iridoids and caffeic-acid

The effect of micronization of granulometrically fractionated olive pomace (OP) on the bioaccessibility of polyphenols and the antioxidant capacity was investigated during sequential in vitro static digestion. Crude OP was fractionated in a 2-mm sieve (F1: > 2 mm; F2: < 2 mm) and then micronized (300 r min

Topics: Antioxidants; Caffeic Acids; Chromatography, High Pressure Liquid; Dietary Supplements; Digestion; Food Handling; Iridoid Glucosides; Iridoids; Olea; Olive Oil; Plant Extracts; Polyphenols; Principal Component Analysis; Tandem Mass Spectrometry

Catechol-functionalized polymers are of particular interest because of their strong water-resistant adhesive properties. Hydroxymethyl chitosan (HECTS) has been used as an implantable biomaterial having good water solubility, biodegradability and biocompatibility. Here, hydrocaffeic acid (HCA) grafted HECTS (HCA-g-HECTS) was prepared through carbodiimide coupling and the tethered catechol underwent periodate (

Topics: Animals; Caffeic Acids; Catechols; Cell Line; Chitosan; Cross-Linking Reagents; Female; Hydrogels; Iridoids; Materials Testing; Mice; Rats; Rats, Sprague-Dawley; Tissue Adhesives

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Discriminant Analysis; Drugs, Chinese Herbal; Iridoids; Mass Spectrometry; Multivariate Analysis

The antimicrobial properties of olive leaf extract (OLE) have been well recognized in the Mediterranean traditional medicine. Few studies have investigated the antimicrobial properties of OLE. In this preliminary study, commercial OLE and its major phenolic secondary metabolites were evaluated in vitro for their antimicrobial activities against Escherichia coli and Staphylococcus aureus, both individually and in combination with ampicillin. Besides luteolin 7-O-glucoside, OLE and its major phenolic secondary metabolites were effective against both bacteria, with more activity on S. aureus. In combination with ampicillin, OLE, caffeic acid, verbascoside and oleuropein showed additive effects. Synergistic interaction was observed between ampicillin and hydroxytyrosol. The phenolic composition of OLE and the stability of olive phenols in assay medium were also investigated. While OLE and its phenolic secondary metabolites may not be potent enough as stand-alone antimicrobials, their abilities to boost the activity of co-administered antibiotics constitute an imperative future research area.

Topics: Ampicillin; Anti-Bacterial Agents; Bacteria; Caffeic Acids; Drug Synergism; Escherichia coli; Flavones; Glucosides; Herb-Drug Interactions; Iridoid Glucosides; Iridoids; Medicine, Traditional; Olea; Phenols; Phenylethyl Alcohol; Plant Extracts; Plant Leaves; Staphylococcus aureus

The bark, seeds, fruits and leaves of the genus Fraxinus (Oleaceae) which contain a wide range of phytochemicals, mostly secoiridoid glucosides, have been widely used in folk medicine against a number of ailments, yet little is known about the metabolism and uptake of the major Fraxinus components. The aim of this work was to advance in the knowledge on the bioavailability of the secoiridoids present in a Fraxinus angustifolia Vahl seed/fruit extract using both targeted and untargeted metabolomic analyses. Plasma and urine samples from nine healthy volunteers were taken at specific time intervals following the intake of the extract and analyzed by UPLC-ESI-QTOF. Predicted metabolites such as tyrosol and ligstroside-aglycone glucuronides and sulfates were detected at low intensity. These compounds reached peak plasma levels 2 h after the intake and exhibited high variability among the participants. The ligstroside-aglycone conjugates may be considered as potential biomarkers of the Fraxinus secoiridoids intake. Using the untargeted approach we additionally detected phenolic conjugates identified as ferulic acid and caffeic acid sulfates, as well as hydroxybenzyl and hydroxyphenylacetaldehyde sulfate derivatives which support further metabolism of the secoiridoids by phase I and (or) microbial enzymes. Overall, the results of this study suggest low uptake of intact secoiridoids from a Fraxinus angustifolia Vahl extract in healthy human volunteers and metabolic conversion by esterases, glycosidases, and phase II sulfo- and glucuronosyl transferases to form smaller conjugated derivatives.

