In vitro Antileishmanial and Antimalarial Activities of Tetrahydrofuran Lignans isolated from Nectandra megapotamica (Lauraceae)

Seven tetrahydrofuran lignans, isolated from Nectandra megapotamica (Lauraceae), were evaluated for their in vitro antileishmanial and antimalarial activities. Among the evaluated compounds, machilin-G (1a) and veraguensin (2a) showed the highest antileishmanial activities, displaying for both compounds an IC(50) value of 18 mu g/mL and an IC(50) value of 36 mu g/mL, while galgravin (1b), nectandrin-A (1c), nectandrin-B (1d), calopeptin (2b) and ganshisandrine (3) were inactive against Leishmania donovani. In the antimalarial assay against Plasmodium falciparum, it was observed that calopeptin (2b) displayed moderate activity, with IC(50) values of 3800 ng/mL (136 clone) and 3900 ng/mL (W2 clone), while the lignans 1a-1d, 2a and 3 were inactive. In order to compare the effect on the parasites with toxicity to mammalian cells, the cytotoxic activity of the isolated compounds were evaluated against the Vero cells, showing that all evaluated tetrahydrofuran lignans exhibited no cytotoxicity at the maximum dose tested. Copyright (C) 2008 John Wiley & Sons, Ltd.

Trypanocidal Activity of Pimarane Diterpenes from Viguiera arenaria (Asteraceae)

Five structurally related pimarane diterpenes isolated from the roots of Viguiera arenaria and a further compound obtained by chemical derivatization were evaluated in vitro against the trypomastigote forms of Trypanosoma cruzi. The natural compound ent-15-pimarene-8 beta,19-diol and the derivative ent-8(14),15-pimaradiene-3 beta-acetoxy showed the highest trypanocidal activity, displaying IC50 values of 116.5 +/- 1.21 and 149.3 +/- 1.07 mu M, respectively, while the positive control, violet gentian, showed an IC50 of 76 mu M. Based on the results, it can be concluded that minor structural differences among the tested diterpenes influence significantly the trypanocidal activity, thus bringing new perspectives to the establishment of structure-activity relationships among this type of metabolites to the treatment of Chagas` disease. Copyright (C) 2008 John Wiley & Sons, Ltd.

Antileishmanial, antimalarial and antimicrobial activities of the extract and isolated compounds from Austroplenckia populnea (Celastraceae)

Austroplenckia populnea (Celastraceae), known as ""marmelinho do campo"", is used in Brazilian folk medicine as antimicrobial, anti-inflammatory, and antitumoural agent. The aim of the present work was to evaluate the antimicrobial. antileishmanial and antimalarial activities of the crude hydroalcoholic extract of A. populnea (CHE) and some of its isolated compounds. The phytochemical study of the CHE was carried Out affording the isolation of methyl populnoate (1), populnoic acid (2), and stigmast-5-en-3-O-beta-(D-glucopyranoside) (3). This is the first time that the presence of compound 3 in A. populnea is reported. The results showed that the CHE presents antifungal and antibacterial activities, especially against Candida glabrata and Candida albicans, for which the CHE showed IC(50) values of 0.7 mu g mL(-1) and 5.5 mu g mL(-1), respectively, while amphotericin B showed an IC(50) value of 0.1 mu g mL(-1) against both microorganisms. Compounds 1-3 were inactive against all tested microorganisms. In the antileishmanial activity test against Leishmania donovani, the CHE showed an IC(50) value of 52 mu g mL(-1), while compounds 2 and 3 displayed an IC(50) value of 18 mu g mL(-1). In the antimalarial assay against Plasmodium falciparum (D6 and W2 clones), it was observed that all evaluated samples were inactive. In order to compare the effect on the parasites with the toxicity to mammalian cells, the cytotoxicity activity of the isolated compounds was evaluated against Vero cells, showing that all evaluated samples exhibited no cytotoxicity at the maximum dose tested.

Further sesquiterpene lactones from viguiera robusta and the potential anti-inflammatory activity of a heliangolide: Inhibition of human neutrophil elastase release

In addition to known heliangolides, a new eudesmanolide was isolated from the leaf rinse extract of Viguiera robusta (Asteraceae). Structural elucidation was based oil spectral analysis. It is the first report on eudesmanolides in members of the subgenus Calanticaria of Viguiera. In this work, the main isolated compound, the furanoheliangolide budlein A, besides its previously, reported in vitro and in vivo anti-inflammatory activities, inhibited human neutrophil elastase release. The inhibition was at the concentration of (16.83 +/- 1.96) mu M for formylated bacterial tripeptide (fMLP) stimulation and (11.84 +/- 1.62) mu M for platelet aggregation factor (PAF) stimulation, being slightly less active than the reference drug parthenolide. The results are important to demonstrate the potential anti-inflammatory activities of sesquiterpene lactones and corroborate the previous studies using other targets.

