Use of Novel Homochiral Thioureas Camphor Derived as Asymmetric Organocatalysts in the Stereoselective Formation of Glycosidic Bonds.

We synthesized six new camphor-derived homochiral thioureas 1-6, from commercially available (1R)-(-)-camphorquinone. These new compounds 1-6 were evaluated as asymmetric organocatalysts in the stereoselective formation of glycosidic bonds, with 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl and 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates as donors, and several alcohols as glycosyl acceptors, such as methanol, ethanol, 1-propanol, 1-butanol, 1-octanol, iso-propanol, tert-butanol, cyclohexanol, phenol, 1-naphtol, and 2-naphtol. Optimization of the asymmetric glycosylation reaction was achieved by modifying reaction conditions such as solvent, additive, loading of catalyst, temperature, and time of reaction. The best result was obtained with 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl trichloroacetimidates, using 15 mol% of organocatalyst 1, in the presence of 2 equiv of MeOH in solvent-free conditions at room temperature for 1.5 h, affording the glycosidic compound in a 99% yield and 1:73 α:ß stereoselectivity; under the same reaction conditions, without using a catalyst, the obtained stereoselectivity was 1:35 α:ß. Computational calculations prior to the formation of the products were modeled, using density functional theory, M06-2X/6-31G(d,p) and M06-2X/6-311++G(2d,2p) methods. We observed that the preference for ß glycoside formation, through a stereoselective inverted substitution, relies on steric effects and the formation of hydrogen bonds between thiourea 1 and methanol in the complex formed.

Use of activated carbon and camphor carbon as cathode and clay cup as proton exchange membrane in a microbial fuel cell for the bioenergy production from crude glycerol biodegradation.

This work characterizes two alternative materials to substitute the most expensive microbial fuel cells (MFCs) components: proton exchange membrane (PEM) and cathode. Crude glycerol biodegradation was studied in MFCs using a clay cup as a PEM and activated carbon and camphor carbon mixture (CAC) as a cathode. The cathode performance was compared with Platinum on carbon cloth. Two clay cup single-chamber MFCs were operated with each cathode and fed with 2000 mg/L of crude glycerol. Electrochemical properties were characterized by linear sweep voltammetry, electrochemical impedance spectroscopy, and chronoamperometry. Biodegradation efficiencies were estimated with the chemical oxygen demand (COD) removal percentage. MFCs with CAC showed a maximum power density of 100 mW/m2. This result was a 43.47% power response regarding MFCs with Platinum. COD removal efficiencies of 94% were achieved in 37 days for both cells. The Columbic efficiencies were 24.04% and 22.78% for the MFCs with Platinum and CAC. The economic analysis showed a cost of USD 9.97 for MFCs with CAC. This cost is five times lower than when using Platinum. MFCs utilizing clay cups and CAC showed an acceptable performance for the bioenergy production from crude glycerol biodegradation above all economic advantage in the cell cost.

Camphor nitroimine: a key building block in unusual transformations and its applications in the synthesis of bioactive compounds.

The development of new drugs requires a lot of time and high financial investments. It involves a research network in which there is the participation of several researchers from different areas. For a new drug to reach the market, thousands of substances must be evaluated. There are several tools for this and the use of suitable building blocks can facilitate the process by allowing a lead compound to have suitable parameters. These compounds are key structures containing special functional groups that also permit adequate synthetic transformations, leading to several structures of interest in a short period of time. In this review, the use of camphor nitroimine as a potential key building block is explored. Derived from camphor, an abundant natural product present in various plant species, this nitroimine has proved to be quite versatile, allowing the access to substances with miscellaneous biological activities, ligands to asymmetric catalysis, asymmetric oxidants, O-N transfer agents and other applications. Its easy conversion to camphecene and other derivatives is described, as well as their applications in medicinal chemistry. Druglikeness analyses were performed on these studied agents as well as on their bioactive derivatives in order to assess their use in the development of potential drugs.

Essential Oil of Rosmarinus officinalis Ecotypes and Their Major Compounds: Insecticidal and Histological Assessment Against Drosophila suzukii and Their Impact on a Nontarget Parasitoid.