Topics: Adult; Biological Availability; Biotransformation; Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Female; Fraxinus; Fruit; Glucosides; Glucuronides; Healthy Volunteers; Humans; Hydroxybenzoates; Iridoids; Male; Plant Extracts; Pyrans; Seeds; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Sulfates

To study the chemical constituents from the flower of Lonicera fragrantissima.. The chemical constituents were isolated and purified by means of several chromatographic techniques, and their structures were elucidated by spectroscopic methods.. Nine compounds were isolated and identified as chlorogenic acid (1), caffeic acid (2), secologanoside (3), secoxyloganin(4), loganin (5), sucrose (6), myo-inositol (7), rutin (8), and chrysoeriol-7-O-β-D-glucoside (9).. Compounds 2-9 are obtained from this plant for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Flavones; Flowers; Glucosides; Inositol; Iridoid Glucosides; Iridoids; Lonicera; Rutin; Sucrose

To research the chemical constituents from stems and leaves of Lonicera macranthoides.. Various column chromatographies were employed to isolate and purify the constituents. Their structures were elucidated by spectral analysis (IR, MS, 1H-NMR, 13 C-NMR) and chemical evidence.. Nine constituents were obtained and identified as loganin (I), loganic acid (II), morroniside (III),7-O-ethyl-morroniside (IV), scopoletin (V), caffeic acid (VI), chlorogenic acid (VII), beta-sitosterol (VIII), daucosterol (IX).. Compounds I-VI are isolated from the plant for the first time. All the compounds are found for the first time from the stems and leaves of Lonicera macranthoides.

Topics: Caffeic Acids; Glycosides; Iridoids; Lonicera; Molecular Structure; Plant Leaves; Plant Stems; Plants, Medicinal; Scopoletin

The antioxidant principles isolated from the various parts of the plant are verminoside (leaf, stem bark and flowers; EC(50) = 2.04 µg/ml), Specioside (flowers; EC(50) = 17.44 µg/ml), Kampeferol diglucoside (leaf; EC(50) = 8.87 µg/ml) and Caffeic acid (leaf and fruits). The non anti-oxidant components isolated in the study include ajugol (stem bark and fruits) and phytol (leaf).

Topics: Antioxidants; Bignoniaceae; Caffeic Acids; Flowers; Fruit; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Iridoids; Kaempferols; Phytol; Plant Extracts; Plant Leaves; Plant Stems; Pyrans

Olive oil and its minor constituents have been recommended as important dietary therapeutic interventions in preventive medicine. However, a question remains to be addressed: what are the effects of olive oil and its phenolic compounds on obesity-induced cardiac metabolic changes?. Male Wistar rats were divided into two groups (n = 24/group): (C) receiving standard-chow; (Ob) receiving hypercaloric-chow. After 21 days C and Ob groups were divided into four subgroups (n = 6/group):(C) standard-chow and saline; (C-Olive)standard-chow and olive-oil (3.0 g/kg.day); (C-Oleuropein)standard-chow and oleuropein (0.023 mg/kg/day); (C-Cafeic) standard-chow and cafeic-acid (2.66 mg/kg/day); (Ob)receiving hypercaloric-chow and saline;(Ob-Olive) hypercaloric-chow and olive-oil;(Ob-Oleuropein) hypercaloric-chow and oleuropein;(Ob-Cafeic) hypercaloric-chow and cafeic-acid. Treatments were given twice a week during 21 days.. After 42 days, obesity was evidenced in Ob rats from enhanced body-weight, surface-area, and body-mass-index. Energy-expenditure, oxygen consumption(VO2) and fat-oxidation were lower in Ob-group than in C. Despite no morphometric changes, Ob-Olive, Ob-Oleuropein and Ob-Cafeic groups had higher VO2, fat-oxidation, myocardial beta-hydroxyacyl coenzyme-A dehydrogenase and lower respiratory-quotient than Ob. Citrate-synthase was highest in Ob-Olive group. Myocardial lipid-hydroperoxide(LH) and antioxidant enzymes were unaffected by olive-oil and its compounds in obesity condition, whereas LH was lower and total-antioxidant-substances were higher in C-Olive and C-Oleuropein than in C.. The present study demonstrated for the first time that olive-oil, oleuropein and cafeic-acid enhanced fat-oxidation and optimized cardiac energy metabolism in obesity conditions. Olive oil and its phenolic compounds improved myocardial oxidative stress in standard-fed conditions.

