Histochemical investigation of Cochlospermum regium (Schrank) Pilg. leaves and chemical composition of its essential oil

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Seasonal Variation of Essential Oil Yield and Composition of Sage (Salvia officinalis L.) Grown in Castilla - La Mancha (Central Spain)

Links between phenology, yield and composition of the essential oil of common sage, Salvia officinalis L., grown in Guadalajara (Central Spain) were determined in the different phases of the biological cycle during one year. Data showed an average yield about 1.0%. The analysis of the oil components was carried out by GC-FID and GC/MS. The main oil constituent was alpha thujone (40.1 - 46.5%). Other identified compounds are beta pinene (2.6 - 4.5%), cineole (3.5 - 8.7%), beta thujone (4.1 - 5.6%), camphor (4.1 - 8.0%), borneol (1.3 - 3.7%), alpha humulene (3.8 - 7.3%), viridiflorol (3.4-12.6%) and manool (0.1-4.5%). The highest yield of oil was obtained in the period of full flowering and the highest concentration of alpha thujone in the period of initial flowering.

Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase

Peppermint (Mentha × piperita L.) was independently transformed with a homologous sense version of the 1-deoxy-d-xylulose-5-phosphate reductoisomerase cDNA and with a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter. Two groups of transgenic plants were regenerated in the reductoisomerase experiments, one of which remained normal in appearance and development; another was deficient in chlorophyll production and grew slowly. Transgenic plants of normal appearance and growth habit expressed the reductoisomerase transgene strongly and constitutively, as determined by RNA blot analysis and direct enzyme assay, and these plants accumulated substantially more essential oil (about 50% yield increase) without change in monoterpene composition compared with wild-type. Chlorophyll-deficient plants did not afford detectable reductoisomerase mRNA or enzyme activity and yielded less essential oil than did wild-type plants, indicating cosuppression of the reductoisomerase gene. Plants transformed with the antisense version of the menthofuran synthase cDNA were normal in appearance but produced less than half of this undesirable monoterpene oil component than did wild-type mint grown under unstressed or stressed conditions. These experiments demonstrate that essential oil quantity and quality can be regulated by metabolic engineering. Thus, alteration of the committed step of the mevalonate-independent pathway for supply of terpenoid precursors improves flux through the pathway that leads to increased monoterpene production, and antisense manipulation of a selected downstream monoterpene biosynthetic step leads to improved oil composition.

Composition and screening of antifungal activity against Cladosporium sphaerospermum and Cladosporium cladosporioides of essential oils of leaves and fruits of Piper species

This study investigated the composition and antifungal activity against Cladosporium sphaerospermum and Cladosporium cladosporioides of essential oils of leaves of Piper cernuum, Piper diospyrifolium, Piper crassinervium, Piper solmsianum and Piper umbelata and fruits of P. cernuum and P. diospyrifolium. The essentials oils were analyzed by GC-MS and submitted of the antifungal activity tests. The essential oils of fruits from P. cernuum and leaves of P. crassinervium and P. solmsianum showed potential antifungal activity against C. sphaerospermum and C. cladosporioides. In addition, this is the first report of the composition of essential oils of fruits of P. cernuum and P. diospyrifolium.

Antiulcerogenic Activity of the Essential Oil of Baccharis dracunculifolia on Different Experimental Models in Rats

Baccharis dracunculifolia DC (Asteraceae), a native plant from Brazil, commonly known as `Alecrim-do-campo` is widely used in folk medicine to treat inflammation, hepatic disorders and stomach ulcers, and it is the most important botanical source of Southeastern Brazilian propolis, known as green propolis. Its essential oil is composed of non-oxygenated and oxygenated terpenes. In this work, the effects of the essential oil obtained from the aerial parts of R dracunculifolia on gastric ulcers were evaluated. The antiulcer assays were undertaken using the following protocols in rats: nonsteroidal antiinflammatory drug (NSAID)-induced ulcer, ethanol-induced ulcer, stress-induced ulcer, and determination of gastric secretion using ligated pylorus. The treatment in the doses of 50, 250 and 500 mg/kg of R dracunculifolia essential oil significantly diminished the lesion index, the total lesion area and the percentage of lesions in comparison with both positive and negative control groups. With regard to the model of gastric secretion a reduction of gastric juice volume and total acidity was observed, as well as an increase in the gastric pH. No sign of toxicity was observed in the acute toxicity study. Considering the results, it is suggested that the essential oil of B. dracunculifolia could probably be a good therapeutic agent for the development of new phytotherapeutic medicine for the treatment of gastric ulcer. Copyright (C) 2009 John Wiley & Sons, Ltd.

