose of investigating the effect of prolonged glucidic starving on the amount of tannins and starch that they contain. During the first two months the tannin contents undergoes a fast decrease. The starch variations are different : a transitory increase simultaneous with the fall in tannin; a decrease after the disappearance of 3/4 of the tannin contents; and lastly, a new amylogenese which precedes the prothallus necrosis. It seems that the gametophytes, in order to survive, degrade first their tannoidic reserves, and they utilize the starch that they contain only with difficulty. This behaviour can be explained by the distribution of the two metabolites; by the acid pH of the medium, which is not very propitious to the phosphorylases activity and lastly by the presence of chlorogenic acids, which are inhibitors of those enzymes.

Cells, Cultured↗
PubMed2003

Hepatobiliary elimination of bile acid-modified oligodeoxynucleotides in Wistar and TR- rats: evidence for mrp2 as carrier for oligodeoxynucleotides.

As therapeutic antisense tools, oligonucleotides (ODNs) must enter cells to bind to their target structures. ODNs distribute in nearly each tissue with relatively high concentrations in kidney and liver from where excretion into urine and bile occurs. To investigate mechanisms involved in hepatic ODN transport, normal mixed backbone phosphodiester/phosphorothioate ODNs (n-ODN) and two different bile acid-conjugated mixed backbone ODNs (1BA-ODN and 2BA-ODN) were applied to two different rat strains, normal Wistar rats and Wistar TR- rats. In normal Wistar rats, concentration-dependent hepatobiliary elimination of the ODNs was observed with a remarkable increase of excretion of the cholic acid BA-ODN conjugates. In contrast to normal Wistar rats, n-ODN excretion into bile by TR- rats, a mutant Wistar rat strain lacking a functional multidrug resistance-associated protein 2 (mrp2) at the canalicular membrane, was strongly diminished, whereas these rats excreted an ODN conjugated with two cholic acid molecules (2BA-ODN) into bile. Concomitant application of substrates transported by mrp2 such as bromosulfophthalein (BSP) or the synthetic chlorogenic acid derivative S 3025 significantly reduced the biliary appearance of normal ODN and 2BA-ODN in Wistar rats and also in TR- rats. To inhibit the expression of cRNA derived from the Na+ -dependent taurocholate cotransporting polypeptide (Ntcp), antisense ODNs were constructed which fully retained the antisense properties when coupled with two bile acid molecules. The results indicate that ODNs are secreted via the mrp2 into bile. In the absence of mrp2, further excretory transport systems with affinity for bile acids seem to be relevant for their excretion. The results further indicate that bile acid tagged ODNs are useful tools for liver specific antisense therapy.

ATP-Binding Cassette Transporters↗
PubMed2005

Phenolic profile, antioxidant property, and anti-influenza viral activity of Chinese quince (Pseudocydonia sinensis Schneid.), quince (Cydonia oblonga Mill.), and apple (Malus domestica Mill.) fruits.

To evaluate the phenolic extracts of Chinese quince, quince, and apple fruits, their phenolic profiles, antioxidant properties, and anti-influenza viral activities were investigated. Chinese quince had the largest amount of phenolics consisting mainly of high polymeric procyanidins. Quince had considerable amounts of hydroxycinnamic derivatives mainly composed of 3-caffeoylquinic acid and 5-caffeoylquinic acid and polymeric procyanidins. Apple (cv. Fuji) had the lowest amount of phenolics, mainly 5-caffeoylquinic acid and monomeric and oligomeric procyanidins. The antioxidant functions of Chinese quince and quince phenolic extracts were superior to that of chlorogenic acid standard or ascorbic acid evaluated in both the linoleic acid peroxidation system and the DPPH radical scavenging system. However, those extracts were less effective than apple phenolics or (-)-epicatechin in linoleic acid peroxidation system. On the other hand, Chinese quince phenolics showed the strongest anti-influenza viral activity on the hemagglutination inhibition test.

Antioxidants↗
PubMed2001

Anticholestatic activity of flavonoids from artichoke (Cynara scolymus L.) and of their metabolites.