Azaphilones from the Endophyte Chaetomium globosum

Six new azaphilones, 5`-epichaetoviridin A (7), 4`-epichaetoviridin F (9), 12 beta-hydroxychaetoviridin C (10), and chaetoviridins G-I (11-13), and six known azaphilones, chaetoviridins A E (1-5) and 4`-epichaetoviridin A (8), were isolated from the endophytic fungus Chaetomium globosum cultivated in PDB medium for 21 days. The structure elucidation and the assignment of the relative configurations of the new natural products were based on detailed NMR and MS spectroscopic analyses. The structure of compound 1 was confirmed by single-crystal X-ray diffraction analysis. were determined using Mosher`s method. The antibiotic activity of the elegans infection model. The absolute configurations of compounds 4, 7, 8, and 12 compounds was evaluated using an in vivo Caenorhabditis elegans infection model.

An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatorium perfoliatum

The CH(2)Cl(2) extract of aerial parts of Eupatorium perfoliatum L. exhibits antiprotozoal activity under in vitro conditions, especially against Plasmodium falciparum (IC(50)=2.7 mu g/ml). The search for active compounds yielded seven sesquiterpene lactones: Four structurally similar guaianolides, one dimeric guaianolide, and two germacranolides. The guaianolides differ in the degree of oxidation at C-14, ranging from a hydroxyl group up to a free carboxylic acid. The dimeric guaianolide, structurally closely related to the monomers, displays an unusual type of interguaianolide linkage between C-14 and C-4. Except for the germacranolide euperfolitin, all STLs described here were hitherto unknown. Furthermore, the flavonoid aglycones eupafolin, hispidulin, patuletin, and kaempferol were identified in the extract, which, except for kaempferol, have not been described as constituents of E. perfoliatum before. The dimeric guaianolide was shown to be the most active constituent against Plasmodium falciparum (IC(50) = 2.0 mu M) and was less cytotoxic against rat skeletal myoblasts (IC(50) = 16.2 mu M, selectivity index of about 8). (C) 2011 Elsevier Ltd. All rights reserved.

Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae)

Baccharis dracunculifolia D. C. (Asteraceae) is the most important plant source of the Brazilian green propolis. Since propolis is known for its antimicrobial activity, the aim of this work was to evaluate the showed that the leaves extract of B. dracunculifolia (BdE) presents antifungal and antibacterial activities, especially against Candida krusei and Cryptococcus neoformans, for which the BdE showed IC50 values of 65 mu g mL(-1) and 40 mu g mL(-1), respectively In comparison to the BdE, it was observed that the green propolis extract (GPE) showed better antimicrobial activity, displaying an IC50 value of 9 mu g mL(-1) against C krusei. Also, a phytochemical study of the BdE was carried out, affording the isolation of ursolic acid (1), 2 alpha-hydroxy-ursolic acid (2), isosakuranetin (3), aromadendrin-4`-methylether (4), baccharin (5), viscidone (6), hautriwaic acid lactone (7), and the clerodane diterpene 8. This is the first time that the presence of compounds 1, 2, and 8 in B. dracunculifolia has been reported. Among the isolated compounds, 1 and 2 showed antibacterial activity against methicillin-resistant Staphylococcus aureus, displaying IC50 values of 65 mu g mL(-1) and 40 mu g mL(-1), respectively. 3 was active against C neoformans, showing an IC50 value of 15 mu g mL(-1) and a MIC value of 40 mu g mL(-1), while compounds 4-8 were inactive against all tested microorganisms. The results showed that the BdE, similar to the GPE, displays antimicrobial activity, which may be related to the effect of several compounds present in the crude extract.

