Supercritical Carbon Dioxide Extraction of Coumarins from the Aerial Parts of Pterocaulon polystachyum.

Pterocaulon polystachyum is a species of pharmacological interest for providing volatile and non-volatile extracts with antifungal and amebicidal properties. The biological activities of non-volatile extracts may be related to the presence of coumarins, a promising group of secondary metabolites. In the present study, leaves and inflorescences previously used for the extraction of essential oils instead of being disposed of were subjected to extraction with supercritical CO2 after pretreatment with microwaves. An experimental design was followed to seek the best extraction condition with the objective function being the maximum total extract. Pressure and temperature were statistically significant factors, and the optimal extraction condition was 240 bar, 60 °C, and pretreatment at 30 °C. The applied mathematical models showed good adherence to the experimental data. The extracts obtained by supercritical CO2 were analyzed and the presence of coumarins was confirmed. The extract investigated for cytotoxicity against bladder tumor cells (T24) exhibited significant reduction in cell viability at concentrations between 6 and 12 µg/mL. The introduction of green technology, supercritical extraction, in the exploration of P. polystachyum as a source of coumarins represents a paradigm shift with regard to previous studies carried out with this species, which used organic solvents. Furthermore, the concept of circular bioeconomy was applied, i.e., the raw material used was the residue of a steam-distillation process. Therefore, the approach used here is in line with the sustainable exploitation of native plants to obtain extracts rich in coumarins with cytotoxic potential against cancer cells.

Polyphenolic Composition and in Vitro Antihypertensive and Anti-Inflammatory Effects of Cuphea lindmaniana and Cuphea urbaniana.

The present study investigates the chemical composition, anti-inflammatory, and antihypertensive activities, in vitro, from extracts of Cuphea lindmaniana and Cuphea urbaniana leaves. The extraction was performed ultrasound-assisted, and UHPLC/MS analysis was in positive mode ionization. The anti-inflammatory activity of the extracts and miquelianin were assayed at concentrations 0.001-10 µg/mL by chemotaxis on rat polymorphonuclear neutrophils. The antihypertensive activity was performed by angiotensin-converting enzyme (ACE) inhibition. From the nineteen proposed compounds, six of them are described for the first time in this genus. The extracts displayed antichemotactic effect with a reduction of 100 % of the neutrophil migration, in vitro, in most concentrations. The ACE-inhibition presented results ranging from 19.58 to 22.82 %. In conclusion, C. lindmaniana and C. urbaniana extracts contain a rich diversity of flavonoids and display in vitro anti-inflammatory and antihypertensive potential. Thus, this study could serve as a scientific baseline for further investigation, on developmental novel products with therapeutic actions.

Chemical Constituents and Pharmacology properties of Aristolochia triangularis: a south brazilian highly-consumed botanical with multiple bioactivities.

Aristolochia triangularis Cham., is one of the most frequently used medicinal plant in Southern Brazil. Preparations containing the leaves and/or stems are traditionally used as anti-inflammatory, diuretic, as well as antidote against snakebites. This study screened A. triangularis extracts, fractions and isolated compounds for different bioactivities. A weak antiproliferative activity against human lung cancer cell line (A549) was observed only for chloroform fraction obtained from stems (CFstems - CC50: 2.93 µg/mL). Also, a moderate antimicrobial activity against Staphylococcus aureus was detected just for chloroform fraction obtained from leaves (CFleaves -13-16 mm inhibition zone). Additionally, two semi-purified fractions (CFstems-4 and CFleaves-4) selectively inhibited HSV-1 replication (IC50 values of 0.40 and 2.61 µg/mL, respectively), while only CFleaves showed promising results against Leishmania amazonensis. Fractionation of extracts resulted in the isolation of one neolignan (-) cubebin and one lignan (+) galbacin. However, these compounds are not responsible for the in vitro bioactivities herein detected. The presence of aristolochic acid I and aristolochic acid II in the crude ethanol extract of stems (CEEstems) and leaves (CEEleaves) was also investigated. The HPLC analysis of these extracts did not display any peak with retention time or UV spectra comparable to aristolochic acids I and II.

