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Brasiliensic acid (Bras) is a chromanone isolated from Calophyllum brasiliense Cambèss. bark extracts with confirmed potential activity on gastric ulcer and Helicobacter pylori infection. This study aimed to investigate the in vitro and in vivo toxicity of Bras and molecular docking studies on its interactions with the H. pylo ri virulence factors and selected gastric cancer-related proteins. Cytotoxicity was evaluated by alamarBlue© assay, genotoxicity by micronucleus and comet assays, and on cell cycle by flow cytometry, using Chinese hamster epithelial ovary cells. Bras was not cytotoxic to CHO-K1 cells, and caused no chromosomal aberrations, nor altered DNA integrity. Furthermore, Bras inhibited damages to DNA by H 2 O 2 at 1.16 µM. No cell cycle arrest was observed, but apoptosis accounted for 31.2% of the cell death observed in the CHO-K1 at 24 h incubation of the IC 50 . Oral acute toxicity by Hippocratic screening test in mice showed no relevant behavioral change/mortality seen up to 1,000 mg/kg. The molecular docking approach indicated potential interactions between Bras and the various targets for peptic ulcer and gastric cancer, notably CagA virulence factor of H. pylori and VEGFR-2. In conclusion, Bras is apparently safe and an optimization for Bras can be considered for gastric ulcer and cancer.Communicated by Ramaswamy H. Sarma.

Floodplains were the first deforested areas for agriculture use all over the world. In Brazil these areas can be restored by the growth of guanandi Calophyllum brasiliense, a slow-growing native forest species adapted to flooding. The aims of this study were to: (i) evaluate the taro, Colocasia esculenta, management under two agroforestry systems (AFS) (Simple and Biodiverse) in succession to a reforestation with guanandi, (ii) evaluate the contribution of macronutrients from the green manure Flemingia macrophylla and Sesbania virgata, both managed using pruning for green manure in the respective AFSs, and (iii) the effects on soil nutrients levels compared to monoculture of guanandi (control). The randomized block was designed with eight replication and 216.0 m² plots with four rows of six guanandi trees in each line. In the simple AFS (SAFS), the taro was intercropped with Flemingia and in the biodiverse AFS (BAFS), Sesbania, banana shrub (Musa sp.), edible palm (Euterpe edulis) and fourteen species of native trees were included. Production was evaluated in seasons with high rainfall and water scarcity. With floods the taro has produced around 15 Mg ha-1 of marketable corms in the SAFS and 9 Mg ha-1 in the BAFS, but the drought has made commercial production unfeasible, with no differences between cormels and corms planting. However, enough rhizomes were harvested for a new planting. Flemingia has accumulated 17 Mg ha-1 of fresh matter and Sesbania contributed with 2 Mg ha-1. Soil pH and macronutrient content, especially K, were significantly higher in AFSs areas compared to guanandi monoculture.

Introduction: The species Calophyllum brasiliense Cambés (Calophyllaceae) is widespread throughout Central and South America. The stem bark infusion is used for lowering blood glucose. Aim: To optimize the spray dry extract of this plant using a D-optimal experimental design. Materials and methods: As factors were used the air-drying speed (3.5-4.5 m3/h), the feed flow rate of the suspension (5-11 mL/min), and the inlet air temperature (90-130 °C). The dried extract was characterized by measuring the phenolics and flavonoids content, moisture, the water activity, apparent densities, flowability, and compressibility. The antioxidant activity, the inhibitory activity of lipase and alpha-glycosidase, and the antiglycant activity of the spray dried extract (SDE) were evaluated. Subsequently, the hypoglycemic activity was evaluated in rats by monitoring the blood glucose level, triglycerides, and cholesterol. Results: Inlet air temperature and feed flow rate were the factors that most affected the yield and phenolic content. SDE showed a potent antioxidant effect (IC50 1.83 μg/mL), a potent α-glycosidase (IC50 74.45 μg/mL) and pancreatic lipase (IC50 27.33 μg/mL) inhibition. A potent antiglycation effect (IC50 9.45μg/mL) was also observed. Conclusion: the SDE showed a potent hypoglycemic effect at 100 mg/kg. These results suggest that SDE could activate four important pathways that can contribute to diabetes control. [ABSTRACT FROM AUTHOR]

Objective: The objective was to quantify the morphological diversity of Calophyllum brasiliense Cambes from four municipalities of the State of Tocantins employing morphological characteristics, to strengthen information on conservation and future breeding of the species. Methodology: Seeds were collected from four municipalities in the State of Tocantins and one in the State of São Paulo. The following were evaluated: plant height, stem diameter, root length, number of leaves, leaf area, root dry mass, shoot dry mass, total dry mass, and Dickson's quality index. The data were subjected to univariate analysis of variance, Tocher grouping method, and UPGMA, obtaining a dendrogram through the generalized Mahalanobis distance. Results: The results showed a statistical difference of 1 and 5% probability. Dueré stood out in stem diameter (5.52 mm), Sandolandia in height (34.84 cm) and root length (42.13 cm). Formoso stood out in the number of leaves (34 leaves). Lagoa da Confusão in leaf area (856.28 cm ) and São Paulo in root dry mass (16.20 g), shoot dry mass (12.38 g), total dry mass (16.20 g), and Dickson's quality index (1.57). Implications: Variations in morphological characteristics can be used as a tool for genetic studies of guanandi progeny according to their similarity and/or differences. Conclusions: The morphological divergence evidenced that among the five studied areas it is possible to direct the collection of seeds to subsidize conservation strategies and future breeding of the species. [ABSTRACT FROM AUTHOR]

