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The aim of the present study was to assess the commercial potential of the Origanum vulgare ssp. hirtum essential oil (OEO) as a natural intrinsic hurdle against common spoilage and pathogenic microbes in tomato juice. The main volatile compounds of the OEO identified by gas chromatography mass spectrometry (GC/MS) analysis were thymol and carvacrol, accounting for approximately 48% and 27%, respectively. Its activity against common food spoilage and pathogenic microbes was confirmed and the minimum inhibitory concentration (MIC), non-inhibitory concentration (NIC), and minimum lethal concentration (MLC) values were determined. OEO effectiveness was further validated in commercial tomato juice. Supplementation of tomato juice with OEO at concentrations lower than the MIC (350 ppm) resulted in significant delay of food spoilage and extension of the product’s shelf-life, as well as in inhibition of Listeria monocytogenes, Clostridium difficile, Saccharomyces cerevisiae, and Aspergillus niger growth after deliberate inoculation in both room and refrigerated temperatures. In conclusion, the results suggested that OEO may be used as an efficient intrinsic inhibitor of food spoilage and growth of pathogenic microbes in tomato juice.

Aqueous solution of potassium hydroxide (KOH) was used in order to obtain rich in antioxidant activity extracts from Origanum dictamnus, Origanum hirtum, Origanum onites, Rosmarinus officinalis and Satureja thymbra, after removal of the essential oil via hydrodistillation. The increase of extraction time induced lower values of total phenolic content and DPPH radical scavenging ability of the extracts, while lower alkaline concentrations, i.e. 1% and 3%, proved to be more effective than 5% (v/w) KOH. The antioxidant activity of the extracts in sunflower oil was also measured by the oxidative stability index (OSI) method. OSI values decreased as extraction time increased, while the effect of KOH concentration at short extraction time was not significant. S. thymbra, O. hirtum and R. officinalis extracts showed high total phenolic content and good antiradical and antioxidant activity in just 30 min of extraction with KOH 1% (w/v). LC–MS analysis showed that all extracts were rich in phenolic acids, such as caffeic acid and rosmarinic acid, while R. officinalis was also rich in carnosic acid.

Background : Nowadays, there has been an increased interest in essential oils from various plant origins as potential antimicrobial, antioxidant, and antiproliferative agents. This trend can be mainly attributed to the rising number and severity of food poisoning outbreaks worldwide along with the recent negative consumer perception against artificial food additives and the demand for novel functional foods with possible health benefits. Origanum dictamnus ( dittany ) is an aromatic, tender perennial plant that only grows wild on the mountainsides and gorges of the island of Crete in Greece. Objective : The aim of the present study was to investigate the antimicrobial, antioxidant, and antiproliferative properties of O. dictamnus essential oil and its main components and assess its commercial potential in the food industry. Design : O. dictamnus essential oil was initially analyzed by gas chromatography–mass spectrometry (GC–MS) to determine semi-quantitative chemical composition of the essential oils. Subsequently, the antimicrobial properties were assayed and the minimum inhibitory and non-inhibitory concentration values were determined. The antioxidant activity and cytotoxic action against the hepatoma adenocarcinoma cell line HepG2 of the essential oil and its main components were further evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and by the sulforhodamine B (SRB) assay, respectively. Results : The main constituents of O. dictamnus essential oil identified by GC–MS analysis were carvacrol (52.2%), γ-terpinene (8.4%), p -cymene (6.1%), linalool (1.4%), and caryophyllene (1.3%). O. dictamnus essential oil and its main components were effective against Staphylococcus aureus , Staphylococcus epidermidis , Escherichia coli , Listeria monocytogenes , Salmonella Enteritidis, Salmonella typhimurium , Saccharomyces cerevisiae , and Aspergillus niger . In addition, the estimated IC 50 value for the DPPH radical scavenging activity for O. dictamnus essential oil was 0.045±0.0042% (v/v) and was mainly attributed to carvacrol. The EC 50 value for the essential oil in the 72h SRB assay in HepG2 cells was estimated to be 0.0069±0.00014% (v/v). Among the individual constituents tested, carvacrol was the most bioactive compound and accounted for the observed antiproliferative activity of the essential oil. Conclusions : The results revealed that O. dictamnus essential oil is a noteworthy growth inhibitor against the microbes studied. It also possesses significant antioxidant activity and demonstrated excellent cytotoxicity against HepG2 cells. Taken together, O. dictamnus essential oil may represent an effective and inexpensive source of potent natural antimicrobial agents with health-promoting properties, which may be incorporated in food systems. Keywords: O. dictamnus essential oil; antimicrobial; antioxidant; antiproliferative; GC–MS analysis (Published: 6 May 2015) Citation: Microbial Ecology in Health & Disease 2015, 26: 26543 - http://dx.doi.org/10.3402/mehd.v26.26543