Attainment of O/W emulsions containing liquid crystal from annatto oil (Bixa orellana), coffee oil, and tea tree oil (Melaleuca alternifolia) as oily phase using HLB system and ternary phase diagram

Emulsions containing liquid crystals present interesting properties and advantages such as the skin moisturize increase, active release modulation, and emulsion stabilization. In this work, emulsions containing annatto, coffee and tea tree oils, and nonionic surfactants were developed. The HLB method was used for selection of surfactants. The required HLB value was established (9.0). Liquid crystals were attained when used the surfactant mixture Ceteareth-5 and Steareth-2 and identified as lamellar. The emulsions showed pseudoplastic behavior and tixotropy. The ternary diagram was useful in the selection of the proportion of surfactant and oily phase considering skin compatibility and liquid crystal presence.

Antimicrobial Activity of Terpenoids from Copaifera langsdorffii Desf. Against Cariogenic Bacteria

In the present work, the anticariogenic activities of nine labdane type-diterpenes and four sesquiterpenes were investigated. Among these metabolites, (-)-copalic acid (CA) was the most active compound displaying MIC values very promising (ranging from 2.0 to 6.0 mu g/mL) against the main microorganisms responsible for dental caries: Streptococcus salivarius, S. sobrinus, S. mutans, S. mitis, S. sanguinis and Lactobacillus casei. Time kill assays performed with CA against the primary causative agent (S. mutans) revealed that, in the first 12 h, this compound only inhibits the growth of the inoculum (bacteriostatic effect). However, its bactericidal effect is clearly noted thereafter (between 12 and 24 h). Also, CA did not show a synergistic effect when combined with the anticariogenic gold standard (chlorhexidine, CHD) in the checkerboard assays against S. mutans. In conclusion, the results points out CA as an important metabolite in the search for new effective anticariogenic agents. Copyright (C) 2010 John Wiley & Sons, Ltd.

Spray Drying of Extracts from Red Yeast Fermentation Broth

Red yeast rice is a pigmented material that is traditionally used in Asia as a food colorant. In addition to food applications, red yeast rice is known in traditional Chinese medicine for its therapeutic actions. The aim of this work was to study the quality interactions during spray drying of extracts from the Monascus ruber van Tiegham fermentation broth. The quality indicators used for the dry powder properties were the levels of monacolin K, ratio of red to yellow pigments, as well as their antioxidant activity. The experiments followed a Box-Behnken design to study the effects of the adjuvant/drug ratio, adjuvant incorporation time, and oulet drying temperature on the pharmacotechnical, chemical, and biological properties of the dry extract. The influences of these factors on the characteristics of the dry powder were evaluated by the bulk density, tapped density, Carr index, Hausner factor, residual moisture content, water activity, antioxidant activity, monacolin K, yellow-to-red pigment ratio, and antioxidant activity. The analysis of variance (ANOVA) on experimental data revealed that an increase in drying temperature significantly increased the dry powder yield and caused an improvement in powder flow properties, which may be related to lower moisture contents. The drying temperature did not affect the monacolin K content in dry powder but showed a complex influence on its antioxidant activity. The increase in drying adjuvant-to-drug ratio affected the yield and also indicated a protective effect on the monacolin K content. The duration of drying adjuvant incorporation had little or negligible effect on powder properties. The dry extracts of red yeast rice showed adequate properties and the process proposed herein can be used to prepare nutraceutical products.

Chemical Constituents of Papulaspora immersa, an Endophyte from Smallanthus sonchifolius (Asteraceae), and Their Cytotoxic Activity

Papulaspora immersa H. H. HOTS ON was isolated from roots and leaves of Smallanthus sonchifolius (POEPP. and ENDL.) H. ROB. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)-8,14-epoxyergosta-4,22-diene-3,6-dione (4), 2,3-epoxy-1,2,3,4-tetrahydronaphthalene-c-1,c-4,8-triol (10), and the chromone papulasporin (13) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)stigmast 4 en 3 one (1), 24-methylenecycloartan-3 beta-ol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (-)-(3R,4R)-4-hydroxymellein (5), (-)-(3R)-5-hydroxymellein (6), 6,8-dihydroxy-3-methylisocoumarin (7), (-)-(4S)-4,8-dihydroxy-alpha-tetralone (8), naphthalene-1,8-diol (9), 6,7,8-trihydroxy-3-methylisocoumarin (11), 7-hydroxy-2,5-dimethylchromone (12), and tyrosol (14). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA-MB435 (melanoma), HCT-8 (colon), SF295 (glioblastoma), and HL-60 (promyelocytic leukemia), with IC(50) values of 3.3, 14.7, 5.0 and 1.6 mu m, respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds.