Topics: 3-Hydroxyacyl CoA Dehydrogenases; Animals; Caffeic Acids; Calorimetry; Citrate (si)-Synthase; Iridoid Glucosides; Iridoids; Male; Myocardium; Obesity; Olive Oil; Phenols; Plant Oils; Pyrans; Rats; Rats, Wistar

This study presents a new HPLC method for the simultaneous determination of seven major components, namely chlorogenic acid, caffeic acid, loganin, sweroside, secoxyloganin, rutin and luteolin 7-O-glucoside in Caulis Lonicerae Japonicae, a commonly used traditional Chinese medicinal herb derived from the caulis of Lonicera japonica Thunb. These seven compounds, belonging to the chemical types of phenolic acids, iridoids and flavonoids, were separated on a C18 column (250 x 4.6 mm, 5.0 microm) with the column temperature at 30 degrees C. The mobile phase was composed of (A) aqueous acetic acid (0.4%, v/v) and (B) acetonitrile using a gradient elution of 10% B at 0-12 min, 10-17% B at 12-25 min and 17% B at 25-35 min. The flow rate was 1.0 mL/min and detection wavelength was set at 245 nm. The limit of detection (S/N = 3) ranged from 0.10 to 0.23 microg/mL and the limit of quantification (S/N = 10) ranged from 0.69 to 3.56 microg/mL. All calibration curves showed good linear regression (r2 > 0.9990) within the test ranges. The intra- and inter-day precisions as determined from sample solutions were below 1.24 and 2.28%, respectively. The recoveries for seven compounds were found to range from 94.2 to 103.6%. This verified method has been successfully applied to evaluation of commercial samples of Caulis Lonicerae Japonicae from different markets in China.

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonoids; Glucosides; Hydroxybenzoates; Iridoid Glucosides; Iridoids; Linear Models; Lonicera; Luteolin; Molecular Structure; Reproducibility of Results; Rutin; Sensitivity and Specificity; Spectrophotometry, Ultraviolet

In search for compounds, able to protect nuclear DNA in cells exposed to oxidative stress, extracts from olive leaves, olive fruits, olive oil and olive mill waste water were tested by using the "single cell gel electrophoresis" methodology (comet assay). Jurkat cells in culture were exposed to continuously generated hydrogen peroxide (11.8+/-1.5 microM per min) by direct addition into the growth medium of the appropriate amount of the enzyme "glucose oxidase" in the presence or absence of the tested total extracts. The protective effects of the tested extracts or isolated compounds were evaluated from their ability to decrease hydrogen peroxide-induced formation of single strand breaks in the nuclear DNA, while the toxic effects were estimated from the increase of DNA damage when the extracts or isolated compounds were incubated directly with the cells. Significant protection was observed in extracts from olive oil and olive mill waste water. However, above a concentration of 100 microg/ml olive oil extracts exerted DNA damaging effects by themselves in the absence of any H2O2. Extracts from olive leaves and olive fruits although protective, were also able to induce DNA damage by themselves. Main compounds isolated from the above described total extracts, like oleuropein glucoside, tyrosol, hydroxytyrosol and caffeic acid, were tested in the same experimental system and found to exert cytotoxic (oleuropein glucoside), no effect (tyrosol) or protective effects (hydroxytyrosol and caffeic acid). In conclusion, cytoprotective as well as cytotoxic compounds with potential pharmaceutical properties were detected in extracts from olive oil related sources by using the comet assay methodology.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Comet Assay; DNA; DNA Damage; Humans; Hydrogen Peroxide; Iridoid Glucosides; Iridoids; Jurkat Cells; Nuclear Magnetic Resonance, Biomolecular; Olea; Olive Oil; Phenylethyl Alcohol; Plant Extracts; Plant Oils; Pyrans

