carnosol and 1-1-diphenyl-2-picrylhydrazyl

Topics: Abietanes; Biphenyl Compounds; Cell Line, Tumor; Cell Proliferation; Chromatography, Liquid; Colonic Neoplasms; Gas Chromatography-Mass Spectrometry; HCT116 Cells; HT29 Cells; Humans; Mass Spectrometry; Picrates; Plant Extracts; Rosmarinus

Ethanol extracts from dried leaves of wild Lepechinia salvia (Lindl) Epling, collected during the flowering period (September-November), contained 15% to 25% carnosic acid and 2 to 8% carnosol, depending on the month of collection. The highest concentration of carnosic acid in extracts was in October, while carnosol concentration had a peak in September, which suggests that it is not a product of carnosic acid oxidation. A comparison of extracts obtained in September 2008 to 2011 shows that the production of both abietanes increased in years with less winter rainfall and higher temperatures, which induced an early blooming. EC50 values in DPPH radical scavenging and antiproliferative (CCRF-CEM tumor cells) bioassays confirm that the high bioactivity of the extracts of rosemary, sage and L. salviae does not arise only from carnosol and carnosic acid. The cytotoxic activity was significantly higher in extracts of L. salviae, probably due to water stress differences between the cultivars and the wild species. These results correlate well with the close phylogenetic relationship between the three species, and their similar medicinal uses.

Topics: Abietanes; Antineoplastic Agents; Antioxidants; Biphenyl Compounds; Cell Line, Tumor; Cell Proliferation; Ethanol; Humans; Lamiaceae; Picrates; Plant Extracts; Plant Leaves

Rosmarinus officinalis extracts were investigated by a combination of bioassays and biochemical analysis to identify bioactive compounds. The 2,2-diphenyl-2-picrylhydracyl hydrate (DPPH) radical scavenging method, Folin-Ciocaulteau method and HPLC chromatography were used to study the distribution and levels of antioxidants (AOXs). Antimicrobial activity analysis was carried out using the disk diffusion and broth dilution techniques. A good correlation between the AOX activities and total phenol content in the extracts was found. Although all rosemary extracts showed a high radical scavenging activity, a different efficacy as antimicrobial agent was observed. Methanol extract containing 30% of carnosic acid, 16% of carnosol and 5% of rosmarinic acid was the most effective antimicrobial against Gram positive bacteria (minimal inhibition concentration, MIC, between 2 and 15 mug/ml), Gram negative bacteria (MIC between 2 and 60 mug/ml) and yeast (MIC of 4 mug/ml). By contrast, water extract containing only 15% of rosmarinic acid showed a narrow activity. MIC value of the methanol and water extracts is in a good correlation with the values obtained with pure carnosic acid and rosmarinic acid, respectively. Therefore, our results suggested that the antimicrobial rosemary extracts efficacy was associated with their specific phenolic composition. Carnosic acid and rosmarinic acid may be the main bioactive antimicrobial compounds present in rosemary extracts. From a practical point of view, rosemary extract may be a good candidate for functional foods as well as for pharmaceutical plant-based products.

Topics: Abietanes; Anti-Infective Agents; Antioxidants; Bacteria; Biphenyl Compounds; Chromatography, High Pressure Liquid; Cinnamates; Depsides; Flavonoids; Free Radicals; Indicators and Reagents; Phenanthrenes; Phenols; Picrates; Plant Extracts; Polyphenols; Rosmarinic Acid; Rosmarinus; Saccharomyces cerevisiae

Preparative-scale incubations with Nocardia sp. NRRL 5646 were conducted to produce new derivatives of the abietane diterpene chemoprotectant and antioxidant carnosic acid (1). Reductive biotransformation of the C-20 carboxylic acid functional group followed by biological methylation at the C-11 phenol afforded 4. Oxidative cyclization of 1 to carnosol 5 followed by dihydroxylation at the isopropyl moiety afforded 6. Metabolites 4 and 6 are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of 4-6 using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging assay showed activities similar to that of mixed tocopherols and carnosic acid.

Topics: Abietanes; Antioxidants; Biphenyl Compounds; Cyclization; Diterpenes; Free Radical Scavengers; Mass Spectrometry; Methylation; Molecular Structure; Nocardia; Nuclear Magnetic Resonance, Biomolecular; Oxidation-Reduction; Picrates; Plant Extracts; Rosmarinus; Structure-Activity Relationship

Carnosol 1, rosmanol 2, carnosic acid 3 and 20-deoxocarnosol 4, the main phenolic abietanes present in aerial parts of the Chilean medicinal plant Sphacele salviae were tested for antioxidant activity of measuring the decay of the radical cation diphenyl-picrylhydrazyl (DPPH). All compounds displayed higher antioxidant levels than BHT under the same conditions and carnosic acid was more efficient than vitamin E.

Topics: Abietanes; Antioxidants; Biphenyl Compounds; Butylated Hydroxytoluene; Chile; Diterpenes; Dose-Response Relationship, Drug; Lamiaceae; Medicine, Traditional; Phenanthrenes; Picrates; Plant Extracts; Plant Leaves; Plants, Medicinal; Structure-Activity Relationship; Time Factors; Vitamin E