Essential oils (EOs) produced by plants in the Lamiaceae family may provide new insecticidal molecules. Novel control compounds are needed to control Drosophila suzukii (Matsumura), a severe economic invasive pest of thin-skinned fruit crops. Thus, we characterized the main compounds of EOs from three rosemary Rosmarinus officinalis ecotypes (ECOs) and evaluated their toxicity to D. suzukii adults, deterrence of oviposition behavior, and histological alterations in larvae. Additionally, we analyzed the lethal and sublethal effect on the pupal parasitoid Trichopria anastrephae. The main compounds identified in the R. officinalis ECOs were α-pinene, camphor and 1,8-cineole. In bioassays via topical application or ingestion, ECOs and their major compounds showed high toxicity on D. suzukii adults and a lower concentration could kill 50% and 90% of flies compared to spinetoram. The dry residues of a-pinene, 1,8-cineole, and camphor provided a repellent effect by reducing D. suzukii oviposition by ~47% compared to untreated fruit. Histological sections of 3rd instar larval D. suzukii posttreatment revealed damage to the fat body, Malpighian tubules, brain, salivary gland, and midgut, which contributed to high larval and pupal mortality. Survival and parasitism by adult T. anastrephae were not affected. Thus, R. officinalis EO and their compounds have potential for developing novel insecticides to manage D. suzukii.

Effects of 24 h Compression Interventions with Different Garments on Recovery Markers during Running.

Compression and temperature manipulation are discussed as strategies to improve performance markers and recovery in sports. Here, we investigate the effects of compression stockings made with fabric, either combined or not with heating and cooling substances, on variables related to running performance and recovery. Ten trained runners (mean ± standard deviation age 45 ± 9 years old, body mass 69 ± 7 kg, height 166 ± 4 cm) with no experience of using compression garments performed an intense running session of 10 km, then wore a stocking for 24 h (randomized; without compression, compression, compression with camphor, and compression with menthol), and were evaluated on the following day, after running 5 km. The different types of compression stockings used 24 h before exercise did not affect running kinematics (p > 0.14), skin temperature (p > 0.05), heart rate (p > 0.12; mean value of maximal heart rate 156 bpm), comfort perception (p = 0.13; mean value of 7/10 points), or perception of recovery (p = 0.13; mean value of 7/10 points). In general, there were no effects of 24 h pre-exercise lower leg compression, including those treated with menthol and camphor applications on running kinematics, skin temperature, heart rate, or recovery perception in athletes undertaking consecutive running exercises.

Investigation of the relaxing effect of a camphor nanoemulsion on rat isolated trachea.

Asthma is a chronic inflammatory disease that targeting lower airways, being characterized by bronchial smooth muscle hyper responsiveness and mucus hypersecretion. Asthma is considered the most common respiratory disease in the world, affecting approximately 235 million individuals. The main therapy sometimes fails to establish clinical improvement in patients, which leads to a constant search for new alternatives. Camphor is a transparent solid monoterpene with a strong aroma, which due to its high lipophilicity is insoluble in water. Nanostructured carrier systems have shown promise as a delivery system for lipophilic compounds such as monoterpenes. Therefore, the objective of this work was to evaluate the relaxant effect of nanoemulsified camphor (NEC), as well as the mechanism of action of that monoterpene, in isolated rat trachea. The results obtained demonstrated that NEC promote relaxation of the isolated rat trachea when smooth muscle contraction was induced by both carbachol (CCh) and KCl, presenting a pCE50 of 2.25 ± 0.27 and 3.30 ± 0.07, respectively. In the presence of dexamethasone (DEXA), tetraethylammonium (TEA), glibenclamide (GLIB), 1H-[1,2,4]-oxadiazole-[4,3,-a]-quinoxaline-1-one (ODQ) and ruthenium red (RR) there was a significant difference in at least one of the evaluated pharmacological parameters, such as concentration-response curves shape, Emax or pCE50. As conclusion, NEC may be involved with ß-adrenergic receptors, channels for K+ sensitive to ATP (KATP) or Channels for K+ opened by Ca2+ (KCa), increase in prostanoids and with receptor channel with transient potential (TRPv). In conclusion, ß-adrenergic receptors, prostanoids, nitric oxide (NO), ATP-sensitive K+ channels (KATP), Ca2+-opened K+ channels (KCa), and transient receptor potential cation channel subfamily V (TRPV) are involved in the relaxing effect of NEC. In addition, the mechanism of action of NEC may be involved with the signal transduction pathway Nitric Oxide/soluble guanylyl cyclase/cGMP/cGMP-activated protein kinase. NEC, therefore, demonstrates spasmolytic activity when presenting tracheal relaxation compared to CCh and KCl contracturants.

