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Ratios of cis- and trans-Sabinene Hydrate in Origanum majorana L. and Origanum microphyllum (Bentham) Vogel.

(+)-cis-Sabinene hydrate and (+)-trans-sabinene hydrate are the main monoterpenes found in marjoram (Origanum majorana), but can also be found in other Origanum species as well, as in e.g. Melaleuca alternifolia. The synthesis of sabinene hydrate in marjoram (Origanum majorana) is performed by sabinene hydrate synthase. It is claimed, that both, (+)-cis- and (+)-trans-sabinene hydrate are produced by the same enzyme in an exact ratio of 10:1. To verify this in vitro result in vivo, we analysed single plants of 20 different genotypes of Origanum majorana and of three different populations of Origanum microphyllum and calculated the ratios of (+)-cis- to (+)-trans-sabinene hydrates. In Origanum majorana a constant ratio of 20:1 could be found, whereas in Origanum microphyllum the ratio did not prove to be constant.

Journal Article↗

Antifungal activities of origanum oil against Candida albicans.

The antimicrobial properties of volatile aromatic oils from medicinal as well as other edible plants has been recognized since antiquity. Origanum oil, which is used as a food flavoring agent, possesses a broad spectrum of in vitro antimicrobial activities attributed to the high content of phenolic derivatives such as carvacrol and thymol. In the present study, antifungal properties of origanum oil were examined both in vitro and in vivo. Using Candida albicans in broth cultures and a micro dilution method, comparative efficacy of origanum oil, carvacrol, nystatin and amphotericin B were examined in vitro. Origanum oil at 0.25 mg/ml was found to completely inhibit the growth of C. albicans in culture. Growth inhibitions of 75% and >50% were observed at 0.125 mg/ml and 0.0625 mg/ml level, respectively. In addition, both the germination and the mycelial growth of C. albicans were found to be inhibited by origanum oil and carvacrol in a dose-dependent manner. Furthermore, the therapeutic efficacy of origanum oil was examined in an experimental murine systemic candidiasis model. Groups of mice (n = 6) infected with C. albicans (5 x LD50) were fed varying amounts of origanum oil in a final vol. of 0.1 ml of olive oil (vehicle). The daily administration of 8.6 mg of origanum oil in 100 microl of olive oil/kg body weight for 30 days resulted in 80% survivability, with no renal burden of C. albicans as opposed to the group of mice fed olive oil alone, who died within 10 days. Similar results were obtained with carvacrol. However, mice fed origanum oil exhibited cosmetically better clinical appearance compared to those cured with carvacrol. The results from our study encourage examination of the efficacy of origanum oil in other forms of systemic and superficial fungal infections and exploration of its broad spectrum effect against other pathogenic manifestations including malignancy.

Animals↗

Chemical composition and extraction yield of the extract of Origanum vulgare obtained from sub- and supercritical CO2.

In this work sub- and supercritical CO(2) were used to obtain extracts from two origanum samples, one commercial, and another cultivated under agronomic control. The experiments were performed in the temperature range of 293-313 K and from 100 to 200 bar in pressure, employing around 26 g of origanum samples. Results show that the commercial sample provides a higher yield of extract if compared to the other sample. It is also achieved that a raise in temperature at constant pressure leads to an increase in the extraction yield despite solvent density changes. Chemical analyses were carried out in a GC-MSD, allowing the identification of around 24 compounds by use of the library of spectra of the equipment and injection of some standard compounds for both commercial and cultivated origanum samples. It was also found that the distribution of chemical components as a function of extraction time differs appreciably between the origanum species. The chromatographic analysis permitted the identification of thymol and cis-sabinene hydrate as the most prominent compounds present in commercial oregano sample and carvacrol and cis-sabinene hydrate in the cultivated Origanum vulgare.

Carbon Dioxide↗

Inhibitory effect of ursolic acid purified from Origanum majorana L on the acetylcholinesterase.

