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Venlafaxine (VFX) is a serotonin and norepinephrine reuptake inhibitor chiral drug used in therapy as an antidepressant in the form of a racemate consisting of R- and S-VFX. The two enantiomers of VFX exhibit different pharmacological activities: R-VFX inhibits both norepinephrine and serotonin synaptic reuptake, whereas S-VFX inhibits only the serotonin one. R- and S-VFX are metabolized in the liver to the respective R- and S-O-desmethylvenlafaxine (ODVFX), R- and S-N-desmethylvenlafaxine (NDVFX), and R- and S-N,O-didesmethylvenlafaxine (NODVFX). The pharmacological profile of ODVFX is close to that of VFX, whereas the other two chiral metabolites (NDVFX and NODVFX) have lower affinity for the receptor sites. The pharmacokinetics of the VFX enantiomers appear stereoselective, including the metabolism process. In the past 20 years, several studies describing the enantioselective analysis of R- and S-VFX in pharmaceutical formulations and its chiral metabolites in biological matrices were published. These methods encompass liquid chromatography coupled with UV detection, mass spectrometry, or tandem mass spectrometry, and capillary electrophoresis. This paper reviews the published methods used for the determination of the individual enantiomers of VFX and its chiral metabolites in different matrices., (© 2020 John Wiley & Sons, Ltd.)

Since the beginning of life on Earth, cyanobacteria have been exposed to natural ultraviolet-A radiation (UV-A, 315-400 nm) and ultraviolet-B radiation (UV-B, 280-315 nm), affecting their cells' biomolecules. These photoautotrophic organisms have needed to evolve to survive and thus, have developed different mechanisms against ultraviolet radiation. These mechanisms include UVR avoidance, DNA repair, and cell protection by producing photoprotective compounds like Scytonemin, carotenoids, and Mycosporine-like amino acids (MAAs). Lyngbya marine species are commercially important due to their secondary metabolites that show a range of biological activities including antibacterial, insecticidal, anticancer, antifungal, and enzyme inhibitor. The main topic in this review covers the Lyngbya sp., a cyanobacteria genus that presents photoprotection provided by the UV-absorbing/screening compounds such as MAAs and Scytonemin. These compounds have considerable potentialities to be used in the cosmeceutical, pharmaceutical, biotechnological and biomedical sectors and other related manufacturing industries with an additional value of environment friendly in nature. Scytonemin has UV protectant, anti-inflammatory, anti-proliferative, and antioxidant activity. MAAs act as sunscreens, provide additional protection as antioxidants, can be used as UV protectors, activators of cell proliferation, skin-care products, and even as photo-stabilizing additives in paints, plastics, and varnishes. The five MAAs identified so far in Lyngbya sp. are Asterina-330, M-312, Palythine, Porphyra-334, and Shinorine are capable of dissipating absorbed radiation as harmless heat without producing reactive oxygen species., (Copyright © 2019 Elsevier B.V. All rights reserved.)

This study evaluated the anti-inflammatory potential of a grasshopper ketone (GK) isolated from the brown alga Sargassum fulvellum on lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophage cell line. GK was isolated and purified from the n -hexane fraction and its structure was verified on the basis of NMR spectroscopic data. GK up to 100 μg/ml is not cytotoxic to RAW 264.7, and is an effective inhibitor of LPS-induced NO production in RAW 264.7 cells. The production of pro-inflammatory cytokines, including IL-6, IL-1β, and TNF-α was found significantly reduced in 0.1-100 μg/ml dose ranges of GK treatment ( p < 0.05). We confirmed the dose-dependent and significant inhibition of iNOS and COX-2 proteins expression. In addition, it has been shown that GK induces anti-inflammatory effects by inhibiting MAPKs (ERK, JNK, and p38) and NF-κB p65 phosphorylation. Our results show that the anti-inflammatory properties of GK may be due to the inhibition of the NF-κB and MAPKs pathways, which are associated with the attenuation of cytokine secretion.

Our earliest phytochemical separation of Miliusa sinensis aided us in the isolation of a class of unique miliusanes, which were demonstrated as anticancer lead molecules. In the present study, we isolated 19 miliusanes (1-19), including 11 novel ones (5 and 10-19) from another Miliusa plant ( M. balansae), and synthesized additional derivatives to elucidate the structure-activity relationship of miliusanes. When extrapolated to various carcinoma xenograft mouse models, miliusol (1) and its derivatives 20, 26, and 27 (7.5-40 mg/kg) were demonstrated with tumor inhibitory efficacy comparable or even superior to the mainstay chemotherapeutics paclitaxel or fluorouracil. To gain a molecular insight into their anticancer mechanism, 1-3 (GI 50 0.03-4.79) were administered to a wide spectrum of human cancer cell lines, including those with specific drug resistance. We further revealed that the antiproliferative properties of miliusanes in carcinoma cells were highly associated with the p21-dependent induction of cellular senescence.

The safety and stability of synthetic UV-filters and the procedures for evaluating the photoprotective capability of commercial sunscreens are under continuous review. The influence of pH and temperature stressors on the stability of certain Mycosporine-like amino acids (MAAs) isolated at high purity levels was examined. MAAs were highly stable at room temperature during 24 h at pH 4.5⁻8.5. At 50 °C, MAAs showed instability at pH 10.5 while at 85 °C, progressive disappearances were observed for MAAs through the studied pH range. In alkaline conditions, their degradation was much faster. Mycosporine-serinol and porphyra-334 (+shinorine) were the most stable MAAs under the conditions tested. They were included in four cosmetically stable topical sunscreens, of which the Sun Protection Factor (SPF) and other Biological Effective Protection Factors (BEPFs) were calculated. The formulation containing these MAAs showed similar SPF and UVB-BEPFs values as those of the reference sunscreen, composed of synthetic UV absorbing filters in similar percentages, while UVA-BEPFs values were slightly lower. Current in vitro data strongly suggest that MAAs, as natural and safe UV-absorbing and antioxidant compounds, have high potential for protection against the diverse harmful effects of solar UV radiation. In addition, novel complementary in vitro tests for evaluation of commercial sunscreens efficacy are proposed.

Chemical examination of the EtOAc extract of the sponge-associated fungus Truncatella angustata in solid culture led to the isolation of eight undescribed isoprenylated cyclohexanols, namely truncateols O-V together with 14 known analogues. Their structures were determined on the basis of extensive spectroscopic analyses, including the modified Mosher's method and ECD data for the assignment of their absolute configurations. Truncateol O exhibited significant inhibition toward both HIV-1 and H 1 N 1 virus, while truncateol P exerted inhibitory effect against HIV-1 virus., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Eight new 4-hydroxy-2-pyridone alkaloids arthpyrones D⁻K ( 1 ⁻ 8 ), along with two known analogues apiosporamide ( 9 ) and arthpyrone B ( 10 ), were isolated from a deep-sea-derived fungus Arthrinium sp. UJNMF0008. The structures of the isolated compounds were elucidated on the basis of spectroscopic methods with that of 1 being established by chemical transformation and X-ray diffraction analysis. Compounds 1 and 2 bore an ester functionality linking the pyridone and decalin moieties first reported in this class of metabolites, while 3 and 4 incorporated a rare natural hexa- or tetrahydrobenzofuro[3,2- c ]pyridin-3(2 H )-one motif. Compounds 3 ⁻ 6 and 9 exhibited moderate to significant antibacterial activity against Mycobacterium smegmatis and Staphylococcus aureus with IC 50 values ranging from 1.66⁻42.8 μM, while 9 displayed cytotoxicity against two human osteosarcoma cell lines (U2OS and MG63) with IC 50 values of 19.3 and 11.7 μM, respectively.