Antichemotactic and Antifungal Action of the Essential Oils from Cryptocarya aschersoniana, Schinus terebinthifolia, and Cinnamomum amoenum.

The purpose of this work was to determine the chemical composition and evaluate the antichemotactic, antioxidant, and antifungal activities of the essential oil obtained from the species Cryptocarya aschersoniana Mez, Cinnamomum amoenum (Ness & Mart.) Kosterm., and Schinus terebinthifolia Raddi, as well as the combination of C. aschersoniana essential oil and terbinafine against isolates of dermatophytes. Allo-aromadendrene, bicyclogermacrene, and germacrene B were identified as major compounds in essential oils. The essential oil of C. aschersoniana shown 100 % inhibitory effect on leukocyte migration at the concentration of 10 µg/mL while S. terebinthifolia oil presented 80.1 % inhibitory effect at the same concentration. Only S. terebinthifolia oil possessed free-radical-scavenging activity which indicates its antioxidant capacity. The essential oils were also tested against fungal isolates of dermatophyte species (Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis and Microsporum gypseum), resulting in MIC ranging from 125 µg/mL to over 500 µg/mL. C. aschersoniana oil combined with terbinafine resulted in an additive interaction effect. In this case, the essential oil may act as a complement to conventional therapy for the topical treatment of superficial fungal infections, mainly because it is associated with an anti-inflammatory effect.

A Chemometrics Approach to the Investigation of the Intraspecific Variability of the Volatile Oil of Eupatorium tremulum from Southern Brazil.

Eupatorium tremulum is a South American shrub reported to cause cattle digestive intoxication, of which the volatile oil, mainly composed by bisabolane- and amorphane-type sesquiterpenoids, exhibits high quantitative variability. This report describes the application of chemometric tools for the identification of volatile compounds that characterize phenophasical changes in the plant. Preblooming, blooming, and postblooming specimens were paired-sampled and submitted to hydrodistillation and GC-MS analysis. Differential results were analyzed by orthogonal projection to latent structures-discriminant analysis (OPLS-DA), and the substances with different distribution in each phase were highlighted. Mean results between phases were submitted to factor analysis (FA), and correlations between the variables were demonstrated. Preblooming to blooming phase change was characterized by decreased levels of amorpha-4-en-7-ol (13) and epi-α-bisabolol (19) and increased amounts of amorpha-4,7(11)-diene (1). Blooming to postblooming change was characterized by decreases in 1, germacrene D (2), and ß-bisabolene (4) and increases in 13 and 19. Finally, enhanced levels of 1, 4, and 2 reflected the change from the postblooming to the preblooming phase. FA revealed a strong correlation in the variability between the bisabolane hydrocarbons, possibly related to its common enzymatic origin. Another strong source of negative correlation showed bisabolane- and amorphane-type alcohols, on one side, and amorphane-type furans, on the other side, to occur in two alternative oxidation routes. Finally, 1 was strongly negatively correlated to its oxidized furan and ketofuran derivatives [verboccidentafuran (16) and 3-oxo-verboccidentafuran (23)] and additionally to a third compound, putatively identified as a biosynthetic intermediate between this hydrocarbon and the furans, amorpha-4,7(11)-dien-8-one (20).

Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice.

A new dimeric acylphloroglucinol, denudatin A (1), was isolated from the flowering aerials parts of Hypericum denudatum, along with the known phloroglucinols selancin A (2), hyperbrasilol A (3), uliginosin B (4), and isouliginosin B (5). The structure of 1 was elucidated using 1D, 2D NMR, and MS experiments, and by comparison with previously reported data for Hypericum dimeric acylphloroglucinols. Denudatin A (1) and selancin A (2) were administered orally to mice displaying antinociceptive activity in the hot plate test. The compounds did not induce motor impairment in the rotarod apparatus.

Characterization of Phloroglucinol-enriched Fractions of Brazilian Hypericum Species and Evaluation of Their Effect on Human Keratinocytes Proliferation.

