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The antinociceptive and anti-inflammatory activities of crude ethanolic extract of Celtis iguanaea leaves and their active fractions are reported. The oral treatment with crude ethanolic extract (CEE; 100, 300 or 1000 mg/Kg) inhibited the number of writhings in a dose-dependent manner. The intermediate dose also inhibited formalin-induced nociception in both phases. The oral treatment with dichloromethane fraction (DF; 9 mg/Kg) produced antinociceptive effect in both phases of formalin test; however, the treatment with ethyl acetate fraction (EAF; 16 mg/Kg) reduced pain only in the second phase of this test. The oral treatments with CEE (300 mg/Kg) or DF (9 mg/Kg) reduced the nociception induced by capsaicin and pre-treatment with naloxone did not change these effects. The oral administration of CEE (300 mg/Kg), DF (9 mg/Kg) or ethyl EAF (16 mg/Kg) reduced ear edema, leukocytes migration and myeloperoxidase activity. Furthermore, the oral treatment with CEE (300 mg/Kg) or EAF (16 mg/Kg) reduced the level of Tumor Necrosis Factor - Alpha (TNF-α) in the pleurisy test. In conclusion, the DF showed antinociceptive activity that involves the vanilloid system as well as anti-inflammatory effect and the EAF showed anti-inflammatory activity involving the reduction of TNF-α cytokine.

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ABSTRACT In this work, we developed and validated a HPLC-PDA method for the quantification of hibalactone in Hydrocotyle umbellata L., Araliaceae, subterraneous parts extracts and optimized its ultrasound-assisted extraction. Chromatographic separations were carried out with an isocratic mobile phase of acetonitrile/methanol/water (10:65:25), a flow of 0.8 ml min−1, detection at 290 nm and C18 column (250 × 4.6 mm, 5 µm). The method validation parameters were determined according to Brazilian legislation. The optimization of the hibalactone ultrasound-assisted extraction was performed using Box-Behnken design and response surface methodology. The HPLC method for hibalactone quantification proved to be selective, linear, precise, accurate and robust, being useful for the analysis of hibalactone in H. umbellata subterraneous parts extracts. The optimal ultrasound-assisted extraction conditions were obtained with solid-to-liquid ratio of 1:5 g ml−1, ethanolic strength of 70% (v/v) and temperature of 65 °C. The results can provide support of the quality control and standardization of raw materials from H. umbellata.

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Abstract Trembleya parviflora (D. Don) Cogn., Melastomataceae, also known as "quaresmeira-branca", is a subshrub that is commonly used to treat verminosis, scabies, dermatoses, rheumatism, vaginal infections, ulcerations and wounds. The aim of this work was to perform a morphological study of T. parviflora, evaluate the composition and chemical variability of the volatile oils from the leaves, perform phytochemical screening of the powder from the leaves and to define parameters for quality control of the plant material. Macroscopic characterization of T. parviflora was carried out by naked eye in Serra dos Pireneus, Pirenópolis, Goiás for 12 months. Volatile oils were subjected to hydrodistillation with Clevenger apparatus and analyzed by gas chromatography-mass spectrometry. Phytochemical screening and ash and volatile compound content determination were performed by conventional techniques. T. parviflora has simple, oppositely crossed and petiolate leaves. The inflorescence of this plant is a cyme. The presence of coumarins, steroids, triterpenes, flavonoids and tannins was observed. The total ash content was 4.05 ± 0.02%; the insoluble ash content was 0.10 ± 0.03%; and the volatile compound content was 9.53 ± 0.02%. The major compounds present in the volatile oils were α-terpineol (2.7-16.5%), α-pinene (0.6-25.4%), β-pinene (2.7-23.1%), sabinene (1.2-14.1%), acetoxyeudesman-4-α-ol (0.6-6.3%) and 2,4a-8,8-tetramethyldecahydrocyclopropanaphtalene (2.4-24.4). Two clusters were identified: Cluster I represented the period with low levels of rainfall, and Cluster II represented the period with high levels of rainfall. This study provides data that can be applied for the quality control of powdered leaves and is the first description of the chemical composition and variability of the volatile oils from the leaves of T. parviflora.

