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The work focuses on the phytochemical and biological study (antimicrobial activity) of the essential oil (EO) from the underground parts ofCymbopogon schoenanthus, collected from the cultural park of Ahaggar in southern Algeria. The extraction of the essential oil gives a yield of more than 4 ml per 100 g of dry matter (gdm). Chromatographic analysis of the essential oil of this species shows a richness in monoterpenes (59.7%) with a predominance of piperitone (50.25%) and secondarily α-elemol (11.06%). The antimicrobial activity of the essential oil, tested on six microorganisms, shows a strong antifungal and antibacterial action. This bioactivity is mainly due to the richness of this essence in piperitone known for its effectiveness against microbial agents. The limit test of toxicity shows that a dose of 2 g of essential oil/kg of body weight is not toxic.

The redbay ambrosia beetle, Xyleborus glabratus, was detected in Georgia, USA, in 2002 and has since spread to 11 additional states. This wood-boring weevil carries a symbiotic fungus, Harringtonia lauricola, that causes laurel wilt, a lethal disease of trees in the Lauraceae family. Native ambrosia beetles that breed in infected trees can acquire H. lauricola and contribute to the spread of laurel wilt. Since 2002, laurel wilt has devastated native Persea species in coastal forests and has killed an estimated 200,000 avocado trees in Florida. Since laurel wilt is difficult to manage once it has entered a susceptible agrosystem, this study evaluated piperitone as a candidate repellent to deter attacks by X. glabratus and other ambrosia beetles. Additionally, piperitone was compared to the known repellent verbenone as a potential cost-effective alternative. The repellent efficacy was determined by comparing captures in traps baited with commercial beetle lures containing α-copaene versus captures in traps baited with lures plus a repellent. In parallel 10-week field tests, the addition of piperitone reduced the captures of X. glabratus in α-copaene-baited traps by 90%; however, there was no significant reduction in the captures of native ambrosia beetles in ethanol-baited traps. In two replicate 10-week comparative tests, piperitone and verbenone both reduced X. glabratus captures by 68–90%, with longevity over the full 10 weeks. This study identifies piperitone as a new X. glabratus repellent with potential for pest management.

Introduction: One of plants that may have therapeutic potential is the Cymbopogon schoenanthus (L.) Spreng, also known as camel grass. Aim: This review aims to investigate and gather comprehensive information about camel grass plants and their potential to be developed into a nanotechnology drug delivery system. Methods: This review examined a variety of online literature. Results: It was found that camel grass contains essential oil such as piperitone. Piperitone is efficacious as an antioxidant, antimicrobial and anti-inflammatory, in addition to other properties . The development of camel grass essential oil into lipid-based nanotechnology preparations can improve its bioavailability, solubility, and stability, thereby improving its potential effectiveness.

The objective of this work was to evaluate the effect of the Chrysactinia mexicana A. Gray essential oil, on C. glabrata clinical isolates. The essential oil was obtained by steam entrainment of flowers, leaves and secondary branches of C. mexicana. Gas chromatography and mass spectrometry were performed to determine the oil composition. Logarithmic and stationary phase microdilution assays were performed with Saccharomyces cerevisiae and clinical isolates of C. gla­brata to determine the Minimum Inhibitory Concentration (MIC) of the oil. The cultures were incubated in liquid YPD medium, for 7 h in fresh medium (logarithmic phase) or 3 h in recovering medium (stationary phase), with the oil and microdilution tests were performed. The three main oil compounds identified were piperitone (29.57%), eucalyptol (26.86%) and α-terpineol (14.65%). The MICs obtained were, a) stationary phase: S. cerevisiae (BY4741) 2.78 mg/mL and C. glabrata (CBS138), (NY66) and (AN400) 6.50 mg/mL and (NY62) 9.29 mg/mL; b) logarithmic phase: S. cerevisiae (BY4741) 3.71 mg/mL and C. glabrata (CBS138) 4.64 mg/mL, (NY66) 6.5 mg/mL, (AN400) 8.36 mg/mL, and (NY62) 18.5 mg/ mL. This work constitutes the first report of the fungicidal effect of the C. mexicana essential oil on human pathogenic fungi such as C. glabrata.

Mentha species are medicinally used worldwide and remain attractive for research due to the diversity of their phytoconstituents and large therapeutic indices for various ailments. This study used the metabolomics examination of five Mentha species (M. suaveolens, M. sylvestris, M. piperita, M. longifolia, and M. viridis) to justify their cytotoxicity and their anti-Helicobacter effects. The activities of species were correlated with their phytochemical profiles by orthogonal partial least square discriminant analysis (OPLS-DA). Tentatively characterized phytoconstituents using liquid chromatography high-resolution electrospray ionization mass spectrometry (LC-HR-ESI-MS) included 49 compounds: 14 flavonoids, 10 caffeic acid esters, 7 phenolic acids, and other constituents. M. piperita showed the highest cytotoxicity to HepG2 (human hepatoma), MCF-7 (human breast adenocarcinoma), and CACO2 (human colon adenocarcinoma) cells using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. OPLS-DA and dereplication studies predicted that the cytotoxic activity was related to benzyl glucopyranoside-sulfate, a lignin glycoside. Furthermore, M. viridis was effective in suppressing the growth of Helicobacter pylori at a concentration of 50 mg mL−1. OPLS-DA predicted that this activity was related to a dihydroxytrimethoxyflavone. M. viridis extract was formulated with Pluronic® F127 to develop polymeric micelles as a nanocarrier that enhanced the anti-Helicobacter activity of the extract and provided minimum inhibitory concentrations and minimum bactericidal concentrations of 6.5 and 50 mg mL−1, respectively. This activity was also correlated to tentatively identified constituents, including rosmarinic acid, catechins, carvone, and piperitone oxide.