In this study, a phytochemical and biological investigation on five South Brazilian Hypericum species (Hypericum caprifoliatum, Hypericum carinatum, Hypericum connatum, Hypericum myrianthum, and Hypericum polyanthemum) was carried out. The phloroglucinol-enriched fractions (PEF) of the flowering aerial parts were analyzed by high-performance liquid chromatography for the content of uliginosin A (1), japonicin A (2), uliginosin B (3), hyperbrasilol B (4), and the three benzopyrans, that is, 6-isobutyryl-5,7-dimethoxy-2,2-dimethyl-benzopyran (HP1) (5), 7-hydroxy-6-isobutyryl-5-methoxy-2,2-dimethyl-benzopyran (HP2) (6), and 5-hydroxy-6-isobutyryl-7-methoxy-2,2-dimethyl-benzopyran (HP3) (7). After chemical characterization, the PEF were assayed for cell proliferation on human keratinocyte cell line by MTT. The H. carinatum and H. polyanthemum PEF demonstrated better results with an increase in cell proliferation (138.7% and 120.6%, respectively). The cell counting and Ki-67 assay with H. carinatum PEF confirmed the MTT results. The cell cycle distribution indicates an increase in the cells at S and G2/M phases, which is indicative of proliferation induction. In summary, the results indicate an induction of HaCaT proliferation by the treatment with H. carinatum PEF (at 10 and 15 µg/mL), suggesting a possible use as wound healing agent. Copyright © 2016 John Wiley & Sons, Ltd.

The monoamine oxidase inhibitory activity of essential oils obtained from Eryngium species and their chemical composition.

CONTEXT: Monoamine oxidase (MAO) inhibitors are used in the treatment of depression, anxiety disorders, and the symptomatic treatment of Parkinson's disease. Eryngium, the most representative of the Apiaceae family, is well known for the presence of essential oils (EOs), which have already demonstrated MAO inhibitory potential. OBJECTIVE: The objective of this study is to evaluate the MAO inhibitory capacity of the EOs obtained from Eryngium floribundum Cham. & Schlecht. (EF), E. eriophorum Cham. & Schlecht. (EE), E. nudicaule Lam. (EN), E. horridum Malme (EH), and E. pandanifolium Cham. & Schlecht. (EP). MATERIALS AND METHODS: EOs were obtained from fresh whole plants by hydrodistillation (3 h). Chemical analyses were performed by GC/MS using apolar and polar columns, with oven temperature from 60 to 300 °C at 3 °C/min. The MAO-A and -B activities were evaluated in vitro by an end-point method using kynuramine as the substrate and mitochondrial suspension or human recombinant enzymes as the enzymatic source. DMSO 2%, clorgyline 10(-7) M, and pargyline 10(-6) M were used as controls. RESULTS AND DISCUSSION: EFEO, EEEO, ENEO, EHEO, and EPEO GC/MS analysis showed (E)-caryophyllene (4.9-10.8%), germacrene D (0.6-35.1%), bicyclogermacrene (10.4-17.2), spathulenol (0.4-36.0%), and globulol (1.4-18.6%) as main constituents. None of the EOs inhibited MAO-A activity (4 and 40 µg/mL). However, EHEO inhibited MAO-B activity with an IC50 value of 5.65 µg/mL (1-200 µg/mL). Pentadecane (10 µM), its major constituent (53.5%), did not display significant MAO-B inhibition. CONCLUSION: The study demonstrates the promising application of Eryngium species as a source of potential central nervous system bioactive secondary metabolites, specially related to neurodegenerative disorders.

Chemical analysis and in vitro antiviral and antifungal activities of essential oils from Glechon spathulata and Glechon marifolia.