Biomass production and essential oil yield from leaves, fine stems and resprouts using pruning the crown of Aniba canelilla (H.B.K.) (Lauraceae) in the Central Amazon

Aniba canelilla (H.B.K.) Mez. is a tree species from Amazon that produces essential oil. The oil extraction from its leaves and stems can be an alternative way to avoid the tree cutting for production of essential oil. The aim of this study was to analyse factors that may influence the essential oil production and the biomass of resprouts after pruning the leaves and stems of A. canelilla trees. The tree crowns were pruned in the wet season and after nine months the leaves and stems of the remaining crown and the resprouts were collected, in the dry season. The results showed that the essential oil yield and chemical composition differed among the stems, leaves and resprouts. The stems' essential oil production differed between the seasons and had a higher production in the resprouting stems than the old stems of the remaining crown. The production of essential oil and leaf biomass of resprouts were differently related to the canopy openness, indicating that light increases the production of the essential oil and decreases the biomass of resprouting leaves. This study revealed that plant organs differ in their essential oil production and that the canopy openness must be taken into account when pruning the A. canelilla tree crown in order to achieve higher oil productivity.

Larvicidal activity of the essential oil from Lippia sidoides cham. against Aedes aegypti linn

The aim of this work was to study the larvicidal activity of Lippia sidoides essential oil against Aedes aegypti larvae. The essential oil and its hydrolate (saturated solution of essential oil in water) were obtained by vapor extraction and their chemical composition determined by GL-chromatography coupled to mass spectroscopy. Bioassays were run with the essential oil, pure and diluted hydrolate and with their main constituents thymol and carvacrol. The results obtained showed that L. sidoides essential oil and its hydrolate have larvicidal action against the mosquito A. aegypti, causing an almost instantaneous mortality. Thymol, an alkylated phenol derivative and one of the major components of L. sidoides essential oil, was identified as the active principle responsible for the larvicidal action, causing 100% larval mortality at the lowest tested concentration of 0.017% (w/v). These results suggest that the essential oil of L. sidoides is promising as larvicide against A. aegypti and could be useful in the search of newer, more selective, and biodegradable larvicidal natural compounds to be used in official combat programs and at home.

Composition and antifungal activity of essential oils from Piper aduncum, Piper arboreum and Piper tuberculatum

The composition of essential oils from leaves, stems and fruits of Piper aduncum, P. arboreum and P. tuberculatum was examined by means of GC-MS and antifungal assay. There was a predominance of monoterpenes in P. aduncum and P. tuberculatum and of sesquiterpenes in P. arboreum. P. aduncum showed the richest essential oil composition, including linalool. The essential oils from fruits of P. aduncum and P. tuberculatum showed the highest antifungal activity with the MIC of 10 µg as determined against Cladosporium cladosporioides and C. sphaerospermum, respectively. This is the first report of the composition of essential oils from P. tuberculatum.

Towards new botanical pesticides: the toxic effect of Eremanthus goyazensis (Asteraceae) leaves essential oil against Brevipalpus phoenicis (Acari: Tenuipalpidae)

This work reports the chemical characterization of Eremanthusgoyzensis essential oil and its toxic effect over Brevipalpus phoenicis. The essential oil displayed a major composition of sesquiterpenes (61.87%) including trans-caryophillene (26.81%) and germacrene-D (13.31%). The fumigation test indicated a promising bioactivity over adult B. phoenicis individuals at 24 h (2.03 µL/L of air) and 48 h (1.08 µL/L of air) of exposition. A brief discussion of essential oils composition and their singular role on the toxic effect over B. phoenicis is provided here. Our results may contribute to a new and profitable use of a species of Brazilian flora on agribusiness.

CONSTITUENTS OF ESSENTIAL OIL AND HYDROLATE OF LEAVES OF Campomanesia viatoris LANDRUM

The chemical composition of the essential oil and hydrolates of Campomanesia viatoris Landrum were investigated by gas chromatography/mass spectrometry (GC/MS) and a GC flame ionization detector (GC-FID). The major constituents were tasmanone (70.50, essential oil; 74.73%, hydrolate), flavesone (12.77, essential oil; 12.24%, hydrolate) and agglomerone (6.79, essential oil; 10.84%, hydrolate). Tasmonone was isolated and its structure was characterized by spectrometric analysis, specifically 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS). These findings supports the quimiotaxonomic relationship with Campomanesia and Eucalyptus genera.

Antimicrobial activity of the essential oil from Lippia sidoides, carvacrol and thymol against oral pathogens