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ABSTRACT Campomanesia adamantium (Cambess.) O. Berg., Myrtaceae, is a plant popularly used for its anti-inflammatory, anti-diarrhoeal and urinary antiseptic activities. The aims of this study were to obtain the crude ethanolic extract and the hexane, dichloromethane, ethyl acetate, aqueous and concentrated aqueous tannin fractions from C. adamantium leaves, perform biomonitored fractionation to isolate and identify chemical compounds, study the chemical composition of the volatile oils of the leaves and flowers and test the antimicrobial activity of the ethanolic extract, fractions, isolated substances and volatile oils. Phytochemical screening and chromatographic and spectrometric techniques were used. Volatile oils were isolated by hydrodistillation in a Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The antimicrobial activity was tested by a broth microdilution test. The component stictane-3,22-diol was isolated and identified from the hexane fraction, while valoneic and gallic acid were isolated and identified from the concentrated aqueous tannin fraction. The major constituents of the volatile oils of the leaves were verbenene (13.91%), β-funebrene (12.05%) and limonene (10.32%), while those of the volatile oils of the flowers were sabinene (20.45%), limonene (19.33%), α-thujene (8.86%) and methyl salicylate (8.66%). Antibacterial activity was verified for the hexane fraction, while antifungal activity was observed for the aqueous fraction and concentrated aqueous tannin fraction and for vanoleic acid. These results may justify the popular use of C. adamantium.

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ABSTRACT Spiranthera odoratissima A. St.-Hil., Rutaceae, known as "manacá" is a shrub native of the Brazilian Cerrado. Their leaves and roots are popularly used to treat rheumatism, infection and abdominal pain. This study analyzed the chemical composition of volatile oils from leaves of S. odoratissima and verified the seasonal variability of its chemical composition. The volatile oils were obtained by hydrodistillation using a Clevenger type apparatus and analyzed by gas chromatography coupled to mass spectrometry. The main chemical components found in samples of volatile oils were β-caryophyllene, bicyclogermacrene, δ-cadinene, amorphous-4,7(11)-diene, α-epi-muurolol, α-cadinol, α-muurolol and γ-cadinene. The hierarchical clustering identified three groups: the first was characterized by α-epi-muurolol, the second by amorphous-4,7(11)-diene and the third group was characterized by α-muurolol. The discriminant canonical analysis was used to differentiate between clusters on the basis of oil composition. The results suggest that the rainfall presented a relationship with the chemical composition of the volatile oil. This is the first study conducted on the seasonal behavior of the chemical constituents in volatile oil from leaves of S. odoratissima.

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Abstract This paper describes the quantification of catechin in the spray-dried extract of Pimenta pseudocaryophyllus (Gomes) Landrum, Myrtaceae, citral chemotype using a validated HPLC-PDA method. The method employs a RP-18 column with acetonitrile:water-orthophosphoric acid 0.05% (gradient system) and UV detection at 210 nm. The method was demonstrated to be simple, sensitive, specific, linear, precise, accurate and robust. The response was linear over a range of 5-200 µg/ml (r > 0.999). The range of recoveries was 92.27-102.54%. The relative standard deviation values for intra- and inter-day precision studies were 4.30 and 3.78%, respectively. This assay can be readily utilized as quality control method for catechin in the dried extract of P. pseudocaryophyllus.

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ABSTRACT Trembleya phlogiformis DC., Melastomataceae, is a shrub whose leaves are used as a dye for dyeing wool and cotton. The present article aimed to carry out the morphological description of the species, to study the chemical composition of volatile oils from the leaves and flowers and the seasonal variability from the leaves during a year. Macroscopic characterization was carried out with the naked eye and with a stereoscopic microscope. Volatile oils were isolated by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The major components of the volatile oil of T. phlogiformis flowers were: n-heneicosane (33.5%), phytol (12.3%), n-tricosane (8.4%) and linoleic acid (6.1%). It was verified the existence of a large chemical variability of the volatile oils from the leaves of T. phlogiformis over the months, with the majority compound (oleic alcohol, ranging from 5.7 to 26.8%) present in all samples. A combination of Cluster Analysis and Principal Component Analysis showed the existence of three main clusters, probably related to the seasons. The results suggested that the volatile oils of T. phlogiformis leaves possess high chemical variability, probably related to variation associated with rainfall and the variation in the behavior of specimens throughout the year. This research provides insights for future studies on the volatile oils obtained from the T. phlogiformis leaves and flowers, mainly related to biological markers of applications monitored in the leaves and flowers of this species.