Abstract: The objective of this work was to determine the relationship of the morphological and physiological characteristics of guanandi (Calophyllum brasiliense) fruit and seeds with ripening and harvesting time. The reproductive cycle of a native plant population, located in the coast of the state of Paraná, Brazil, was monitored from anthesis until fruit dispersion, during three years. Monthly harvests were performed, and the morphological and physical aspects (color, size, dry mass, and moisture content) of fruit and embryos were evaluated, as well as the physiological ones (germination and vigor) of seeds. The ripening process of guanandi seeds occurred between 200 and 240 days after anthesis (DAA), with anthesis peak in February and fruit dispersion in October. The maximum dry matter mass accumulation was not synchronized with the maximum physiological potential of the seeds. Germination potential was reached close to the middle of the maturation process, and maximum vigor at the end of the cycle. Fruit external color did not change from 110 DAA onwards. The morphological characteristics related to harvesting time are fruit pulp and embryo weakly adherent to the endocarp and to the tegument, respectively, as well as the dark-brown color of these tissues.

The objective of this work was to evaluate the growth of guanandi (Calophyllum brasiliense Cambess.) in floodplain, as homogeneous planting (control) and as two agroforestry systems - AFS (simple and biodiverse). Guanandi was planted in the Paraíba Valley, State of São Paulo in 2007. From 2011 to 2014, guanandi growth was evaluated in a randomized block design experiment with eight replications. The AFS consisted of planting annual crops between guanandi lines. The biodiverse AFS was formed with 16 tree species, banana shrubs (Musa sp.) and juçara palm (Euterpe edulis Mart.). Guanandi presented morphological similarity in homogeneous planting and agroforestry systems and reached, on average, 5.40 m of total height at seven years of age. The relative growth rate was similar in the three treatments with higher values attributed to the canopy radius (2.59%) and the circumference at 1.30 m above ground level (1.86%). Agroforestry systems are promising to combine the benefits of income generation and ecological restoration in planting guanandi in floodplain. [ABSTRACT FROM AUTHOR]

Background: The influence of soil nutrients on biosynthesis of secondary metabolites from tropical trees has been poorly investigated. Questions: Does the deprival of Ca2+ and K+ influence the production of pharmacologically active compounds in the seedling of Calophyllum brasiliense? Species study: Calophyllum brasiliense Cambess. Study site: Los Tuxtlas, Veracruz, Mexico; November 2005 to November 2009. Methods: The seedlings were obtained from seeds and subjected to different hydroponic treatments: 1) modified Hoagland solution (MHS), 2) MHS-Ca2+, and 3) MHS-K+. Growth, height, foliar biomass, and HPLC analysis were performed after 7 months. Results: Under hydroponic conditions Ca2+ and K+ deficiency induced the mortality of 53 % and 28 % of the seedlings, respectively. The foliar biomass, and plant height of the survivors were also drastically reduced. MHS-K+ treatment induced a 15, 4.2 and 4.3-fold decrease for calanolides B, C, and apetalic acid in the leaves, respectively. MHS-Ca2+ treatment induced a decrease of 4.3, and 2.4-fold for calanolide B, and C, respectively. Conclusion: Ca2+ is essential for survival of C. brasiliense seedlings under hydroponic conditions, Ca2+ and K+ are critical for growth, foliar production, and biosynthesis of apetalic acid, and calanolide B.

Guanandi is a native forest species with particularities that make it difficult to store of seeds, because of its recalcitrant behavior and since a specific and practical protocol to determine the moisture content of its seeds is not available yet. This work had the purpose to test procedures to determine the moisture content and to study different environmental conditions of the storage of the guanandi seeds. In order to determine the moisture content, the low-temperature oven method at 101 - 105°C was used, testing seed preparation methods (intact, cut in half and fragments smaller than 7.0 mm) and different drying periods. Four environments (wet chamber, dry chamber, cooler and laboratory environment) were tested for the storage of the seeds, with two packaging types, during four periods (0, 1, 2, 3 and 4 months). For the statistical analysis, a completely randomized design, with a factorial arrangement, was used for moisture content; a split-split plot design was used for storage. A regression analysis was performed to evaluate the physiological potential and moisture content during the storage, adjusting the significant equation by Tukey's test. From the obtained results, it was observed that the low-temperature oven method 101 - 105°C / 17 h, using intact seeds, should be used to determine the moisture content of guanandi seeds. The best combination of environment and packaging to store seeds was the laboratory environment condition (average between 19.6 - 23.1 °C and RH 53-62%) in polyethylene packaging. [ABSTRACT FROM AUTHOR]