We screened 139 herbal spices in search of the acetylcholinesterase (AChE) inhibitor from natural resources. AChE inhibitors, which enhance cholinergic transmission by reducing the enzymatic degradation of acetylcholine, are the only source of compound currently approved for the treatment of Alzheimer's Disease (AD). Among these herbs, edible plants and spices, the ethanol extract from Origanum majorana L. showed the highest inhibitory effect on AChE in vitro. By sequential fractionation of Origanum majorana L. the active component was finally identified as ursolic acid (3 beta-Hydroxyurs-12-en-28-oic acid). The ursolic acid of Origanum majorana L. inhibited AChE activity in a dose-dependent and competitive/non-competitive type. The Ki value (representing the affinity of the enzyme and inhibitor) of Origanum majorana L. ursolic acid was 6 pM, and that of tacrine was 0.4 nM. The concentration required for 50% enzyme inhibition of the active component (IC50 value) was 7.5 nM, and that of tacrine was 1 nM. This study demonstrated that the ursolic acid of Origanum majorana L. appeared to be a potent AChE inhibitor in Alzheimer's Disease.

Acetylcholinesterase↗

Essential oils of Satureja, Origanum, and Thymus species: chemical composition and antibacterial activities against foodborne pathogens.

The chemical composition of the essential oils obtained from the species restricted to Greece and the eastern Mediterranean region, Satureja spinosa L. and Thymus longicaulis L.; species endemic to central and south Greece, Satureja parnassica ssp. parnassica Heldr. and Sart ex Boiss.; species endemic to the island of Crete, Origanum dictamnus L.; and species widely distributed in the Mediterranean region, Satureja thymbra L. and Origanum vulgare L. subsp. hirtum, were determined by gas chromatography (GC) and GC/mass spectrometry (MS) analysis. The in vitro antibacterial activities of the essential oils were evaluated against a panel of five foodborne bacteria (Escherichia coli 0157:H7 NCTC 12900, Salmonella enteritidis PT4, Staphylococcus aureus ATCC 6538, Listeria monocytogenes ScottA, and Bacillus cereus FSS 134). The analytical data indicated that various monoterpene hydrocarbons and phenolic monoterpenes constitute the major components of the oils, but their concentrations varied greatly among the oils examined. The antibacterial assay results showed that 5 muL doses of the essential oils extracted from the endemic Satureja species in Greece possess remarkable bactericidal properties, which are clearly superior as compared to those of Origanum and Thymus species essential oils. Therefore, they represent an inexpensive source of natural mixtures of antibacterial compounds that exhibit potentials for use in food systems to prevent the growth of foodborne bacteria and extend the shelf life of the processed food.

Anti-Bacterial Agents↗

Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities.

The composition of the essential oils of Origanum and Thymus species restricted to Algeria and the North Africa region was determined. Antioxidant and antibacterial activities of the isolated essential oils were also determined. The oils of oregano plants were strongly characterized by p-cymene (16.8-24.9%), gamma-terpinene (16.8-24.9%), thymol (8.4-36.0%), and carvacrol (1.1-29.7%), a thymol chemotype for Origanum floribundum and a alpha-terpineol chemotype for Thymus numidicus being described for the first time. The strains of Listeria monocytogenes tested were relatively resistant to the action of essential oils of either Origanum or Thymus species. All essential oils possessed antioxidant activity, but this was dependent on the specific chemical composition and the method employed to determine such activity.

Algeria↗

Superheated water extraction of essential oils of Origanum micranthum.

Superheated water extraction is used to extract essential oil of leaves of Origanum micranthum. The effect of different temperatures on the essential oil profile and rate of extraction as a function of time is investigated. The components of essential oil of Origanum micranthum are removed from the aqueous extract by C18 solid-phase extraction. The identification of components is carried out using comprehensive gas chromatography-time of flight-mass spectrometry. The number of extracted components is almost the same; however, the concentrations change with changing temperature. The highest yield (0.64%) is found at a temperature of 150 degrees C, 2 mL/min and 60 bar for 30 min. The increasing temperature from 100 degrees C to 175 degrees C increased the rate of extraction of six selected components of essential oil of Origanum micranthum. cis-Sabinenehydrate exhibits the fastest rate of extraction at all temperatures studied. Some degradation products are observed at a temperature of 175 degrees C.

Chemical Fractionation↗

A study of the larvicidal activity of Origanum (Labiatae) species from southwest Turkey.

The insecticidal activity of essential oils isolated from two species of Origanum (Origanum onites L. and Origanum minutiflorum (O. Schwarz and P.H. Davis) (Labiate)) was investigated against 3rd and 4th instar larvae of the mosquito, Culex pipiens L. (Diptera: Culicidae). The LC50 and LC90 values were 24.8 and 61.3 ppm, and 73.8 and 118.9 ppm, respectively. This activity was attributed to the carvacrol, the major constituent of these oils.

Animals↗

Experimental study on the antibacterial effect of origanum volatile oil on dysentery bacilli in vivo and in vitro.

