In this paper, we have applied state-of-the-art technologies and new investigations were developed focusing on obtaining simple and inexpensive molecules for treating cardiovascular diseases, as they are considered the leading cause of death in the world. For the first time, the inclusion complex of sulcatone (SU) and β-cyclodextrin (β-CD) was achieved (using a spray drier) and characterized making use of spectroscopic, thermal and computational methods. In addition, the system was evaluated regarding its vasorelaxant properties. Evidence of the inclusion complex formation was provided using different techniques, such as X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), Fourier transform infrared (FTIR), and 1H nuclear magnetic resonance (NMR) spectroscopies and then deduced by pharmacological experiments, which showed significant changes in relation to the initial material.

Abstract The essential oils obtained by hydrodistillation from fresh leaves of Vitex agnus-castus and Ocimum campechianum, and from fresh inflorescences of Ocimum carnosum were analysed by GC-FID and GC-MS. The major components of V. agnus-castus essential oil were identified as 1,8-cineole (47.9%), terpinyl α-acetate (11.6%), sabinene (11.2%) and caryophyllene oxide (9.7%), while in the O. campechianum essential oil were eugenol (72.1%), β-elemene (6.8%), (E)-caryophyllene (6.4%) and bicyclogermacrene (5.2%). Linalool (79.0%), α-epi-cadinol (5.4%), terpinen-4-ol (3.2%) and 1,8-cineole (2.8%) were the major constituents in the O. carnosum essential oil. The essential oils were subsequently evaluated for their larvicidal and cytotoxic activities. Larval bioassay against Aedes aegypti of V. agnus-castus, O. campechianum and O. carnosum essential oils showed LC50 values of 97.55 ± 0.35, 81.45 ± 0.35 and 109.49 ± 0.35 μg/mL, respectively. The in vitro cytotoxic activities of the essential oils has been evaluated on breast adenocarcinoma (MCF-7), lung carcinoma (NCI-H292), pro-myelocytic leukemia (HL-60), and cervical adenocarcinoma (HEP-2) human cell lines, and pro-myelocytic leukemia cells lines (HL-60) were found to be the most sensitive to all the essential oils tested than the others. This is the first report on larvicidal and cytotoxic activities of these essential oils.

RESUMO Objetivou-se avaliar o efeito da qualidade de luz e da disponibilidade de nitrogênio na produção de fitomassa, rendimento e composição do óleo essencial de erva cidreira (Lippia alba). Estudaram-se cinco doses de N (0; 40; 80; 120 e 160 kg ha-1), tendo como fonte a ureia e três condições de qualidade de luz, obtidas com o uso de malhas fotoconversoras coloridas (azul e vermelha) com 50% de irradiância e sob pleno sol. O arranjo experimental foi em esquema fatorial 5x3, em delineamento em parcelas subdivididas, com sete repetições. Após 60 dias de cultivo sob as malhas, observou-se maior fitomassa seca das folhas (4,83 g per planta) nas plantas submetidas ao cultivo sob malha azul na dose de 102 kg ha-1 de N. As plantas cultivadas sob pleno sol apresentaram maior quantidade de neral e geranial, componentes majoritários do óleo essencial da erva cidreira, que atribuem valor comercial à espécie. O uso de malhas não exerce influência na qualidade do óleo essencial, mas aumenta a quantidade de compostos encontrados no mesmo. O nitrogênio não afeta a qualidade do óleo essencial, mas proporciona maior (0,27g per planta) rendimento de óleo, sob dose 65 kg ha-1 de N.

ABSTRACT The aim of this study was to evaluate the effect of light quality and nitrogen availability on the biomass production, yield and composition of essential oil of lemon balm (Lippia alba). Five doses of N (0; 40; 80; 120 and 160 kg ha-1) were studied, using urea and three light quality conditions obtained with the use of colored shading nets (blue and red), 50% irradiance and under full sun. The experiment was arranged in a 5x3 factorial scheme, in split plots, with seven replicates. After 60 days of cultivation under the shading nets, a higher dry leaf biomass (4.83 g per plant) was observed in the plants under blue net cultivation at a dose of 102 kg ha-1 of N. The plants grown under full sun presented greater amount of neral and geranial, major components of the essential oil of the lemon balm, which give commercial value to the species. The use of colored shading nets does not influence the composition of the essential oil of lemon balm, but increases the concentration of the compounds found in it. Nitrogen does not affect the quality of the essential oil of lemon balm, but it provides higher oil yield (0.27 g per plant) at the dose of 65 kg ha-1 of N.