It is well known that water-soluble extracts of artichoke (Cynara scolymus L.) leaves exert choleresis. When studying this effect in vitro using primary cultured rat hepatocytes and cholephilic fluorescent compounds, it was noticed that the artichoke leaf extracts not only stimulated biliary secretion, but that they also reestablished it when secretion was inhibited by addition of taurolithocholate to the culture medium. Furthermore, taurolithocholate-induced bizarre bile canalicular membrane distortions detectable by electron microscopy could be prevented by artichoke leaf extracts in a dose-dependent manner when added simultaneously with the bile acid. These effects were exerted by the flavonol luteolin and, to a lesser extent, by luteolin-7-O-glucoside, while chlorogenic acid and 1.5-dicaffeoyl quinic acid were almost ineffective. Surprisingly, metabolites produced by the cultured hepatocytes were able to stimulate biliary secretion substantially as well as prevent canalicular membrane deformation. These results demonstrate that artichoke leaf extracts exert a potent anticholestatic action at least in the case of taurolithocholate-induced cholestasis. Flavonoids and their metabolites may contribute significantly to this effect.

Animals↗
PubMed2005

Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS(n).

The fragmentation behavior of all six dicaffeoylquinic acids (diCQA) has been investigated using LC-MS(4). It is possible to discriminate between each of the isomers including those for which commercial standards are not available. For diCQA, the ease of removal of the caffeoyl residue during fragmentation is 1 approximately = 5 > 3 > 4. The distinctive fragmentation observed for the little-studied 1,4-dicaffeoylquinic acid involves elimination of the C1 caffeoyl residue, repeated dehydrations leading to the aromatization of the quinic acid moiety, and its decarboxylation. It is suggested that this process is initiated by the C1 carboxyl protonating the C5 hydroxyl in the inverted chair conformer, followed by its protonating the C1 caffeoyl residue in the favored chair conformation. The fragmentation of 1-caffeoylquinic acid is indistinguishable from that of the commercially available 5-caffeoylquinic acid, but these two isomers can be distinguished easily by their facile chromatographic resolution on reversed phase packings. The hierarchical key previously developed for characterizing chlorogenic acids has been extended to accommodate 1-caffeoylquinic acid and the 1-acyl dicaffeoylquinic acids.

Caffeic Acids↗
PubMed1970

Biogenesis of rosmarinic acid in Mentha.

The biogenesis of rosmarinic acid (alpha-O-caffeoyl-3,4-dihydroxyphenyl-lactic acid), the second most common ester of caffeic acid in the plant kingdom, was studied in Mentha arvense and Mentha piperita. Administration of (14)C-labelled compounds showed that, whereas the caffeoyl moiety was formed from phenylalanine via cinnamic acid and p-coumaric acid, the 3,4-dihydroxyphenyl-lactic acid moiety was formed from tyrosine and 3,4-dihydroxyphenylalanine. Time-course studies and the use of labelled rosmarinic acid showed that endogenous rosmarinic acid had a low turnover rate. The caffeoyl moiety did not appear to contribute to the formation of insoluble polymers, as has been suggested for chlorogenic acid in other plants.

Carbon Isotopes↗
PubMed2006

Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development.

BACKGROUND AND AIMS: Caffeoylquinic acids are cinnamate conjugates derived from the phenylpropanoid pathway. They are generally involved in plant responses to biotic and abiotic stress and one of them, chlorogenic acid (5-O-caffeoylquinic acid, 5-CQA), is an intermediate in the lignin biosynthesis pathway. Caffeoylquinic acids, and particularly 5-CQA, are accumulated in coffee beans, where they can form vacuolar complexes with caffeine. Coffea canephora beans are known to have high caffeoylquinic acid content, but little is known about the content and diversity of these compounds in other plant parts. To gain new insights into the caffeoylquinic acid metabolism of C. canephora, caffeoylquinic acid content and in situ localization were assessed in leaves at different growth stages. METHODS: HPLC analyses of caffeoylquinic acid content of leaves was conducted in conjunction with detailed histochemical and microspectrofluorometrical analysis. KEY RESULTS AND CONCLUSIONS: HPLC analyses revealed that caffeoylquinic acid content was 10-fold lower in adult than in juvenile leaves. The most abundant cinnamate conjugate was 5-CQA, but dicaffeoylquinic acids (particularly in juvenile leaves) and feruloylquinic acids were also present. Using specific reagents, histochemical and microspectrofluorometrical analysis showed that caffeoylquinic acids (mono- and di-esters) were closely associated with chloroplasts in very young leaves. During leaf ageing, they were found to first accumulate intensively in specific chlorenchymatous bundle sheath cells and then in phloem sclerenchyma cells. The association with chloroplasts suggests that caffeoylquinic acids have a protective role against light damage. In older tissues, their presence in the leaf vascular system indicates that they are transported via phloem and confirms their involvement in lignification processes. In accordance with the hypothesis of a complex formation with caffeine, similar tissue distribution was observed for alkaloids and this is further discussed.