A priority in restoration research is to seek methods that reach high levels of plant establishment at the lowest possible cost. Here, we test how direct seeding works with and without a plastic protector that covers seeds and seedlings in an early‐successional rainforest in Veracruz (Mexico). Two native species, Calophyllum brasiliense (barí) and Vochysia guatemalensis (corpo), at three topographic positions, were used. Germination rates with and without the protector were 84 versus 79% for C. brasiliense, and 98 versus 89% for V. guatemalensis, respectively. The protector significantly improved the germination only of V. guatemalensis. Plant survivorship of V. guatemalensis 27 months after seeding was significantly higher with the protector (78%) than without it (46%). For C. brasiliense, there were no differences in survivorship after 22 months with (61%) and without (54%) protector. In both species, the protector had no effect on height growth, which was significantly larger for seedlings located at the toeslope position. We developed a cost–benefit model that provides a threshold value at which the investment for protectors is justified by a resulting higher survivorship: If 27 months after seeding a treelet of V. guatemalensis is worth at least 0.83 USD on our sites, then the effect of the protector is worth the cost of its implementation (for C. brasiliense, survivorship was statistically undistinguishable with and without protector). We suggest that direct seeding with a plastic protector could be a promising alternative for forest restoration with suitable tree species. [ABSTRACT FROM AUTHOR]

Soulattrolide is a natural coumarin synthesized by the leaves of species of Calophyllum (Calophyllaceae) rain forest trees, including the American C. brasiliense, and the Asian C. teysmanii. Soulattrolide is a potent inhibitor of the reverse transcriptase from HIV‐1 (RT‐HIV‐1), and active against Mycobacterium tuberculosis. However, the effects of this coumarins on other systems, remains to be evaluated. C. brasiliense is used in traditional medicine for the treatment of pain and inflammation. Therefore, we decided to explore the antinociceptive, anti‐inflammatory activity of soulattrolide in mice, as well as, some of its possible effects on the CNS. Soulattrolide showed antinociceptive effects in the writhing test (ED50 = 33.8 mg/kg), as well as, in the formalin test with an ED50 = 7.9, and 22.1 mg/kg for Phases 1 and 2, respectively. The highest dose of soulattrolide (50 mg/kg) induced 40% of antinociception in the hot plate test. Regarding to anti‐inflammatory activity, in the 12‐O‐Tetradecanoylphorbol‐13‐acetate (TPA) test, soulattrolide showed an IC50 = 1.81 μmol/ear, whereas in the myeloperoxidase assay, it showed an inhibition of 87% (1 μmol/ear). Soulattrolide showed sedative effects on the pentobarbital‐induced sleeping time test, and the rotarod test, but lacked antidepressant activity on the tail suspension test. In conclusion, we report for the first time, the antinociceptive effects of soulattrolide in mice, like those of naproxen; soulattrolide also showed mild anti‐inflammatory activity, as well as mild sedative and anxiolytic properties, therefore, it has also activity on the CNS. [ABSTRACT FROM AUTHOR]

The phytoremediation potential of Brazilian trees species Calophyllum brasiliense, Eremanthus crotonoides, Hymenaea courbaril, Inga striata, and Protium heptaphyllum was investigated for contaminated soils containing ametryn and hexazinone. Visual injury, chlorophyll content, plant height, leaf temperature, leaf number, and water-efficient use were evaluated. Residual herbicides at soil substrates were analyzed by LC/MS. Among the species C. brasiliense and H. courbaril were tolerant to both herbicides. P. Heptaphyllum presented tolerance at ametryn treatment. E. crotonoides, I. striata, and P. heptaphyllum died in hexazinone treatment. A high content of residual ametryn was found for E. crotonoides. In ametryn treatment, residual herbicide has decreased for C. brasiliense and E. crotonoides species. C. brasiliense highlighted among others becoming a good agent for phytoremediation of soils contaminated with traces of ametryn and hexazinone. [ABSTRACT FROM AUTHOR]

Mast cells (MCs) are important effectors in allergic reactions since they produce a number of pre-formed and de novo synthesized pro-inflammatory compounds in response to the high affinity IgE receptor (FcεRI) crosslinking. IgE/Antigen-dependent degranulation and cytokine synthesis in MCs have been recognized as relevant pharmacological targets for the control of deleterious inflammatory reactions. Despite the relevance of allergic diseases worldwide, efficient pharmacological control of mast cell degranulation has been elusive. In this work, the xanthone jacareubin was isolated from the heartwood of the tropical tree Callophyllum brasilense , and its tridimensional structure was determined for the first time by X-ray diffraction. Also, its effects on the main activation parameters of bone marrow-derived mast cells (BMMCs) were evaluated. Jacareubin inhibited IgE/Ag-induced degranulation in a dose-response manner with an IC 50  = 46 nM. It also blocked extracellular calcium influx triggered by IgE/Ag complexes and by the SERCA ATPase inhibitor thapsigargin (Thap). Inhibition of calcium entry correlated with a blockage on the reactive oxygen species (ROS) accumulation. Antioxidant capacity of jacareubin was higher than the showed by α-tocopherol and caffeic acid, but similar to trolox. Jacareubin shown inhibitory actions on xanthine oxidase, but not on NADPH oxidase (NOX) activities. In vivo , jacareubin inhibited passive anaphylactic reactions and TPA-induced edema in mice. Our data demonstrate that jacareubin is a potent natural compound able to inhibit anaphylactic degranualtion in mast cells by blunting FcεRI-induced calcium flux needed for secretion of granule content, and suggest that xanthones could be efficient anti-oxidant, antiallergic, and antiinflammatory molecules. [ABSTRACT FROM AUTHOR]