A new class of 2-pyrrolidinone derivatives was designed, synthesized, and tested for their antioxidant and anti-inflammatory activities. The compounds were evaluated for their inhibitory activity against LOX. The most potent among them, 14d [IC 50 0.08 (±0.005) mM], and 14e [IC 50 0.0705 (±0.003) mM], were also tested in vivo. The compound 14d induced equipotent inhibition against rat paw edema, which is very close to the effect produced by the commonly used standard, namely indomethacin (47%). The LOX inhibitory activity of the compound 14e proceeds in parallel to the % inhibitory value of lipid peroxidation meaning that this LOX inhibitory activity is supported by the lipid peroxidation inhibition. The molecular features that govern their bioactivity were explored through in silico docking experiments. The results showed that acidic moieties must be placed in certain distance and orientation in the active site of LOX enzyme in order to productively exhibit inhibitory activity. In addition, the 2-pyrrolidinone template significantly contributes in the inhibitory properties of the new compounds.

Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.

A new class of optically active 2-pyrrolidinones was synthesized, starting from S-pyroglutamic acid, a well known natural chiral synthon. The synthetic design followed led to the insertion of various substituents at positions 1 and 5 of the 2-pyrrolidinone ring, including the imidazole moiety. Some of them possess two or three stereogenic centers, the configuration of which was retained under the mild conditions used. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes.

A new class of 2-pyrrolidinone derivatives was designed, synthesized, and tested for their antioxidant and anti-inflammatory activities. The compounds were evaluated for their inhibitory activity against LOX. The most potent among them, 14d [IC50 0.08 (±0.005) mM], and 14e [IC50 0.0705 (±0.003) mM], were also tested in vivo. The compound 14d induced equipotent inhibition against rat paw edema, which is very close to the effect produced by the commonly used standard, namely indomethacin (47%). The LOX inhibitory activity of the compound 14e proceeds in parallel to the % inhibitory value of lipid peroxidation meaning that this LOX inhibitory activity is supported by the lipid peroxidation inhibition. The molecular features that govern their bioactivity were explored through in silico docking experiments. The results showed that acidic moieties must be placed in certain distance and orientation in the active site of LOX enzyme in order to productively exhibit inhibitory activity. In addition, the 2-pyrrolidinone template significantly contributes in the inhibitory properties of the new compounds

The new molecule 4-[(2S)-2-(1H-imidazol-1-ylmethyl)-5-oxotetrahydro-1H-pyrrol-1-yl]methylbenzenecarboxylic acid (MMK16) was found to have promising anti-inflammatory activity. This biological behavior of MMK16 triggered our interest to study its binding affinity using NMR spectroscopy in LOX and its docking and molecular dynamics (MD) properties in LOX and COX enzymes. The present NMR and docking binding studies not only rationalize the obtained biological results since in all three receptors MMK16 shows high affinity and scoring but also make it a potential dual LOX-5/COX-2 inhibitor. Thus, this class of molecules must be further investigated for discovering compounds possessing better biological activity and more lasting biological effect.

Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.