The volatile components of kuromoji oil (Lindera umbellata Thunb.) obtained in Shizuoka Pref. were analyzed by GC/MS. Linalool, α-pinene, limonene, camphene, cis- and trans-dihydrocarvone, 1,8-cineol, 4-terpinenol, α-terpineol, piperitone, geranyl acetate, geraniol, and trans-nerolidol were identified as major components. Using enantio-MDGC-MS, the enantiomeric ratio ((R)-(-) vs (S)-(+)) of linalool in this oil was determined to be 67.8/32.2. Touch care treatment while sniffing this oil was done on cancer patients. We found that the relaxation effect persisted longer after the treatment compared to treatment without aroma.

Altitudinal variations in the content of main bioactive secondary metabolites namely, hypericin, pseudohypericin, hyperforin, the chlorogenic, neochlorogenic, caffeic and 2,4-dihydroxybenzoic acids, isoquercitrin, quercitrin, avicularin, hyperoside, rutin, biapigenin, (+)-catechin, (-)-epicatechin and in the composition of essential oil (EO) among Hypericum perforatum populations from two growing sites of Northern Turkey were investigated in detail for the first time. Aerial parts of 30 individuals at full flowering were collected at five different altitudes (391, 631, 1318, 1586 and 1733 m) of “Anzer” upland and six different altitudes (1311, 1447, 1968, 2068, 20169 and 2210 m) of “Cimil” upland in territory of Rize province, Turkey. Air dried plant samples were assayed for polar ingredients by high-performance liquid chromatography (HPLC) and for EO components by solid-phase microextraction (SPME) supported gas chromatography-mass spectrometry (GC-MS) analyses. All the tested polar phytochemicals were detected at various levels depending on altitude in both uplands and the accumulation level of each compound showed a positive consistent and significant response to altitudinal gradient. A considerable diversity in quality and quantity of major EO components was also observed and 2,2,6-trimethyl-cyclohexanone, caryophyllene oxide, tricycloheptane, hexanoic acid, tetradecanol, 2-methyl-dodecane, tetradecane, α-amorphene, eicosene, β-cedrene, piperitone, spathulenol, β-caryophyllene, δ-cadinene and linalool were identified as major EO components depending on altitude. The present results suggest that altitude of plant habitat has an ultimate effect on secondary metabolism of Hypericum perforatum and indicate the investigated populations as new chemotypes in terms of their EO composition. Such kind of findings could be useful to characterize the unique strains with desired chemical composition and can provide new viewpoints for investigations on this valuable medicinal plant.

Buchu (Barosma betulina) is a small flowering plant found in the family Rutaceae in Western Cape of South Africa, Namibia and Australia, capable of growing up to 2 meters with a simple rounded leaf that produced essential oil of strong peppermint and sweetish smell. The Buchu oil as an essential oil consist of many chemical constituents, the main components includes piperitone, pulegone, piperitone epoxide, iso-menthone, P-menthane-8-thiol3-one, 4-diosphenol. The piperitone epoxide and Pmenthane-8-thiol-3-one constituents in Buchu oil have high commercial values, which extensively used as fragrances in perform, flavor, food additives, tonic and medicinal stimulant in modern medicine in the manufacture of insecticides, antimicrobial, antiinflammatory and antioxidant in cosmetic products. The extinction threat of the plant and chemistry benefit of these chemical constituents initiate scientist with synthetic route for synthesizing the compounds from Eucalyptus dives oil and pennyroyal oil, which are also an essential oils and abundant in nature. In the synthesis, purified piperitone and pulegone from the Eucalyptus dives oil and pennyroyal oil produced two enatiotiomers of piperitone epoxide and P-menthane-8- thiol-3-one respectively. The analytical analysis such infrared and GC-Mc conducted for the starting materials, synthesis processes and synthesize products showed results of significant value in terms chemical reactions and structural re-arrangement.

The volatile chemical constituents derived from two Asteraceae species (Artemisia judaica and A. herba-alba) were analyzed and compared for the first time using gas chromatography techniques (GC–MS, GC–FID, Co-GC, LRI determination, database and literature searches) on two different stationary phase columns (polar and nonpolar). This analysis led to the identification of a total of 110 and 81 components from whole plant (stems, leaves and flowers) oils of A. judaica and A. herba-alba respectively. The major classes of compounds in both plants included oxygenated monoterpenes, sesquiterpenes and hydrocarbons. The prominent components in the oil of A. judaica were β-eudesmol, hexadecanoic acid, spathulenol, eudesma-4 (15),7-dien-1-β-ol, carvacrol and thymol which account for 67.3% of the total essential oils composition (96.7%). While the main oil constituents from A. herba-alba were piperitone, (E)-ethylcinnamate, (Z)-ethylcinnamate, thymol, isophrone which account for 78.0% of the total oil composition (99.6%). Comparison showed similar composition in thymol and spathulenol while in others major constituents, have opposite values. To the best of our knowledge, both plant species (A. judaica and A. herba-alba) from Saudi Arabia were considered for the first time in this study. In addition, the oils of these plants were screened for their bio-activities and were found to possess significant anti-microbial activities. Keywords: Artemisia judaica, A. herba-alba, Essential oils, β-eudesmol, Piperitone, (Z) and (E)-ethylcinnamate, Thymol, Anti-microbial activities

Objective: Boswellia papyrifera (Del.) Hochst and Ruta chalepensis L. are aromatic plants used in the Republic of Djibouti, both as food and medicine. The importance of essential oils of these two species in the treatment of certain pathologies such as inflammations and infections has led to an assessment of their composition in volatile organic compounds and their hepato-protective properties on rats poisoned by carbon tetrachloride (CCl4). Methods: The chemical composition of essential oils studied was determined by GC-MS. The hepato-protective properties of the essential oils of Boswellia papyrifera and Ruta chalepensis were assessed through inhibition of hepato toxicity in rats by CCl4 poisoning. The hepato-protection of essential oils was estimated by measuring biochemical and hematological parameters. Results: Essential oils of Boswellia papyrifera and Ruta chalepensis reduced the blood level of transaminases and triglycerides at the dependent dosage, and restored liver proteins (0.27 g/l) to levels similar to those rats not poisoned by CCl4. Blood levels of uric acid, urea, creatinine and HDL have also been restored to values similar to those of non-poisoned rats. The chemical composition of the essential oils studied shows that Boswellia papyrifera contains incensole acetate (43.76%) and isoincensole (18.42%), and that Ruta chalepensis contains menthyl acetate (29.8%) and piperitone (22.22%). Conclusion: The studies carried out have shown that the essential oils of Boswellia papyrifera and Ruta chalepensis have a hepato-protective potential similar to that of sylimarin (reference hepato-protective substances). The results show that the essential oils of Boswellia papyrifera and Ruta chalepensis could present good prospects in the formulation of phytomedicines for the management of liver diseases.