To observe the germistatic and germicidal effects of origanum volatile oil (OVI) on the dysentery bacteria, the abdominal cavity of mice was infected with Shigella sonne (Sh. sonnei) and Shigella flexneri (Sh. flexneri) F2a. After OVI was given to the mice via gastric lavage, the effects of OVI on the infected mice were observed. The minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) for dysentery bacteria were determined in vitro. The results showed that origanum volatile oil showed obvious protective effect on mice infected with Sh. sonnei and Sh. flexneri F2a and it had germistatic and germicidal effects on dysentry bacteria. We are led to conclude that origanum volatile oil is an effective medicine against the infection of dysentery bacteria.

Animals↗

Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.

From the polar extracts of Origanum vulgare L. ssp. hirtum 19 compounds have been isolated. The structures and relative stereochemistry have been elucidated by spectroscopic analysis and determined as apigenin, luteolin, chrysoeriol, diosmetin, quercetin, eriodictyol, cosmoside, vicenin-2, caffeic acid, p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, thymoquinol 2-O-beta-glucopyranoside, thymoquinol 5-O-beta-glucopyranoside, thymoquinol 2,5-O-beta-diglucopyranoside, 12-hydroxyjasmonic acid, 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside, lithospermic acid B, rosmarinic acid, 10-epi-lithospermic acid, and epi-lithospermic acid B. The three latter products display unusual stereochemistry of the 3,4-hydroxyphenyllactic acid unit(s), which to the authors' best knowledge has never been reported before in similar compounds. Moreover, lithospermic acid B (and its stereoisomers), p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, 12-hydroxyjasmonic acid, and 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside were isolated for the first time from Origanum species.

Circular Dichroism↗

Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey.

In the present study, essential oil from the leaves of Syrian oreganum [Origanum syriacum L. (Lauraceae)] grown in Turkish state forests of the Dortyol district, Turkey, was obtained by steam distillation. The chemical composition of oil was analysed by GC and GC-MS, and was found to contain 49.02% monoterpenes, 36.60% oxygenated monoterpenes and 12.59% sesquiterpenes. The major components are as follows: gamma-terpinene, carvacrol, p-cymene and beta-caryophyllene. Subsequently, the reducing power, antioxidant and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activities of the essential oil were studied. The reducing power was compared with ascorbic acid, and the other activities were compared with 2,6-di-tert-butyl-4-methyl phenol (BHT, butylated hydroxytoluene). The results showed that the activities were concentration dependent. The antioxidant activities of the oil were slightly lower than those of ascorbic acid or BHT, so the oil can be considered an effective natural antioxidant. Antimicrobial activities of the essential oil from the leaves of Origanum syriacum was also determined on 16 microorganisms tested using the agar-disc diffusion method, and showed antimicrobial activity against 13 of these.

Ampicillin↗

Effect of an aqueous distillate of Origanum onites L. on isolated rat fundus, duodenum and ileum: evidence for the role of oxygenated monoterpenes.

The aqueous distillate of Origanum onites L. (Labiatae) was reported to have various ethnomedical uses including effects on the gastrointestinal tract. The effects of three different doses (0.1, 0.2 and 0.4 mL) of the aqueous distillate of Origanum onites on isolated rat fundus, duodenum and ileum against acetylcholine induced contractions were investigated in this study. The aqueous distillate inhibited contractions in a dose dependent manner. Inhibitions were lowest on fundus. Carvacrol, being the major compound of the test substance, did not inhibit acetylcholine induced contractions of the isolated rat fundus, indicating the presence of other active principles including menthane diols. As being one of the first pharmacological studies on aqueous distillates, a possible pharmacological activity of cis-p-menth-4-ene-1,2-diol and 3,7-dimethyl-1-octen-3,7-diol is proposed in this study.

Acetylcholine↗

[Analysis on the volatile oil in Origanum vulgare].

OBJECTIVE: To analysis compositions of the volatile oil in Origanum vulgare. METHODS: GC-MS condition: using programmed temperature gas chromatography cinitial temperature was 60 degrees C, and then raising the temperature (5 degrees C/min) to 240 degrees C, mass-to-electric charge ratio was 10 to 425. RESULTS: GC-MS identified 29 kinds of contents. CONCLUSION: Thymol and carvacrol are main compositions of the volatile oil in Origanum vulgare.

Cymenes↗

Analysis of Origanum vulgare volatiles by direct thermal desorption coupled to gas chromatography-mass spectrometry.