Evidence for cometabolic transformation of weathered toxaphene under aerobic conditions using camphor as a co-substrate.

AIMS: Toxaphene is a persistent organic pollutant, composed of approximately 1000 highly chlorinated bicyclic terpenes. The purpose of this study was to evaluate if camphor, a structural analogue of toxaphene, could stimulate aerobic biotransformation of weathered toxaphene. METHODS AND RESULTS: Two enrichment cultures that degrade camphor as the sole carbon source were established from contaminated soil and biosolids. These cultures were used to evaluate aerobic transformation of weathered toxaphene. Only the biosolids culture could transform compounds of technical toxaphene (CTTs) in the presence of camphor, while no transformation was observed in the presence of glucose or with toxaphene as a sole carbon source. The transformed toxaphene had lower concentration of CTTs with longer retention times, and higher concentration of compounds with lower retention times. Gas chromatography with electron capture negative ion mass spectrometry (GC/ECNI-MS) showed that aerobic biotransformation mainly occurred with Cl8 - and Cl9 -CTTs compounds. The patterns of Cl6 - and Cl7 -CTTs were also simplified albeit to a much lesser extent. Seven camphor-degrading bacteria were isolated from the enrichment culture but none of them could degrade toxaphene. CONCLUSION: Camphor degrading culture can aerobically transform CCTs via reductive pathway probably by co-metabolism using camphor as a co-substrate. SIGNIFICANCE AND IMPACT OF THE STUDY: Since camphor is naturally produced by different plants, this study suggests that stimulation of aerobic transformation of toxaphene may occur in nature. Moreover plants, which produce camphor or similar compounds, might be used in bioremediation of contaminated soils.

Synthesis, crystal structure and Hirshfeld analysis of a crystalline compound comprising a 1/1 mixture of 1-[(1R,4S)- and 1-[(1S,4R)-1,7,7-trimethyl-2-oxobi-cyclo[2.2.1]heptan-3-yl-idene]hydrazinecarbo-thio-amide.

The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thio-semicarbazide yielded the title compound, C11H17N3OS [common name: (R)- and (S)-camphor thio-semicarbazone], which maintains the chirality of the methyl-ated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c. There are two mol-ecules in general positions in the asymmetric unit, one of them being the (1R)-camphor thio-semicarbazone isomer and the second the (1S)- isomer. In the crystal, the mol-ecular units are linked by C-H⋯S, N-H⋯O and N-H⋯S inter-actions, building a tape-like structure parallel to the (01) plane, generating R 2 1(7) and R 2 2(8) graph-set motifs for the H⋯S inter-actions. The Hirshfeld surface analysis indicates that the major contributions for crystal cohesion are from H⋯H (55.00%), H⋯S (22.00%), H⋯N (8.90%) and H⋯O (8.40%) inter-actions.

In vitro Assessment of Camphor Hydrazone Derivatives as an Agent Against Leishmania amazonensis.

PURPOSE: Due to serious problems with the treatment of leishmaniasis all around the world, here is an urgent need in the search for new drugs that are more effective and safer for the treatment of the various forms of leishmaniasis. Actual therapy is limited and lacks sufficient efficacy due to incomplete elimination of the parasites form of patients. In this sense, we decided to evaluate, by first-time, a series of seventeen camphor hydrazone derivatives (2a-2p) against Leishmania amazonensis. METHODS: The compounds previously synthesized from camphor, an abundant natural compound, were evaluated in vitro against the extra and intracellular forms of Leishmania amazonensis, and murine macrophages. RESULTS: The majority of compounds, fourteen, displayed activity against the intracellular form of the parasite (amastigote) with IC50 values ranging from 21.78 to 58.23 µM, being six compounds active for both forms of the parasite. The compound 2i exhibited higher activity against the amastigote form with the value of IC50 (21.78 µM) close to standard utilized miltefosine (12.74 µM) and selectivity index of at least 6.9. Six compounds displayed activity against promastigote form of Leishmania amazonensis 2g, 2j-2n (41.17-69.59 µM), with the compound 2m being the more active with IC50 = 41.17 µM, 1.9 times less active than the reference drug (IC50 = 21.39 µM). The compound 2m was the more selective to this form, with a selectivity index of at least 3.6. All the compounds were non-cytotoxic to macrophages. CONCLUSIONS: Most compounds showed activity against amastigote form of Leishmania amazonensis, being that they were not cytotoxic to macrophage at the maximum tested concentration, showing the selective property of these compounds. Since amastigotes are the parasite stages that cause the disease in humans, these results highlight the antileishmanial effect of the compounds. This study indicates the possible development of candidates to leishmanicidal drugs from an abundant natural compound of easy access.