Replanting obstacles of Panax notoginseng caused by complex factors, including pathogens, have received great attention. In this study, essential oils (EOs) from either Alpinia officinarum Hance or Amomum tsao-ko (Zingiberaceae) were found to inhibit the growth of P. notoginseng -associated pathogenic fungi in vitro. Subsequent GC-MS analysis revealed the chemical profiles of two plant derived EOs. Linalool and eucalyptol were found to be abundant in the EOs and tested for their antifungal activities. In addition, the synergistic effects of A. tsao-ko EOs and hymexazol were also examined. These findings suggested that Zingiberaceae EOs might be a good source for developing new green natural pesticides fighting against root-rot of P . notoginseng .

The species Croton rhamnifolioides, belonging to the Croton genus, is known in ethnomedicine as "quebra faca" and is used in the treatment of stomach pain, vomiting and fever. This study aims to evaluate the anti-edematogenic and anti-inflammatory effect of Croton rhamnifolioides leaf essential oil (OEFC) and its major constituent: 1,8-cineole (eucalyptol). The essential oil was extracted from fresh leaves through a hydrodistillation system. The chemical analysis was determined by gas chromatography-mass spectrometry (GC-MS). The acute anti-inflammatory activity was determined from the models of: ear edema by the single application of croton oil, paw edema induced by: carrageenan, dextran, histamine and arachidonic acid, while vascular permeability was determined by Evans blue extravasation and chronic anti-inflammatory activity by granuloma induction using the implantation of cotton pellets. The GC-MS results identified and quantified 11 constituents, with the major component being 1,8-cineole (41.33%). The OEFC (20mg/mL) and 1,8-cineole (8.26mg/mL) significantly reduced the edema induced by croton oil by 42.1 and 34.9%, respectively. The OEFC (25, 50, 100 and 200mg/kg) and 1,8-cineole (10.33, 20.66, 41.33 and 82.66mg/kg) statistically reduced paw edema induced by carrageenan, dextran as well as vascular permeability (protein extravasation). The OEFC (25mg/kg) and 1,8-cineole (10.33mg/kg) demonstrated efficacy in reducing edema induced by histamine and arachidonic acid and granuloma. In conclusion, the OEFC and 1,8-cineole have anti-inflammatory activity in the acute and chronic phase, suggesting therapeutic potential as a source for the development of new anti-inflammatory agents., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)

Monogenean parasites are important ectoparasites of fish, and are responsible for severe economic impacts in the aquaculture industry. They are usually treated with chemicals, but the chemicals can have harmful side effects in the fish and may pose threats to human health. Rosemary (Rosmarinus officinalis) is a common medicinal herb, with antimicrobial and antitumor properties. Here, we examined the anthelmintic activity of rosemary extract against the monogenean (Dactylogyrus minutus) in vitro and in vivo using bath treatment and oral administration. The in vitro experiments showed that parasite survival was affected by both rosemary extract concentration and the solvent (water and ethanol). Parasites were dead at 61.8±5.6 and 7.8±1.4min when exposed to 100 and 200g aqueous rosemary extract solution/L of water respectively. It took 166.7±48.2 and 5.4±1.01min to kill the parasites when exposed to 1 and 32g ethanol rosemary extract solution/L of water respectively. Moreover, pure component of rosemary extract obtained commercially used in in vitro experiments showed that 1,8-Cineole was the most toxic component of the main components tested. Parasite intensity and prevalence in fish exposed to 50 and 100g aqueous rosemary solution/L water for 30min were significantly lower than they were in controls (p<0.05). In oral treatment experiments, diets of Cyprinus carpio were supplemented with eight different concentrations of aqueous rosemary extract. The intensity of parasites was significantly less in fish fed for 30days with feed containing 60, 80 and 100ml aqueous extract/100g feed than in control (p<0.05). Together these results indicate that rosemary is a promising candidate for prevention and control of monogenean infection., (Copyright © 2017. Published by Elsevier B.V.)

The aim of this study was to investigate the essential oil (EO) compositions and antioxidant activities from petals of three wild tree peony species (Paeonia delavayi, P. lutea, and P. rockii) and eleven P. suffruticosa cultivars from different cultivar groups. The EOs yields varied from 0.63% to 1.25% (v/v) among samples when using supercritical CO 2 extraction. One hundred and sixty-three components were detected by GC/MS; and among them, linalool oxide, (Z)-5-dodecen-1-yl acetate, nonadecane, (Z)-5-nonadecene, heneicosane, phytol, and linoleic acid ethyl ester were dominant. According to hierarchical cluster analysis, principal component analysis and correspondence analysis, P. lutea, P. delavayi, and 'High Noon' were clustered in a group described as having a refreshing herbal-like note due to high rates of phytol and linalool oxide. Notably, P. lutea and P. delavayi also had strong DPPH and ABTS radical scavenging activities. These results suggest that P. lutea and P. delavayi are the most promising candidates as useful sources of fragrances and natural antioxidants., (© 2017 Wiley-VHCA AG, Zurich, Switzerland.)

The chemical composition of the essential oils from the leaves and fruit of Eucalyptus camaldulensis grown in Mersin, Turkey was analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. The biological activities (antibacterial and antifungal) were examined using the agar well diffusion method. The main leaf oil constituents were p-cymene (42.1%), eucalyptol (1,8-cineole) (14.1%), α-pinene (12.7%) and α-terpinol (10.7%). The main constituents of the fruit oil were eucalyptol (1,8-cineole) (34.5%), p-cymene (30.0%), α-terpinol (15.1%) and α-pinene (9.0%). Our results showed that both types of oils are rich in terms of monoterpene hydrocarbons and oxygenated monoterpenes. The leaf and fruit essential oils of E. camaldulensis significantly inhibited the growth of Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli and Streptococcus sp.) bacteria (p<0.05). The oils also showed fungicidal activity against Candida tropicalis and C. globrata. Leaf essential oils showed more activity than fruit essential oils, probably due to the higher p-cymene concentration in leaves.

Background: Rosmarinus officinalis L. from Tunisia, popularly known as rosemary, is of a considerable importance for its medicinal uses and aromatic value. The aim of this study was to examine the chemical composition of Rosmarinus officinalis essential oil (ROEO) and to evaluate its antibiofilm activity on biofilm-forming bacterium and its anticancer activity on cancer cell lines., Methods: The chemical composition of Rosmarinus officinalis essential oil (ROEO) was analyzed by GC-MS and its antibacterial activity was evaluated by micro-dilution method. The antibofilm activity of ROEO was evaluated using the crystal violet test and the cytotoxicity activity was determined by the MTT assay., Results: In this research, thirty-six compounds were identified in ROEO using GC-MS analyses. The main components were 1,8-cineole (23.56%), camphene (12.78%), camphor (12.55%) and β-pinene (12.3%). The antibacterial activity of ROEO was evaluated by micro-dilution method. The oil exhibited inhibition and bactericidal effect against two strains: Staphylococcus aureus ATCC 9144 and Staphylococcus epidermidis S61. It was found that the minimum inhibitory concentration (MIC) obtained for S. aureus and S. epidermidis ranged from 1.25 to 2.5 and from 0.312 to 0.625 μl ml -1 , respectively and the minimum bactericidal concentration (MBC) were in the order of 5 and 2.5 μl ml -1 , respectively. Furthermore, this oil showed a S. epidermidis biofilm inhibition more than 57% at a concentration of 25 μl ml -1 . The eradication of 67% of the established biofilm was observed at a concentration of 50 μl ml -1 of ROEO, whereas the dose of 25 μl ml -1 removed only 38% of preformed biofilm. ROEO strongly inhibited the proliferation of Hela and MCF-7 cells with IC 50 values of 0.011 and 0.253 μl ml -1 , respectively., Conclusion: Our results demonstrate that ROEO could have a potential role in the treatment of diseases related to infection by microorganisms or proliferation of cancer cells.