Chloroplasts↗
PubMed2004

In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans.

Seven kinds of hydroxycinnamic acid derivatives identified as 3-caffeoylquinic acid (3-CQA), 4-caffeolyquinic acid (4-CQA), 5-caffeoylquinic acid (5-CQA), 5-feruloylquinic acid (5-FQA), 3,4-dicaffeoylquinic acid (3,4-diCQA), 3,5-dicaffeoylquinic acid (3,5-diCQA), and 4,5-dicaffoylquinic acid (4,5-diCQA) by MS, 1H NMR, and HPLC analyses were isolated from low-quality (immature) and commercial quality green coffee beans. The quantity of chlorogenic acid isomers (10.4 g/100 g), especially 5-CQA, in commercial green coffee beans [West Indische Bereiding (West India processing beans from Sumatra Island, Indonesia, WIB)] was higher than that in low-quality beans [9.1 g/100 g, Eerste Kwaliteit (Export low-quality beans from Java Island, Indonesia, EK-1, grade 4)], whereas little difference in diCQAs was detected between the two kinds of beans. The free radical scavenging activity of these isolates was evaluated in assay systems using DPPH free radicals and superoxide anion radicals generated by xanthine-XOD. The diCQAs showed strong (1.0-1.8-fold) free radical scavenging activity compared to commonly used antioxidants such as alpha-tocopherol and ascorbic acid. The potency order of superoxide anion radical scavenging activity was diCQAs > caffeic acid, CQAs > 5-FQA. The activities of the diCQAs were twice as effective as those of CQAs and 4 times as effective as that of 5-FQA. The diCQAs also exhibited more potent (2.0-2.2-fold) tyrosinase inhibitory activities compared to CQAs, arbutin, and ascorbic acid. The isolates exhibited antiproliferation activities in four cancer cell lines, U937, KB, MCF7, and WI38-VA. Among these, KB cells were most sensitive (IC50 = 0.10-0.56 mM).

Animals↗
PubMed2002

New insights into the acid-promoted reaction of caffeic acid and its esters with nitrite: decarboxylation drives chain nitrosation pathways toward novel oxime derivatives and oxidation/fragmentation products thereof.

In 0.05 M acetate buffer, pH 4, containing 1% methanol, caffeic acid (1a) (2 x 10(-3) M) reacted smoothly with nitrite (NO(2)(-)) (4 x 10(-3) M) to afford as main products the novel 2-hydroxy- and 2-methoxyaldoximes 7a,b, the 2-oxoaldoxime 9a, 3,4-dihydroxybenzoic acid, 3,4-dihydroxybenzaldehyde, and the known furoxan 3c and benzoxazinone 4b in smaller amounts. At lower 1a concentration (e.g., 1 x 10(-4) M), 7a was the main product, whereas with 0.1 M 1a and 0.5 M NO(2)(-) 3c and 9a were prevailing. At pH 2, 7a was still the most abundant product, together with 3,4-dihydroxybenzaldehyde and some 9a, whereas at pH 1 9a and 3,4-dihydroxybenzaldehyde were formed in higher yields. No evidence for ring nitration products, including the previously reported 4,5-dihydroxy-2-nitrobenzaldehyde, was obtained. At 2 x 10(-3) M concentration and at pH 4, caffeic acid methyl ester (1b) reacted with NO(2)(-) chiefly via ring nitration and/or dimerization to give 5a, the novel nitrated neolignan derivative 10, and the parent 6. Chlorogenic acid (1c) afforded only the ring nitrated derivative 5b. A unifying mechanism for the reaction of 1a and its esters with NO(2)(-) is proposed involving reversible formation of nitroso intermediates via chain nitrosation at the 2-position of the (E)-3-(3,4-dihydroxyphenyl)propenoic system. In the case of 1a, decarboxylation would drive the nitroso intermediates toward the formation of oximes 7a,b and 3c, reflecting nucleophilic addition of water, methanol, and NO(2)(-), and their oxidation or breakdown products, viz. 9a, 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic acid, and the benzoxazinone 4b. In the case of esters 1b,c, to which decarboxylation is precluded, ring nitration or dimerization become the favored routes, triggered by preliminary oxidation at the catechol moiety.