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ABSTRACT A 33 Box–Behnken design and Response Surface Methodology were performed to evaluate the influence of extract feed rate, drying air inlet temperature and spray nozzle airflow rate on the process yield, stability parameters (moisture content and water activity) and on several physicomechanical properties of spray-dried rosemary extracts. Powder yield ranged from 17.1 to 74.96%. The spray-dried rosemary extracts showed moisture content and water activity below 5% and 0.5%, respectively, which indicate their chemical and microbiological stabilities. Even without using drying aids, some sets of experimental conditions rendered dried products with suitable flowability and compressibility characteristics for direct preparation of solid dosage forms. Analysis of variance and Response Surface Methodology proved that studied factors significantly affected most of the spray-dried rosemary extract quality indicators at different levels. The main processing parameter affecting the spray-dried rosemary extract characteristics was inlet temperature. The best combination of parameters used to obtain a reasonable yield of stable dry rosemary extracts with adequate technological properties for pharmaceutical purpose involves an extract feed rate of 2 ml/min, 80 °C inlet temperature and 40 l/min SA. The design of experiments approach is an interesting strategy for engineering spray-dried rosemary extracts with improved characteristics for pharmaceutical industrial purpose.

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ABSTRACT Hyptis carpinifolia Benth., Lamiaceae, is a species known popularly as "rosmaninho" and "mata-pasto", and leaves are employed in Brazilian folk medicine to treat colds, flu, and rheumatism. The aim of this study was to perform a morphological description of H. carpinifolia and to evaluate the seasonal chemical variability of the leaf essential oils during 12 months. Macroscopic characterization of H. carpinifolia was carried out with the naked eye and with a stereoscopic microscope. Essential oils were isolated from leaves by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. Major compounds were found to be 1,8-cineole (39.6-61.8%), trans-cadina-1(6),4-diene (2.8-17.5%), β-caryophyllene (4.4-10.0%), prenopsan-8-ol (4.2-9.6%) and β-pinene (2.9-5.3%). Results of essential oils compositions were processed by cluster analysis and principal component analysis. Data showed high variability in the concentration of the components. Besides, there was a seasonal variability of chemical composition, probably related mainly to the rainfall regime.

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Memora nodosa is popularly known as "caroba" and widely found in the Cerrado regions of Brazil. In traditional medicine, the leaves and stems are used for the healing of external ulcer and the roots for abdominal pain. This study investigated the effect of ethanolic roots extract of Memora nodosa (EMN) on the gastric mucosa of mice. In the indomethacin induced gastric ulcer model, the treatments of the animals with EMN at doses of 100, 300 and 1000 mg/kg, p.o., markedly reduced the index of lesions. In the gastric ulcer models induced by ethanol and cold restraint-stress the previous treatment with EMN at dose of 300 mg/kg showed 69% and 43% of protection, respectively. Seven days after food-restriction, the animals treated with EMN (300 mg/kg p.o.) showed reduction in the index of lesion by 65% as compared to control group. The intraduodenal administration of EMN (300 mg/kg) did not alter the gastric acid secretion parameters. The treatment with EMN (300 mg/kg p.o.) did not alter glutathione levels (GSH), but showed an increase of adhered gastric mucus as compared to the control group with lesion. These results showed that EMN has gastroprotective activity probably due with an increase of adhered gastric mucus.

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Trichogonia cinerea is endemic to Brazil and occurs in areas of cerrado and campo rupestre. In this study, we characterized the glandular and non-glandular trichomes on the aerial parts of this species, determined the principal events in the development of the former, and identified the main constituents of the volatile oil produced in its aerial organs. Fully expanded leaves, internodes, florets, involucral bracts, and stem apices were used for the characterization of trichomes. Leaves, internodes, florets, and involucral bracts were examined by light microscopy and scanning electron microscopy, whereas stem apices were examined only by light microscopy. Branches in the reproductive phase were used for the extraction and determination of the composition of the volatile oil. The species has three types of glandular trichomes, biseriate vesicular, biseriate pedunculate, and multicellular uniseriate, which secrete volatile oils and phenolic compounds. The major components identified in the volatile oil were 3,5-muuroladiene (39.56%) and butylated hydroxytoluene (13.07%).

