An expeditious and consistent procedure for tetrahydrofuran (THF) drying and deoxygenation by the still apparatus

Despite the availability of alternative methods for drying tetrahydrofuran (THF), the use of the still apparatus, wherein a THF solution containing Na-bezophenone ketyl is heated to reflux, remains widespread. We herein propose a set of procedures to solve the problems usually faced in applying this drying technique. Moreover, a discussion is made on the chemical knowledge underlying such procedures. Safety and economy issues concerned with the operation of the THF still apparatus are also discussed.

Chemical composition and antibacterial activities from the essential oils of myrtaceae species planted in Brazil

The essential oils of seven Myrtaceae species were investigated for its chemical composition and antibacterial activity. The volatile oils were characterized by a high content of monoterpenoids of which 1,8-cineole (88.0, 65.0 and 77.0% for Melaleuca hypericifolia, Callistemon viminalis and Callistemon citrinus respectively), terpinen-4-ol (47.0 and 49.8% for Melaleuca thymifolia and Callistemon polandii respectively) and α-pinene (54.5% for Kunzea ericoides) were the major components. The oil from M. linariifolia was characterized by a high concentration of methyleugenol (87.2%). The oil from Melaleuca thymifolia was the most active, exhibiting high antimicrobial activity against all tested bacteria.

Chemical composition of volatile oils from leaves of Nectandra megapotamica Spreng. (Lauraceae)

The volatile oils from Nectandra megapotamica Spreng. leaves, collected in February and August of 2007 and at 7:00 and 12:00 h (samples A - D), were extracted by hydrodistillation and the chemical composition was analyzed by GC-FID and GC/MS. A total of nineteen compounds were identified with predominance of oxygenated sesquiterpenes, among them, α-bisabolol, was the main constituent (62.3-69.4 %). After chromatographic separation procedures, this compound was purified from crude oil and its structure was confirmed by analysis of NMR data. This paper describes for the first time the composition of the leaves volatile oil from N. megapotamica.

Interespecific variation in the composition of volatile oils from the leaves of Swietenia macrophylla King (Meliaceae)

The volatile oils from leaves of five Brazilian specimens of Swietenia macrophylla King (Meliaceae) collected in three different Amazon Rainforest Conservation Areas in the States of Mato Grosso, Pará, and Rondônia were extracted and analyzed by GC and GC/MS. The oils showed to be composed by terpenoids, majority hydrocarbon sesquiterpenes, being germacrene D (20.5-46.8%) and bicyclogermacrene (8.3-11.1%) the main components. Besides these derivatives, only α-cubebene, β-caryophyllene, β-gurjunene and γ-cadinene were detected in all of the analyzed samples. This analysis indicated a great diversity of constituents in the oils obtained from specimens collected in these regions, which could be associated to the different susceptibility in the attack of H. grandella in S. macrophylla cultures.

Quantitative structure-retention relationships analysis of retention index of essential oils

Genetic algorithm and multiple linear regression (GA-MLR), partial least square (GA-PLS), kernel PLS (GA-KPLS) and Levenberg-Marquardt artificial neural network (L-M ANN) techniques were used to investigate the correlation between retention index (RI) and descriptors for 116 diverse compounds in essential oils of six Stachys species. The correlation coefficient LGO-CV (Q²) between experimental and predicted RI for test set by GA-MLR, GA-PLS, GA-KPLS and L-M ANN was 0.886, 0.912, 0.937 and 0.964, respectively. This is the first research on the QSRR of the essential oil compounds against the RI using the GA-KPLS and L-M ANN.