This work aimed to study the effect of the Calophyllum brasiliense seed coat on the seed germination process. To this end, three experiments were conducted in laboratory, greenhouse and screenhouse. From a total of six treatments, five are related to the seed coat (mechanical scarification; mechanical scarification followed by 2 hours in water, chemical scarification, hot water immersion and complete seed coat removal) and one control. Laboratory and greenhouse experiments were conducted in a completely randomized design (CRD). Screenhouse experiment was conducted in a completely randomized block design (RBD). We evaluated the total percentage, the speed index and the average time of germination or emergence. Data were subjected to analysis of variance and means compared by LSD test, at 5%. Under the conditions of this work, it was possible to infer that, in laboratory, mechanical scarification followed by 2 hours in water increases the proportion and germination speed index (GSI), in the greenhouse, the complete seed coat removal increases the percentage and emergence speed index (ESI), and in the screenhouse, mechanical scarification followed by 2 hours in water and chemical scarification presented the best results. The average germination time was not significantly different in the three experiments evaluated.

O objetivo deste trabalho foi avaliar tipos de preparo de sementes de guanandi (Calophyllum brasiliense), com vistas à superação da dormência física e mecânica, e verificar a influência da temperatura e do substrato sobre a germinação. Foram avaliados três substratos (papel, areia e vermiculita), duas temperaturas de germinação (25 e 30ºC) e quatro tipos de preparo das sementes: sementes íntegras; sementes nuas, sem tegumento e endocarpo; sementes com punctura no endocarpo, na região próxima ao eixo embrionário ou na região oposta ao eixo embrionário; e sementes cortadas a 1/3 da região oposta ao eixo embrionário. Foram realizados testes de vigor (índice de velocidade de germinação e emergência de plântulas em campo), e a curva de embebição foi obtida para os diferentes tipos de preparo da semente. A retirada total do envoltório (endocarpo e tegumento) é necessária para a completa superação da dormência física e mecânica das sementes de guanandi. A germinação das sementes deve ser realizada em substrato papel à temperatura de 30ºC.

Antecedentes: Calophyllum brasiliense Cambess. Es un árbol de la familia Calophyllaceae, separada recientemente de Clusiaceae (Guttiferae). Se distribuye ampliamente en selvas tropicales lluviosas del continente americano, desde Brasil hasta México. Esta especie sintetiza diversos metabolitos secundarios en hojas, flores, frutos, corteza y raíz, tales como cumarinas, cromanonas, xantonas, terpenos, flavonoides y compuestos fenólicos, los cuales presentan múltiples propiedades biológicas. Objetivos: Ofrecer una visión general de las características botánicas, químicas y farmacológicas de C. brasiliense, así como evidencias químicas, anatómicas y genéticas que sugieren la existencia de quimiotipos (fenotipos químicos) en la especie. Métodos: Se revisó la información disponible en las bases de datos NCBI y SciFinder®, se seleccionaron investigaciones relevantes que permitieron conocer los compuestos químicos aislados y su actividad biológica. Resultados: Entre los compuestos sintetizados por C. brasiliense destacan calanólidos e inofilums, especialmente el (+)-calanólido A, como inhibidores potentes de la enzima transcriptasa reversa del virus de inmunodeficiencia humana tipo 1 (VIH-1) y baja toxicidad a linfocitos humanos. El (+)-calanólido A, una dipiranocumarina tetracíclica, podría ser el primer fármaco de origen natural aprobado por la FDA (EUA) en el tratamiento del VIH/SIDA. Otros compuestos, tales como cumarinas tipo mammea, cromanonas, xantonas y triterpenos, mostraron actividad contra protozoarios, células tumorales humanas, como bactericidas y antiespasmódicos. La actividad más importante de cumarinas tipo mammea es contra protozoarios como Leishmania y Trypanosoma. En relación a L. amazonensis, destacó (-)-mammea A/BB presentando buena actividad y selectividad contra amastigotes y promastigotes, y baja toxicidad en macrófagos humanos. La (-)-mammea A/BA, y las xantonas preniladas mostraron alta citotoxicidad sobre líneas celulares tumorales humanas y T. cruzi. Las evidencias químicas, anatómicas y genéticas indican que existen quimiotipos en C. brasiliense, sugiriendo un proceso de especiación en curso en el taxón. Las secuencias ribosomales (ITS) discriminaron al quimiotipo 1 (produce coumarinas tipo mammea) de los quimiotipos 2 y 3 (biosintetizan calanólidos e inofilums), siendo útiles como posibles códigos de barras. Conclusiones: El adecuado manejo de C. brasiliense mediante técnicas silvícolas y biotecnológicas, así como el conocimiento científico y tecnológico, podrían aportar soluciones a países en desarrollo, por ejemplo mediante producción de fitomedicamentos, a enfermedades como el VIH/ SIDA, Leshmaniasis y la Enfermedad de Chagas.