Volatile components of samples of a population of Spanish Origanum vulgare have been analyzed by direct thermal desorption coupled to GC-MS. The method is fast and reliable and requires a low amount of sample, allowing analysis of leaves and flowers from a single individual plant. Volatile yield is highly variable among individual plants and concentration also presents a high variation for most Origanum volatile compounds, linalool being the main component in most samples. Statistical analyses are applied in order to find patterns in composition data.

Adsorption↗

Ursolic acid of Origanum majorana L. reduces Abeta-induced oxidative injury.

Amyloid beta protein (Abeta) increases free radical production and lipid peroxidation in PC12 nerve cells, leading to apoptosis and cell death. The effect of ursolic acid from Origanum majorana L. on Abeta-induced neurotoxicity was investigated using PC12 cells. Pretreatment with isolated ursolic acid and vitamin E prevented the PC12 cell from reactive oxygen species (ROS) toxicity that is mediated by Abeta. The ursolic acid resulted in decreased Abeta toxicity assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), lactate dehydrogenase (LDH), and trypan blue assay. Thus, treatment with these antioxidants inhibited the Abeta-induced neurotoxic effect. Therefore, these results indicate that micromolar Abeta-induced oxidative cell death is reduced by ursolic acid from Origanum majorana L.

Alzheimer Disease↗

[Action of essential oils of chamomile, cinnamon, absinthium, mace and origanum on operant conditioning behavior of the rat].

The Chamomile, Cinnamon, Absinthium, Mace, Origanum essential oils have been experimented on rat's operant conditioning behaviour. At the highest doses all the oils caused a depressive effect (probably due to toxicity) while at the lowest doses they caused weak or doubtful effects. Only the Origanum oil caused a depressive effect which clearly seems related to a direct action on the CNS.

Animals↗

Superheated water extraction, steam distillation and Soxhlet extraction of essential oils of Origanum onites.

Superheated water extraction (SWE) at various temperatures (100, 125, 150 and 175 degrees C), steam distillation, and Soxhlet extraction were compared in the extraction of essential oils from two samples of the plant Origanum onites, one cultivated, the other wild. C18 solid-phase extraction was used to elute the essential oils from the SWE aqueous extract. The compositions of the extracted essential oils obtained from all three methods were then characterized by comprehensive GCxGC/time-of-flight mass spectrometry (TOF/MS). The highest essential oil yields were obtained by using SWE at 150 degrees C with a flow rate of 2 mL min(-1) and a pressure of 60 bar for 30 min: these were 3.76 and 4.11% for wild and cultivated O. onites samples, respectively, expressed as a percentage of 100 g of dry (leaf) matter. The yields obtained using SWE at 150 degrees C were slightly higher than those from conventional methods. Steam distillation was performed for 3 h, and Soxhlet extraction was completed in 12 h. The major compounds found were borneol, terpinen-4-ol and carvacrol.

Chromatography, Gas↗

Effect of oregano (Origanum vulgare L.) and thyme (Thymus vulgaris L.) essential oils on Trypanosoma cruzi (Protozoa: Kinetoplastida) growth and ultrastructure.

In the present work, we have investigated the effect of essential oils obtained from Origanum vulgare L. (oregano) and Thymus vulgaris L. (thyme) on growth and ultrastructure of diverse evolutive forms of Trypanosoma cruzi. Culture epimastigotes and bloodstream trypomastigotes were incubated for 24 h with different concentrations of oregano or thyme essential oils and with thymol (the main constituent of thyme), and the inhibitory concentration (IC)(50) was determined by cell counting. Crude extract of oregano essential oil inhibited epimastigote growth (IC(50)/24 h = 175 microg/ml) and also induced trypomastigote lysis (IC(50)/24 h = 115 microg/ml). Thyme essential oil presented IC(50)/24 h values of 77 microg/ml for epimastigotes and 38 mug/ml for trypomastigotes, while treatment with thymol resulted in an IC(50)/24 h of 62 microg/ml for epimastigotes and 53 microg/ml for trypomastigotes. Scanning electron microscopy of treated cells showed few morphological alterations at the plasma membrane. Observation by transmission electron microscopy showed cytoplasmic swelling with occasional morphological alterations in plasma and flagellar membrane. Our data indicate that oregano and thyme essential oils are effective against T. cruzi, with higher activity of thyme, and that thymol may be the main component responsible for the trypanocidal activity.

Animals↗