Assessment of the performance of the Brazilian Portuguese Nottingham Health Profile in adult growth hormone deficiency and pulmonary hypertension.

Background: The Nottingham Health Profile (NHP) is a generic measure of perceived distress that has been used widely as an outcome measure in clinical practice and trials. The availability of two Brazilian datasets provided the opportunity to assess the psychometric performance of the NHP in different populations - adult growth hormone deficiency (GHD) and pulmonary hypertension (PH). The purpose of the study was to see how valuable the NHP could be in assessing outcomes in diseases where no disease-specific measures are available. Methods: Secondary analyses were performed with NHP data. Patients diagnosed with adult GHD or PH were administered the NHP during clinic visits on two occasions, two weeks apart. A disease-specific measure of quality of life (QoL) was also administered to the relevant sample of patients on each occasion. Results: The psychometric properties of the NHP were good for both disease groups. As expected, both samples reported high scores on energy level, the PH sample scored high on physical functioning and the GHD sample on emotional reactions. For both samples, most of the NHP sections were able to distinguish between groups of respondents with different ratings of perceived general health. While most sections of the NHP were relatively highly correlated with the QoL measures, pain and sleep did not seem to be important predictors of QoL in either of the samples. Conclusions: The use of the NHP in adult GHD and PH populations in Brazil is not recommended as there are high-quality disease-specific measures available for each disease. However, where no disease-specific measures are available, the NHP can provide good descriptive information of the impact of disease on different patient populations.

Camphor, Applied Epidermally to the Back, Causes Snout- and Chest-Grooming in Rats: A Response Mediated by Cutaneous TRP Channels.

Thermoregulatory grooming, a behavioral defense against heat, is known to be driven by skin-temperature signals. Because at least some thermal cutaneous signals that drive heat defenses are likely to be generated by transient receptor potential (TRP) channels, we hypothesized that warmth-sensitive TRPs drive thermoregulatory grooming. Adult male Wistar rats were used. We showed that camphor, a nonselective agonist of several TRP channels, including vanilloid (V) 3, when applied epidermally to the back (500 mg/kg), caused a pronounced self-grooming response, including paw-licking and snout- and chest-"washing". By the percentage of time spent grooming, the response was similar to the thermoregulatory grooming observed during exposure to ambient warmth (32 °C). Ruthenium red (a non-selective antagonist of TRP channels, including TRPV3), when administered intravenously at a dose of 0.1 mg/kg, attenuated the self-grooming behavior induced by either ambient warmth or epidermal camphor. Furthermore, the intravenous administration of AMG8432 (40 mg/kg), a relatively selective TRPV3 antagonist, also attenuated the self-grooming response to epidermal camphor. We conclude that camphor causes the self-grooming behavior by acting on TRP channels in the skin. We propose that cutaneous warmth signals mediated by TRP channels, possibly including TRPV3, drive thermoregulatory self-grooming in rats.

Intratubular decontamination ability and physicochemical properties of calcium hydroxide pastes.

OBJECTIVE: This in vitro study compared the penetration, pH, calcium ion release, solubility, and intradentinal decontamination capacity of calcium hydroxide (CH) pastes with different vehicles and additives. MATERIALS AND METHODS: Infected standard bovine dentine contaminated with Enterococcus faecalis were treated with propolis extract, chlorhexidine, and camphorated paramonochlorophenol (CPMC) loaded in CH paste for the bacterial viability evaluation made by confocal laser scanning microscopy (CLSM) and microbiological culture. Beside this, 50 acrylic teeth were filled with the previously mentioned pastes to evaluate the pH and calcium ion release (pHmeter and atomic absorption spectrophotometer at time intervals of 7, 15, and 30 days) and solubility (micro-computed tomographic imaging before and after 15 days). RESULTS: After treatment, all samples decreased intra-dentinal contamination, specially, the CH paste with CPMC. There was no statistically significant difference between the groups when evaluating the intra-canal paste penetration. In the pH measurements, CH with distilled water showed the smallest pH values. Regardless the solubility percentage of the pastes, the paste of CH + PG presented the highest values. CONCLUSION: The vehicles and additives tested may increase CH antimicrobial effect, but with small differences. In general, all CH pastes tested here were effective in reducing Enterococcus faecalis and were similar in the penetration, pH, calcium ion release, and solubility of calcium hydroxide when compared to distilled water. CLINICAL RELEVANCE: The use of calcium hydroxide pastes as intracanal medication with an aqueous or viscous vehicle, as propylene glycol, can be useful, since all formulations of the tested pastes resulted in great bacterial reduction inside root canals.