We evaluated the in vitro anti-Mycobacterium tuberculosis activity and the cytotoxicity of dichloromethane extract and pure compounds from the leaves of Calophyllum brasiliense. Purification of the dichloromethane extract yielded the pure compounds (-) mammea A/BB (1), (-) mammea B/BB (2) and amentoflavone (3). The compound structures were elucidated on the basis of spectroscopic and spectrometric data. The contents of bioactive compounds in the extracts were quantified using high performance liquid chromatography coupled to an ultraviolet detector. The anti-M. tuberculosis activity of the extracts and the pure compounds was evaluated using a resazurin microtitre assay plate. The cytotoxicity assay was performed in J774G.8 macrophages using the 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyl tetrazolium bromide colourimetric method. The quantification of the dichloromethane extract showed (1) and (2) at concentrations of 31.86 ± 2.6 and 8.24 ± 1.1 µg/mg of extract, respectively. The dichloromethane and aqueous extracts showed anti-M. tuberculosis H37Rv activity of 62.5 and 125 µg/mL, respectively. Coumarins (1) and (2) showed minimal inhibitory concentration ranges of 31.2 and 62.5 µg/mL against M. tuberculosis H37Rv and clinical isolates. Compound (3) showed no activity against M. tuberculosis H37Rv. The selectivity index ranged from 0.59-1.06. We report the activity of the extracts and coumarins from the leaves of C. brasiliense against M. tuberculosis.

Calophyllum brasiliense is used as anti-inflammatory and analgesic in Brazilian traditional medicine. Thus, the main purpose of this study is to evaluate the antinociceptive effect of the chloroform fraction of C. brasiliense (CFCB) roots and to investigate its main mechanism of action. The antinociceptive effect of CFCB was evaluated in mice using acetic acid-induced writhing, formalin-induced paw licking, and hot-plate tests and capsaicin- and glutamate-induced nociception. Brasiliensic acid and 1,2-dimethoxyxanthone were isolated and evaluated in writhing test. The amount of 1,2-dimethoxyxanthone was determined in the fraction by UPLC-DAD. CFCB inhibited abdominal constrictions induced by acetic acid up to 97%, with an ID of 9.4 mg/kg (i.p.) and 131.8 mg/kg (p.o.). In the formalin test, CFCB impaired paw licking with an ID of 26.3 mg/kg for the first phase and 27.5 mg/kg for the second phase (i.p.). The painful response evoked by capsaicin and glutamate was significantly reduced (ID 26.7 and 47.9 mg/kg, i.p.). The latency time was increased up to 76% at 60 mg/kg (i.p.) in the hot-plate test. 1,2-Dimethoxyxanthone was almost three times more potent (ID 27.6 μmol/kg, i.p.) than brasiliensic acid (72.0 μmol/kg) in acetic acid-induced writhing test. The amount of the xanthone was estimated as 92.5 mg/g in the extract. CFCB inhibited the nociceptive response associated to several agents. TRPV1 channels play an important role in the mechanism of action of the fraction. In addition, 1,2-dimethoxyxanthone largely contributes to the antinociceptive effect of CFCB. [ABSTRACT FROM AUTHOR]

Calophyllum brasiliense is a rich source of bioactive coumarins, xanthones and biflavonoids. The aim of the study was to compare the phenol contents and the antioxidant activity of C. brasiliense extracts obtained by conventional and supercritical fluid extraction (SFE) methods, as well as the quantification of crude extracts and (−)-mammea A/BB yields. Dichloromethane and hexane were used as solvents for the conventional extractions and SFE was developed using supercritical CO2; the kinetic curves were modeled using a second-order empirical model. The dichloromethane extract presented the best total yield, although it showed the lowest content of (−)-mammea A/BB. The concentration of the coumarin was considerably higher in extracts obtained by the supercritical fluid method and a higher antioxidant activity was assigned to extracts obtained by this technique. Concerning the total phenolic contents, both the dichloro-methane and the supercritical extractions produced satisfactory amounts. The SFE method proved to be more promising than conventional methods.

Se realizó un experimento en invernadero, cuyo objetivo fue determinar la dependencia micorrícica de barcino (Calophyllum brasiliense Cambers). Para lo cual se utilizó un diseño experimental completamente al azar. Los tratamientos tuvieron un arreglo factorial 3 x 2 con cinco repeticiones, que consistieron en la combinación de tres concentraciones de fósforo (P) en la solución del suelo (0,002, 0,02 y 0,2 mg l-1) con 2 niveles de inoculación micorrizal de Glomus agreggatum Schenck y Smith, modificado por Koske (inoculado y no inoculado). Se emplearon como variables respuesta el contenido de P foliar en función del tiempo. Al momento de la cosecha, se determinaron la masa seca aérea (MSA), el P total absorbido (PTA) en la parte aérea, la colonización micorrizal y la dependencia micorrizal (DM). Los resultados indican que el contenido de P foliar no tuvo variaciones significativas en relación a la inoculación micorrizal. El contenido de P total absorbido no varió al igual que la masa seca aérea. No se presentó colonización micorrizal en ninguno de los tratamientos. Finalmente, no hubo dependencia micorrizal con G. agreggatum de barcino, ubicando a esta especie dentro de la categoría independiente, al menos en las condiciones del estudio.A greenhouse bioassay was carried out to determine the mycorrhizal dependency of barcino (Calophyllum brasiliense Cambers), using a completely randomized experimental design. Treatments were arranged in a 3 x 2 factorial design with five repetitions, that consisted of combinations of three concentrations of phosphorus (P) in the soil solution (0.002, 0.02, and 0.2 mg l-1), with two levels of mycorrhizal inoculation with Glomus agreggatum Schenck and Smith, modified by Koske (inoculated and not innoculated). Leaf P content as a function of time was the response variable. Shoot dry matter (MSA), shoot P content (PTA), mycorrhizal colonization of roots, and mycorrhizal dependency (DM) were measured at harvest. The results indicated that foliar P content did not vary significantly with micorrizal inoculation. The total P content absorbed did not vary, nor did aerial dry mass. Micorrizal colonization with G. agreggatum was not documented in any of the treatments. Finally, barcino showed no mycorrhizal dependence to G. aggreggatum, placing this species in the independent category, at least under the conditions of this study.