A method was established for the simultaneous quantification of nine components of five different structural types in Qingkailing injection. High performance liquid chromatography coupled with a photo diode array detector and an evaporative light scattering detector (HPLC-DAD-ELSD) was employed in the determination. Four monitoring wavelengths of 240, 254, 280 and 330 nm were set to determine nucleosides (uridine and adenosine), iridoid glucoside (geniposide), flavone glycoside (baicalin) and organic acids (chlorogenic acid and caffeic acid) respectively, and a combined evaporative light scattering detector was used to detect three steroid compounds (cholic acid, ursodesoxycholic acid and hyodeoxycholic acid). The proposed method permitted the simultaneous separation and determination of five groups of compounds in Qingkailing injection, and acceptable validation results of the precision, repeatability, stability and accuracy tests were achieved. The method was applied to the analysis of 19 Qingkailing injection samples from three different plants, and the results indicated that the method could be used as a convenient and reliable method in the multi-component determination and quality control of traditional Chinese medicines.

Topics: Adenosine; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonoids; Iridoids; Medicine, Chinese Traditional; Scattering, Radiation; Uridine

Several epidemiological and experimental studies have associated the intake of antioxidants, which are abundant in the Mediterranean diet, with a low incidence of cardiovascular disease. One possible mechanism of this action is the oxidative protection in low density lipoproteins (LDL). The aim of our study was to compare the antioxidative activity of diverse phenolic compounds present in virgin olive oil on these lipoproteins.. LDL was isolated from blood plasma of healthy volunteers by sequential ultracentrifugation. This was followed by oxidation with CuC12 in the presence of different concentrations of phenolic compounds and virgin olive oil extract. Production of conjugated dienes was determined by the continuous monitoring of increased absorbency at 234 nm as an indicator of LDL oxidation.. Virgin olive oil extract prolonged the latency phase and significantly lowered the progression rate (p < 0.05) at low concentrations (2 g/ml). This antioxidative effect was also observed with low concentrations (2 M) of caffeic acid and oleuropein (p < 0.05). However, it was necessary to increase the concentration of flavone up to 50 times to observe a similar effect (p < 0.05).. Both virgin olive oil extract enriched in phenolic compounds and phenolic compounds present in olive oil (caffeic acid and oleuropein) are potent antioxidants at very low concentrations. Thus, the beneficial effects of a Mediterranean diet may be partly due to the protective action of these compounds.

Topics: Antioxidants; Caffeic Acids; Diet, Mediterranean; Dietary Fats, Unsaturated; Flavones; Flavonoids; Humans; In Vitro Techniques; Iridoid Glucosides; Iridoids; Lipid Peroxidation; Lipoproteins, LDL; Olive Oil; Oxidation-Reduction; Phenols; Plant Oils; Pyrans; Vasodilator Agents

The major phenolics from the polar fraction of virgin olive oil (caffeic acid, oleuropein, tyrosol and hydroxytyrosol) have well-established antioxidant activities but their effects on reactive nitrogen species and nitrergic neurotransmission have not been fully investigated. The three catechol compounds were active as scavengers of nitric oxide generated spontaneously from the decomposition of sodium nitroprusside (approximately 50% inhibition achieved at 75 microM), and had similar ability to scavenge chemically generated peroxynitrite, as determined by an alpha1-antiproteinase inactivation assay (67.2%-92.4% reduction when added at 1 mM). Tyrosol was less active in these tests, but does not possess the catechol functionality. Despite their ability to interact with chemically prepared nitric oxide, neither oleuropein nor hydroxytyrosol at 5 microM altered NO*-mediated relaxations of the nerve-stimulated rat anococcygeus preparation, but this may be because the nitrergic transmitter is protected from the effects of externally applied scavengers. In conclusion, the phenolics found in virgin olive oil possess ability to scavenge reactive oxygen and nitrogen species that are implicated in human pathologies, but their impact may be restricted to those species present in the extracellular environment.