Partial characterization of proteins from baru (Dipteryx alata Vog) seeds

BACKGROUND: Baru (Dipteryx alata Vog.) is a fruit distributed throughout the Brazilian savanna and contains a seed with a high protein content, whose properties have been rarely explored. The purpose of this study was to characterize this protein, especially by isolation and quantifying its fractions and measuring some of its molecular properties. RESULTS: Baru seeds contain 244 g kg(-1) protein on a dry weight basis. Solubility profiles showed a preponderance of globulins. This fraction dominated the seed composition, with 61.7 wt% of the total soluble proteins. Albumins and glutelins accounted for 14 and 3.3 wt%, respectively. SDS-PAGE resolution of albumin and globulin showed main bands with molecular weights of 84 kDa and 64,66 and 73 kDa, respectively. The total protein of the flour and the globulin showed values of in vitro digestibility of 85.59% and 90.54%, relative to casein. Total globulin produced only one chromatographic peak, both on Sepharose CL-6B gel filtration and on DEAE-cellulose ion-exchange columns, eluted at a concentration of 0.12 mol L(-1) NaCl. CONCLUSION: The baru seed had high protein content with large quantities of storage proteins. The chromatographic and solubility profiles indicate the predominance of a fraction with characteristics of a legumin-type protein. (C) 2011 Society of Chemical Industry

Eudesmanolides and Methyl Ester Derivatives from Dimerostemma arnottii

The phytochemical investigation of Dimerostemma arnottii (Asteraceae) afforded, in addition to a known eudesmanolide, two unusual eudesmane methyl ester derivatives and a new eudesmanolide. Structural elucidation of the compounds was based on their ID and 2D NMR spectroscopic as well as HR-ESI-MS data. There is a remarkable similarity between the structures of the eudesmanes from D. arnottii and those previously encountered in other Dimerostemma species, which is in agreement with the results of a previous phylogenetic study based on molecular data. The chemotaxonomic relevance of the isolated compounds is briefly discussed.

Gene expression analysis of Paracoccidioides brasiliensis transition from conidium to yeast cell

Paracoccidioides brasiliensis infectious process relies on the initial expression of virulence faactors that are assumed to be controlled by molecular mechanisms through which the conidia and/or mycelial fragments convert to yeast cells. In order to analyze the profile of the thermally-induced dimorphic gene expression, 48 h C-L transition cultures which had been incubated at 36 degrees C were studied. By this time approximately 50% of the conidial population had already reverted to yeast form cells. At this transition time, an EST-Orestes library was constructed and characterized. As a result, 79 sequences were obtained, of which 39 (49.4%) had not been described previously in other libraries of this fungus and which could represent novel exclusive C-Y transition genes. Two of these sequences are, among others, cholestanol delta-isomerase, and electron transfer flavoprotein-ubiquinoneoxidoreductase (ETF-QO). The other 40 (50.6%) sequences were shared with Mycelia (M), Yeast (Y) or Mycelia to yest transition (M-Y) libraries. An important component of this group of sequences is a putative response regulator receiver SKN7, a protein of high importance in stress adaptation and a regulator of virulence in some bacteria and fungi. This is the first report identifying genes expressed during the C-Y transition process, the initial step required to understand the natural history of P brasiliensis conidia induced infection.

Antiprotozoal, Schistosomicidal, and Antimicrobial Activities of the Essential Oil from the Leaves of Baccharis dracunculifolia

Baccharis dracunculifolia DC. (Asteraceae), popularly known as alecrim do campo, is a native plant from Brazil used in folk medicine as febrifuge, anti-inflammatory, antiseptic, and to treat skin sores. Also, B. dracanculifolia is the most important plant source of the Brazilian green propolis. which is recognized for its antiseptic and antiprotozoal activities. This study aimed at investigating the in vitro antiprotozoal. schistosomicidal, and antimicrobial activities of the essential oil from the leaves of R. dracunculifolia. The essential oil was obtained by hydrodistillation and analyzed by CC and GC/MS, which allowed the identification of 14 compounds, mainly oxygenated sesquiterpenes, such as ( E)nerolidol (33.51%) and spathulenol (16.24%). The essential oil showed activity against promzistigote forms of Leishmania donovani, with IC(50), values of 42 mu g/ml. The essential oil displayed high activity in the schistosomicidal assay, since all pairs of Schistosoma mansoni adult worms were dead after incubation with the essential oil (10, 50, and 100 fig/m1). B. dracunculifolia essential oil was neither cytotoxic against Vero cells, nor active in the antimicrobial and antiplasmodial assays.