Purpose. To study the impact of clonal micropropagation and sanitation in vitro by viricide Ribavirin on ex vitro plant productivity, quantitative content and qualitative composition of peppermint essential oil components obtained from four breeding samples of peppermint plants (Mentha piperita L.) and the ‘Chornolysta’ variety. Methods . The study used methods of field agrotechnical one-factor experiment, essential oil distillation with water vapor according to the Ginzberg method, capillary gas chromatography and statistical analysis. Results. Due to the sanitation process in vitro, the yield of air-dried leaves of breeding samples increased by 2.9–7.1%, the ‘Chornolysta’ variety by 51.4% and rhizomes by 2.2–3.8% and 28.5% respectively, which amounted 0.35–2.74 t/ha. A significant increase of essential oil yield of breeding samples from 4.0 to 9.9 kg/ha was shown, and of the ‘Chornolysta’ variety – up to 28.6 kg/ha. After in vitro sanitation and clonal cropropagation of the breeding sample M 01-12, the content of essential oil was more than 4%. The following components of peppermint essential oil were identified: limonene, cineole, menton, mentofuran, isomenton, menthyl acetate, β-caryophyllene, isomenthol, menthol, pulegon, piperitone and carvone. A clear tendency to a decrease in the amount of menton and isomenthol with isomenton and menthol increase in plants, sanitated and propagated in vitro, was revealed. Conclusions . The use of tissue and organ culture methods and in vitro sanitation improves the qualitative composition of terpenoids by increasing the amount of menthol and menton reducing. The data obtained on the composition of terpenoids should be considered in peppermint selection as one of the integral criteria, which should be included in the list of economically valuable characteristics of peppermint plants, such as foliage, biomass of air-dried leaves, plant rhizomes and the amount of peppermint essential oil. Six indicators of the essential oil of the breeding sample M 01-02, namely citric acid, cineole, mentofuran, isomentone, pulegon, carvone, as well as the cineole / limonene ratio, meet the criteria of the European Pharmacopoeia, so it can be considered as promising for cultivation among the studied samples.

Background Wild medicinal plants are suffering natural environmental stresses and habitat destruction. The genetic diversity evaluation of wild accessions and their in vitro raised genotypes using molecular markers, as well as the estimation of substances of pharmaceutical value in wild plants and their regenerated genotypes are convenient approaches to test the genetic fidelity of regenerated plants as a source of substances of pharmaceutical value. In this study, the genetic diversity of 12 accessions of the medicinal plant Achillea fragrantissima, representing five sites in the mountains of South Sinai, Egypt, were estimated by the inter simple sequence repeats (ISSR) fingerprinting and their volatile oil components were identified using gas chromatography-mass spectrometry (GC-MS) analysis. The same accessions were regenerated in vitro and the genetic diversity and volatile oil components of propagated genotypes were determined and compared to their wild parents. Results Clustering and principal component analyses indicated that the wild accessions and their regenerated genotypes were genetically differentiated, but the regenerated plants are relatively more diverse compared to their wild parents. However, genetic variation between wild accessions is inherited to their in vitro propagated genotypes indicating genotypic differentiation of the examined accessions. The number of volatile oil compounds in the wild A. fragrantissima accessions was 31 compounds while in the in vitro propagated plants only 24 compounds were detected. Four major compounds are common to both wild and regenerated plants; these are artemisia ketone, alpha-thujone, dodecane, and piperitone. Conclusions Genome profiling and essential oil components analysis showed variations in A. fragrantissima accessions from different populations. Genetic differences between wild and regenerated genotypes were analyzed and validated with the final conclusion that in vitro conditions elicited higher genetic variation that is associated with reduced amount and diversity in the essential oil components.

Clinopodium nepeta subsp. glandulosum (Req.) Govaerts is a natural perennial grass belonging to the Lamiaceae family, growing spontaneously on the Mediterranean coast. It is locally known as “kedi fesleğeni” in Turkey. This aromatic plant is used as a mint-like spice in food preparations and in the composition of some recipes during religious feasts. In folk medicine, it is used as stimulant, antiseptic and antispasmodic. Aerial parts of C. nepeta subsp. glandulosum were collected from Bilecik in July 2017, and was air dried. The essential oil was isolated by hydrodistillation using a Clevenger-type apparatus and the composition of the essential oil was simultaneously analysed by GC-FID and GC-MS. Piperitenone oxide (47.8%), limonene (18.6%) and piperitone oxide II (13.6%) were found as major components. Antibacterial activity of the essential oil was tested against Escherichia coli NRRLB-3008, Pseudomonas aeruginosa ATCC 27853, Salmonella typhimurium ATCC 13311, Bacillus cereus NRRL-B3711 and Streptococcus sanguinis ATCC 10556 were used by broth microdilution method. Ciprofloxacin was used as control and Minimal Inhibitory Concentrations (MIC) were determined. The highest activity was found against S. typhimurium (1250 µg/mL). The essential oil is more effective against B. cereus (2500 µg/mL) and S. sanguinis (2500 µg/mL). The lowest activities were determined against E. coli (5000 µg/mL) and P. aeruginosa (10000 µg/mL).