Application of GA-PLS and GA-KPLS calculations for the prediction of the retention indices of essential oils

Genetic algorithm and partial least square (GA-PLS) and kernel PLS (GA-KPLS) techniques were used to investigate the correlation between retention indices (RI) and descriptors for 117 diverse compounds in essential oils from 5 Pimpinella species gathered from central Turkey which were obtained by gas chromatography and gas chromatography-mass spectrometry. The square correlation coefficient leave-group-out cross validation (LGO-CV) (Q²) between experimental and predicted RI for training set by GA-PLS and GA-KPLS was 0.940 and 0.963, respectively. This indicates that GA-KPLS can be used as an alternative modeling tool for quantitative structure-retention relationship (QSRR) studies.

Chemical composition and antibacterial activity of essential oils from verbenaceae species: alternative sources of (E)-caryophyllene and germacrene-D

Volatile oils from the leaves of Verbenaceae species Aloysia virgata, Lantana camara, Lantana trifolia, Lantana montevidensis, Lippia brasiliensis and Lippia sericea were investigated for its chemical composition and antibacterial activity. The volatile oils were characterized by a high content of sesquiterpenes of which (E)-caryophyllene (10-35%), germacrene-D (5-46%) and bicyclogermacrene (7-17%) were the major components for all studied species. For the flowers, a higher concentration of monoterpenes was observed for the species L. camara, L. trifolia and L. brasiliensis. These compounds probably act as attractive to specific pollinators. The volatile oils from A. virgata was the most active, exhibiting moderate antimicrobial activity against the bacteria Staphylococcus aureus, Bacillus cereus and Escherichia coli.

In vitro trypanocidal evaluation of pinane derivatives from essential oils of ripe fruits from Schinus terebinthifolius Raddi (Anacardiaceae)

Essential oils of ripe fruits from Schinus terebinthifolius (Anacardiaceae), obtained using a pilot extractor and a Clevenger apparatus were chemically characterized. Due the high amount of (-)- α-pinene in both oils, this monoterpene was tested against the protozoan parasite Trypanosoma cruzi, showing a moderate potential (IC50 63.56 µg/mL) when compared to benznidazole (IC50 43.14 µg/mL). Otherwise, (-)- α-pinene oxide did not showed anti-trypanosomal activity (IC50 > 400 µg/mL) while (-)-pinane showed an IC50 of 56.50 µg/mL. The obtained results indicated that the epoxydation of α-pinene results to the loss of the anti-parasitic activity while its hydrogenation product, contributed slightly to the increased activity.

Evaluation of chitosan microparticles containing curcumin and crosslinked with sodium tripolyphosphate produced by spray drying

The aim of this study was to encapsulate curcumin into chitosan, using sodium tripolyphosphate (TPP) as an ionic crosslinker by the spray drying method. The influence of TPP on the properties of the final product, such as solubility, morphology, loading efficiency, thermal behavior, swelling degree and release profiles, was evaluated. The microparticles had a spherical morphology (0.5-20 µm) with no apparent porosity or cracks. Results indicated the formation of a polymeric network, which ensures effective protection for curcumin. Controlled-release studies were carried out at pH 1.2 and 6.8, to observe the influence of pH on curcumin release while the mechanism was analyzed using the Korsmeyer-Peppas equation.

Hydrolytic activity of bacterial lipases in amazonian vegetable oils

The data presented describe the development of an enzymatic process in vegetable oils. Six bacterial lipases were tested for their ability to hydrolyze. For each lipase assay, the p-NPP method was applied to obtain maximum enzymatic activities. The lipase from Burkholderia cepacia (lipase B-10) was the most effective in buriti oil, releasing 4840 µmol p-NP mL-1. The lipase from Klebsiella variicola (lipase B-22) was superior in passion fruit oil, releasing 4140 µmol p-NP mL-1 and also in babassu palm oil, releasing 2934 µmol p-NP mL-1. Research into the bioprocessing of oils aims to provide added value for this regional raw material.

