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Our previous study showed that kaempferitrin, the main flavonoid from Bauhinia forficataLink leaves, induces diuresis and saluresis when orally given to rats. Since afzelin (AFZ) and kaempferol (KFL) are active compounds from the biometabolism of kaempferitrin, the diuretic and renal protective properties of these two compounds were evaluated. While the acute treatment with AFZ evoked a diuretic action associated with an increase in Cl–excretion and a Ca2+-sparing effect, KFL did not present any activity. The pretreatment with a muscarinic receptor blocker or with an inhibitor of the cyclooxygenase fully avoided AFZ-induced diuresis. AFZ also induced a prolonged (7-day treatment) diuretic effect in normotensive (NTR) and hypertensive rats (SHR), with an increase of urinary Na+and Cl–excretion, while it decreased the elimination of Ca2+. AFZ was able to decrease ROS and nitrite generation on kidney homogenates in comparison with the SHR group treated with the vehicle, as well as mitigated the changes in the renal corpuscle region (glomerulus and Bowman’s capsule). Moreover, AFZ significantly reduced calcium oxalate crystal formation in urine, with inhibition rates of 41% for the NTR and 92% for the SHR group. Taken together, this study shows that AFZ exerts acute and prolonged diuretic effects plus protective renal properties.

Oral mucositis is a common inflammatory complication among patients undergoing hematopoietic stem cell transplantation (HSCT). Among its therapeutic properties, Chamomilla recutitahas anti-inflammatory effects.

(−)-Hinokinin (1) is a dibenzylbutyrolactone lignan obtained by the partial synthesis of (−)-cubebin. This study reports the antigenotoxic and anticarcinogenic potential of 1by the comet and aberrant crypt focus assays in the peripheral blood and colon of 4–5-week-old Wistar rats, respectively. The rats were exposed to 1,2-dimethylhydrazine (40 mg/kg) and were treated by gavage with doses of 10, 20, and 40 mg/kg of 1. The results showed that the dose of 40 mg/kg was neither genotoxic nor carcinogenic. In the comet assay, all 1doses displayed antigenotoxic effects. In addition, this compound (20 and 40 mg/kg) exhibited an anticarcinogenic effect in the aberrant crypt focus assay.

Three new azaphilones with an unusual methylene bridge, named mycoleptones A, B, and C (2, 4, and 5), were isolated from cultures of Mycoleptodiscus indicus, a fungus associated with the South American medicinal plant Borreria verticillata. Additionally, four known polyketides, austdiol (1), eugenitin (3), 6-methoxyeugenin (6), and 9-hydroxyeugenin (7), were also isolated. The structural characterization of compounds was carried out by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, electronic circular dichroism spectroscopy, time-dependent density functional theory calculations, and X-ray crystallography. Compounds 1–9were weakly active when tested in antileishmanial and cytotoxicity assays.

The Copaifera langsdorffiiDesf., Fabaceae, is a Brazilian native tree, known as copaiba, which oil is commonly used in folk medicine as muscle relaxant, wound healing, antiseptic and anti-inflammatory to respiratory and urinary tracts. Despite of the wide use of the oil of Copaiferaspecies, scientific works related to the study of its leaves are rarely found. In fact, processes for flavonoid extraction from C. langsdorffiileaves have not been studied yet leaving a wide field to be investigated. In this work, the 25–2fractional factorial design was selected in order to study how the factors of a dynamic maceration process influence the responses of total flavonoids, total phenols, quercetrin and afzelin contents, and antioxidant activity in extracts from C. langsdorffiileaves. The results demonstrated that the significant factors studied were the drug load in extractor, the ethanol/water ratio and the stirring speed whereas the temperature and the extraction time were not significant. In conclusion, this study allowed visualizing which factors were considered the most important in copaiba leaves dynamic maceration and their effect in extract antioxidant activity. Furthermore, this technological study gives directions to optimize future extraction experiments from C. langsdorffii.

The antimycobacterial activity of (-)-cubebin (1), hinokinin (2), and some of their semisynthetic derivatives, namely (-)-O-acetyl-cubebin (3), (-)-O-methyl-cubebin (4), (-)-O-(N,Ndimethylamine- ethyl)-cubebin (5) and (-)-6,6´-dinitrohinokinin (6), was evaluated against Mycobacterium tuberculosis (ATCC 27294), M. kansasii (ATCC 12478), and M. avium (ATCC 15769). The MIC values ranged from 31.25 to 2000 μg/mL. Among the evaluated compounds, 2 displayed a MIC value of 62.5 μg/mL against M. tuberculosis, while 3 and 4 displayed MIC values of 62.5 and 31.25 μg/mL, respectively, against M. avium. All compounds were inactive against M. kansasii. These are promising results concerning the search for biologically active natural products, highlighting that new approaches to the prevention, treatment, and cure of tuberculosis are extremely important.