Separation of Volatile Metabolites from the Leaf-Derived Essential Oil of Piper mollicomum Kunth (Piperaceae) by High-Speed Countercurrent Chromatography.

The technique of high-speed countercurrent chromatography was applied to the isolation of compounds in essential oil derived from the leaves of Piper mollicomum species. Plant leaves (200.0 g) were submitted to hydrodistillation in a modified Clevenger apparatus. The resulting crude leaf essential oil was analyzed by gas chromatography with flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) to determine the profile of the components. The purified fractions were composed of monoterpenes and sesquiterpenes such as camphor (85.0 mg at 98.5% purity), (E)-nerolidol (100.0 mg at 92.8% purity), and camphene (150.0 mg at 82.0% purity). A minor component of the essential oil, bornyl acetate (16.2 mg at 91.2% purity) was also isolated in the one-step separation protocol in 2 h. The countercurrent chromatography technique proved to be a fast and efficient method for the separation of volatile metabolites that conserved the solvent while delivering various fractions of high purity.

Anti-hyperalgesic effect of Lippia grata leaf essential oil complexed with ß-cyclodextrin in a chronic musculoskeletal pain animal model: Complemented with a molecular docking and antioxidant screening.

BACKGROUND: Due to its unclear pathophysiology, the pharmacological treatment of fibromyalgia is a challenge for researchers. Studies using medicinal plants, such as those from the genus Lippia, complexed with cyclodextrins (CDs) have shown innovative results. OBJECTIVE: The present research intended to evaluate the effect of an inclusion complex containing ß-cyclodextrin (ßCD) inclusion complex with Lippia grata (LG) essential oil in a chronic musculoskeletal pain model, its central activity and its possible interaction with neurotransmitters involved in pain. METHODS: After acid saline-induced chronic muscle pain, male mice were evaluated for primary and secondary hyperalgesia and muscle strength. Moreover, an antagonist assay was performed to assess the possible involvement of the opioidergic, serotonergic and noradrenergic pathways. In addition, Fos protein in the spinal cord was assessed, and a docking study and antioxidant assays were performed. RESULTS: The treatment with LG-ßCD, especially in the dose of 24mg/kg, was able to significantly decrease (p<0.05) the paw withdrawal and muscle threshold. Furthermore, LG-ßCD was shown to affect the opioidergic and serotonergic pathways. There were no significant changes in muscle strength. Fos protein immunofluorescence showed a significant decrease in expression in the dorsal horn of the spinal cord. The main compounds of LG showed through the docking study interaction energies with the alpha-adrenergic and µOpioid receptors. In all antioxidant assays, LG exhibited stronger antioxidant activities than LG-ßCD. CONCLUSION: This study suggested that LG-ßCD could be considered as a valuable source for designing new drugs in the treatment of chronic pain, especially musculoskeletal pain.

Flexible camphor diamond-like carbon coating on polyurethane to prevent Candida albicans biofilm growth.

Camphor was incorporated in diamond-like carbon (DLC) films to prevent the Candida albicans yeasts fouling on polyurethane substrates, which is a material commonly used for catheter manufacturing. The camphor:DLC and DLC film for this investigation was produced by plasma enhanced chemical vapor deposition (PECVD), using an apparatus based on the flash evaporation of organic liquid (hexane) containing diluted camphor for camphor:DLC and hexane/methane, mixture for DLC films. The film was deposited at a low temperature of less than 25°C. We obtained very adherent camphor:DLC and DLC films that accompanied the substrate flexibility without delamination. The adherence of camphor:DLC and DLC films on polyurethane segments were evaluated by scratching test and bending polyurethane segments at 180°. The polyurethane samples, with and without camphor:DLC and DLC films were characterized by Raman spectroscopy, scanning electron microscopy, atomic force microscopy, and optical profilometry. Candida albicans biofilm formation on polyurethane, with and without camphor:DLC and DLC, was assessed. The camphor:DLC and DLC films reduced the biofilm growth by 99.0% and 91.0% of Candida albicans, respectively, compared to bare polyurethane. These results open the doors to studies of functionalized DLC coatings with biofilm inhibition properties used in the production of catheters or other biomedical applications.