In the present study the ability of supercritical carbon dioxide (SCO2) extracts of M. longifolia L. leaves to modulate low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9) expression was evaluated in cultured human hepatoma cell lines Huh7 and HepG2. Two SCO2 extracts, one oil (ML-SCO2) and a semisolid (MW-SCO2), were subjected to detailed chemical characterization by mono- and bidimensional nuclear magnetic resonance (1D, 2D-NMR), gas chromatography coupled with mass spectrometry (GC-MS) and liquid chromatography coupled with mass spectrometry (LC-MS). Chemical analysis revealed significant amounts of fatty acids, phytosterols and terpenoids. ML-SCO2 was able to induce LDLR expression at a dose of 60 µg/mL in HuH7 and HepG2 cell lines. Furthermore, ML-SCO2 reduced PCSK9 secretion in a concentration-dependent manner in both cell lines. Piperitone oxide, the most abundant compound of the volatile constituent of ML-SCO2 (27% w/w), was isolated and tested for the same targets, showing a very effective reduction of PCSK9 expression. The overall results revealed the opportunity to obtain a new nutraceutical ingredient with a high amount of phytosterols and terpenoids using the SCO2 extraction of M. longifolia L., a very well-known botanical species used as food. Furthermore, for the first time we report the high activity of piperitone oxide in the reduction of PCSK9 expression.

Introduction: Solenostemma oleifolium is a species that grows in extremely dry conditions. It is widespread at the foot of cliffs and in rocky areas. It is a medicinal plant used for the treatment of diabetes, respiratory disorders, rheumatism, stomach pain, urinary tract infections and febrifuge. As a part of this research program on natural compounds with antioxidant properties, the main objective of this study was to determine the chemical composition and the antioxidant activity of essential oil of S. oleifolium. Material and Methods: In this study, the aerial parts of the plant were hydrodistilled in a Clevenger-type apparatus. The isolated essential oil was analyzed using gas chromatography mass spectrometry (GC-MS). The antioxidant activity of the essential oil was assessed using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric-reducing power (FRAP). Results: The essential oil of S. oleifolium was principally characterized by oxygenated monoterpenes (94.3%) represented by linalool (59.0%), α-terpineol (14.5%) and geraniol (12.4%), followed by small amounts of nerol (3.7%) and piperitone (3.6%). The results of the antioxidant activity of essential oil showed an interesting propriety in the quenching of DPPH radical, with an IC50 of 3.3 g/L. On the other hand, essential oil showed the presence of the reductive effect, which increased with an increase in concentration. Conclusions: The results of this research showed that the S. oleifolium essential oil presented an interesting antioxidant property. Actually, it could be proposed as a new potential source of natural additives for the food or pharmaceutical industries.

Mints are perennial herbs that are cultivated for medicinal and aromatic purposes. They are highly polymorphic and their taxonomy is difficult. Sixty mint accessions, representing seven Mentha species (M. aquatica L., M. longifolia L., M. piperita L., M. pulegium., M. rotundifolia L., M. spicata L. and M. spicata var. crispa 'moroccan'), were collected at full flowering from 51 Tunisian localities. Essential oil yields were found to vary from 0.45 to 2.5%, (w/w). Analyses of these oils by GC/FID and GC/MS and their subsequent classification by statistical analysis resulted in six clusters with significant variations in their terpenoid compositions: i) pulegone/isomenthone/menthone; ii) isomenthone/pulegone; iii) menthone/pulegone ; iv) piperitenone oxide; v) linalool/linalyl acetate/1,8 cineol/myrcene; and vi) carvone/limonene/1.8 cineol. M. pulegium accessions grouped two chemotypes: one rich in pulegone and the second rich in isomenthone. M. longifolia grouped one chemotype rich in pulegone and a second rich in menthone. M. spicata grouped one chemotypes characterized by a moderate to high carvone content and the second pulegone-rich. M. rotoundifolia accessions were piperitone oxide-rich. M. aquatica and M. piperita have linalool and linalyl acetate as major compounds. These results clearly indicate that there were a large biochemical diversity among the investigated Tunisian Mentha spp. accessions. Genetic and ecological diversities may explain this chemical diversity.

Aim of the present study was to determine the In-vitro antibacterial activity of ethanolic extract of E. globulus leaves against common multidrug resistant poultry pathogens. Phytochemical analysis through HPLC revealed that kaempeferol (7.315min) followed by querecetin (6.655min) and myrecetin (3.655min). Percent area of kaempeferol (6826.88%) was highest, followed by myrecetin (5516.22%) and querecetin (163.748%). Phytochemical investigation of ethanolic extract of E. globulus leaves through GCMS showed highest retention time (min) α-pinene (20.43) and α-terpineol (20.15) accompanied by spathulenol (11.97), piperitone (11.04). The ethanolic extracts of E. globulus leaves showed a highest zone of inhibition against S. pullorum SP6; 20.64± 2.08, E. coli SE 12; 19.75± 2.83, C. perfringens type A (CPM38-01); 19.46± 2.02. The highest level of MIC of E. globulus noted were against S. gallinarum S22; 133.37±53.294, S. gallinarum S1; 130.20±45.10, S. gallinarum S4; 129.47±24.182, S. gallinarum S3; 126.83±72.392. In conclusion, the study confirmed that the ethanolic extract of E. globulus is composed of active ingredients having antibacterial activity and can be referred as an alternate to antibiotics.