This manuscript describes the biooxidation of rac-camphor using whole cells of marine-derived fungus Botryosphaeria sp. CBMAI 1197. The main biotransformation products of this monoterpene were achieved via a hydroxylation reaction and occurred with 5 days of rac-camphor incubation. Products were identified by means of gas chromatography mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) data. The major hydroxylated products were 6-endo-hydroxycamphor, 6-exo-hydroxycamphor, 5-exo-hydroxycamphor, 5-endo-hydroxycamphor, 3-exo-hydroxycamphor and 8-hydroxycamphor. The 6-exo-hydroxycamphor was obtained through a retro-aldol reaction when 6-endo-hydroxycamphor was maintained in presence of CDCl3; this isomerization was confirmed by 1H NMR and GC-MS data.

Plantas de orégano foram cultivadas em diferentes ambientes de luz, obtidos com o uso de malhas coloridas, com o objetivo de avaliar o teor e a composição de óleo essencial e características anatômicas nas folhas destas plantas. Para isto, foi realizado o cultivo em vasos com capacidade para 3 dm³ submetidas aos seguintes tratamentos: cultivo sob pleno sol (testemunha absoluta), malha azul, malha vermelha e malha cinza. Foi adotado o DIC com seis repetições. Foram avaliadas características anatômicas de pecíolo e folhas, teor e composição do óleo essencial. Observa-se que a modificação no ambiente de luz possibilita modificações no aumento do teor de óleo essencial, assim como influencia na composição química deste metabólito secundário.

Oregano's plants were grown in different light environments, obtained with the use of colorful fabrics, in order to evaluate the content and composition of essential oil and anatomical characteristics in leaves of these plants. For this, the plants were grown in pots with capacity for 3 dm³ submitted to the following treatments: cultivation under full sun (absolute witness), shading with blue, red and gray colors. It was adopted the DIC with six repetitions. Anatomical features were evaluated of petiole and leaf, content and composition of essential oil. It is observed that modification in the light environment allows increasing the content of essential oil and it influences in the chemical composition of this secondary metabolite.

Many species from Croton genus have been used in traditional medicine and its pharmacological activities demonstrated. Croton argyrophyllus Kunth, Euphorbiaceae, is a shrub that grows in the flora of Northeastern Brazilian. The essential oil of C. argyrophyllus leaves was tested in rodents (10-100 mg/kg, p.o.) in classical models of inflammation (carrageenan-induced paw oedema and peritonitis) and its chemical constituents were determined by GC-MS/FID analysis. Nitric oxide radical-scavenging activity and lipidic peroxidation were determined to evaluate the antioxidant capacity of the essential oil (0.001-100 µg/mL). Forty-two components were identified, among them, bicyclogermacrene (14.60%) and spathulenol (8.27%) were the most abundant ones. C. argyrophyllus essential oil reduced significantly the oedema (30 and 100 mg/kg, p<0.05) and, besides, reduced the carrageenan increase in mieloperoxidase activity (10, 30, and 100 mg/kg, p<0.001). The carrageenan-induced peritonitis was significantly reduced (p<0.001) by the essential oil (10, 30, and 100 mg/kg). The essential oil (100 mg/kg) reduces the total peritoneal lavage NOx- concentration (p<0.01). Nitric oxide radical generated from sodium nitroprusside was found to be inhibited by the essential oil (p<0.001). C. argyrophyllus essential oil was able to prevent Fe2+- or Fe2+ plus H2O2-induced lipid peroxidation (p<0.001). This study suggests that the anti-inflammatory effect of the essential oil of C. argyrophyllus observed in the present study can be related, at least in part, its antioxidant capacity.