Chemical composition, circadian rhythm and antibacterial activity of essential oils of piper divaricatum: a new source of safrole

The essential oils from leaves, stems and fruits of Piper divaricatum were analyzed by GC-MS. The tissues showed high safrole content: leaves (98%), fruits (87%) and stems (83%), with yields of 2.0, 4.8 and 1.7%, respectively. This is a new alternative source of safrole, a compound widely used as a flavoring agent and insecticide. The leaf's oil showed antibacterial activity against gram-negative bacteria while safrole was active against Salmonella Typhimurium and Pseudomonas aeruginosa. In addition, the study of circadian rhythm of the safrole concentration in the essential oils of leaves showed a negligible variation of 92 to 98%.

In vitro activity of essential oils of Lippia sidoides and Lippia gracilis and their major chemical components against Thielaviopsis paradoxa, causal agent of stem bleeding in coconut palms

Essential oils of Lippia sidoides, Lippia gracilis and their main chemical components were investigated for in vitro control of Thielaviopsis paradoxa. Mycelial growth and a number of pathogen conidia were inhibited by the essential oil of L. sidoides at all concentrations tested (0.2; 0.5; 1.0; 3.0 µL mL-1). L. sidoides oil contained 42.33% thymol and 4.56% carvacrol, while L. gracilis oil contained 10% thymol and 41.7% carvacrol. Mycelial growth and conidial production of T. paradoxa were completely inhibited by thymol at a 0.3 µL m-1 concentration. The results suggest that thymol could potentially be used for controlling coconut stem bleeding.

Imobilização de lipase por encapsulação em sílica aerogel

Lipase from Burkholderia cepacia was immobilized in a silica matrix and dried in high pressure carbon dioxide media (aerogel). The protic ionic liquid (PIL) was used in the immobilization process by encapsulation. The objective of this work was to evaluate the influence of the drying technique using supercritical carbon dioxide in biocatalysts obtained through the sol-gel technique by evaluating temperature and pressure and, after selecting the best drying conditions, to investigate the application of the technique for the biocatalyst using ionic liquid as an additive in the immobilization process. The results for immobilized biocatalysts showed that the best conditions of pressure and temperature were 100 bar and 25 ºC, respectively, giving a total activity recovery yield of 37.27% without PIL (EN) and 44.23% with PIL (ENLI). The operational stability of the biocatalysts showed a half-life of 11.4 h for ENLI and 6 h for EN. Therefore, solvent extraction using supercritical CO2, besides shortening drying time, offers little resistance to the immobilization of lipases, since their macropores provide ample room for their molecules. The use of the ionic liquid as an additive in the process studied for the immobilization of enzymes produced attractive yields for immobilization and therefore has potential for industrial applications in the hydrolysis of vegetable oils.

MICROWAVE ACTIVATION OF IMMOBILIZED LIPASE FOR TRANSESTERIFICATION OF VEGETABLE OILS

This work investigated the effect of microwave irradiation (MW) on the ethanolysis rate of soybean and sunflower oils catalyzed by supported Novozyme 435 (Candida antarctica). The effects of tert-butanol, water addition and oil:ethanol molar ratio on transesterification were evaluated under conventional heating (CH), and under optimum reaction conditions (with no added water in the system, 10% tert-butanol and 3:1 ethanol-to-oil molar ratio). The reactions were monitored up to 24 h to determine the conditions of initial reaction velocity. The investigated variables under MW (50 W) were: reaction time (5.0-180 min) and mode of reactor operation (fixed power, dynamic and cycles) in the absence and presence of tert-butanol (10% (w/w). The measured response was the reaction conversion in ethyl esters, which was linked to the enzyme catalytic activity. The results indicated that the use of microwave improved the activity at fixed power mode. A positive effect of the association of tert-butanol and MW irradiation on the catalytic activity was observed. The reaction rate improved in the order of approximately 1.5 fold compared to that under CH with soybean oil. Using soybean oil, the enzymatic transesterification under MW for conversion to FAEE (fatty acid ethyl esters) reached >99% in 3h, while with the use of CH the conversions were about 57% under similar conditions.