The sedative effects of volatile components in the essential oil of Artemisia montana ("Yomogi") were investigated and measured using gas chromatography-mass spectrometry (GC-MS). Major components identified included 1,8-cineol, camphor, borneol, α-piperitone, and caryophyllene oxide. Among them, 1,8-cineol exhibited the highest flavor dilution (FD) value in an aroma extract dilution analysis (AEDA), followed by borneol, o-cymene, β-thujone, and bornyl acetate. The sedative effects of yomogi oil aroma were evaluated by sensory testing, analysis of salivary α-amylase activity, and measurement of relative fluctuation of oxygenated hemoglobin concentration in the brain using near-infrared spectroscopy (NIRS). All results indicated the stress-reducing effects of the essential oil following nasal exposure, and according to the NIRS analysis, 1,8-cineol is likely responsible for the sedative effects of yomogi oil.

The phytochemical profile of decoction and infusion, obtained from the dried leaves of M. nivellei, consumed as tea in Saharan region, was characterized by UHPLC-PDA-HRMS. Fourteen compounds were characterized and, to confirm the proposed structures a preparative procedure followed by NMR spectroscopy was applied. Compound 3 (2-hydroxy-1,8-cineole disaccharide) was a never reported whereas a bicyclic monoterpenoid glucoside (2), two ionol glucosides (1 and 12), a tri-galloylquinic acid (4), two flavonol glycosides (5 and 9), and a tetra-galloylglucose (7), were reported in Myrtus spp. for the first time. Five flavonol O-glycosides (6, 8, 10-11, and 14) togheter a flavonol (13) were also identified. Quantitative determination of phenolic constituents from decoction and infusion has been performed by HPLC-UV-PDA. The phenolic content was found to be 150.5 and 102.6mg/g in decoction and infusion corresponding to 73.8 and 23.6mg/100mL of a single tea cup, respectively. Myricetin 3-O-β-d-(6″-galloyl)glucopyranoside (5), isomyricitrin (6) and myricitrin (8) were the compounds present in the highest concentration. The free-radical scavenging activities of teas and isolated compounds was measured by the DPPH assay and compared with the values of other commonly used herbal teas (green and black teas). Decoction displayed higher potency in scavenging free-radicals than the infusion and green and black teas., (Copyright © 2017 Elsevier B.V. All rights reserved.)

The essential oil isolated from the bark of Cinnamomum glanduliferum (Wall) Meissn grown in Egypt was screened for its composition as well as its biological activity for the first time. The chemical composition was analyzed by GC and GC/MS. The antimicrobial activity of the oil was assessed using agar-well diffusion method toward representatives for each of Gram-positive bacteria, Gram-negative bacteria, and fungi. The cytotoxic activity was checked using three human cancer cell lines. Twenty seven compounds were identified, representing 99.07% of the total detected components. The major constituents were eucalyptol (65.87%), terpinen-4-ol (7.57%), α-terpineol (7.39%). The essential oil possessed strong antimicrobial activities against Escherichia coli, with an activity index of one and minimum inhibitory concentration (MIC) equaling to 0.49 μg/ml. The essential oil possessed good antimicrobial activities against methicillin-resistant Staphylococcus aureus, Geotrichum candidum, Pseudomonas aeruginosa, Bacillus subtilis, Helicobacter pylori, Aspergillus fumigatus (MIC: 7.81, 1.95, 7.81, 0.98, 31.25, and 32.5 μg/ml, respectively). A considerable activity was reported against S. aureus and Mycobacterium tuberculosis (MIC; 32.5 and 31.25 μg/ml, respectively). The extracted oil was cytotoxic to colon (HCT-116), liver (HepG2), and breast (MCF-7) carcinoma cell lines with IC 50 of 9.1, 42.4, and 57.3 μg/ml, respectively. These results revealed that Egyptian Cinnamomum glanduliferum bark oil exerts antimicrobial and cytotoxic activities mainly due to eucalyptol and other major compounds., (© 2017 Wiley-VHCA AG, Zurich, Switzerland.)

The volatile organic compounds (VOCs) of four monofloral and one multifloral of Thai honeys produced by Apis cerana, Apis dorsata and Apis mellifera were analyzed by headspace solid-phase microextraction (HS-SPME) followed by gas chromatography and mass spectrometry (GC-MS). The floral sources were longan, sunflower, coffee, wild flowers (wild) and lychee. Honey originating from longan had more VOCs than all other floral sources. Sunflower honey had the least numbers of VOCs. cis-Linalool oxide, trans-linalool oxide, ho-trienol, and furan-2,5-dicarbaldehyde were present in all the honeys studied, independent of their floral origin. Interestingly, 2-phenylacetaldehyde was detected in all honey sample except longan honey produced by A. cerana. Thirty-two VOCs were identified as possible floral markers. After validating differences in honey volatiles from different floral sources and honeybee species, the results suggest that differences in quality and quantity of honey volatiles are influenced by both floral source and honeybee species. The group of honey volatiles detected from A. cerana was completely different from those of A. mellifera and A. dorsata. VOCs could therefore be applied as chemical markers of honeys and may reflect preferences of shared floral sources amongst different honeybee species., Competing Interests: The authors have declared that no competing interests exist.

Ethnopharmacological Relevance: Mentha longifolia L (Wild Mint or Habak) (ML) is used in traditional medicine in treatment of many gastrointestinal disorders., Aim of the Study: This study aimed to evaluate potential protecting effect of ML and its major constituent, eucalyptol, against acetic acid-induced colitis in rats, a model of human inflammatory bowel disease (IBD)., Materials and Methods: Rats were divided into ten groups (n=8) given orally for three days (mg/kg/day) the following: normal control, acetic acid-induced colitis (un-treated, positive control), vehicle (DMSO), sulfasalazine (500), ML extract (100, 500, 1000), and eucalyptol (100, 200, 400). After 24h-fasting, two ML of acetic acid (3%) was administered intrarectally. On the fifth day, serum and colonic biochemical markers, and histopathological changes were evaluated., Results: Colitis significantly increased colonic myeloperoxidase activity and malonaldehyde level, and serum tumor necrosis factor-α, interleukin-6, and malonaldehyde levels while significantly decreased colonic and serum glutathione levels. All treatments (except ML 100, ML 1000, and eucalyptol 100) significantly reversed these changes where eucalyptol (400) showed the highest activity in a dose-dependent manner. The colitis-induced histopathological changes were mild in sulfasalazine and eucalyptol 400 groups, moderate in ML 500 and eucalyptol 200 groups, and severe in ML 100, ML 1000, and eucalyptol 100 groups nearly similar to colitis-untreated rats., Conclusion: ML (in moderate doses) and eucalyptol (dose-dependently) exerted protective effects against acetic acid-induced colitis in rats possibly through antioxidant and antiinflammatory properties suggesting a potential benefit in treatments of IBD. To our knowledge this is the first report addressing this point., (Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.)