Foi avaliado o efeito da intensidade e da qualidade espectral da luz transmitida pelas malhas fotoconversoras em relação ao crescimento, teor e composição química do óleo essencial das plantas de Mentha arvensis. Foram realizadas duas avaliações, aos 85 dias após o plantio e aos 80 dias após a rebrota das plantas. O delineamento experimental utilizado foi inteiramente casualizado, dispostos em quatro tratamentos e cinco repetições, sendo cada parcela composta de três vasos (uma planta por vaso) em cada corte. Os tratamentos foram caracterizados por plantas de hortelã-japonesa cultivadas a pleno sol e sob malhas com 50% de sombreamento na cor preta, vermelha ou azul. Foram avaliados a biomassa seca de folhas, caules, parte aérea, raízes e estolões e total, razão raiz/parte aérea, área foliar total, razão de área foliar, área foliar específica, número de brotações, teor, rendimento e composição química do óleo essencial. O crescimento da planta, teor e rendimento de óleo essencial são mais afetados pela intensidade do que pela variação espectral da luz imposta pelas malhas. O sombreamento de 50% provocado pelas malhas é excessivo, independente da cor. A composição química do óleo essencial não foi afetada consideravelmente pelas malhas.

This research was carried out to evaluate the intensive effect and spectral light quality transmitted by the shading nets related to Mentha arvensis plants growth, content and chemical composition. Two evaluations were performed, one 85 days after planting and the other one 80 days after plants reshoot. The experimental design was randomized complete blocks with 4 treatments and 5 replications, each plot with 3 pots (one plant per pot) in each cutting. The treatments consisted of mint cultured under full sun light and under shading net with 50% of black, red or blue screen. We evaluated the yield of dry leaves biomass, stalks, shoots, roots and stolons and total biomass, root/shoot ratio, total foliar area, foliar area ratio, foliar weight ratio, specific foliar area, shoots number after reshoots, content, yield and chemical composition of essential oil. The plants growth, essential oil content and yield were more affected by light intensity than spectral light quality transmitted by the shading nets. The shading of 50% by nets is excessive, independently on color. The chemical composition of essential oil was not affected considerably by color shading nets.

Insecticidal activity of essential oils of Pelargonium graveolens, Lippia alba and compounds geraniol, linalool, 1,8-cineole, limonene, carvone, citral and Azamax® were evaluated against Spodoptera frugiperda. Topical application assay showed essential oil of P. graveolens has acute toxicity against Spodoptera frugiperda larvae (third instar) with LD50 1.13 µg/mg per insect and LD90 2.56 µg/mg per insect. Three essential oils of L. alba also exhibited insecticidal activity with LD50 ranging from 1.20 to 1.56 µg/mg per insect and LD90 from 2.60 to 3.75 µg/mg per insect. Geraniol, linalool, carvone and citral caused significant mortality of 30, 90, 84 and 64% respectively, compared to negative control. The bioinsecticide, Azamax®, caused lower mortality than the compounds of the essential oils.

Chrysopogon zizanioides (L.) Roberty, Poaceae, is a plant widely used in northeast Brazil in folk medicine for the treatment of various pathological conditions, including inflammatory pain. The present study evaluated the antinociceptive and anti-inflammatory effects of C. zizanioides essential oil (EO) in rodents. EO was further characterized by GC/MS. The major components of EO were identified as khusimol (19.57%), E-isovalencenol (13.24%), α-vetivone (5.25%), β-vetivone (4.87%) and hydroxy-valencene (4.64%). Following intraperitoneal injection (i.p.), EO at 50 and 100 mg/kg significantly reduced the number of writhes (51.9 and 64.9%, respectively) and the number of paw licks during phase 2 (56.7 and 86.2%, respectively) of a formalin model when compared to control group animals. However, EO-treated mice were ineffective at all doses in hot-plate and rota-rod tests. The EO inhibited the carrageenan-induced leukocyte migration to the peritoneal cavity in a dose-dependent manner (34.7, 35.4, and 62.5% at doses of 25, 50 and 100 mg/kg, respectively). In the paw edema test, the EO (100 mg/kg) inhibited all three phases of the edema equally well, suggesting that the EO has a non-selective inhibitory effect on the release or actions of these mediators. Our results suggest possible antinociceptive and anti-inflammatory effects of the EO.