CONTEXT: Glechon spathulata Benth. and Glechon marifolia Benth. (Lamiaceae, Mentheae) are aromatic plants used in traditional medicine for the treatment of viral infections. OBJECTIVE: The chemical composition and antiviral and antifungal activities of Glechon spathulata and Glechon marifolia essential oils were investigated. MATERIALS AND METHODS: The oils were obtained by hydrodistillation and analyzed by GC-FID and GC-MS. Anti-herpes virus (HSV-1) activity was examined in Vero cells by yield reduction assay, in doses of 0.0095% v/v and 0.039% v/v, for G. spathulata and G. marifolia oil, respectively. Antifungal activity was carried by the broth microdilution method, in oil concentrations that ranged from 5.2 to 500 µg/mL. RESULTS: ß-Caryophyllene (14.2% and 32.2% for G. spathulata and G. marifolia, respectively) and bicyclogermacrene (17.1% and 16.5%, respectively) were the major components of both oils. At noncytotoxic concentrations of the essential oils, the viral titer was reduced by up to 2 log10 for KOS and VR-733 strains. The antifungal activity was observed against Trichophyton rubrum (MIC 10-83 µg/mL) and Epidermophyton floccosum (MIC 83-500 µg/mL). The oil of G. spathulata exhibited activity against the three strains tested (KOS, VR733, and 29-R), whereas G. marifolia oil was active against two strains, KOS and VR733. DISCUSSION AND CONCLUSION: The chemical composition for G. spathulata and G. marifolia essential oils is very similar. The oil of G. spathulata can be promising as a new antifungal agent against dermatophytes. The findings add important information to the biological activity of Glechon species essential oils, specifically its antiviral and antidermatophytic properties.

Taxonomic notes on Lyroglossa and Pteroglossa (Orchidaceae: Spiranthinae): two new generic records for the flora of Rio Grande do Sul.

Lyroglossa and Pteroglossa (Orchidaceae: Spiranthinae) are first recorded for Rio Grande do Sul. Descriptions, illustrations, taxonomic notes and distribution are presented. We also provide an artificial key to distinguish the genera of the "Stenorrhynchos Clade" reported so far in Rio Grande do Sul.

Anti-Leishmania effect of icetexanes from Salvia procurrens.

BACKGROUND AND PURPOSE: Leishmaniasis is a globally prevalent vector-borne disease caused by parasites of the genus Leishmania. The available chemotherapeutic drugs present problems related to efficacy, emergence of parasite resistance, toxicity and high cost, justifying the search for new drugs. Several classes of compounds have demonstrated activity against Leishmania, including icetexane-type diterpenes, previously isolated from Salvia and other Lamiaceae genera. Thus, in this study, compounds of Salvia procurrens were investigated for their leishmanicidal and immunomodulatory activities. METHODS: The exudate of S. procurrens was obtained by rapidly dipping the aerial parts in dichloromethane. The compounds were isolated by column and centrifugal planar chromatography over silica gel. The effects on L. amazonensis growth, survival, membrane integrity, reactive oxygen species (ROS) generation, mitochondrial membrane potential and cytotoxicity of the compounds towards human erythrocytes, peripheral blood mononuclear cells and macrophages were evaluated. The effects on intracellular amastigote forms, nitric oxide (NO) and TNF-α production were also investigated. RESULTS: The exudate from the leaves afforded the novel icetexane 7-hydroxyfruticulin A (1) as well as the known demethylisofruticulin A (2), fruticulin A (3) and demethylfruticulin A (4). The compounds (1-4) were tested against promastigotes of L. amazonensis and showed an effective inhibition of the parasite survival (IC50 = 4.08-16.26 µM). In addition, they also induced mitochondrial ROS production, plasma membrane permeability and mitochondrial dysfunction in treated parasites, and presented low cytotoxicity against macrophages. Furthermore, all diterpenes tested reduced the number of parasites inside macrophages, by mechanisms involving TNF-α, NO and ROS. CONCLUSION: The results suggest the potential of 7-hydroxyfruticulin A (1) as well as the known demethylisofruticulin A (2),fruticulin A (3) and demethylfruticulin A (4) as candidates for use in further studies on the design of anti-leishmanial drugs.

Alkaloid profiling and anticholinesterase activity of South American Lycopodiaceae species.