Green prickly ash (Zanthoxylum armatum) and red prickly ash (Zanthoxylum bungeanum) fruit have unique flavor and aroma characteristics that affect consumers' purchasing preferences. However, differences in aroma components and relevant biosynthesis genes have not been systematically investigated in green and red prickly ash. Here, through the analysis of differentially expressed genes (DEGs), differentially abundant metabolites, and terpenoid biosynthetic pathways, we characterize the different aroma components of green and red prickly ash fruits and identify key genes in the terpenoid biosynthetic pathway. Gas chromatography-mass spectrometry (GC-MS) was used to identify 41 terpenoids from green prickly ash and 61 terpenoids from red prickly ash. Piperitone was the most abundant terpenoid in green prickly ash fruit, whereas limonene was most abundant in red prickly ash. Intergroup correlation analysis and redundancy analysis showed that HDS2, MVK2, and MVD are key genes for terpenoid synthesis in green prickly ash, whereas FDPS2 and FDPS3 play an important role in the terpenoid synthesis of red prickly ash. In summary, differences in the composition and content of terpenoids are the main factors that cause differences in the aromas of green and red prickly ash, and these differences reflect contrasting expression patterns of terpenoid synthesis genes.

The aim of the study was to investigate the micromorphology of Mentha pulegium leaves and flowers harvested in three different Sicilian (Italy) areas with peculiar pedo-climatic conditions, and to characterize the phytochemical profile, the phytotoxic activity, and the eco-compatibility of their essential oils (EOs) for potential use as safe bioherbicides. Light microscopy (LM) and scanning electron microscopy (SEM) highlighted that M. pulegium indumentum consists of non-glandular and glandular trichomes of different types. Peltate trichomes of plants from the different sites showed few significant differences in dimension and abundance, but they were characterized by a surprisingly high number of secretory cells both in leaves and flowers. Phytochemical analyses showed that oxygenated monoterpenes were the most abundant class in all the EOs investigated (92.2–97.7%), but two different chemotypes, pulegone/isomenthone and piperitone/isomenthone, were found. The complex of morphological and phytochemical data indicates that soil salinity strongly affects the expression of the toxic metabolite pulegone, rather than the EO yield. Phytotoxicity tests showed a moderate activity of EOs against the selected species as confirmed by α-amylase assay. Moreover, the low toxicity on brine shrimp provided a rationale for the possible use of investigated EOs as eco-friendly herbicides.

A novel automated method was developed for the quantitative determination of nine terpenoids that could contribute to the minty notes of red wine bouquet. The method couples headspace SPME-Arrow extraction with GC-MS/MS analysis. PDMS/DVB fiber was chosen for the extraction and an ionization energy of 30 eV permitted to optimize the analyte detection. The optimal sample preparation consists of a two-fold dilution of the wine sample with addition of 4 g of sodium chloride while the most suitable extraction conditions take place at 50 °C for 1 h. The method shows good linearity, intraday variations between 2 and 25%, interday variations between 7 and 23% and recoveries between 80 and 119%. The method exhibits the required low detection (between 3 and 60 ng/L) and quantification (between 6 ng/L and 200 ng/L) limits. These limits have permitted the quantification of the pool of minty terpenoids in fourteen red Bordeaux wines.

Background Marigold (Tagetes erecta L) accounts for over half of the world’s loose flower production, and marigold crop residue (MCR) are abundantly available and should be used as a forage. In this study, MCR from the last commercial flower pickings was ensilaged with lactic acid bacteria (LAB) and the shift in their volatile organic compounds (VOCs) profiles was monitored. Samples were collected at 6 different times during ensilage (3, 6, 9, 12, 15, 30 days) to determine and quantify the VOCs changes using a solid-phase microextraction (SPME) technique and gas chromatography – mass spectrometry (GC-MS). Results After 30 days, the caryophyllene and piperitone, which account for 14.7 and 12.1% of total VOCs, decreased by 32.9 and 9.6% respectively, alcohols increased from 2.8 to 8.1%, and the acetic acid content increased by 560%. Conclusion We have confirmed LAB can degrade the content of terpenes and enhance the content of alcohols and acids in MCR, which was for the first time on terpene degradation in fodder by ensilage. These results have shed light on our understanding of how to improve fodder odor and to enhance terpene degradation by lactic acid bacteria fermentation.

This study evaluated the larvicidal activity of Origanum majorana Linnaeus essential oil, identified the chemical composition, evaluated the antimicrobial, cytotoxic and antioxidant potential. The larvicidal activity was evaluated against larvae of the third stage of Aedes aegypti Linaeus, whereas the chemical composition was identified by gas chromatography coupled to mass spectrometer, the antimicrobial activity was carried out against the bacteria Pseudomonas aeruginosa, Escherichia coli and Staphylococcus auereus, the antioxidant activity was evaluated from of 2.2-diphenyl-1-picryl-hydrazila sequestration and Artemia salina Leach cytotoxicity. Regarding to the results, the larvicidal activity showed that O. majorana L. essential oil caused high mortality in A. aegypti L. larvae. In the chromatographic analysis, the main component found in O. majorana L. essential oil was pulegone (57.05%), followed by the other components verbenone (16.92%), trans-p-menthan-2-one (8.57%), iso-menthone (5.58%), piperitone (2.83%), 3-octanol (2.35%) and isopulegol (1.47%). The antimicrobial activity showed that E. coli and P. aeruginosa bacteria were more sensitive to oil than S. aureus, which was resistant at all concentrations. Essential oil did not present antioxidant activity, but it has high cytotoxic activity against A. salina L.

The chemical composition of Essential Oils Satureja montana and Mentha longifolia was determined, and their activity against important phytopathogenic and post-harvest fungi was studied, to evaluate their potential as natural food preservatives. The major compounds were carvacrol (24.0%), γ-terpinene (15.9%) and p-cymene (14.2%) in S. montana, and piperitenone oxide (52.7%) and piperitone oxide (23.5%) in M. longifolia. EOs were tested in vitro on Alternaria alternata, Botryotinia fuckeliana, Curvularia hawaiiensis, Fusarium equiseti, F. oxysporum lycopersici, Rhizoctonia solani and Verticillium dahliae. S. montana demonstrated excellent results. At 300 μg mL−1 the growth of all fungi was inhibited with 100% mycelial growth inhibition (MGI), except for B. fuckeliana (92%). M. longifolia was less effective, and its best result was against Verticillium dahliae (100% MGI) at 400 and 300 μg mL−1. S. montana EO was selected for in vivo antifungal tests in Cherry tomatoes and kaki “Persimmon” against A. alternata. The S. montana EO biofilm reduced post-harvest fungi development. In tomato, it inhibited up to 90% after 20 days. Necrosis did not occur for 2 months in the persimmon fruits. S. montana EO is an effective non-toxic preservative that can be considered to develop a botanical and enviro-friendly low-risk biofungicide., Graphical abstract Image 1, Highlights • Satureja montana and Mentha longifolia EOs were tested as food preservatives. • The in vitro tested Satureja montana EO showed great antifungal activity. • A natural biodegradable Satureja montana EO biofilm was developed. • The S. montana EO biofilm controlled Alternaria alternata in tomato and kaki. • The composition of the EOs was determined by CG and GC/MS.