A number of natural compounds have been used as immunomodulatory agents, enabling the function of the immune system to be modified by stimulating or suppressing it. There has been increasing interest in the study of therapeutic action of plant extracts regarding their immunomodulatory activity. The aim of this study was to identify and evaluate the action of extracts of the medicinal plants Calophyllum brasiliense, Ipomoea pes-caprae, Matayba elaeagnoides, Maytenus robusta, Rubus imperialis and Vernonia scorpioides on the development of spleen cells from mice, using the in vitro cellular proliferation assay. The cells, obtained by mechanical rupture of mice spleen (5x10(4) cells/mL), were incubated with methanol extracts (10, 50, 100 and 200 µg/mL) and phytohemagglutinin (PHA, 5 µg/mL). The basal control for proliferation consisted of cells alone, while the positive control consisted of cells and PHA. The cell culture was kept at 37 ºC in 5% CO2 for 72 hours, and cell proliferation was revealed by the blue tetrazolium reduction assay (MTT). The results were expressed as percentage of growth and were analyzed using the Kruskal-Wallis and Mann-Whitney tests. The C. brasiliense, I. pes-caprae and M. elaeagnoides extracts showed dose-dependent induction of cell proliferation, with a significant increase in cell proliferation (pVárias substâncias de origem natural têm sido utilizadas como agentes imunomoduladores, permitindo modificar a função do sistema imune e propiciando o estudo de atividades terapêuticas de extratos de plantas. Este trabalho objetivou identificar a atividade imunomodulatória dos extratos de seis plantas medicinais da flora brasileira, Calophyllum brasiliense, Ipomoea pes-caprae, Matayba elaeagnoides, Maytenus robusta, Rubus imperialis e Vernonia scorpioides, sobre a proliferação de células esplênicas de camundongos. As células esplênicas murinas obtidas por ruptura mecânica do baço (5x14³ células/mL) foram incubadas com os extratos metanólicos das plantas (10, 50, 100, 200 µg/mL) e fito-hemaglutinina (PHA, 5 µg/mL). O controle basal de proliferação foi constituído de células apenas e o controle positivo formado por células e PHA. O cultivo celular foi mantido a 37 ºC, 5% de CO2, 72 horas, com quantificação da proliferação celular pelo ensaio de redução do azul de tetrazólio. Os resultados expressos em percentagem de crescimento foram analisados pelos testes de Kruskal-Wallis e Mann-Whitney. Os extratos de C. brasiliense, I. pes-caprae e M. elaeagnoides mostraram indução dose-dependente da proliferação celular (p

En el presente trabajo se da a conocer el hallazgo de Calophyllum brasiliense Cambess. en Argentina. Se presenta la descripción, ilustraciones, usos, distribución geográfica y caracterización ecológica de la especie.In this paper, the finding of C. brasiliense Cambess. in Argentina is presented. The description, illustrations, uses, geographical distribution, and ecological characterization of the species are included.

Calophyllum brasiliense and Mammea americana (Clusiaceae) are two trees from the tropical rain forests of the American continent. A previous screening showed high trypanocidal activity in the extracts of these species. Several mammea-type coumarins, triterpenoids and biflavonoids were isolated from the leaves of C. brasiliense. Mammea A/AA was obtained from the fruit peels of M. americana. These compounds were tested in vitro against epimastigotes and trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas disease. The most potent compounds were mammea A/BA, A/BB, A/AA, A/BD and B/BA, with MC100 values in the range of 15 to 90 g/ml. Coumarins with a cyclized ,-dimethylallyl substituent on C-6, such as mammea B/BA, cyclo F + B/BB cyclo F, and isomammeigin, showed MC100 values > 200 g/ml. Several active coumarins were also tested against normal human lymphocytes in vitro, which showed that mammea A/AA and A/BA were not toxic. Other compounds from C. brasiliense, such as the triterpenoids, friedelin, canophyllol, the biflavonoid amentoflavone, and protocatechuic and shikimic acids, were inactive against the epimastigotes. The isopropylidenedioxy derivative of shikimic acid was inactive, and its structure was confirmed by X-ray diffraction. Our results suggest that mammea-type coumarins could be a valuable source of trypanocidal compounds.