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The occurrence of thickened underground systems in Asteraceae is widely reported in the literature. Given the great complexity of underground systems, which may originate from roots, stems, or both, morpho-anatomical analyses are essential to ensure the use of correct terminology. The goals of this study were to describe the morpho-anatomy and ontogeny, investigate the occurrence of secondary metabolites and evaluate the effects of seasonality on the underground system of Chrysolaena simplex (Less.) Dematt. Samples were studied using standard protocols of plant anatomy, scanning electron microscopy, histochemical and phytochemical. The underground system of C. simplex was categorised as a rhizophore which started from cotyledonary node. In adult individuals, with rhizophores completely developed, the primary roots degenerated and adventitious radicular systems are formed. The buds in the subterranean portions promote the rhizophore growing, and form aerial stems when exposed to light. Lipophilic droplets were evident in the parenchymatous cells of the cortex and pith, endodermis and buds. Inulin-type fructans were observed in the stem axis and buds of the rhizophore. The presence of buds, secondary metabolites and the storage of fructans and lipids in the rhizophore can be seen as adaptive traits.

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Abstract Hortia oreadica Groppo, Kallunki & Pirani, Rutaceae, known as “para-tudo”, “quina”, and “quina-do-campo”, is used in traditional medicine locally to treat stomach pain and fevers. The aims of this study were: analyze the chemical composition of essential oils from leaves, flowers and fruits of H. oreadica and verify the seasonal variation of the chemical components of essential oils from leaves. The essential oils were obtained by hydrodistillation using a Clevenger type apparatus and analyzed by GC/MS. The major components found in the samples of the essential oils were the amorpha-4,7(11)-diene (29.27% – flowers, 20.26% – fruits, 27.66–37.89% – leaves), bicyclogermacrene (23.28% – flowers, 20.64% – fruits, 14.71% to 31.37% – leaves). This work represents the first study of the chemical composition of essential oils from leaves, flowers and fruits and seasonal variation in the essential oils from leaves of H. oreadica.

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ETHNOPHARMACOLOGICAL RELEVANCE: Lafoensia pacari A. St.-Hil. (Lythraceae), known popularly as "pacari" or "mangaba-brava" is popularly used in the state of Goiás, Brazil. The stem bark or leaves are used to treat cancer, gastric disorders, inflammation and as a tonic to treat loss of enthusiasm. AIM OF THE STUDY: Previous results suggest that the ethanol:water 7:3 extract of the stem bark of L. pacari (PEx) has antidepressant-like activity in male mice. Our aim was to perform the PEx׳s bioguided fractionation and evaluate the monoaminergic system involvement in the antidepressant effect as well as progress in the study of L. pacari mechanism of action. MATERIAL AND METHODS: Mice (30-35g) orally treated (24, 5 and 1h) with PEx (100, 300 or 1000mg/kg), chloroform (ChloF-70mg/kg), ethyl acetate (180mg/kg), n-butanol (370mg/kg) and aqueous (1g/kg) fractions were submitted to the forced swimming test. To assess the mechanism of action, different groups of mice were pretreated with p-chlorophenylalanine (PCPA-100mg/kg, 4 days, i.p.) and alpha-methyl-p-tyrosine (AMPT-100mg/kg, 4h, i.p.) to assess the involvement of serotoninergic and catecholaminergic systems in the ChloF effects, respectively. A putative in vitro inhibition of monoamine oxidase (MAO) activity as well as the ex vivo hippocampal brain-derived neurotrophic factor (BDNF) quantification were carried out. Phytochemical screening, spectroscopy and chromatography analysis were used for identification of compounds present in ChloF. RESULTS AND DISCUSSION: After the fractionation, the ChloF 70mg/kg was the most active fraction, reducing the immobility time by 22%. Pre-treatments with both PCPA and AMPT abolished the ChloF effects, suggesting that ChloF antidepressant-like effect is dependent on serotonergic and catecholaminergic systems. ChloF did not inhibited MAO-A or MAO-B activity, excluding this as possible mechanism of action. ChloF augmented hippocampal BDNF level, which could be accounted for its antidepressant-like effect. Phytochemical screening showed the presence of saponins, tannins, steroids and triterpene in the PEx, and the presence of triterpene and steroids in ChloF. The spectroscopy and chromatography analysis identified lupeol, ß-sitosterol and stigmasterol in ChloF. CONCLUSION: ChloF is the fraction that better retained the crude extract active constituents. ChloF presents antidepressant-like effect that involves both serotonergic and catecholaminergic systems without inhibiting MAO enzymatic activity; this fraction also increases the hippocampal BDNF levels.