The present study investigated the antinociceptive effects of Ocimum basilicum L. (Lamiaceae) leaf essential oil (LEO) and (-)-linalool (LIN) in formalin (2%)-, glutamate (25 µM)- and capsaicin (2.5 µg)- induced orofacial nociception models in mice. The involvement of these substances was further evaluated on the neuronal excitability of the hippocampal dentate gyrus. Male mice (n=8/group) were pretreated separately with LEO and by LIN (50, 100, and 200 mg/kg, i.p.), morphine (5 mg/kg, i.p.) and vehicle (saline + Tween 80 0.2%), before injection of nociceptive agent into the right upper lip (perinasal area). The LEO and LIN reduced the nociceptive face-rubbing behaviour in both phases on formalin test. LEO and LIN, at high doses, produced significantly antinociceptive effect in the capsaicin and glutamate tests. In hippocampal slices, LEO inhibited the population spike generated by stimulation of the hylus (antidromic stimulation), with an IC50 of 0.1±0.05 mg/mL. This response was reversibly blocked by lidocaine (0.5 mg/mL), a known voltage-dependent sodium channel antagonist and by LIN (0.5 mg/mL). Our results suggest that LEO and LIN modulate neurogenic and inflammatory pain in the tests of orofacial nociception induced by formalin, capsaicin and glutamate. Part of these effects may be associated with decreased peripheral and central neuronal excitability.

The composition of six samples of essential oil (EO) extracted from leaves, flowers and seeds of several plants of Hyptis fruticosa Salzm. ex Benth., Lamiaceae, was investigated by GC/MS and GC/FID. 1,8-Cineole, spathulenol, α-pinene, β-pinene were the major constituents. Ten constituents that have not been previously described in the composition of the oil of H. fruticosa were identified. Hydrocarbons sesquiterpenes represented the main group, followed by hydrocarbons monoterpenes. The results were submitted to Cluster Analysis which allowed three groups of EO to be distinguished with respect to the content of α-pinene/β-pinene, 1,8-cineole and spathulenol. Growth stages of the plants and geographical parameters seem to be important factors determining the variability of the oil. Sesquiterpenes were mainly produced in the seeds.

C. citratus é utilizada na medicina popular para tratar hipertensão. Este trabalho investigou a composição química e os efeitos cardiovasculares do óleo essencial do C. citratus (OECC). Foram identificados oito constituintes no OECC, sendo geranial o majoritário (43,08%). Em ratos, o OECC (1, 5, 10 e 20 mg/kg, i.v.) induziu hipotensão e bradicardia que foram atenuadas pela atropina e tiopental sódico, mas não por L-NAME ou indometacina. Em anéis de artéria mesentérica de ratos pré-contraídos com fenilefrina, o OECC (1 a 3000 µg/mL) induziu relaxamento que não foi afetado após remoção do endotélio, após TEA ou em anéis pré-contraídos com KCl (80 mM). Além disso, o OECC (1000 µg/mL) não induziu efeito adicional sobre o relaxamento máximo da nifedipina (10 µM). Em conclusão, o OECC induz hipotensão possivelmente devido à redução da resistência vascular que pode ser causada por inibição do influxo de Ca2+, e bradicardia provavelmente devido à ativação de receptores muscarínicos cardíacos.