Dental caries and periodontal disease are associated with oral pathogens. Several plant derivatives have been evaluated with respect to their antimicrobial effects against such pathogenic microorganisms. Lippia sidoides Cham (Verbenaceae), popularly known as "Alecrim-pimenta" is a typical shrub commonly found in the Northeast of Brazil. Many plant species belonging to the genus Lippia yield very fragrant essential oils of potential economic value which are used by the industry for the commercial production of perfumes, creams, lotions, and deodorants. Since the leaves of L. sidoides are also extensively used in popular medicine for the treatment of skin wounds and cuts, the objective of the present study was to evaluate the composition and antimicrobial activity of L. sidoides essential oil. The essential oil was obtained by hydro-distillation and analyzed by GC-MS. Twelve compounds were characterized, having as major constituents thymol (56.7%) and carvacrol (16.7%). The antimicrobial activity of the oil and the major components was tested against cariogenic bacterial species of the genus Streptococcus as well as Candida albicans using the broth dilution and disk diffusion assays. The essential oil and its major components thymol and carvacrol exhibited potent antimicrobial activity against the organisms tested with minimum inhibitory concentrations ranging from 0.625 to 10.0 mg/mL. The most sensitive microorganisms were C. albicans and Streptococcus mutans. The essential oil of L. sidoides and its major components exert promising antimicrobial effects against oral pathogens and suggest its likely usefulness to combat oral microbial growth.

Essential oil of Lippia alba and its main constituent citral block the excitability of rat sciatic nerves

Lippia alba is empirically used for infusions, teas, macerates, and hydroalcoholic extracts because of its antispasmodic, analgesic, sedative, and anxiolytic effects. Citral is a mixture of trans-geranial and cis-neral and is the main constituent of L. alba essential oil and possesses analgesic, anxiolytic, anticonvulsant, and sedative effects. The present study evaluated the effects of the essential oil of L. alba (EOLa) and citral on compound action potentials (CAPs) in Wistar rat sciatic nerves. Both drugs inhibited CAP in a concentration-dependent manner. The calculated half-maximal inhibitory concentrations (IC50) of peak-to-peak amplitude were 53.2 µg/mL and 35.00 µg/mL (or 230 µM) for EOLa and citral, respectively. Peak-to-peak amplitude of the CAP was significantly reduced by 30 µg/mL EOLa and 10 µg/mL citral. EOLa and citral (at 60 and 30 µg/mL, values close to their respective IC50 for CAP blockade) significantly increased chronaxy and rheobase. The conduction velocity of the first and second CAP components was statistically reduced to ∼86% of control with 10 µg/mL EOLa and ∼90% of control with 3 µg/mL citral. This study showed that EOLa inhibited nerve excitability and this effect can be explained by the presence of citral in its composition. Both EOLa and citral showed inhibitory actions at lower concentrations compared with other essential oils and constituents with local anesthetic activity. In conclusion, these data demonstrate that EOLa and citral are promising agents in the development of new drugs with local anesthetic activity.

HIGH PRESSURE PHASE EQUILIBRIUM: PREDICTION OF ESSENTIAL OIL SOLUBILITY

This work describes a method to predict the solubility of essential oils in supercritical carbon dioxide. The method is based on the formulation proposed in 1979 by Asselineau, Bogdanic and Vidal. The Peng-Robinson and Soave-Redlich-Kwong cubic equations of state were used with the van der Waals mixing rules with two interaction parameters. Method validation was accomplished calculating orange essential oil solubility in pressurized carbon dioxide. The solubility of orange essential oil in carbon dioxide calculated at 308.15 K for pressures of 50 to 70 bar varied from 1.7± 0.1 to 3.6± 0.1 mg/g. For same the range of conditions, experimental solubility varied from 1.7± 0.1 to 3.6± 0.1 mg/g. Predicted values were not very sensitive to initial oil composition.

Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)

The essential oils isolated by hydrodistillation from trunk bark and leaves of Talauma ovata A. St. Hil. (Magnoliaceae), collected in four seasons, were analyzed by capillary GC and GC/MS. Altogether 52 components were identified, The oils were characterized by predominance of cyclic sesquiterpenes. The main components were linalool, trans-beta-guaiene, germaerene D, germacrene B, spathulenol, caryophyllene oxide, viridiflorol and alpha-endesmol. The content of individual components was variable during the year. All oils were screened against several strains of bacteria and yeasts, using the agar well-diffusion technique. The antimicrobial activity of oils showed strong dependence with the season. Significant activity was found for oils obtained in the spring and summer.

Phase behavior of the orange essential oil/sodium bis(2-ethylhexyl)sulfosuccinate/water system

The ternary phase diagram for the orange essential oil (OEO)/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water system was constructed at 25 degrees C. It indicates a large single phase region, comprising an isotropic water-in-oil (W/O) microemulsion (ME) phase (L(2)), a liquid crystal (LC) (lamellar or hexagonal) and a large unstable emulsion phase that separates in two phases of normal and reverse micelles (L(1) and L(2)). In this communication the properties of the ME are investigated by viscosity, electric conductivity and small angle X-ray scattering (SAXS) indicating that the isotropic ME phase exhibits different behaviors depending on composition. At low water content low viscous ""dry"" surfactant structures are formed, whereas at higher water content higher viscous water droplets are formed. The experimental data allow the determination of the transition from ""dry"" to the water droplet structures within the L(2) phase. SAXS analyses have also been performed for selected LC samples. (C) 2009 Elsevier B.V. All rights reserved.