Aims: To evaluate the phytotoxic, antifungal and antioomycete activity; and, determine the chemical composition of the volatile organic compounds (VOCs) and semi-volatile metabolites produced by the endophyte Hypoxylon anthochroum strain Blaci isolated from Bursera lancifolia., Methods and Results: Based on its macro- and micro-morphological features, the strain Blaci was identified as Nodulisporium sp.; partial analysis of its ITS1-5.8-ITS2 ribosomal gene sequence revealed the identity of the teleomorphic stage of the fungus as H. anthochroum. Phytotoxic and antimicrobial activities of VOCs, and culture medium and mycelium organic extracts from H. anthochroum Blaci were determined by simple and multiple antagonism bioassays, and gas phase and agar dilution bioassays respectively. The volatile and semi-volatile metabolites were identified by gas chromatography-mass spectrometry. VOCs from a 5-day H. anthochroum strain Blaci culture caused the inhibition of seed germination, root elongation and seedling respiration on Amaranthus hypochondriacus, Panicum miliaceum, Trifolium pratense and Medicago sativa. In addition, extracts, phenylethyl alcohol and eucalyptol main compounds present in the VOCs and extract displayed a high phytotoxic activity, inhibiting the three physiological processes on the four test plants in a concentration-dependent manner., Conclusions: The results revealed that H. anthochroum strain Blaci produces a mixture of VOCs. These VOCs showed a strong phytotoxic activity on seed germination, root elongation, and seedling respiration of four plants and slightly affected the growth of phytopathogenic fungi and oomycetes. Also, the culture medium and mycelium extracts of H. anthochroum showed a high phytotoxic activity on the four test plants and, generally, the culture medium extract was more phytotoxic than the mycelium extracts., Significance and Impact of the Study: This work firstly reports the phytotoxic activity of volatile and semi-volatile compounds produced by the endophyte H. anthochroum strain Blaci on seed germination, root elongation, and seedling respiration of four different plants; consequently, these compounds could be useful in biocontrol of weeds and plant pathogens., (Journal of Applied Microbiology © 2016 The Society for Applied Microbiology.)

Citral, eucalyptol, and linalool are widely used as flavorings, fragrances, and cosmetics. Here, we examined their effects on electrophysiological and binding properties of human 5-HT3 receptors expressed in Xenopus oocytes and human embryonic kidney 293 cells, respectively. Data were analyzed using nonlinear mixed-effects modeling to account for random variance in the peak current response between oocytes. The oils caused an insurmountable inhibition of 5-HT-evoked currents (citral IC50 = 120 µM; eucalyptol = 258 µM; linalool = 141 µM) and did not compete with fluorescently labeled granisetron, suggesting a noncompetitive mechanism of action. Inhibition was not use-dependent but required a 30-second preapplication. Compound washout caused a slow (∼180 seconds) but complete recovery. Coapplication of the oils with bilobalide or diltiazem indicated they did not bind at the same locations as these channel blockers. Homology modeling and ligand docking predicted binding to a transmembrane cavity at the interface of adjacent subunits. Liquid chromatography coupled to mass spectrometry showed that an essential oil extracted from Lippia alba contained 75.9% citral. This inhibited expressed 5-HT3 receptors (IC50 = 45 µg ml(-1)) and smooth muscle contractions in rat trachea (IC50 = 200 µg ml(-1)) and guinea pig ileum (IC50 = 20 µg ml(-1)), providing a possible mechanistic explanation for why this oil has been used to treat gastrointestinal and respiratory ailments. These results demonstrate that citral, eucalyptol, and linalool inhibit 5-HT3 receptors, and their binding to a conserved cavity suggests a valuable target for novel allosteric modulators., (Copyright © 2016 by The American Society for Pharmacology and Experimental Therapeutics.)

Patients with chronic diseases such as cardiovascular diseases, chronic respiratory diseases, and neurological diseases have been shown to benefit from treatments such as aromatherapy in addition to medication. Most chronic diseases are caused by chronic inflammation and oxidative stress as well as harmful factors. Eucalyptol (1,8-cineole), a terpenoid oxide isolated from Eucalyptus species, is a promising compound for treating such conditions as it has been shown to have anti-inflammatory and antioxidant effects in various diseases, including respiratory disease, pancreatitis, colon damage, and cardiovascular and neurodegenerative diseases. Eucalyptol suppresses lipopolysaccharide (LPS)-induced proinflammatory cytokine production through the action of NF-κB, TNF-α, IL-1β, and IL-6 and the extracellular signal-regulated kinase (ERK) pathway, and reduces oxidative stress through the regulation of signaling pathways and radical scavenging. The effects of eucalyptol have been studied in several cell and animal models as well as in patients with chronic diseases. Furthermore, eucalyptol can pass the blood-brain barrier and hence can be used as a carrier to deliver drugs to the brain via a microemulsion system. In summary, the various biological activities of eucalyptol such as its anti-inflammatory and antioxidant properties, as well as its physicochemical characteristics, make this compound a potentially important drug for the treatment of chronic diseases.

Lavandin (Lavandula × intermedia Emeric ex Loiseleur) essential oils (EOs), from Abrial, Super and Grosso cultivars, cultivated and extracted in the South East of Spain, were analysed by using GC/MS to determine their composition, in both relative (peak area) and absolute (using standard curves) concentrations. Linalool (34-47%), linalyl acetate (17-34%), camphor (4-9%) and eucalyptol (3-7%) were determined as the main molecules. This characterisation was completed with the enantioselective gas chromatography, where ( - )-linalool, (+)-camphor and ( - )-linalyl acetate were determined as the main components. Antioxidant activity was evaluated positively by several methods: activity against free radicals, chelating and reducing power, probably due to linalool and linalyl acetate. Mild inhibitory activity on lipoxygenase was observed supporting potential anti-inflammatory activity, mainly due to linalool and camphor. These properties support the potential use of L. × intermedia essential oils as natural cosmetic and natural pharmaceutical ingredient to fight several skin diseases.

The rhizome of Hedychium spicatum has been widely used in traditional medicines. The present study deals with the evaluation of the cytotoxic potential of rhizome essential oils from four different regions of the Western Himalaya (India) along with comparative correlation analysis to characterise the bioactive cytotoxic component. The essential oils were coded as MHS-1, MHS-2, MHS-3 and MHS-4, and characterised using GC-FID and GC-MS. The main volatile compounds identified were 1,8-cineol, eudesmol, cubenol, spathulenol and α-cadinol. In vitro cytotoxic activities were assessed against human cancer cell lines such as, the lung (A549), colon (DLD-1, SW 620), breast (MCF-7, MDA-MB-231), head and neck (FaDu), and cervix (HeLa). MHS-4 is significantly active in comparison to other samples against all cancer cell lines. Sample MHS-4 has major proportion of monoterpene alcohol mainly 1,8-cineol. Principal components analysis was performed for the experimental results and all four samples were clustered according to their percentage inhibition at different doses.