Crystal structure of cis-bis-{4-phenyl-1-[(3R)-1,7,7-tri-methyl-2-oxobi-cyclo-[2.2.1]heptan-3-ylidene]thio-semicarbazidato-κ(3) O,N (1),S}cadmium(II) with an unknown solvent mol-ecule.

The reaction between the racemic mixture of the camphor-4-phenyl-thio-semicarbazone derivative and cadmium acetate dihydrate yielded the title compound, [Cd(C17H20N3OS)2]. The Cd(II) ion is six-coordinated in a distorted octa-hedral environment by two deprotonated thio-semicarbazone ligands acting as an O,N,S-donor in a tridentate chelating mode, forming five-membered chelate rings. In the crystal, the mol-ecules are connected via pairs of N-H⋯S and C-H⋯S inter-actions, building centrosymmetric dimers. One of the ligands is disordered in the campher unit over two sets of sites with site-occupancy factors of 0.7 and 0.3. The structure contains additional solvent mol-ecules, which are disordered and for which no reasonable split model was found. Therefore, the data were corrected for disordered solvent using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON. Since the disordered solvents were removed by data processing, and the number of solvent entities was a suggestion only, they were not considered in the chemical formula and subsequent chemical or crystal information.

Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives.

Both sonochemical and classical methodologies have been employed to convert camphor, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, C9H16C=O, into a number of derivatives including hydrazones, C9H16C=N-NHAr 3, imines, C9H16C=N-R 7, and the key intermediate nitroimine, C9H16C=N-NO2 6. Reactions of nitroamine 6 with nucleophiles by classical methods provided the desired compounds in a range of yields. In evaluations of activity against Mycobacterium tuberculosis, compound 7j exhibited the best activity (minimal inhibitory concentration (MIC) = 3.12 µg/mL), comparable to that of the antitubercular drug ethambutol. The other derivatives displayed modest antimycobacterial activities at 25-50 µg/mL. In in vitro tests against cancer cell lines, none of the synthesized camphor compounds exhibited cytotoxic activities.

In vitro inhibition of the bovine viral diarrhoea virus by the essential oil of Ocimum basilicum (basil) and monoterpenes.

The bovine viral diarrhoea virus (BVDV) is suggested as a model for antiviral studies of the hepatitis C virus (HCV). The antiviral activity of the essential oil of Ocimum basilicum and the monoterpenes camphor, thymol and 1,8-cineole against BVDV was investigated. The cytotoxicities of the compounds were measured by the MTT (3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide) test, and the antiviral activities were tested by the plaque reduction assay. The oil or compounds were added to the assay in three different time points: a) pre-treatment of the virus (virucidal assay); b) pre-treatment of the cells; or c) post-treatment of the cells (after virus inoculation). The percentage of plaques inhibition for each compound was determined based on the number of plaques in the viral control. The results were expressed by CC50 (50% cytotoxic concentration), IC50 (inhibitory concentration for 50% of plaques) and SI (selectivity index = CC50/IC50). Camphor (CC50 = 4420.12 µg mL(-1)) and 1,8-cineole (CC50 = 2996.10 µg mL(-1)) showed the lowest cytotoxicities and the best antiviral activities (camphor SI = 13.88 and 1,8-cineol SI = 9.05) in the virucidal assay. The higher activities achieved by the monoterpenes in the virucidal assay suggest that these compounds act directly on the viral particle.

Componentes volátiles de Eriope crassipes, Hyptis conferta, H. dilatata, H. brachiata, H. suaveolens y H. mutabilis (Lamiaceae) / Volatile compounds of analysis of Eriope crassipes, Hyptis conferta, H. dilatata, H. brachiata, H. suaveolens y H. mutabilis (Lamiaceae)