Topics: Animals; Antioxidants; Caffeic Acids; Dose-Response Relationship, Drug; Free Radical Scavengers; Iridoid Glucosides; Iridoids; Male; Muscle Relaxation; Muscle, Smooth; Neural Conduction; Nitrates; Nitric Oxide; Nitroprusside; Olive Oil; Phenols; Phenylethyl Alcohol; Plant Oils; Pyrans; Rats; Rats, Wistar

Interest in the health-promoting effects of virgin olive oil, an important part of the 'Mediterranean diet', prompted us to determine the anti-eicosanoid and antioxidant effects in leukocytes of the principal phenolic compounds from the 'polar fraction': oleuropein, tyrosol, hydroxytyrosol, and caffeic acid. In intact rat peritoneal leukocytes stimulated with calcium ionophore, all four phenolics inhibited leukotriene B4 generation at the 5-lipoxygenase level with effectiveness hydroxytyrosol > oleuropein > caffeic acid > tyrosol (approximate EC50 values: 15, 80, 200, and 500 microM, respectively). In contrast, none of these compounds caused substantial inhibition of thromboxane generation via the cyclo-oxygenase pathway. Hydroxytyrosol, caffeic acid, oleuropein, and tyrosol (decreasing order of effectiveness) also quenched the chemiluminescence signal due to reactive oxygen species generated by phorbol myristate acetate-stimulated rat leukocytes. None of these compounds were toxic to leukocytes at the concentrations tested. We conclude that the phenolics found in virgin olive oil possess an array of potentially beneficial lipoxygenase-inhibitory, prostaglandin-sparing, and antioxidant properties.

Topics: Animals; Antioxidants; Caffeic Acids; Dietary Fats, Unsaturated; Eicosanoids; Iridoid Glucosides; Iridoids; Leukocytes; Lipoxygenase Inhibitors; Male; Olive Oil; Phenylethyl Alcohol; Plant Oils; Pyrans; Rats; Rats, Wistar; Reactive Oxygen Species

The antimicrobial potential of eight phenolic compounds isolated from olive cake was tested against the growth of Escherichia coli, Klebsiella pneumoniae, Bacillus cereus, Aspergillus flavus and Aspergillus parasiticus. The phenolic compounds included p-hydroxy benzoic, vanillic, caffeic, protocatechuic, syringic, and p-coumaric acids, oleuropein and quercetin. Caffeic and protocatechuic acids (0.3 mg/ml) inhibited the growth of E. coli and K. pneumoniae. The same compounds apart from syringic acid (0.5 mg/ml) completely inhibited the growth of B. cereus. Oleuropein, and p-hydroxy benzoic, vanillic and p-coumaric acids (0.4 mg/ml) completely inhibited the growth of E. coli, K. pneumoniae and B. cereus. Vanillic and caffeic acids (0.2 mg/ml) completely inhibited the growth and aflatoxin production by both A. flavus and A. parasiticus, whereas the complete inhibition of the moulds was attained with 0.3 mg/ml p-hydroxy benzoic, protocatechuic, syringic, and p-coumaric acids and quercetin.

Topics: Aflatoxin B1; Anti-Bacterial Agents; Anti-Infective Agents; Antifungal Agents; Antioxidants; Aspergillus; Aspergillus flavus; Bacillus cereus; Bacteria; Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Escherichia coli; Fruit; Gallic Acid; Hydroxybenzoates; Iridoid Glucosides; Iridoids; Klebsiella pneumoniae; Parabens; Phenols; Propionates; Pyrans; Quercetin; Vanillic Acid