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Eugenia calycina, which is described as "red pitanga or pitanga cherry of cerrado," is widely distributed in the Cerrado area of Brazil. Its leaf and bark extracts are used in folk medicine for many applications. In this study, the compositions of the major polar compounds of the bark and leaf extracts and their fractions were obtained from a liquid-liquid extraction using hexane, dichloromethane, ethyl acetate, and water. They were then evaluated using electrospray ionization negative FT-ICR mass spectrometry (ESI(-) FT-ICR MS), which revealed a large number of oxygen-containing compounds, such as flavonoids, terpenes, tanins, steroids, and fat acids. The biological activity of these extracts towards several bacterial and fungal strains was then evaluated. The highest activity was found using aqueous fractions, in which the ESI(-) FT-ICR MS analysis revealed compounds with a high content of oxygen (e.g., glycosed flavonoids, tannins, and polyphenolic compounds) against Cryptococcus sp. D (minimum inhibitory concentration [MIC]=15.62µg/mL). Strong activity was also found using the hexanic fractions-in which the ESI(-) FT-ICR MS analysis revealed that the compounds contained a decreased amount of oxygen (e.g., fat acids and steroids)-towards Cryptococcus gatti L48, Cryptococcus neoformans L3 (MIC=31.2µg/mL), and Cryptococcus sp. D (MIC=62.5µg/mL). Therefore, antimicrobial assays using the bark/leaf extracts of E. calycina present prospects for the research of active substances that may be used for the treatment of cryptococcosis, a disease that is common in immunosuppressed patients.

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BACKGROUND: Stryphnodendron adstringens (Mar.) Coville is a native plant from Brazil, rich in phenolic compounds and used on popular medicine as a wound healing agent, in the treatment of gastric lesions and as antimicrobial. MATERIALS AND METHODS: Ultrassound-assisted extraction (UAE) was applied to extraction of epigallocatechin gallate (EGCG), total polyphenols (TP) and total tannins (TT) content from barks of Stryphnodendron adstringens (Mar.) Coville. Several operating parameters, namely extraction time (min), liquid to solid ratio (mg/mL), ethanolic strength (%, v/v), were optimized using response surface methodology (RSM) with a Box-Behnken design. RESULTS: By using the desirability function approach, the optimum UAE conditions to obtain desirable extraction yields for all these metabolites simultaneously were found at the extraction time of 30 min, solid to liquid ratio of 4 mg/mL and ethanolic strength of 65. Under these conditions, the epigallocatechin gallate, total polyphenols and total tannins content were 0.31; 22.95 and 11.95 % (w/w), respectively. CONCLUSION: The results indicated that knowledge gained from this study should be helpful to further exploit and apply this resource and also showed the feasibility of ultrasound-assisted extraction for obtaining GEGC, TP and TT from barks of S. adstrigens.

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The leaves of Myrcia tomentosa were collected from five sites and four different months in the Brazilian Cerrado and their essential oils were obtained by hidrodistillation and analyzed by GC/MS. The aim of this work was to evaluate the influence of environmental factors on essential oils composition in the leaves of M. tomentosa. The results were submitted to stepwise Multiple Regression and Canonical Correlation Analysis that indicated a relationship between compounds in essential oils and some environmental factors (foliar nutrients, soil nutrients and climatic data). Cluster Analysis indicated a high chemovariability in the essential oils from different sites, also showed that the collection time had a minor effect on oil composition.