This investigation focused on the qualitative and quantitative composition of essential oil compounds of European Origanum vulgare. Extracts of 502 individual O. vulgare plants from 17 countries and 51 populations were analyzed via GC. Extracts of 49 plants of 5 populations of Israeli Origanum syriacum and 30 plants from 3 populations of Turkish Origanum onites were included to exemplify essential oil characteristics of 'high-quality' oregano. The content of essential oil compounds of European O. vulgare ranged between 0.03% and 4.6%. The monoterpenes were primarily made up of sabinene, myrcene, p-cymene, 1,8-cineole, β-ocimene, γ-terpinene, sabinene hydrate, linalool, α-terpineol, carvacrol methyl ether, linalyl acetate, thymol and carvacrol. Among the sesquiterpenes β-caryophyllene, germacrene D, germacrene D-4-ol, spathulenol, caryophyllene oxide and oplopanone were often present in higher amounts. According to the proportions of cymyl-compounds, sabinyl-compounds and the acyclic linalool/linalyl acetate three different main monoterpene chemotypes were defined. The cymyl- and the acyclic pathway were usually active in plants from the Mediterranean climate whereas an active sabinyl-pathway was a characteristic of plants from the Continental climate., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Mycosporine-like amino acids (MAAs), a group of small secondary metabolites found in algae, cyanobacteria, lichens and fungi, have become ecologically and pharmacologically relevant because of their pronounced UV-absorbing and photo-protective potential. Their analytical characterization is generally achieved by reversed phase HPLC and the compounds are often quantified based on molar extinction coefficients. As an alternative approach, in our study a fully validated hydrophilic interaction liquid chromatography (HILIC) method is presented. It enables the precise quantification of several analytes with adequate retention times in a single run, and can be coupled directly to MS. Excellent linear correlation coefficients (R² > 0.9991) were obtained, with limit of detection (LOD) values ranging from 0.16 to 0.43 µg/mL. Furthermore, the assay was found to be accurate (recovery rates from 89.8% to 104.1%) and precise (intra-day precision: 5.6%, inter-day precision ≤6.6%). Several algae were assayed for their content of known MAAs like porphyra-334, shinorine, and palythine. Liquid chromatography-mass spectrometry (LC-MS) data indicated a novel compound in some of them, which could be isolated from the marine species Catenella repens and structurally elucidated by nuclear magnetic resonance spectroscopy (NMR) as (E)-3-hydroxy-2-((5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-((2-sulfoethyl)amino)cyclohex-2-en-1-ylidene)amino) propanoic acid, a novel MAA called catenelline.

The aim of the present study was to investigate the chemical composition of the essential oil of Artemisia vestita and to determine the antibacterial activity of the essential oil and its two major components, grandisol and 1,8‑cineole, against certain respiratory infection‑causing bacterial strains, in vitro and in vivo. The chemical composition of the essential oil was analyzed using gas chromatography‑mass spectrometry. A micro‑well dilution method was used to determine the minimum inhibition concentration (MIC) values of the essential oil and its major constituents. A model of Streptococcus pyogenes infection in mice was used to determine its in vivo activities. Lung and blood samples were obtained to assess bacterial cell counts. Toxicity evaluation of the essential oil and its components was completed by performing biochemical analysis of the serum, particularly monitoring aspartate transaminase, alanine transaminase, urea and creatinine. The essential oil exhibited potent antibacterial activity, whereas the two major constituents were less potent. The essential oil exhibited MIC values between 20 and 80 µg/ml, while the values of the two constituents were between 130 and 200 µg/ml. Scanning electron microscopy results demonstrated that the essential oil inhibited biofilm formation and altered its architecture. Survival curves indicated that the essential oil led to a reduction in the viability of different bacteria. The essential oil also induced significant leakage of potassium ions from S. pyogenes. The essential oil (100 µg/mouse) and grandisol (135 µg/mouse) significantly reduced the number of viable bacterial cells in the lungs (P<0.01). However, intake of 100 µg/mouse of essential oil or grandisol 135 µg/mouse once or twice each day for 9 days did not produce any toxic effects in the mice. In conclusion, the in vitro and in vivo results suggested that the essential oil of A. vestita and one of its major constituents, grandisol, can significantly inhibit the growth of different bacterial strains.

According to distribution of genus Achillea, two main centers of diversity occur in S.E. Europe and S.W. Asia. Diversified essential oil compositions from Balkan Peninsula have been numerously reported. However, report on essential oils of Achillea species growing in Turkey, which is one of the main centers of diversity, is very limited. This paper represents the chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of eleven Achillea species, identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were found to be 1,8-cineole, p-cymene, viridiflorol, nonacosane, α-bisabolol, caryophyllene oxide, α-bisabolon oxide A, β-eudesmol, 15-hexadecanolide and camphor. The chemical principal component analysis based on thirty compounds identified three species groups and a subgroup, where each group constituted a chemotype. This is the first report on the chemical composition of A. hamzaoglui essential oil; as well as the antioxidant and antimicrobial evaluation of its essential oil and methanolic extract.

A virulent strain of Diaporthe gulyae, isolated from stem cankers of sunflower and known to be pathogenic to saffron thistle, has been shown to produce both known and previously undescribed metabolites when grown in either static liquid culture or a bioreactor. Together with phomentrioloxin, a phytotoxic geranylcyclohexenetriol recently isolated from a strain of Phomopsis sp., two new phytotoxic trisubstituted α-pyrones, named gulypyrones A and B (1 and 2), and two new 1,O- and 2,O-dehydro derivatives of phomentrioloxin, named phomentrioloxins B and C (3 and 4), were isolated from the liquid culture filtrates of D. gulyae. These four metabolites were characterized as 6-[(2S)2-hydroxy-1-methylpropyl]-4-methoxy-5-methylpyran-2-one (1), 6-[(1E)-3-hydroxy-1-methylpropenyl]-4-methoxy-3-methylpyran-2-one (2), 4,6-dihydroxy-5-methoxy-2-(7-methyl-3-methyleneoct-6-en-1-ynyl)cyclohex-2-enone (3), and 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methyleneoct-6-en-1-ynyl)cyclohex-3-enone (4) using spectroscopic and chemical methods. The absolute configuration of the hydroxylated secondary carbon of the 2-hydroxy-1-methylpropyl side chain at C-6 of gulypyrone A was determined as S by applying a modified Mosher's method. Other well-known metabolites were also isolated including 3-nitropropionic, succinic, and p-hydroxy- and p-methylbenzoic acids, p-hydroxybenzaldehyde, and nectriapyrone. When assayed using a 5 mM concentration on punctured leaf disks of weedy and crop plants, apart from 3-nitropropionic acid (the main metabolite responsible for the strong phytotoxicity of the culture filtrate), phomentrioloxin B caused small, but clear, necrotic spots on a number of plant species, whereas gulypyrone A caused leaf necrosis on Helianthus annuus plantlets. All other compounds were weakly active or inactive.

Context: 1,8-Cineole, a terpene, characterized as a major constituent occurring in the essential oils of several aromatic plants. It is widely used in pharmaceutical industry, as a food additive and for culinary purposes., Objective: This study investigates the inhibitory effect of 1,8-cineole on transit time and diarrhea in animal models., Materials and Methods: Acute toxicity and lethality of 1-8-cineole was determined by Lork's guidelines. The antidiarrheal effect of 1,8-cineole was investigated by determining the intestinal transit and enterpooling in rats. In all experiments, different doses of 1,8-cineole (20-120 mg/kg), atropine, and loperamide were administered orally., Results: The LD50 of 1,8-cineole for oral administration was estimated to be 1280 mg/kg. 1,8-Cineole (20-120 mg/kg) did not show a significant decrease in small intestine transit (p > 0.05); however, the highest dose displayed a significant decrease in comparison with atropine (p < 0.05). This substance decreased the peristaltic index value to 68 ± 0.36% at a dose of 120 mg/kg compared with the control group (85.22 ± 4.31%) in the castor oil transit test. 1,8-Cineole significantly delayed the onset of diarrhea to -142.33 ± 6.08 min at 120 mg/kg, while the time was 103.66 ± 20.73 min for the control and >240 min for the loperamide. Moreover, 1,8-cineole significantly decreased intestinal fluid accumulation (p < 0.05)., Conclusions: This study demonstrated antispasmodic and antisecretory activities of 1,8-cineole and rationalized the traditional use of the plant containing various levels of this terpene in the treatment of gastrointestinal complains such as diarrhea.