Chemical investigation of the EtOAc fraction (EF) obtained from the ethanolic extract of Zanthoxylum naranjillo (Rutaceae) leaves (EE) by preparative HPLC resulted in the isolation of protocatechuic acid (1), gallic acid (2), p-hydroxybenzoic acid (3), and 5-Ocaffeoylshikimic acid (4). This is the fi rst time that the presence of compounds 1 - 4 in Z. naranjillo has been reported. Compounds 1 - 4, the EE, and EF were tested in vitro against Schistosoma mansoni adult worms. The results showed that the S. mansoni daily egg production decreased by 29.8%, 13.5%, 28.4%, 17.7%, 16.3%, and 6.4%, respectively. Compounds 1 and 3 were also able to separate adult worm pairs into male and female. This activity may be correlated with the reduction in egg production, since 1 and 3 showed better inhibitory properties compared with 2 and 4.

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 antimicrobial activities of B. dracunculifolia and some of its isolated compounds. The results 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 IC50values of 65 µg mL -1and 40 µg mL-1, respectively. In comparison to the BdE, it was observed that the green propolis extract (GPE) showed better antimicrobial activity, displaying an IC50value of 9 µg mL-1against C. krusei. Also, a phytochemical study of the BdE was carried out, affording the isolation of ursolic acid (1), 2a-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 IC50values of 5 µg mL-1and 3 µg mL-1, respectively. 3 was active against C. neoformans, showing an IC50value of 15 µg mL-1and a MIC value of 40 µg 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.

A sensitive and reliable RP‐HPLC method was developed using a C18 CLC‐ODS (M) – 4.6×250 mm2 column and gradient elution for the analysis of phenolic compounds in propolis raw material and its products. A procedure for the extraction of phenolic compounds using aqueous ethanol (90%) with the addition of veratraldehyde as the internal standard (IS) was developed allowing to quantify ten compounds: caffeic acid, coumaric acid, ferulic acid, cinnamic acid, aromadendrin‐4′‐methyl ether (AME), isosakuranetin, drupanin, artepellin C, baccharin, and 2,2‐dimethyl‐6‐carboxyethenyl‐2H‐1‐benzopyran acid (DCBEN). The developed method gave good detection response and linearity in the range of 20.83–533.33 μg/mL.

Diketopiperazines (DKPs) corresponding to cyclic dipeptides have been reported to exhibit antimicrobial, antitumor, antimutagenic and antiviral properties. These compounds are commonly isolated from microorganisms and sponges and from a variety of tissues and body fluids. In this work, we used electrospray ionization tandem mass spectrometry (ESI‐MS/MS) to investigate the fragmentation of a series of DKPs previously isolated from Aspergillus fumigatus, which exhibit the same structural core. Loss of CO directly from the protonated molecule was found to be a fragmentation process common to all the compounds analyzed. However, our results revealed a series of ions that are diagnostic for the substituents at C(4) and C(9). In order to rationalize the differences in the fragmentation pathways of substituted and nonsubstituted DKPs, the relative Gibbs energies (ΔG) of the product ions and intermediate ions were estimated using the B3LYP/6–31 + + G(d,p) model. The data reported here can be used for the structural elucidation of DKPs from low sample amounts, as an alternative to NMR. Copyright © 2007 John Wiley & Sons, Ltd.

We have performed a trypanocidal bioactivity‐guided study of Baccharis dracunculifolia(Asteraceae), the main botanical origin of Brazilian green propolis. The leaf rinse extract of B. dracunculifolia, at a concentration of 3.0 mg mL−1, displayed 100% lysis of trypomastigote forms of the Y strain of Trypanosoma cruzi(2 times 106parasites mL−1). The chromatographic fractionation of the leaf rinse, using several techniques, afforded the isolation of the compounds isosakuranetin (1), aromadendrin‐4′‐methylether (2), baccharis oxide (3), ferulic acid (4), dihydrocinnamic acid (5), 3‐prenyl‐4‐(dihydrocinnamoyloxy)‐cinnamic acid (6), and friedelanol (7). The chemical structures of all compounds were established by UV‐vis, 1H and 13C NMR data analysis in comparison with the literature. Compounds 1and 3were the most active in the trypanocidal assay, showing IC50 values (inhibitory concentration required for 50% inhibition) of 247.6 and 249.8 μM, respectively. Compounds 2, 4, and 6displayed moderate activity, whilst compounds 5and 7were inactive.

The bioactivity‐guided phytochemical investigation of the crude hydralcoholic extract of Nectandra megapotamicawas carried out using the abdominal constriction test in mice, which led to the isolation of three active compounds: α‐asarone (1), galgravin (2) and veraguensin (3). The crude extract (EBCA, 300 mg kg−1) and isolated compounds 1, 2, and 3, at different doses, were evaluated using the acetic acid‐induced abdominal constriction test in mice, carrageenan‐induced paw oedema in rats, and hot plate tests in rats. The EBCA showed a significant effect in the abdominal constriction and hot plate tests, but did not show activity in the rat paw oedema assay. All isolated compounds displayed activity in the abdominal constriction test, but only compound 1was active in the hot plate test. Compounds 2and 3displayed activity in the anti‐inflammatory assay. It was suggested that the analgesic effects obtained for EBCA could be due mainly to the presence of its major compound, α‐asarone (1).