Objective: The new coronavirus type SARS-Cov 2 (severe acute respiratory syndrome), which appeared in autumn 2019 in China, became a global pandemic in a few months. In this work, we looked for the potential anti SARS-Cov 2 of the compounds isolated from three Djiboutian medicinal plants, namely Acacia seyal, Cymbopogon commutatus, and Indigofera caerulea. Methods: We carried out a molecular docking with nine biomolecules, β-Sitosterol, Quercetin, Catechin, Lupeol, Rutin, Kaempferol, Gallic acid, Piperitone and Limonene on three target sites which are SARS-CoV-2 main protease (Mp), SARS-CoV-2 receptor-binding domain (RBD) and human furin protease. These targets are chosen because of their role in the process of penetration of the virus into human cells and its multiplication. Moreover, the predictions of pharmacokinetic parameters as well as toxicological properties have been determined using an online bioinformatics tool named SwissADME and AdmetSAR respectively. Results: The phenolic compounds have a very good affinity on these three target sites with binding energies of up to-9.098 kcal/mol for rutin on SARS-CoV-2 Mp, much better than the two reference drugs hydroxychloroquine (-5.816 kcal/mol) and remdesivir (-7.194 kcal/mol). Except for β-Sitosterol, the tested biomolecules have weak toxicity. Conclusion: These natural compounds can be used against covid 19 pending In vitro and In vivo evaluations.

Thermal stabilities of four major components (l-menthol, l-menthone, piperitone, and l-menthyl acetate) of Japanese mint essential oil were evaluated via subcritical water treatment. To improve experimental throughput for measuring compound stabilities, a small-scale subcritical water treatment method using ampoule bottles was developed and employed. A mixture of the four major components was treated in subcritical water at 180&ndash, 240 &deg, C for 5&ndash, 60 min, and then analyzed by gas chromatography. The results indicated that the order of thermal resistance, from strongest to weakest, was: l-menthyl acetate, l-menthol, piperitone, and l-menthone. In individual treatments of mint flavor components, subsequent conversions of l-menthyl acetate to l-menthol, l-menthol to l-menthone, l-menthone to piperitone, and piperitone to thymol were observed in individual treatments at 240 &deg, C for 60 min. As the mass balance between piperitone and thymol was low, the hydrothermal decomposition of the components was considered to have occurred intensely during, or after the conversion. These results explained the degradation of mint essential oil components under subcritical water conditions and provided the basis for optimizing the extraction conditions of mint essential oils using subcritical water.

International audience; Cognac spirit aromas result from the presence of a wide variety of volatile odorous compounds associated with the modalities of spirit distillation and aging. However, very few studies have been carried out on aging notes of Cognac spirits. An HPLC fractionation approach was used in order to evidence fractions of interest recalling the specific aromatic nuances of aged Cognac. Then, a GC-O/MS analysis of the selected fractions allowed one to detect odorous zones and identify several volatile compounds. Among them, various well-known volatile compounds representative of the terpenoid family were highlighted, such as geraniol, α-terpinene, nerol, α-terpineol, 1,8-cineole (eucalyptol) and, particularly, piperitone, santalol, and α-campholenal, which have not previously been cited in Cognac. These compounds were quantitated and their detection thresholds were determined. Geraniol, α-terpinene, α-terpineol, and 1,8-cineole concentrations increased while spirits were more aged, while nerol tends to decrease. A sensory contribution of terpenes was observed through perceptual synergic effects, along with β-damascenone and whisky lactone.

Euwallacea fornicatus (Eichhoff), the polyphagous shot hole borer (PSHB), is an ambrosia beetle infesting avocado Persea americana Mill. limbs in North America and Israel. We conducted field experiments with sticky traps in avocado orchards to develop push–pull semiochemical methods of managing PSHB. Traps baited with 10-fold increasing doses (0.01 to 100× or 1.26 µg to 12.6 mg/d) of attractant quercivorol were previously shown to increasingly capture female PSHB (males flightless). We converted trap catch of this relationship to a standardized effective attraction radius (EAR) that predicts capture power of baited-traps regardless of insect flight density. Earlier, piperitone and verbenone were shown to strongly inhibit attraction of PSHB to quercivorol-traps. We tested increasing numbers of 1× piperitone dispensers at 0.75-m distance surrounding a quercivorol-trap and found PSHB catch to decline exponentially. Increasing decadic doses (0.01 to 10×) of either verbenone or piperitone released at 1× quercivorol-traps caused a sigmoidal first-order kinetic-decay in catch. Verbenone (1×) placed at increasing distances (0, 0.25, 0.5, 1, and 2 m) from a 1× quercivorol-trap became increasingly ineffective in reducing catch of PSHB. We found no evidence that ethanol released from 7.5 to 480 mg/d affected attraction of PSHB, but Scobicia chevrieri (Villa and Villa) (Coleoptera: Bostrichidae) was increasingly attracted. Due to their relatively short-range (