This work presents the analysis by GC-MS of volatile metabolites of six Lamiaceae from Arauca (Colombia). In stems and leaves of Eriope crassipes were determined as the most abundants: citronellic acid (53,8 percent and 66,2 percent), and methyl citronellate (15,7 percent and 14,5 percent). In the inflorescences of Hyptis conferta were identified: t-cadinol (49,4 percent), and caryophyllene oxide (13,0 percent). From leaves and flowers of Hyptis dilatata were found: delta-3-carene (11,0 percent and 0,5 por ciento), camphor (43,8 percent and 12,2 percent), bornyl acetate (3,2 percent and 25,5 percent), E-caryophyllene (12,8 percent and 22,3 percent), and palustrol (6,0 percent and 10,3 percent). In the leaves of Hyptis brachiata were recognized: E-caryophyllene (8,3 percent), alpha-humulene (19,8 percent), and germacrene D (13,0 percent). The principal compounds in leaves and flowers of Hyptis suaveolens were: alpha-phellandrene (9,4 percent and 0,4 percent), limonene (10,5 percent and 2,5 percent), 1,8-cineole (1,3 percent and 15,2 por ciento), fenchone (10,8 por ciento and tr), E-caryophyllene (26,3 por ciento and 8,0 por ciento), and germacrene D (6,7 por ciento and 14,0 por ciento). In the leaves of Hyptis mutabilis were determined: sabinene (6,6 percent) beta-elemene (6,8 percent), germacrene D (14,9 percent), beta-selinene (8,8 percent), alpha-selinene (9,1 percent), and bicyclogermacrene (6,1 percent), as the most abundants.

Este trabajo presenta el análisis por GC-MS de los metabolitos volátiles de seis Lamiaceae recolectadas en Arauca (Colombia). En tallos y hojas de Eriope crassipes se determinaron como mayoritarios: ácido citronélico (53,8 por ciento y 66,2 por ciento), y citronelato de metilo (15,7 por ciento y 14,5 por ciento). En las inflorescencias de Hyptis conferta se identificaron: t-cadinol (49,4 por ciento), y óxido de cariofileno (13,0 por ciento). En hojas y flores de Hyptis dilatata se encontraron: delta-3-careno (11,0 por ciento y 0,5 por ciento), alcanfor (43,8 por ciento y 12,2 por ciento), acetato de bornilo (3,2 por ciento y 25,5 por ciento), E-cariofileno (12,8 por ciento y 22,3 por ciento), y palustrol (6,0 por ciento y 10,3 por ciento). En las hojas de Hyptis brachiata se reconocieron: E-cariofileno (8,3 por ciento), alfa-humuleno (19,8 por ciento), y germacreno D (13,0 por ciento). Los compuestos principales en hojas y flores de Hyptis suaveolens fueron: alfa-felandreno (9,4 por ciento y 0,4 por ciento), limoneno (10,5 por ciento y 2,5 por ciento), 1,8-cineol (1,3 por ciento y 15,2 por ciento), fenchona (10,8 por ciento y tr), E-cariofileno (26,3 por ciento y 8,0 por ciento), y germacreno D (6,7 por ciento y 14,0 por ciento). En las hojas de Hyptis mutabilis se determinaron: sabineno (6,6 por ciento), beta-elemeno (6,8 por ciento), germacreno D (14,9 por ciento), beta-selineno (8,8 por ciento), alfa-selineno (9,1 por ciento), y biciclogermacreno (6,1 por ciento), como los más abundantes.

In vitro inhibition of the bovine viral diarrhoea virus by the essential oil of Ocimum basilicum (basil) and monoterpenes

The bovine viral diarrhoea virus (BVDV) is suggested as a model for antiviral studies of the hepatitis C virus (HCV). The antiviral activity of the essential oil of Ocimum basilicum and the monoterpenes camphor, thymol and 1,8-cineole against BVDV was investigated. The cytotoxicities of the compounds were measured by the MTT (3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide) test, and the antiviral activities were tested by the plaque reduction assay. The oil or compounds were added to the assay in three different time points: a) pre-treatment of the virus (virucidal assay); b) pre-treatment of the cells; or c) post-treatment of the cells (after virus inoculation). The percentage of plaques inhibition for each compound was determined based on the number of plaques in the viral control. The results were expressed by CC50 (50% cytotoxic concentration), IC50 (inhibitory concentration for 50% of plaques) and SI (selectivity index = CC50/IC50). Camphor (CC50 = 4420.12 µgmL-1) and 1,8-cineole (CC50 = 2996.10 µgmL-1) showed the lowest cytotoxicities and the best antiviral activities (camphor SI = 13.88 and 1,8-cineol SI = 9.05) in the virucidal assay. The higher activities achieved by the monoterpenes in the virucidal assay suggest that these compounds act directly on the viral particle.(AU)