O objetivo deste trabalho foi avaliar, em casa de vegetação, os efeitos de doses de esterco bovino e de calcário na formação de mudas de guanandi (Calophyllum brasiliense Cambèss.). Foram avaliadas quatro doses de cada fator, combinadas em esquema fatorial 4x4. O delineamento experimental foi inteiramente ao acaso com quatro repetições, e cada parcela continha cinco mudas. O substrato foi formado pela mistura, em volume, de oito partes de subsolo e duas partes de areia, e doses de esterco correspondentes a 0, 2, 4 e 6 partes que, em massa, equivalem a 0, 101, 175 e 229 kg m-3. As doses de calcário foram calculadas para elevar a saturação por bases (V%) a 20, 35, 50 e 65%. Aos 120 dias, foram avaliados: altura, diâmetro do colo, número de folhas, área foliar e matéria seca das partes aérea e radicular das mudas. Em substrato constituído de subsolo+areia, a calagem e a adubação com esterco bovino não são necessárias para produção de mudas de guanandi.The effects of cattle manure and lime levels in substrate were evaluated to produce guanandi (Calophyllum brasiliense Cambèss.) seedlings in greenhouse conditions. Four levels of each factor were evaluated, in a factorial scheme 4x4. The experimental design was completely randomized with four replicates, each plot with five seedlings. The substrate was obtained by the mixture of eight subsoil parts and two sand parts (v:v). The manure was applied in 0, 2, 4 and 6 parts, in volume, that correspond, in mass, to 0, 101, 175 and 229 kg m-3. Lime doses were calculated to increase the base saturation degree near to 20% (original subsoil sample), 35, 50 and 65%. Seedlings harvest was performed 120 days after transplant, when height, stem diameter, leaf number, leaf area, shoot and root dry matter were evaluated. For substrate constituted by subsoil+sand, the liming and the cattle manure are not necessary to produce guanandi seedlings.

En Argentina la especie arbórea Calophyllum brasiliense Cambess (Calophyllaceae) constituye poblaciones en los bordes de esteros y en las selvas higrófilas del río Paraná. Las poblaciones de la margen del río forman parte de ecosistemas fuertemente fragmentados por su asociación a las cotas de inundación del embalse Yacyretá, lo cual las ha llevado a reducir drásticamente su tamaño al punto de encontrarse en riesgo de extinguirse localmente. Uno de los efectos de la fragmentación en las especies vegetales es la producción de semillas en menor cantidad, calidad o ambas. El valor ecológico, medicinal, económico y social de la especie y el estado de sus poblaciones suscitaron interés en conservarla. Una de las estrategias implementadas fue el almacenamiento de sus semillas, las cuales son recalcitrantes. Los objetivos del presente trabajo fueron evaluar tres poblaciones en cuanto a su potencialidad de producir semillas capaces de generar individuos y evaluar la calidad fisiológica en relación al momento de cosecha y al tiempo de almacenamiento bajo cuatro modos de almacenamiento. La población de Puerto Valle produjo semillas de buena calidad que conservaron la viabilidad durante treinta y un semanas cuando se almacenaron con endocarpo, en frascos de vidrio.

The occurrence of chromanone derivatives has been noticed as a distinctive feature of the genus Calophyllum (Calophyllaceae). Previous studies have demonstrated that the extract of the stem bark of Calophyllum brasiliense and its chromanone-rich fractions show anti-ulcer activity in murine gastric ulcer models. In this work, brasiliensic and isobrasiliensic acids, the two main compounds of the n-hexane extract of the stem bark extract of C. brasiliense, were isolated by flash chromatography using silica gel impregnated with silver nitrate and their structures were elucidated by NMR techniques and mass spectrometry. 13C NMR data is available for the first time for both compounds. Brasiliensic and isobrasiliensic acids showed good in vitro bacteriostatic activity against Helicobacter pylori, and are responsible, at least in part, for the bacteriostatic anti-H. pylori activity of the n-hexane extract of the stem bark of C. brasiliense. [ABSTRACT FROM AUTHOR]

Calophyllum brasiliense (Calophyllaceae) is a tropical rain forest tree distributed in Central and South America. It is an important source of tetracyclic dipyrano coumarins (Soulatrolide) and Mammea type coumarins. Soulatrolide is a potent inhibitor of HIV-1 reverse transcriptase and displays activity against Mycobacterium tuberculosis . Meanwhile, Mammea A/BA and A/BB, pure or as a mixture, are highly active against several human leukemia cell lines, Trypanosoma cruzi and Leishmania amazonensis . Nevertheless, there are few studies evaluating their safety profile. In the present work we performed toxicogenomic and toxicological analysis for both type of compounds. Soulatrolide, and the Mammea A/BA + A/BB mixture (2.1) were slightly toxic accordingly to Lorke assay classification (DL 50 > 3000 mg/kg). After a short-term administration (100 mg/kg/daily, orally, 1 week) liver toxicogenomic analysis revealed 46 up and 72 downregulated genes for Mammea coumarins, and 665 up and 1077 downregulated genes for Soulatrolide. Gene enrichment analysis identified transcripts involved in drug metabolism for both compounds. In addition, network analysis through protein–protein interactions, tissue evaluation by TUNEL assay, and histological examination revealed no tissue damage on liver, kidney and spleen after treatments. Our results indicate that both type of coumarins displayed a safety profile, supporting their use in further preclinical studies to determine its therapeutic potential. [ABSTRACT FROM AUTHOR]

The bioassay-guided fractionation against Biomphalaria glabrata of hydroalcoholic extracts of Calophyllum brasiliense aerial parts led to the isolation of the coumarin, named (-) mammea A/BB. The compound had its structure determined by both spectroscopic techniques (NMR ¹H, NMR 13C, gHSQC, gHMBC and MS) and some literature comparison data. The probit analysis of (-) mammea A/BB showed LD50 = 0.67 ppm and LD90 = 1.47 ppm. In addition, the dichloromethane extract obtained from C. brasiliense leaves with significant molluscicidal activity against Biomphalaria glabrata was analyzed by HPLC-UV.