The aim of the present study was to develop a capillary gas chromatography method for the quantitative analysis of caffeine in Brazilian guarana as seed powder, dried crude ethanol extracts, and lyophilized water extracts with the addition of 7β‐Hydroxyethyltheophylline as the internal standard. The experimental protocol, the conditions, the analytical instrumentation, the recovery studies, as well as the analysis of seven different commercial batches of guarana, are presented and discussed.

Sulfluramid (N‐Ethylperfluorooctane sulfonamide) is a highly effective insecticide for controlling ants. It is usually incorporated into orange pellets at a concentration of 0.3%, in combination with 4 to 6% soybean oil. The objective of the present study was to develop a capillary gas chromatography method for the quantitative analysis of sulfluramid and its isomers in orange pellet baits with the addition of 1,2,4,5‐tetramethylbenzene as the internal standard. The proposed method proved to be rapid and reliable for the analysis of sulfluramid and its isomers in both raw material and baits. The experimental protocol, the conditions, and the equipment for analysis, as well as the recovery studies, are presented and discussed.

In previous studies, Zanthoxylum naranjillohexane crude extract revealed marked analgesic and antimalarial activities. This paper reports an investigation of preclinical toxicity in acute phase ( 24 h and 15 days with repeated doses ) in which the action of different extract doses ( 15, 150 and 450 mg/kg ) was evaluated. Wistar rats weighing 300 ± 15 g were submitted to toxicological evaluation of clinical chemical, haematological and haemostatic blood parameters including evaluation of liver, pancreas, kidneys, bile ducts, heart, serum lipids, bonc marrow, haematological and haemostatic systems. The initial results showed an alteration of albumin and alkaline phosphatase at some of the doses tested, but without suggesting hepatic or biliary involvement. Copyright © 1998 John Wiley & Sons, Ltd.

Propolis is one of the most widely used products in traditional medicine. One of the most prominent types of Brazilian propolis is the red one, whose primary botanical source is Dalbergia ecastaphyllum(L.) Taub. Despite the potential of Brazilian red propolis for developing new products with pharmacological activity, few studies guarantee safety in its use. The objective of this study was the evaluation of the possible toxic effects of Brazilian red propolis and D. ecastaphyllum, as well as the cytotoxicity assessment of the main compounds of red propolis on tumoral cell lines. Hydroalcoholic extracts of the Brazilian red propolis (BRPE) and D. ecastaphyllumstems (DSE) and leaves (DLE) were prepared and chromatographed for isolation of the major compounds. RP-HPLC-DAD was used to quantify the major compounds in the obtained extracts. The XTT assay was used to evaluate the cytotoxic activity of the extracts in the human fibroblast cell line (GM07492A). The results revealed IC50values of 102.7, 143.4, and 253.1 μg/mL for BRPE, DSE, and DLE, respectively. The extracts were also evaluated for their genotoxic potential in the micronucleus assay in Chinese hamster lung fibroblasts cells (V79), showing the absence of genotoxicity. The BRPE was investigated for its potential in vivotoxicity in the zebrafish model. Concentrations of 0.8–6.3 mg/L were safe for the animals, with a LC50of 9.37 mg/L. Of the 11 compounds isolated from BRPE, medicarpin showed a selective cytotoxic effect against the HeLa cell line. These are the initial steps to determine the toxicological potential of Brazilian red propolis.

Biotransformation of 16α,17-epoxy-ent-kaurane-19-oic acid (1) by Beauveria sulfurescensATCC 7159-F led to the production of a new ent-kaurane diterpenoid, 7β,17-dihydroxy-ent-kaur-15-en-19-oic acid (7), and four other ent-kauranes (8 - 11), all of which were identified as their methyl esters. Compounds 9and 10were found to be new stereoisomers. Structures of these were established by the extensive usage of their spectroscopic characteristics.

Hydroethanolic extracts of C. langsdorffiileaves have therapeutic potential. This work reports a validated chromatographic method for the quantification of polar compounds in the hydroethanolic extract of C. langsdorffiileaves. A reliable HPLC method was developed using two monolithic columns linked in series (100 × 4.6 mm – C18), with nonlinear gradient elution, and UV detection set at 257 nm. A procedure for the extraction of flavonols was also developed, which involved the use of 70% aqueous ethanol and the addition of benzophenone as the internal standard. The developed method led to a good detection response as the values for linearity were between 10.3 and 1000 μg/mL, and those for recovery between 84.2 and 111.1%. The detection limit ranged from 0.02 to 1.70 μg/mL and the quantitation limit from 0.07 to 5.1 μg/mL, with a maximum RSD of 5.24%. Five compounds, rutin, quercetin-3-O-α-L-rhamnopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, quercetin and kaempferol, were quantified. This method could, therefore, be used for the quality control of hydroethanolic extracts of Copaiferaleaves and their cosmetic and pharmaceutical products.