The present investigation was focused on the study of the chemical composition variability and biological activities of the essential oils from Clinopodium nepeta subsp. nepeta and subsp. glandulosum. Essential oils extraction was performed using hydrodistillation and the separation of the constituents was carried out by gas chromatography coupled with mass spectrometry (GC-MS). Antifungal activities were tested against Aspergillus flavus, Aspergillus terreus, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophytes, and Candida albicans. Toxicity and repellency were evaluated against the stored product pests Tribolium confusum and Sitophilus zeamais. Both essential oils were characterized by a high content of oxygenated monoterpenes. Piperitone ranks first in the subspecies nepeta and piperitenone oxide is the dominant constituent in the subspecies glandulosum. All tested samples displayed noteworthy antifungal properties, with the highest activity observed for the essential oil of C. nepeta subsp. glandulosum, collected in B&eacute, ni-M&rsquo, tir, against T. mentagrophytes (MIC = 40 &micro, g/mL). The essential oil samples of C. nepeta subsp. glandulosum were strongly repellent to the insect species (PR &gt, 80%, after 2h) and highly toxic to S. zeamais reaching 97.5%&ndash, 100% mortality after 24 h of exposure. In conclusion, this study showed considerable intra-specific changes in the quality of C. nepeta essential oils, which is reflected in different rates of antifungal and insecticidal activity.

Volatile components of Haplophyllum canaliculatum Boiss. grown in Iran were extracted by hydrodistillation (HD), solvent-free microwave extraction (SFME), and headspace solid-phase microextraction (HS-SPME). The components were analyzed by means of GC and GC-MS. The extraction time and temperature for HS-SPME, microwave, power, and exposure time of extraction for SFME were optimized. Twenty-five compounds that represent 99.88% of total compounds in the oil were obtained by the HD method, and the major components for this method were identified as β-pinene (18.90%), 1,8-cineole (13.94%), and piperitone (12.22%). However, piperitone (34.50%), caryophyllene oxide (9.94%), and a-eudesmol were the main compounds among twenty-one constituents, representing 99.89% of the total composition that were characterized in volatiles extracted by the SFME method. Moreover, thirteen compounds, representing 99.95% of the total constituents, were characterized in volatile fraction extracted by the HS-SPME method, which were dominated by β-pinene (21.13%), a-pinene (13.07%), limonene (11.65%), and δ-2-carene (10.23%) as major constituents.

In an attempt to synthesize carvotacetone analogues, new 3-O-benzyl-carvotacetone (10) and previously reported 3-hydroxy-2-isopropyl-5-methyl-p-benzoquinone (11) were synthesized from piperitone (7). In this work, we describe the synthesis of 10 and other analogues from 7. Luche reduction of 7 to cis-piperitol (8), followed by benzylation yielded 3-O-benzyl-piperitol (9). Riley oxidation of 9 afforded corresponding ketone 10, 11 and 3-benzyloxy-4-isopropylcyclohex-1-enecarbaldehyde (12). Structures of these compounds were determined based on NMR, IR and LC-MS spectral data. Compound 11, exhibited antiplasmodial activities against chloroquine-sensitive (D6) and resistant (W2) strains of Plasmodium falciparum with IC50 values of 0.697 and 0.653 µg/mL, respectively. In addition, compound 11 was active against Cryptococcus neoformans with an IC50 value of 3.11 µg/mL, compared to reference standard fluconazole (IC50 value of 1.87 µg/mL), while 10 and 12 were inactive against both organisms. This is the first report of the antiplasmodial and anticryptococcal activity of compound 11.

The antifungal activity of essential oil from Calamintha nepeta (L.) Savi subspecies nepeta was investigated against some destructive fungal pathogens of postharvest fruit. A preliminary in vitro assay was used to assess the inhibitory effect using vapour contact and direct contact of the essential oil against Botrytis cinerea, Penicillium digitatum, Monilia laxa and Penicillium italicum. Both methods demonstrated that the essential oil was effective against all the fungal species tested in a dose-dependent manner, although the antifungal activity was more potent with the vapour contact test. Additional in vivo tests confirmed the efficacy of the vapour phase of the essential oil against P. digitatum and M. laxa on clementine and plum fruit, respectively. Total control of both brown rot and green mould was achieved on artificially inoculated fruit at doses of 133.3μLL. Furthermore, excellent control efficacy, similar to that obtained with conventional fungicides, was achieved at a dose of 66.6μLL. Chemical analysis of the essential oil by gas chromatography-mass spectrometry showed that pulegone (44.7%), menthone (16.4%), piperitenone (13.3%) and piperitone (6.01%) were the major constituents. These results suggest that the essential oil of C. nepeta subsp. nepeta has the potential to be used by vapour diffusion as an alternative biocontrol agent to conventional fungicides for postharvest management. However, it is important to do further research to validate these results under conditions that mimic commercial facilities and to optimise the application of essential oil vapours.

Ralstonia solanacearum raza 2 es la causante del Moko o marchitez bacteriana, produciendo grandes pérdidas económicas en cultivos como plátano, tabaco y tomate. Se han descrito varios componentes de los extractos y del aceite esencial (AE) de Tagetes patula L., que incluyen: benzofuranos, carotenoides, flavonoides y tiofenos que son biológicamente activos y potencialmente alelopáticos contra muchos organismos patógenos. Las investigaciones del efecto de los extractos y el AE de T. patula L contra R. solanacearum son escasas. El objetivo de esta investigación fue analizar el potencial antioxidante y determinar el efecto de los extractos metanólicos de flores (EMF) y de hojas (EMH) y el AE sobre el crecimiento de la bacteria. El EMF de T. patula posee mayor capacidad captadora de radicales libres (DPPH) que el AE, posiblemente relacionado con su mayor contenido de fenoles. También el EMF tiene un alto contenido en flavonoides y terpenoides. La composición química del AE fue determinada por cromatografía gas/masa, la cual reveló seis componentes mayores, los cuales representan más de 84% del AE: Indano 5.47%, D-limoneno 5.76%, Z-ocimeno 5.98%, terpinoleno 6.73%, Bervenona 19.98% y la piperitona con 40.4%. El EMF como el AE inhibieron el crecimiento de R solanacearum raza 2, pero el AE fue más efectivo (radio de inhibición 16 cm). Basados en estos resultados EMF y AE de flores y hojas de T. patula puede ser una opción para el control R solanacearum raza 2. Fil: Soto Rueda, Eliana Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Centro de Investigaciones en Ciencias de la Tierra. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Centro de Investigaciones en Ciencias de la Tierra; Argentina. Universidad del Quindio; Colombia Fil: Rodriguez Ruiz, Yenni Leandra. Universidad del Quindio; Colombia Fil: Loango Chamorro, Nelsy. Universidad del Quindio; Colombia Fil: Landazuri, Patricia. Universidad del Quindio; Colombia

