1-1-diphenyl-2-picrylhydrazyl and 4-hydroxyphenylethanol

The aim of the present study is to highlight volatile and targeted non-volatile bioactive compounds in Nuragus wines, as a part of Italian DOC (Controlled Origin Designation) white wines. So far there has not been any systematic study of the chemical compositions and antioxidant activity of this monovarietal wine. Phenolic compounds, volatiles and organic acids were analysed and antioxidant capacity was assessed by spectrophotometric assays. Chromaticity coordinates and technological parameters (alcohol, reducing sugars, pH, total and volatile acidity) were also evaluated. Gallic acid (128±87mg/L), trans-caftaric acid (81±27mg/L) and tyrosol (25±8mg/L) were the most abundant phenolic compounds. The major headspace volatiles were isoamyl alcohol (35.8-76.6%) and 2-phenylethanol (5.9-24.9%). In the wine extracts, the most abundant were 2-phenylethanol (12.3-40.0%), 4-hydroxy-2-phenylethanol (12.5-33.3%), diethyl succinate (5.8-30.3%), (Z)-octadec-9-en-1-ol (5.9-18.3%) and tryptophol (2.8-15.6%). Nuragus wines exhibited an excellent antioxidant capacity. The data obtained may help Nuragus wine producers to promote this monovarietal wine as a valid complement associated with the Mediterranean diet.

Topics: Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Gallic Acid; Gas Chromatography-Mass Spectrometry; Molybdenum; Pentanols; Phenols; Phenylethyl Alcohol; Phytochemicals; Picrates; Solid Phase Microextraction; Tungsten Compounds; Volatile Organic Compounds; Wine

In continuation of our search for new antibacterial and antioxidant metabolites from sponge-derived fungi, one new tyrosol derivative, hypocrol A (1), together with four known congeners, trichodenol B (2), 4-hydroxyphenethyl acetate (3), 4-hydroxyphenethyl tetradecanoate (4) and 1-oleyltyrosol (5), was isolated from the strain Hypocrea koningii PF04. Their planar structures were unequivocally elucidated by spectroscopic methods and comparison with the literature data. All the compounds displayed weak antibacterial activities against Staphylococcus aureus, methicillin-resistant S. aureus and Escherichia coli, whereas compounds 1 and 2 exhibited a moderate antioxidant efficacy in the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay with IC50 values of 48.5 and 97.4 μg/mL, respectively.

Topics: Animals; Anti-Bacterial Agents; Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Escherichia coli; Fermentation; Hypocrea; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Phenylethyl Alcohol; Picrates; Porifera; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet

Consumption of phenolic compounds is associated with beneficial effects in humans even though many of them are poorly absorbed. The aim of this study was to investigate the in vitro antioxidant activity of tyrosol (T), resveratrol (R) and their acetylated derivatives (AcD), as increased lipophilicity has been reported to improve absorption. The chemically synthesized AcDs were evaluated by their ability to scavenge DPPH radicals, inhibit non-enzymatic linoleic acid peroxidation, inhibit human serum oxidation in the presence of copper ions and inhibit lipoxygenase activity. T showed an inhibitory effect only in serum oxidation, where the T-acetylated at aromatic-OH was the most active. The T-acetylated at aliphatic-OH and 3,5-diacetyl-R exhibited the most powerful effect in non-enzymatic linoleic acid peroxidation with IC50 values 2.4 mM ± 0.21 and 0.055 mM ± 0.0018, respectively. In all other tests R was the most potent among all its AcD and T. Increasing lipophilicity by acetylation improves antioxidant activity of phenolic compounds in non-enzymatic lipid peroxidation assays.

Topics: Acetylation; Antioxidants; Biphenyl Compounds; Free Radical Scavengers; Glycine max; Humans; In Vitro Techniques; Linoleic Acid; Lipid Peroxidation; Lipoxygenase Inhibitors; Oxidation-Reduction; Phenylethyl Alcohol; Picrates; Resveratrol; Serum; Stilbenes

Two new indole derivatives (3, 4) and three known compounds (1, 2, 5) were isolated as radical scavengers from the culture filtrate of a marine sponge-derived yeast. Their structures were determined to be tyrosol (1), tryptophol (2), 2-(1H-indol-3-yl)ethyl 2-hydroxypropanoate (3), 2-(1H-indol-3-yl)ethyl 5-hydroxypentanoate (4), and cyclo(L-Pro-L-Tyr) (5) on the basis of their spectroscopic data. The absolute configurations of compounds 3 and 5 were determined by chiral HPLC analysis combined with synthesis and Marfey's method, respectively. Each obtained compound was evaluated for DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity, and all compounds exhibited weak activities.

Topics: Animals; Biphenyl Compounds; Chromatography, High Pressure Liquid; Free Radical Scavengers; Indoles; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Peptides, Cyclic; Phenylethyl Alcohol; Pichia; Picrates; Piperazines; Porifera

In the current study, we investigated 2 species of the genus Rhodiola for the inhibition of alpha-amylase,alpha-glucosidase and angiotensin converting enzyme (ACE) inhibitory activity. Water extracts of Rhodiola crenulata had the highest alpha-amylase inhibitory activity (IC50,98.1 microg total phenolic /ml) followed by ethanol extract of R.crenulata (IC50, 120.9 microg total phenolic/ml) and ethanol extract of R.rosea (IC50, 173.4 microg total phenolic /ml). Ethanol R.rosea (IC50, 44.7 microg total phenolic/ml), water extract of R.rosea (IC50, 52.3 microg total phenolic/ml), water extract of R.crenulata (IC50, 60.3 microg total phenolic /ml) and ethanol extract of R.crenulata (IC50, 60.2 microg total phenolic/ml) also showed significant alpha-glucosidase inhibitory activity. The alpha-glucosidase inhibitory activity of the extracts was compared to standard tyrosol, which was significantly detected in the extracts using HPLC. Tyrosol had strong alpha-glucosidase inhibitory activity (IC50, 70.8 microg total phenolic/ml) but did not have any inhibitory effect on the alpha-amylase activity. Results suggested that alpha-glucosidase inhibitory activities of both Rhodiola extracts correlated to the phenolic content, antioxidant activity and phenolic profile of the extracts. The ability of the above Rhodiola extracts to inhibit rabbit lung angiotensin I-converting enzyme (ACE) was investigated. The ethanol extracts of R.rosea had the highest ACE inhibitory activity (38.5 %) followed by water extract of R.rosea (36.2 %) and R.crenulata (15.4 %).

Topics: alpha-Amylases; Angiotensin-Converting Enzyme Inhibitors; Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Diabetes Mellitus, Type 2; Enzyme Inhibitors; Ethanol; Glycoside Hydrolase Inhibitors; Hypertension; Phenols; Phenylethyl Alcohol; Picrates; Plant Extracts; Rhodiola; Water