Background: A detailed phytochemical analysis of Origanum vulgare L. ssp. viride (Boiss.) Hayek was carried out and the antioxidant activities of five different crude extracts were determined. The antiproliferative activities of the extracts were determined using the xCELLigence system (Real Time Cell Analyzer)., Results: Differences between the essential oil and volatile organic compound profiles of the plant were shown. The main component of the essential oil was caryophyllene oxide, while the main volatile organic compounds were sabinene and eucalyptol as determined by HS-GC/MS. Phenolic contents of the extracts were determined qualitatively and quantitatively by HPLC/TOF-MS. Ten phenolic compounds were found in the extracts from O. vulgare and Origanum acutidens: rosmarinic acid (in highest abundance), chicoric acid, caffeic acid, p-coumaric acid, gallic acid, quercetin, apigenin-7-glucoside, kaempferol, naringenin and 4-hydroxybenzaldehyde., Conclusion: This study provides first results on the antiproliferative and antioxidant properties and detailed phytochemical screening of O. vulgare ssp. viride (Boiss.) Hayek., (© 2014 Society of Chemical Industry.)

Croton zehntneri (Euphorbiaceae) is a native aromatic plant from Northeast region of Brazil. The monoterpenoid estragole (ESL) has been isolated by classical chromatographic methods from the essential oil (EO) of C. zehnteneri leaves and characterized by GC-FID and GC-MS, its antimicrobial and cytotoxic potentials being assessed. The analysis of the EO enabled the identification of 100% of the integrated constituents, of which yield was about 1.8%. The main components identified were: eucalyptol, estragole (84.7%) and spathulenol. The dosage of 50 μg/disk of ESL presented fairly significant zones of inhibition against Gram-positive bacteria and fungi. The ESL presented toxicity against Artemia salina with LC50 and LC90 of 4,54 and 8,47 μg mL-1. However, in tumor inhibition assays (human cells), there were no rewarding inhibition in any of the human cancer cell lines (MCF-7, HEP-2 and NCI-H292).

Plants used for traditional medicine contain a wide range of substances that can be used to treat various diseases such as infectious diseases. The present study was designed to evaluate the antileishmanial effects of the essential oil and methanolic extract of Myrtus communis against Leishmania tropica on an in vitro model. Antileishmanial effects of essential oil and methanolic extract of M. communis on promastigote forms and their cytotoxic activities against J774 cells were evaluated using MTT assay for 72 hr. In addition, their leishmanicidal activity against amastigote forms was determined in a macrophage model, for 72 hr. Findings showed that the main components of essential oil were α-pinene (24.7%), 1,8-cineole (19.6%), and linalool (12.6%). Findings demonstrated that M. communis, particularly its essential oil, significantly (P<0.05) inhibited the growth rate of promastigote and amastigote forms of L. tropica based on a dose-dependent response. The IC50 values for essential oil and methanolic extract was 8.4 and 28.9 μg/ml against promastigotes, respectively. These values were 11.6 and 40.8 μg/ml against amastigote forms, respectively. Glucantime as control drug also revealed IC50 values of 88.3 and 44.6 μg/ml for promastigotes and amastigotes of L. tropica, respectively. The in vitro assay demonstrated no significant cytotoxicity in J774 cells. However, essential oil indicated a more cytotoxic effect as compared with the methanolic extract of M. communis. The findings of the present study demonstrated that M. communis might be a natural source for production of a new leishmanicidal agent.

The chemical composition of essential oil extracted from Uncaria Hook ("Chotoko" in Japanese), the branch with curved hook of the herbal medicine Uncaria rhynchophylla has been investigated by GC and GC-MS analyses. Eighty-four compounds, representing 90.8% of the total content was identified in oil obtained from Uncaria Hook. The main components i were (E)-cinnamaldehyde (13.4%), α-copaene (8.0%), methyl eugenol (6.8%), δ-cadinene (5.3%), and curcumene (3.6%). The important key aroma-active compounds in the oil were detected by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA), using the flavor dilution (FD) factor to express the odor potency of each compounds. Furthermore, the odor activity value (OAV) has been used as a measure of the relative contribution of each compound to the aroma of the Uncaria Hook oil. The GC-O and AEDA results showed that α-copaene (FD = 4, OAV = 4376), (E)-linalool oxide (FD = 64, OAV = 9.1), and methyl eugenol (FD = 64, OAV = 29) contributed to the woody and spicy odor of Uncaria Hook oil, whereas furfural (FD = 8, OAV = 4808) contributed to its sweet odor. These results warrant further investigations of the application of essential oil from Uncaria Hook in the phytochemical and medicinal fields.

Rosemary (Rosemarinus officinalis L.) is a well-known medicinal and essential oil plant, utilized by humankind since ancient times. The objective was to determine the effect of steam distillation time (DT) and material (dry or fresh biomass) on essential oil yield, composition, and bioactivity; and to develop regression models that can predict oil yield and composition at specific DT. The oil yield (content) from dry biomass was higher (0.43%) than that from fresh biomass (0.35%) and ranged from 0.18% in the 1.25 min DT to 0.51% in the 40 min DT. There was no yield advantage in extending the DT beyond 40 min, which is much shorter than the DT used by industry. In this study, the antioxidant capacity of the rosemary oil using the ORACoil method was 4,108 μmolVE/L. Rosemary oil did not exhibit significant antileishmanial, antimalarial, or antimicrobial activity. In general, the low-boiling constituents eluted earlier than the higher boiling constituents of the essential oil, resulting in a great variation of essential oil composition obtained at different DT. The most important constituents are α-pinene, eucalyptol, and camphor. The highest α-pinene concentration in the oil (30.4%) was obtained from dry biomass at 2.5 min DT; eucalyptol (23.3% of the total oil) from fresh biomass at 2.5 min DT; and camphor (15.9% of the total oil) from fresh biomass at 160 min DT. The DT could be used as an inexpensive tool to alter essential oil composition of the essential oil from fresh or dried rosemary biomass, and to produce rosemary oils with elevated or lowered concentration of specific targeted oil constituents to meet specific market demands.

Mycosporine-like amino acids (MAAs) are UV-absorbing pigments, and structurally unique glycosylated MAAs are found in the terrestrial cyanobacterium Nostoc commune. In this study, we examined two genotypes of N.commune colonies with different water extract UV-absorption spectra. We found structurally distinct MAAs in each genotype. The water extract from genotype A showed a UV-absorbing spectrum with an absorption maximum at 335nm. The extract contained the following compounds: 7-O-(β-arabinopyranosyl)-porphyra-334 (478Da), pentose-bound shinorine (464Da), hexose-bound porphyra-334 (508Da) and porphyra-334 (346Da). The water extract from genotype B showed a characteristic UV-absorbing spectrum with double absorption maxima at 312 and 340nm. The extract contained hybrid MAAs (1050Da and 880Da) with two distinct chromophores of 3-aminocyclohexen-1-one and 1,3-diaminocyclohexen linked to 2-O-(β-xylopyranosyl)-β-galactopyranoside. A novel 273-Da MAA with an absorption maximum at 310nm was also identified in genotype B. The MAA consisted of a 3-aminocyclohexen-1-one linked to a γ-aminobutyric acid chain. These MAAs had potent radical scavenging activities in vitro and the results confirmed that the MAAs have multiple roles as a UV protectant and an antioxidant relevant to anhydrobiosis in N. commune. The two genotypes of N. commune exclusively produced their own characteristic glycosylated MAAs, which supports that MAA composition could be a chemotaxonomic marker for the classification of N. commune., (Copyright © 2014 Elsevier B.V. All rights reserved.)

