lignans and 4-hydroxyphenylethanol

Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay- and LC/MS-guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS-stimulated RAW 264.7 cells (P<0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p-TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione (1), 3-(3,5-di-tert-butyl-4-hydroxy)phenylpropionic acid (2), variabilone (3), 2,4-di-tert-butylphenol (4), indole-3-carboxylic acid (5), tyrosol (6), ethyl ferulate (7) and a new lignan (8) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan (8), was based on HR-MS,

Topics: Fungi; Lignans; Lipopolysaccharides; Nitric Oxide; Penicillium; Piper nigrum; Plant Extracts

Potato, tomato, eggplant and pumpkin were deep fried, sautéed and boiled in Mediterranean extra virgin olive oil (EVOO), water, and a water/oil mixture (W/O). We determined the contents of fat, moisture, total phenols (TPC) and eighteen phenolic compounds, as well as antioxidant capacity in the raw vegetables and compared these with contents measured after cooking. Deep frying and sautéing led to increased fat contents and TPC, whereas both types of boiling (in water and W/O) reduced the same. The presence of EVOO in cooking increased the phenolics identified in the raw foods as oleuropein, pinoresinol, hydroxytyrosol and tyrosol, and the contents of vegetable phenolics such as chlorogenic acid and rutin. All the cooking methods conserved or increased the antioxidant capacity measured by DPPH, FRAP and ABTS. Multivariate analyses showed that each cooked vegetable developed specific phenolic and antioxidant activity profiles resulting from the characteristics of the raw vegetables and the cooking techniques.

Topics: Antioxidants; Benzothiazoles; Chlorogenic Acid; Chromatography, High Pressure Liquid; Cluster Analysis; Cooking; Cucurbita; Dietary Fats; Furans; Iridoid Glucosides; Iridoids; Lignans; Multivariate Analysis; Olive Oil; Phenols; Phenylethyl Alcohol; Rutin; Solanum lycopersicum; Solanum melongena; Solanum tuberosum; Sulfonic Acids; Vegetables

Different grades of genuine and counterfeit Fraxinus excelsior exudates, marketed as natural sweeteners or mild laxatives, were evaluated for their proximate composition and for saccharidic, organic acids, lipidic and phenolic profile by means of GC-MS and (1)H NMR. Genuine samples contained mannitol (39-48 g/100 g, according to the grade), fructose (9-16 g/100 g), glucose (2-3.7 g/100 g), sorbitol (0,5-0,6 g/100 g), galactose (0.02-0.74 g/100 g), oligosaccharides as mannotriose (13-22 g/100 g) and stachyose (1-11 g/100 g), and traces of myo-inositol, mannose, sucrose. On the contrary, counterfeit samples contained mostly mannitol and sorbitol, with traces of fructose, glucose and mannose. Differences in ash, total polyphenolic content and fatty acid composition allowed a quick identification of counterfeit products, confirmed by a distinct mono-, oligosaccharidic and phenolic pattern. Elenolic acid (63-1628 mg/kg), tyrosol (15-774 mg/kg), homovanillic acid (2,39-52.8 mg/Kg), dopaol (0.8-63 mg/kg), pinoresinol (4.2-18.5 mg/kg) and fraxetin (0.25-11.64 mg/kg), albeit showing a wide concentration range, were the most abundant substances detected in the phenolic fraction of Fraxinus manna, while esculetin, p-hydroxybenzoic acid, 4-hydroxyphenacetic acid, 3,4 hydroxybenzoic acid, hydroxy-pinoresinol, medioresinol and siringaresinol were present in low amounts. The polyphenolic profile may be used as a marker for authentication and should be considered in the evaluation of nutritional and health properties ascribed to Fraxinus manna.

Topics: Coumarins; Fatty Acids; Fraxinus; Furans; Hexoses; Homovanillic Acid; Lignans; Oligosaccharides; Phenylethyl Alcohol; Plant Extracts; Plant Exudates; Polyphenols; Pyrans; Sugar Alcohols

Refined edible oils (viz., oils from maize, soya, high-oleic sunflower, sunflower, olive, and rapeseed) enriched at two concentration levels (200 and 400 μg/mL total phenolic content) with phenolic extracts isolated from olive pomace and leaves have been characterized and compared with nonenriched oils and extra virgin olive oil (EVOO). Enriched oils were analyzed by LC-TOF/MS to generate representative fingerprints and compared with nonenriched oils and EVOO by unsupervised principal component analysis (PCA). The two raw materials reported enriched oils with profiles which were compared with those provided by EVOOs. Correlation analysis enabled us to establish the enriched oils with a composition more similar to EVOO. Discrimination according to the enrichment level depended on the raw material for extracts, and a global discussion about the enrichment on relevant phenolic compounds present in EVOO has reported quantitative results concerning the enrichment level for those significant compounds with known nutraceutical properties.

Topics: Antioxidants; Flavonoids; Furans; Iridoids; Lignans; Mass Spectrometry; Olea; Olive Oil; Phenols; Phenylethyl Alcohol; Plant Extracts; Plant Leaves; Plant Oils; Principal Component Analysis

An RRLC method capable of simultaneous identification and rapid quantification of six biologically active compounds (salidroside, tyrosol, rosarin, rosavin, rosin, rosiridin) in Rhodiola rosea L. and two active compounds (eleutheroside B and eleutheroside E) in Eleutherococcus senticosus Maxim. was developed. The chromatographic analyses were performed on a reversed phase Phenomenex C18 (2)-HST column at 40°C with a neutral mobile phase (purified water and acetonitrile) gradient system at a flow rate of 1.0ml/min and UV detection at 205 and 220nm simultaneously. Baseline separation of eight active compounds was achieved within 8min. This developed method provides good linearity (R>0.9997), precision (RSD<1.99%) and recovery of the bioactive compounds. The RRLC method developed is capable of controlling the quality of R. rosea and E. senticosus raw herbs, commercial extracts, as well as polyherbal formulations containing R. rosea and E. senticosus as ingredients. This RRLC method is accurate and sensitive; in addition, it greatly increases sample analysis throughput with reduced analysis time, which is suitable for routine quality control analysis.

Topics: Calibration; Chemistry Techniques, Analytical; Chemistry, Pharmaceutical; Chromatography; Chromatography, Liquid; Disaccharides; Eleutherococcus; Glucosides; Lignans; Phenols; Phenylethyl Alcohol; Phenylpropionates; Plant Extracts; Plant Preparations; Quality Control; Reproducibility of Results; Resins, Plant; Rhodiola

A capillary zone electrophoresis method has been carried out to determine and quantitate some compounds of the polyphenolic fraction of virgin olive oil which have never previously been determined before using capillary electrophoresis, such as elenolic acid, ligstroside aglycon, oleuropein aglycon, and (+)-pinoresinol. The compounds were identified using standards obtained by semipreparative high-performance liquid chromatography (HPLC). A detailed method optimization was performed to separate the phenolic compounds present in olive oil using a methanol-water extract of Picual extra-virgin olive oil, and different extraction systems were compared (C18-solid phase extraction (SPE), Diol-SPE, Sax-SPE and liquid-liquid extraction). The optimized parameters were 30 mM sodium tetraborate buffer (pH 9.3) at 25 kV with 8 s hydrodynamic injection, and the quantitation was carried out by the use of two reference compounds at two different wavelengths.

Topics: Chromatography, High Pressure Liquid; Electrophoresis, Capillary; Flavonoids; Furans; Glucosides; Iridoid Glucosides; Iridoids; Lignans; Olive Oil; Phenols; Phenylethyl Alcohol; Plant Oils; Polyphenols; Pyrans