Las hojas de Myrcia tomentosa se obtuvieron de cinco sitios diferentes y cuatro meses en el Cerrado brasileño y sus aceites esenciales fueron obtenidos por hidrodistillation y analizados por GC/MS. El objetivo de este trabajo fue evaluar la influencia de los factores ambientales sobre la composición de los aceites esenciales en las hojas de M. tomentosa. Los resultados fueron sometidos a múltiples etapas de regresión y análisis de correlación canónica indicó que la relación entre los compuestos en los aceites esenciales y algunos factores ambientales (nutrientes foliares, fertilizantes y datos climáticos). El análisis de agrupamiento indicó chemovariability un alto en los aceites esenciales de diferentes sitios, también mostró que el equipo de recolección tuvo un efecto menor sobre la composición del aceite.

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Ethnobotanical surveys of Cerrado native plants show that leaves of Celtis iguanaea (Jacq.) Sargent (Cannabaceae), popularly known in Brazil as "esporão de galo", are used in folk medicine for body pain, asthma, cramps, poor digestion, urinary infection, kidney dysfunctions, as well as a stimulant and diuretic. This work aimed at evaluating possible C. iguanaea aqueous leaf extract (CALE) cytotoxicity, genotoxicity, and antigenotoxicity using the mouse bone marrow micronucleous test. To assess CALE genotoxicity, Swiss mice were orally treated with three different extract concentrations (100, 300, and 500 mgkg-1). To evaluate its antigenotoxicity, the same doses were used simultaneously with a single i.p. dose of mitomycin C (MMC, 4mg.kg-1). The frequencies of micronucleated polychromatic erythrocytes (MNPCE) were evaluated 24 h and 48 h after administration except for the negative control (24 h). Genotoxicity was evaluated using the frequency of micronucleated polychromatic erythrocytes (MNPCE), whereas cytotoxicity was assessed by the polychromatic and normochromatic erythrocytes ratio (PCE/NCE). The results showed that CALE did not exhibit a significant reduction in the PCE/NCE ratio, neither a considerable increase in the frequency of MNPCE. Nonetheless, CALE reduced bone marrow toxicity (increased PCE/NCE ratio) and decreased the micronuclei frequency induced by MMC. We can conclude that CALE presented no cytotoxic and genotoxic effects, but showed antigenotoxic and anticytotoxic actions under the experimental conditions applied in this study.

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The Hydrocotyle umbellata L. is a specimen of the Araliaceae family popularly known as acariçoba. Its indications in folk medicine include treatment of skin ulcers, and rheumatism. The aim of this study was to evaluate the antinociceptive and anti-inflammatory activities of the ethanolic extract from acariçoba's underground parts (EEA). EEA reduced the nociceptive response of the animals as evaluated in the acetic acid-induced writhing test and in both phases of formalin test. EEA also presented a supraspinal analgesic activity by increasing the pain latency in the hot plate test. Moreover, EEA reduced the leukocytes migration and plasma extravasation to pleural cavity in the carrageenan-induced pleurisy, besides reducing the edema induced by carrageenan until the second hour and also the edema induced by dextran. In conclusion our results showed that EEA of H. umbellata L. presents analgesic and anti-inflammatory activities, and that a blockade of activity or reduction in the release of different mediators, such as histamine and serotonin, could be involved in these pharmacologic effects.

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This study aimed to impact of different extraction methods on the quality of Dipteryx alata Vogel, Fabaceae, extracts from fruits. The major compounds found were the lipids 38.9% (w/w) and proteins 26.20% (w/w). The residual moisture was 7.20% (w/w), total fiber 14.50% (w/w), minerals 4.10% (w/w) and carbohydrate 9.10 % (w/w). The species studied has great potential in producing oil, but the content and type of fatty acids obtained is dependent on the method of extraction. The Blingh & Dyer method was more selective for unsaturated fatty acids and Shoxlet method was more selective for saturated fatty acids. The tannin extraction by ultrasound (33.70 % w/w) was 13.90% more efficient than extraction by decoction (29 % w/w).