Caffeic Acids↗
PubMed1991

Chemotaxis and nod Gene Activity of Bradyrhizobium japonicum in Response to Hydroxycinnamic Acids and Isoflavonoids.

For Bradyrhizobium japonicum, the chemotactic and the nod gene-inducing effects of hydroxycinnamic acids and two of their derivatives were compared with those of isoflavonoids. Only the hydroxycinnamic acids were strong chemoattractants, while the other substances tested were chemotactically inactive. Besides the known nod gene induction by isoflavonoids, a weak nod gene induction by coniferyl alcohol, chlorogenic acid, and ferulic acid was found.

Journal Article↗
PubMed2005

Effect of ascorbic acid and dehydration on concentrations of total phenolics, antioxidant capacity, anthocyanins, and color in fruits.

The purpose of this investigation was to report on the total phenolics, anthocyanins, and oxygen radical absorbance capacity (ORAC) of strawberry, peach, and apple, the influence of dehydration and ascorbic acid treatments on the levels of these compounds, and the effect of these treatments on fruit color. Results showed that fresh strawberry had the highest levels for total phenolics [5317.9 mg of chlorogenic acid equivalents (CAE)/kg], whereas lower levels were found in fresh apple and peach (3392.1 and 1973.1 mg of CAE/kg, respectively), and for anthocyanins (138.8 mg/kg), whereas lower levels were found in fresh apple and peaches (11.0 and 18.9 mg/kg, respectively; fresh strawberry had an ORAC value of 62.9 mM/kg Trolox equivalents. The fresh apple and peach were found to have ORAC values of 14.7 and 11.4 mM/kg of Trolox equivalents, respectively. The color values indicated that the addition of 0.1% ascorbic acid increased the lightness (L) and decreased the redness (a) and yellowness (b) color values of fresh strawberry, peach, and apple, sliced samples, and the puree made from them. Also, results showed that dehydration is a good method to keep the concentrations of total phenolics and anthocyanins and ORAC values at high levels.

Anthocyanins↗
PubMed2000

Purification and characterization of a highly stable tyrosinase from Thermomicrobium roseum.

Tyrosinase, with an isoelectric point at pH 4.9, was purified to electrophoretic homogeneity from an extremely thermophilic bacterium, Thermomicrobium roseum. Gel filtration, N-terminal amino acid sequencing and SDS/PAGE analysis indicate that T. roseum tyrosinase is composed of two identical subunits, each with a molecular mass of 43000 Da. The enzyme exhibited high substrate specificity towards catechol, chlorogenic acid, L-3-(3,4-dihydroxyphenyl)-L-alanine (L-DOPA) and pyrogallol. The K(m) value of the enzyme for L-DOPA was 0.18 mM. beta-Mercaptoethanol and sodium diethyldithiocarbamate notably inhibited the enzymic activity. The activity of the enzyme was optimal at pH 9.5 and 70 degrees C, and was increased by addition of 1 mM Mg(2+), K(+) or Cu(2+). The enzyme was highly stable against high temperature and guanidine hydrochloride. The N-terminal amino acid sequence of the enzyme was determined to be Asp-Ile-Asn-Gly-Gly-Gly-Ala-Thr-Leu-Pro-Gln-Lys-Leu-Tyr. These facts indicate that T. roseum tyrosinase appears to be distinct from the tyrosinases so far purified from other sources.

Amino Acid Sequence↗
PubMed1973

Inactivity of 3-methyleneoxindole as mediator of auxin action on cell elongation.

The recently reported growth-promoting ability of 3-methyl-eneoxindole was examined in order to test the hypothesis that indole-3-acetic acid acts as a growth promoter only after oxidative conversion to 3-methyleneoxindole. Methyleneoxindole was synthesized from indole-3-acetic acid and N-bromosuccinimide, and its identity was confirmed by ultraviolet absorption, infrared absorption, mass spectrometry, and melting point. Methyleneoxindole was found to lack growth-promoting activity in coleoptile and pea (Pisum sativum) stem segments. Chlorogenic acid, an inhibitor of the oxidation of indole-3-acetic acid, was found to have no inhibitory effect on growth promotion by indole-3-acetic acid. It is concluded that 3-methyleneoxindole is inactive as a growth promoter and therefore does not mediate the action of auxin on cell elongation.

Journal Article↗