The alkaloid extracts of four Huperzia and one Lycopodiella species, from Brazilian habitats, were tested for their in vitro anticholinesterase activities. IC(50) values showed a potent acetylcholinesterase inhibition for H. reflexa (0.11 ± 0.05 µg/mL), followed by H. quadrifariata (2.0 ± 0.3 µg/mL), H. acerosa (5.5 ± 0.9 µg/mL), H. heterocarpon (25.6 ± 2.7 µg/mL) and L. cernua (42.6 ± 1.5 µg/mL). A lower inhibition of butyrylcholinesterase was observed for all species with the exception of H. heterocarpon (8.3 ± 0.9 µg/mL), whose alkaloid extract presented a selectivity for pseudocholinesterase. Moreover, the chemical study of the bioactive extracts performed by GC-MS, revealed the presence of a number of Lycopodium alkaloids belonging to the lycopodane, flabellidane and cernuane groups. Surprisingly, the potent acetylcholinesterase inhibitors huperzines A and B were not detected in the extracts, suggesting that other alkaloids may be responsible for such an effect.

Larvicidal activity of lipophilic extract of Hypericum carinatum (Clusiaceae) against Aedes aegypti (Diptera: Culicidae) and benzophenones determination.

In this study, the larvicidal activity of an enriched fraction of the major lipophilic phenolic compounds from Hypericum carinatum Griseb. (Clusiaceae) was investigated against larvae of Aedes aegypti (Diptera: Culicidae), the main vector of dengue virus in Brazil. The larval mortality rate ranged 37.33 to 72.00 % at concentrations of 66-200 µg/mL. The effect demonstrated to be dose-dependent. The lethal concentration 50 % and confidence interval were 100 and 88-111 µg/mL, respectively. The results could be attributed to the presence of cariphenone A and cariphenone B in concentrations of 1.24 ± 0.04 and 0.56 ± 0.01 %, respectively, determined by high-performance liquid chromatography. Besides, the results reinforce the potential of genus Hypericum as source of alternative insecticides.

Chemical composition and amoebicidal activity of Croton pallidulus, Croton ericoides, and Croton isabelli (Euphorbiaceae) essential oils.

Acanthamoeba is a free-living amoebae genus that causes amoebic keratitis which is a painful sight-threatening disease of the eyes. Its treatment is difficult, and the search for new drugs is very important. Here, essential oils obtained from the aerial parts of Croton pallidulus, Croton isabelli, and Croton ericoides (Euphorbiaceae), native plants of Southern Brazil, were tested against Acanthamoeba polyphaga and analyzed by gas chromatography and gas chromatography-mass spectrometry. The essential oils of C. pallidulus and C. isabelli were characterized by the presence of sesquiterpenes: germacrene D (15.5 %), terpinen-4-ol (13.2 %), and ß-caryophyllene (13.1 %) in C. pallidulus and bicyclogermacrene (48.9 %) in C. isabelli. The essential oil of C. ericoides presented mainly monoterpenes, ß-pinene (39.0 %) being the main component. Laboratory tests were carried out to determine the effect of the essential oils against A. polyphaga trophozoites. The essential oil of C. ericoides was the most active, killing 87 % of trophozoites at the concentration of 0.5 mg/mL. The essential oil of C. pallidulus killed only 29 % of the trophozoites at the same concentration. The essential oil of C. isabelli presented the lowest activity, killing only 4 % of the trophozoites at the concentration of 10 mg/mL. The essential oils of the three species showed cytotoxic effect by the methyl thiazolyl tetrazolium (MTT) method in Vero cells. The oil of C. ericoides, which showed the highest amoebicidal activity, was the most cytotoxic on these mammalian cells.

Chemical composition and anti-inflammatory activity of the essential oils of Piper gaudichaudianum and Piper mikanianum.