Quantitative and qualitative composition of essential oils of peppermint breeds Lebedinaya Pesnya, Lubenchanka, Lidiya, Ukrainskaya Perechnaya, Mama, Chornolista was investigated before and after clonal microreproduction by the method of isolated tissues and bodies culture in vitro. Methods of essential oil steam distillation, capillary gas chromatography and statistical analysis were used in the research. It is established that increase in essential oil quantity was observed for peppermint breeds on which reproduction and improvement іn vіtro technology was applied. As a result of clonal microreproduction of peppermint plants in culture іn vіtro on nutrient medium Murasige and Skug, in which the growth regulators 0.75 mg/l of 6-benzylaminopurine, 0.1 mg/l of adenine, 0.05 mg/l of indolil-3-acetic acid and 0.5 mg/l of gibberellins acid were added and virocide Ribavirin in concentration 10 mg/l, improvement was obtained in comparison with vegetatively reproduced plants; increase in essential oil quantity per hectare was established for the following breeds; Chornolista by 54.2%, Lebedinaya pesnya by 38.2%, Ukrainskaya Perechnaya by 36.7%, Mama by 28.5%, Lubenchanka by 17.1% and Lidiya by 11.6%. For oil content the highest indices were noted for Lubenchanka, Mama and Lebedinaya Pesnya peppermint breeds with product yield 4.02%, 3.98% and 3.84% respectively. It was established that the essential oil component composition in non-clonal peppermint plants raw materials and plants-regenerants after culture in vitro is variable depending on breed. Limonene, cineole, menthone, menthofuran, iso-menthone, menthyl acetate, β-caryophyllene, iso-menthol, menthol, pulegone, germacren, piperitone, carvone were identified in peppermint essential oil. High content of menthol, low content of carvone, piperitone, pulegone (except for Chornolista, Ukrainskaya Perechnaya breeds) and menthofuran (except for Chornolista, Ukrainskaya Perechnaya and Lubenchanka breeds) are characteristic for Ukrainian selection peppermint investigated breeds. A clear tendency to menthol and menthone content ratio increase is observed in plants which were improved in conditions іn vіtro. Pulegone was not detected in essential oil samples of Lebedinaya Pesnya, Lidiya and Mama breeds. Biochemical markers of Lebedinaya Pesnya, Lubenchanka, Mama breeds, which differentiate them within the group of investigated breeds, are higher limonene, piperitone and menthol pool; for Ukrainskaya Perechnaya and Chornolista breeds – pulegone, cineole and menthone; for Lidiya breed – iso-menthone.

Plants of the genus Piper are widely used commercially. Piper chimonanthifolium Kunth. is a species with a dearth of studies on chemistry and biological activities. Essential oils of other species of this genus show good biological activities, especially against microorganisms. This work presents a comparative analysis of chemical composition of essential oils and hydrolates of leaves, inflorescences and stems of this specie. Samples were obtained by co-distillation and analyzed by Gas Chromatography-Mass Spectrometry (GC-MS). The samples were composed of monoterpenes and sesquiterpenes, with predominance of monoterpenes. Piperitone, a monoterpene with important biological activities, was the most important substance. In addition to this compound, L -linalool, cis -?-ocimene, trans -?-ocimene, 1-phellandrene, ?-pinene, limonene, and spathulenol stood out. Some of these substances can exhibit a variation in the composition according to environmental factors or may be biological control agents, demonstrating importance in ecology. The chemical characterization showed chemical differences between leaves, stems and inflorescences and demonstrated pharmacological potential for this species.

WOS: 000500885300001, PubMed: 31808956, Essential oils from the inflorescence of Cymbopogon schoenanthus and C. nervatus growing in Northern Sudan were examined for their chemical composition, antiproliferative activity against human breast carcinoma and human colon adenocarcinoma cell lines, antioxidant activity (phosphomolybdenum, antiradical, reducing power, and ferrous chelating), and enzyme inhibition activity against acetylcholinesterase butyrylcholinesterase, tyrosinase, alpha-glucosidase, and alpha-amylase. In silico study on the inhibition of tyrosinase and alpha-amylase was also performed. Piperitone (59.1%) and isomers of para-menthadienols (35.3%) were the main compounds in C. schoenanthus and C. nervatus oils, respectively. Oil from C. nervatus possessed higher antioxidant activity than that from C. schoenanthus except for its metal chelating ability. Both oils showed high antiproliferative activity. In silico study showed that trans-p-mentha-2,8-dien-1-ol and piperitone (both isomers) revealed the best docking scores for alpha-amylase and tyrosinase, respectively. In conclusion, oils from these two Cymbopogon species could be new natural agents with functional properties for food, cosmetics, and pharmaceutical industries. Practical applications Recently, there is a growing tendency to replace synthetic oils by natural ones in the cosmetic, food, and pharmaceutical products. In this context, we investigated the chemical characterization and biological activities of two Cymbopogon species essential oils (C. schoenanthus (L.) Spreng. and C. nervatus). Antioxidant capacity, enzyme inhibition, and antiproliferative effects were tested for biological activities. Chemical characterization was identified by GC-MS. Based on our findings, the Cymbopogon species may be utilized as sources of natural bioactive agents in food industries.