Artemisia stolonifera, a perennial herb, is widely distrbuted in China. The aim of this study was to analyze the essential oil from the aerial parts of Artemisia stolonifera, as well as to evaluate the bioactivity of the oil and its main constituents. The essential oil was analyzed by gas chromatography-flame ionization detector and gas chromatography-mass spectrometry that allowed characterizing 22 compounds. The main components were eucalyptol (32.93%), β-pinene (8.18%), camphor (6.12%) and terpinen-4-ol (6.11%), and obtained from the essential oil after a further isolation. During the contact toxicity tests, the essential oil (LD50 = 8.60 μg/adult) exhibited stronger toxicity against Tribolium castaneum adults than those isolated constituents, however, camphor and terpinen-4-ol showed 1 and 2 times toxicity against Lasioderma serricorne adults than the essential oil (LD50 = 12.68 μg/adult) with LD50 values of 11.30 and 5.42 μg/adult, respectively. In the fumigant toxicity tests, especially on Tribolium castaneum, the essential oil (LC50 = 1.86 mg/L air) showed almost the same level toxicity as positive control, methyl bromide (LC50 = 1.75 mg/L air). Moreover, the essential oil and its four isolated constituents also exhibited strong repellency against two stored-product insects.

In this paper, for the first time, an inorganic-organic hybrid material based on ZnO nanoparticles was anchored to a composite made from polythiophene and hexagonally ordered silica (ZnO/PT/SBA-15) for use in solid-phase fibre microextraction (SPME) of medicinal plants. A homemade SPME apparatus was used for the extraction of volatile components of Ziziphora tenuior L. A simplex method was used for optimisation of five different parameters affecting the efficiency of the extraction. The main constituents extracted by ZnO/PT/SBA-15 and PDMS fibres and hydrodistillation (HD) methods, respectively, included pulegone (51.25%, 53.64% and 56.68%), limonene (6.73%, 6.58% and 8.3%), caryophyllene oxide (5.33%, 4.31% and 4.53%) and 1,8-cineole (4.21%, 3.31% and 3.18%). In comparison with the HD method, the proposed technique could equally monitor almost all the components of the sample, in an easier way, in a shorter time and requiring a much lower amount of the sample.

Dendranthema indicum (L.) Des Moul. is a perennial herb commonly used as a traditional Chinese medicine for a long time. In this work, we took Dendranthema indicum as a target plant and two stored insects which include Tribolium castaneum and Stegobium paniceum adults as target insects. Essential oil obtained from Dendranthema indicum was analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 31 components representing 92.44% of the oil were identified and the main compounds were found to be chamazulene (15.93%), β-caryophyllene (13.78%), germacrene D (9.11%), and b-cis-farnesene (6.59%). With a further isolation, three constituents were obtained from the essential oil and identified as chamazulene, β-caryophyllene and eucalyptol. Significantly, in the progress of assay, it showed that the essential oil and chamazulene exhibited stronger insecticidal and repellent activities against Stegobium paniceum than Tribolium castaneum. The results indicate that additional to its traditional use as Chinese medicinal herb, the essential oil of Dendranthema indicum aerial parts and isolated compounds have potential to be developed into natural insecticides or repellents for control of insects in stored grains.

The capability of electrospray ionization-conventional ion mobility spectrometry (ESI-IMS) for direct analysis of the samples extracted by solid phase microextraction (SPME) was investigated and evaluated for the first time. To that end, an appropriate new desorption chamber was designed and constructed, resulting in the possibility of direct exposure of the SPME fiber to the electrospray solvent flow. Two different elution methods in dynamic and static modes were exhaustively investigated. The results indicated that the interface could help us to have an accurate and sensitive analysis without disturbing the electrospray process, in static elution method. Venlafaxine as a test compound was extracted from human urine and plasma by a convenient headspace SPME method. The positive ion mobility spectrum of the extracted drug was obtained and the analyte responses were calculated. The coupled method of SPME-ESI-IMS was comprehensively validated in terms of sensitivity, dynamic range, and recovery percentage. Finally, various real samples of human urine and plasma were analyzed, all verifying the feasibility and success of the proposed method for the easy routine analysis., (Copyright © 2014 Elsevier B.V. All rights reserved.)

Alkenyl cyclohexenones (1a-d), alkenyl cyclohexenols (2a-c and 3b-d) and cardanols (4a-d) were isolated from the stem bark and root of Lannea schimperi. The alkenyl cyclohexenones (1a and 1d) and cardanols (4a and 4d) have side chains which have not been reported previously, in combination with the core skeletal structures. In addition, compounds 2a-c and 3b-d are all new cyclohexenols. Also isolated were the triterpenes, taraxerone and taraxerol, and sitosterol. The suite of compounds isolated (cyclohexenones and cyclohexenols) make up a nice biosynthetic pathway to the cardanols. The 5-[alkenyl]-4,5- dihydroxycyclohex-2-enone mixture (1a-d) exhibited good in vitro cytotoxicity against the Chinese Hamster Ovarian mammalian cell-line. The compounds were identified mainly from GCMS and NMR spectroscopic techniques.

The present study focuses on the volatile compounds with characteristic odor of essential oil from the leaves of Magnolia obovata by hydrodistillation (HD) and solvent-assisted flavor evaporation (SAFE) method. Eighty-seven compounds, representing 98.0% of the total oil, were identified using HD. The major compounds of HD oil were (E)-β-caryophyllene (23.7%), α-humulene (11.6%), geraniol (9.1%), and borneol (7.0%). In SAFE oil, fifty-eight compounds, representing 99.7% of the total oil, were identified. The main compounds of SAFE oil were (E)-β-caryophyllene (48.9%), α-humulene (15.7%), and bicyclogermacrene (4.2%). In this study, we newly identified eighty-five compounds of the oils from M. obovata leaves. These oils were also subjected to aroma evaluation by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). As a result, twenty-four (HD) and twenty-five (SAFE) aroma-active compounds were detected. (E)-β-Caryophyllene, α-humulene, linalool, geraniol, 1,8-cineole, and bicyclogermacrene were found to impart the characteristic odor of M. obovata leaves. These results imply that the oils of M. obovata leaves must be investigated further to clarify their potential application in the food and pharmaceutical industries.

Four new norsesquiterpenes wilfordonols A-D (1-4), along with three known compounds, sarmentol B (5), boscialin (6), and (+)-loliolide (7), were isolated from the leaves of Tripterygium wilfordii Hook.f.. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of the compounds was confirmed by CD and modified Mosher's method. At a concentration of 10 μM, compounds 4, 6, and 7 inhibited signal transducer and activator of transcription 1 translocation by 34.27 ± 1.02%, 48.93 ± 1.76%, and 70.31 ± 2.20%, respectively.

Artemisia species possess pharmacological properties that are used for medical purposes worldwide. In this paper, the essential oils from the aerial parts of Artemisia nilagirica and Artemisia maritima from the western Indian Himalaya region are described. The main compounds analyzed by simultaneous GC/MS and GC/FID were camphor and 1,8-cineole from A. maritima, and camphor and artemisia ketone from A. nilagirica. Additionally, the oils were evaluated for their antibacterial, antifungal, mosquito biting deterrent, and larvicidal activities. A. nilagirica essential oil demonstrated nonselective antifungal activity against plant pathogens Colletotrichum acutatum, Colletotrichum fragariae, and Colletotrichum gloeosporioides, whereas A. maritima did not show antifungal activity. Both Artemisia spp. exhibited considerable mosquito biting deterrence, whereas only A. nilagirica showed larvicidal activity against Aedes aegypti. Antibacterial effects assessed by an agar dilution assay demonstrated greater activity of A. maritima essential oil against Staphylococcus aureus and Pseudomonas aeruginosa compared to A. nilagirica., (Georg Thieme Verlag KG Stuttgart · New York.)