ETHNOPHARMACOLOGICAL RELEVANCE: Inflammation is the body's normal protective response to injury and is stimulated by pathogens, toxic compounds, damaged cells or radiation, promoting healing and restoring homeostasis to the injured tissue. Leaves of Piper gaudichaudianum Kunth, known as "pariparoba" are widely used in folk medicine for the relief of toothache, while the fresh roots are used as anti-inflammatory and to treat liver disorders. For P. mikanianum (Kunth) Steud is known as "aguaxima", is widely used in the treatment of inflammation, rheumatism and ulcer, with its roots being used for stomach disorders and as a diaphoretic in intermittent fevers. AIM OF THE STUDY: Therefore, this work aims to chemically characterize the essential oil of Piper gaudichaudianum and Piper mikanianum, as well as the evaluation of neutrophil antichemotactic activity of both essential oils in order to complement the information of its traditional use, taking the leaves as plant material and, with that, corroborating its use in folk medicine for the treatment of inflammatory diseases. MATERIALS AND METHODS: The essential oil from leaves of both Piper species were obtained from crushed fresh samples, by hydrodistillation using a Clevenger type-apparatus for 4 h. The yield determination was performed as vol/wt (v/w) and in triplicate. The amount of essential oil obtained was quantified in mL. The identification and quantification of the compounds was performed using gas chromatography-mass spectrometry (GC-MS) and gas chromatography-flame ionization detection (GC-FID). The in vitro anti-inflammatory activity was evaluated using the model of modified Boyden chamber. In this test the essential oils were tested for their ability to inhibit leukocyte chemotaxis stimulated by Escherichia coli lipopolysaccharide. RESULTS: The chemical composition of the essential oils revealed the identification of 26 constituents for P. gaudichaudianum being the sesquiterpenes ß-selinene (14.0%) and viridiflorene (10.5%) the main compounds, followed by caryophyllene oxide (9.3%) and (E)-nerolidol (9.0%). For P. mikanianum essential oil, ß-myrcene (17.2%) and bicyclogermacrene (26.3%) were the major components in the monoterpenes and sesquiterpene fractions, respectively. The essential oils were also tested for their ability to inhibit neutrophil chemotaxis in vitro when stimulated by Escherichia coli lipopolysaccharide. Both essential oils showed antichemotactic effect with reduction in migration of 0-72.2% for P. gaudichaudianum and 8.6-100% for P. mikanianum to same concentrations, suggesting a response to acute inflammatory processes. CONCLUSIONS: Since up to date there is no report of this biological activities by this mechanism (antichemotactic assay) for essential oils this species. These results showed that the essential oils of P. gaudichaudianum and P. mikanianum have a great capacity to inhibit neutrophil chemotaxis in an inflammatory process, in a dose-dependent way, suggesting anti-inflammatory potential, by preventing its accumulation at the injury site with the possibility of tissue damage. Findings of these studies support the traditional use of these species in the treatment of inflammatory processes.

Antimicrobial activity of dimeric acylphloroglucinols isolated from southern Brazilian Hypericum species against to resistant bacterial.

The hexanic extracts of Hypericum austrobrasiliense, H. caprifoliatum, H. denudatum, H. pedersenii and H. polyanthemum, and three isolated dimeric acylphloroglucinols (uliginosin B, japonicine A and hyperbrasilol B) were assayed for their antimicrobial activity against some Gram-positive and Gram-negative bacteria (including resistant strains). These extracts were assayed using the disc diffusion test, and the results indicated that the tested species did non exhibit activity on the Gram-negative strains. Subsequently, the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were measured using the broth dilution technique adopted to macrodillution. The most susceptible strains were the MRSA and the S. aureus MLSb. Regarding these pathogens, the better MIC values were obtained with the extracts from H. austrobrasiliense, H. caprifoliatum and H. pedersenii. The acylphloroglucinols uliginosin B and hyperbrasilol B presented the lowest MIC values against Enterococcus faecalis, Staphylococcus aureus, MRSA and S. aureus MLSb resistance.

Two morphotypes versus two chemotypes of Psidium cattleyanum: Chemical and pharmacological comparison and a rational approach for marker selection.

Psidium cattleyanum has two morphotypes: one with yellow fruits and other with red fruits. The leaves are popularly used as anti-inflammatory. However, no distinction is made between the types. Therefore, this study compared chemical and pharmacological data of both morphotypes to select proper biomarkers to ensure P. cattleyanum leaves quality. After extraction optimization by experimental design, 28 samples were analyzed by HPLC. Using Principal Component Analysis, it was possible to detect two chemotypes, unrelated to the color of the fruits. However, the extracts obtained from both chemotypes seemed to play similar anti-inflammatory effect, demonstrated by anti-chemotactic activity. The compounds common to both chemotypes were isolated and identified as hyperoside, miquelianin and quercitrin; these compounds also demonstrated anti-inflammatory potential. Since both chemotypes played similar activity, along with the isolated flavonoids, these flavonoids were selected as biomarkers for quality control of P. cattleyanum leaves. Following ICH guidelines, a HPLC method was validated. In summary, this study demonstrated that hyperoside, miquelianin and quercitrin can be used as biomarkers for quality control of P. cattleyanum leaves and a method was developed and validated to be used interchangeably for both morpho- and chemotypes.

Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae.

Volatile oils (VOs) obtained from the aerial parts of species from the Disynaphiinae subtribe (genera Acanthostyles, Campovassouria, Disynaphia, Grazielia, Raulinoreitzia, and Symphyopappus) of Eupatorieae (Asteraceae) collected in Rio Grande do Sul, southern Brazil, were characterized using GC-MS. The yield of VOs relative to fresh material ranged from 0.2 to 1.7% between the Disynaphiinae subtribe samples (Acanthostyles buniifolius, Campovassouria cruciata, Disynaphia ericoides, D. ligulifolia, D. spathulata, Symphyopappus casarettoi, S. reticulatus, S. itatiayensis, Grazielia gaudichaudieana, G. intermedia, G. nummularia, G. serrata, Raulinoreitzia crenulata, and R. tremula). The VOs in this subtribe were mainly composed of terpene compounds. Compositional multivariate analysis demonstrated clustering between the samples of Grazielia and Raulinoreitzia on one side, which contain relatively higher proportions of monoterpenes, and Disynaphia and Campovassouria, which contain more oxygenated sesquiterpenes. The samples of Symphyopappus and Acanthostyles, which contain more sesquiterpene hydrocarbons, were located between these two main groups. Multivariate analysis accounting for the recent proposals of subtribal recircumscription of Eupatorieae was also performed. The odd chemistry of S. itatiayensis was in accordance with the recent attempts to exclude it from the genus Symphyopappus.

Cuphea spp.: antichemotactic study for a potential anti-inflammatory drug.

Cuphea genus (Lythraceae) popularly known in Brazil as "sete-sangrias", it's described as antimicrobial, anti-inflammatory, diuretic and antihypertensive mainly. Investigating the chemotactic ability plays an important role in the identification of new anti-inflammatory agents. Thus, this research aims to assay the antichemotactic activity of hydroethanolic extracts of C. calophylla, C. carthagenensis, C. glutinosa, and C. racemosa as well as the compounds miquelianin and myricitrin. The antichemotactic activity of the hydroethanolic extracts, miquelianin, and myricitrin were assayed at concentrations 0.001 to 10 µg/mL in the lipopolysaccharide-induced chemotaxis on rat polymorphonuclear neutrophils. All the assayed samples displayed antichemotactic activity with reduction of the neutrophil migration in the range of 4.46-100%, and an IC50 value in the range of 0.30-1.24 µg/mL. Thus, this study demonstrates that the extracts hydroethanolic of Cuphea species, miquelianin, and myricitrin display a significant antichemotactic activity. Therefore, in future studies, extracts from Cuphea spp. could be used as anti-inflammatory drugs.

Acaricidal activity and chemical composition of the essential oil from three Piper species.

The chemical composition of the essential oil obtained by hydrodistillation of the aerial parts of Piper amalago, Piper mikanianum, and Piper xylosteoides was elucidated by gas chromatography (GC) and GC/mass spectrometry analyses. P. mikanianum and P. xylosteoides essential oils presented phenylpropanoids as their main compounds (67.89% and 48.53%, respectively) whereas P. amalago was rich in monoterpene and sesquiterpene hydrocarbons (84.95%). The essential oils obtained were investigated for their effect on newly hatched larvae of the cattle tick, Rhipicephalus (Boophilus) microplus. The essential oil of P. mikanianum (LC(50) 2.33 microL/mL) was more active than that of P. xylosteoides (LC(50) 6.15 microL/mL) against the larvae, while the oil of P. amalago was inactive. These results suggest that phenylpropanoids, mainly apiol and safrole, are responsible for the acaricidal activity.