Cymbopogon citratus DC. Stapf, Poaceae, is used in the folk medicine for hypertension treatment. This work investigated the chemical composition and cardiovascular effects in rats of C. citratus essential oil (EOCC). A phytochemical screening demonstrated the presence of eight constituents, being geranial the major compound (43.08%). In rats, EOCC (1, 5, 10, and 20 mg/kg, i.v.) induced transient hypotension and bradycardia that were attenuated by atropine and sodium thiopental, but not by L-NAME or indomethacin. In rings of rat superior mesenteric artery pre-contracted with phenylephrine, EOCC (1 to 3000 µg/mL) induced relaxation that was not affected after removal of the endothelium, after TEA or in rings pre-contracted with KCl (80 mM). Furthermore, EOCC (1000 µg/mL) was not able to induce additional effect on maximal relaxation of nifedipine (10 µM). In conclusions, EOCC induces hypotension, possibly by reduction in vascular resistance caused by inhibition of the Ca2+ influx, and bradycardia probably due to an activation of cardiac muscarinic receptors.

Genótipos de manjericão (Ocimum basilicum L.) apresentam diferentes teores, rendimentos e composições químicas de óleos essenciais. Fatores influenciam na produção do óleo essencial de manjericão, como a cultivar plantada e o método de cultivo. O estudo dos parâmetros genéticos tem sido ferramenta útil na identificação de genótipos superiores. Este trabalho teve o objetivo de estimar alguns parâmetros genéticos associados ao comportamento produtivo de seis populações de manjericão nos anos agrícola 2004/05 e 2005/06. As características massa seca de folha + inflorescência e rendimento de óleo essencial apresentaram grande variabilidade por forte influência dos anos estudados. Já o teor de linalol manteve sua produtividade estável ao longo dos dois anos. Teor e rendimento de óleo essencial e teor de linalol no óleo essencial apresentaram herdabilidades altas na análise conjunta, indicando controle genético e grande possibilidade de serem transmitidas para as gerações futuras. Na análise conjunta as populações PI 197442-S3-bulk 3, PI 197442-S3-bulk 5 e PI 197442-S3-bulk 8 apresentaram os maiores teores e rendimentos de óleo essencial. Quanto ao constituinte químico majoritário do óleo essencial, o linalol, todas as populações apresentaram teores semelhantes, diferindo apenas na presença de alguns constituintes químicos minoritários.

Basil (Ocimum basilicum L.) genotypes present different contents, yields and chemical constituents in its essential oils. Factors influence the essential oil production of basil, such as cultivar and cultivation method. The study of genetic parameters is a useful tool to identify superior genotypes. In this work we estimated some genetic parameters associated to the production behavior of six basil populations cultivated in 2004/05 and 2005/06. The variables dry weight of leaves + inflorescences and essential oil yield presented high variability because of strong influence of the studied years. Linalool content presented constant values during the two years. Essential oil content and yield and linalool content in the essential oil presented high herdability in the combined analyses, indicating genetic control and great possibilities to transmit them to the following generations. The combined analyses showed highest essential oil content and yield for the populations PI 197442-S3-bulk 3, PI 197442-S3-bulk 5 and PI 197442-S3-bulk 8. For the major chemical constituent of the essential oil, linalool, all the populations presented similar content. Only the minor chemical constituents were different.

Reduction of camphor to a mixture of borneol and isoborneol was performed using NaBH4 as the reducing agent under suitable conditions. Although more effective reduction was accomplished using toxic methanol, an alternative non-toxic ethanolic system is described. This experiment is important to introduce undergraduate students in reductive procedures, and can be used to show details on stereoselective procedures on carbonyl moieties (facial diastereoselectivity, Bürgi-Dunitz trajectory, diastereomeric excess).

Essential oil was extracted from leaves of Hyptis pectinata using hydrodistillation, and its composition determined using GC-FID and GC-MS. Chemical analysis showed that there was a predominance of sesquiterpenes, of which β-caryophyllene (18.34%), caryophyllene oxide (18.00%) and calamusenone (24.68%) were measured for the first time in the genus Hyptis. Twenty-one compounds were identified, and calamusenone was isolated using preparative thin layer chromatography with a silica gel plate (60 PF254). The minimal inhibitory concentration (MIC) and minimal microbicidal concentration (MMC) were determined for various pathogenic microorganisms. H. pectinata oil was most effective against Gram (+) bacteria and yeasts.