Four cyclohexanol analogues, dendrodochols A-D (1-4), were isolated from a Dendrodochium sp. fungus associated with the sea cucumber Holothuria nobilis Selenka collected from the South China Sea. The structures were elucidated by means of detailed spectroscopic analysis. The absolute configurations were assigned using a solution TDDFT/ECD calculation approach and the modified Mosher's method. In an in vitro bioassay, these compounds exhibited no growth inhibition activity against the A549 and MG63 cell lines. Dendrodochols 1 and 3 exhibited modest antifungal activity against Candida strains, Cryptococcus neoformans, and Trichophyton rubrum, whereas 2 and 4 showed no activity against the tested strains.

The aim of this research was to determine the chemical constituents and toxicities of the essential oil derived from Amomum tsaoko Crevost et Lemarie fruits against Tribolium castaneum (Herbst) and Lasioderma serricorne (Fabricius). Essential oil of A. tsaoko was obtained from hydrodistillation and was investigated by gas chromatography-mass spectrometry (GC-MS). GC-MS analysis of the essential oil resulted in the identification of 43 components, of which eucalyptol (23.87%), limonene (22.77%), 2-isopropyltoluene (6.66%) and undecane (5.74%) were the major components. With a further isolation, two active constituents were obtained from the essential oil and identified as eucalyptol and limonene. The essential oil and the two isolated compounds exhibited potential insecticidal activities against two storedproduct insects. Limonene showed pronounced contact toxicity against both insect species (LD50 = 14.97 μg/adult for T. castaneum; 13.66 μg/adult for L. serricorne) and was more toxic than eucalyptol (LD50 = 18.83 μg/adult for T. castaneum; 15.58 μg/adult for L. serricorne). The essential oil acting against the two species of insects showed LD50 values of 16.52 and 6.14 μg/adult, respectively. Eucalyptol also possessed strong fumigant toxicity against both insect species (LC50 = 5.47 mg/L air for T. castaneum; 5.18 mg/L air for L. serricorne) and was more toxic than limonene (LC50 = 6.21 mg/L air for T. castaneum; 14.07 mg/L air for L. serricorne), while the crude essential oil acting against the two species of insects showed LC50 values of 5.85 and 8.70 mg/L air, respectively. These results suggested that the essential oil of A. tsaoko and the two compounds may be used in grain storage to combat insect pests.

Phomentrioloxin is a phytotoxic geranylcyclohexenetriol produced in liquid culture by Phomopsis sp. (teleomorph: Diaporthe gulyae), a potential mycoherbicide proposed for the control of the annual weed Carthamus lanatus. In this study, seven derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on nonhost weedy and agrarian plants, fungi, Gram+ and Gram- bacteria, and on brine shrimp larvae. The results provide insights into an investigation of the structural requirements for activity. The hydroxy groups at C-2 and C-4 appeared to be important features for the phytotoxicity, as well as an unchanged cyclohexentriol ring. A role seemed also to be played by the unsaturations of the geranyl side chain. These findings could be useful for understanding the mechanisms of action of new natural products, for identifying the active sites, and possibly in devising new herbicides of natural origin.

Wastewater from a pharmaceutical formulation facility (TevaKS, Israel) was treated with a biological activated-sludge system followed by ozonation. The goal was to reduce the concentrations of the drugs carbamazepine (CBZ) and venlafaxine (VLX) before discharging the wastewater to the municipal wastewater treatment plant (WWTP). Both drugs were detected at extremely high concentrations in TevaKS raw wastewater ([VLX]=11.72 ± 2.2mg/L, [CBZ]=0.84 ± 0.19 mg/L), and resisted the biological treatment. Ozone efficiently degraded CBZ: at an O3 dose-to-dissolved organic carbon ratio of 0.55 (O3/DOC), the concentration of CBZ was reduced by >99%. A lower removal rate was observed for VLX, which was decreased by ≈ 98% at the higher O3/DOC ratio of 0.87. Decreasing the pH of the biologically treated effluent from 7 to 5 significantly increased the ozone degradation rate of CBZ, while decreasing the degradation rate of VLX. Ozone treatment did not alter the concentration of the effluent's DOC and filtered chemical oxygen demand (CODf). However, a significant increase was recorded (following ozonation) in the effluent's biological oxygen demand (BOD5) and the BOD5/CODf ratio. This implies an increase in the effluent's biodegradability, which is highly desirable if ozonation is followed by a domestic biological treatment. Different organic byproducts were formed following ozone reaction with the target pharmaceuticals and with the effluent organic matter; however, these byproducts are expected to be removed during biological treatment in the municipal WWTP., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Four new cyclohexanone derivatives (2-5) and one known analog, (-)-Palitantin (1) were isolated from the EtOAc extract of Penicillium commune, a fungal strain of low-temperature habitats. The structures of 2-5 were determined on the basis of extensive spectroscopic analysis. Furthermore, the absolute configuration of 2 was assigned by electronic circular dichroism (ECD) calculations, whereas that 3-5 were deduced via the CD data. Cytotoxicities of 2-5 against five human carcinoma cell lines (Hela, A549, MCF7, HCT116, T24) were evaluated., (Copyright © 2013 Elsevier B.V. All rights reserved.)

In the age of the Internet, the variety of drugs offered online is constantly increasing, and new drugs emerge every month. One group of drugs showing such an enormous increase is that of synthetic cannabinoids. Since their first identification in 'herbal mixtures', new structural modifications continue to appear on the market. In order to keep up with this process, toxicological screening methods need to be up to date. This can become extremely difficult if no reference material is available. In this article, a fast and effective way to extract and purify synthetic cannabinoids from 'herbal mixtures' is presented. This method opens a new opportunity for a timely reaction by obtaining reference material straight out of the 'herbal mixtures' ordered via the Internet. Isolation was carried out on a flash chromatography system with gradient elution on a C18 column using methanol and 0.55 % formic acid as mobile phases. The obtained purity of all compounds exceeded 99 %. In addition to the isolation of single compounds, the method proved to be suitable for the separation of various synthetic cannabinoids in one mixture, including the diastereomers cis- and trans-CP-47,497-C8. This approach for obtaining pure standards of new drugs proved to be effective, inexpensive and much quicker than waiting for the substances to be commercially available as reference material.

Background: An enantioselective analytical method was developed and validated for determination of venlafaxine and its metabolites O-desmethylvenlafaxine and N-desmethylvenlafaxine in plasma samples. The method employed LC-MS/MS analysis and hollow-fiber liquid-phase microextraction (HF LPME) for sample preparation., Results: After HF LPME optimization the following condition was established: sample volume of 4 ml, sample agitation at 1750 rpm, 20 min of extraction, 0.1 mol/l acetic acid as acceptor phase, 1-octanol as organic phase and donor phase pH adjustment to 10. Under these conditions, the method was linear over the concentration range of 5-500 ng/ml with quantification limits of 5 ng/ml., Conclusion: The use of HF LPME for sample preparation provided suitable recoveries, efficient clean-up and low consumption of organic solvent.