This study evaluated the wound healing effects of topical application of an emulsion containing the HPLC-standardised extract from Calophyllum brasiliense Cambess (Clusiaceae) leaves in rats. The macroscopic analysis demonstrated that the wounds treated with the C. brasiliense emulsion healed earlier than the wounds treated with emulsion base and Dersani®. The percentage of wound healing in the group treated with the C. brasiliense emulsion was significantly higher than in the other groups at 7 and 14 days. On day 14, the animals treated with the C. brasiliense emulsion exhibited a 90.67% reduction of the wound areas. The histological evaluation revealed that on day 21, the group treated with the C. brasiliense emulsion exhibited a significant increase in fibroblasts compared with the other groups. Thus, the C. brasiliense emulsion had healing properties in the topical treatment of wounds and accelerated the healing process. [ABSTRACT FROM AUTHOR]

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Ethnopharmacological relevance Calophyllum brasiliense Camb., Clusiaceae, is commonly known as "guanandi" and its stem bark is used in Brazilian traditional medicine to treat rheumatism, vein problems, hemorrhoids and gastric ulcers. The aim of this study was to evaluate the toxicity of hexane extract of Calophyllum brasiliense stem bark (HECb) using in vitro and in vivo experimental models. Materials and methods In vitro toxicity was evaluated by Alamar Blue cytotoxicity assay and micronucleus test, using Chinese hamster ovary (CHO-k1) epithelial cells. in vivo toxicity was evaluated by oral acute and subchronic toxicity assays. In the oral acute toxicity screening, a single dose of HECb was administered to mice at doses ranging from 250 to 1000 mg/kg. In the subchronic study, HECb was administered orally for 30 days to Wistar rats at doses of 100 mg/kg and 500 mg/kg. Phytochemical analyses were performed by HPLC/UV-vis, secondary metabolites were quantified by spectrophotometric methods. Results HECb presented IC50=119.94±4.31 µg/mL after a 24 h cytotoxicity test using CHO-k1 cells, showing low cytotoxicity. However, when the cells were exposed to HECb for 72 h, the IC50 value was 8.39±2.00 µg/mL, showing in this case, a pronounced cytotoxic effect. In the oral acute toxicity studies, doses up to 500 mg/kg of HECb did not cause any changes in both male and female mice. At 1000 mg/kg, male mice showed signs typical of depression and stimulation that were reversed at 72 h. Besides, female mice were more sensitive to the toxic effect of HECb at 1000 mg/kg, which initially presented typical agitation signals, followed by depression signals, leading to death of all the animals at 24 h. In subchronic assay with rats, HECb administered orally at doses of 100 and 500 mg/kg did not cause significant changes in all clinical parameters evaluated. Histopathological analyses showed no deleterious effect in the vital organs of rats. Preliminary phytochemical analysis revealed the presence of phenolic compounds, steroids, and volatile coumarins. Analysis by HPLC showed two major peaks characteristic of chromanones. Conclusions In vitro toxicological tests showed that HECb exhibited cytotoxicity especially after 72 h of exposition, and mutagenicity on the highest tested dose. The in vivo studies demonstrated that HECb produced some toxicity signs at the highest dose tested, particularly, in the acute toxicity test but showed no significant signs of toxicity in the subchronic assay. Based on these and previous pharmacological studies, it is possible to say that HECb did not exhibit significant toxicity at its effective dose. This suggests that HECb is relatively safe in humans at its effective dose. [ABSTRACT FROM AUTHOR]

Objectives The aim of this study was to determine the cellular and molecular mechanisms of cell death induced by mammea A/ BA and A/ BB (3 : 1) on K562 cells. Methods These compounds were isolated from C alophyllum brasiliense and its cytotoxicity was tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Cell death was evaluated by Terminal deoxynucleotidyl transferase dUTP nick end labeling ( TUNEL) assay and immunocytofluorescence of active caspase-3. Genotoxicity was tested using comet assay. Lastly, a chemoinformatic analysis was performed with Osiris- Molinspiration software. Key findings The mixture of mammea A/ BA and A/ BB (3 : 1) showed cytotoxic activity against K562 cells ( IC50 = 43.5 μ m). TUNEL positive cells and active caspase-3 were detected after treatment. Genotoxicity of mammea A/ BA and A/ BB on K562 was detected since first hour of treatment. Additionally, mammea A/ BA and A/ BB were found to be in compliance with Lipinski 'rule of 5' suggesting that they possess strong potential of druglikeness. Conclusions The overall results confirm and extend the knowledge about coumarins as an important resource of antitumor drugs, and indicate that these compounds could be used in further preclinical studies against leukaemia. [ABSTRACT FROM AUTHOR]

Highlights: [•] The application of organic wastes to soils during reforestation induced higher CO2 and N2O emissions. [•] The greatest of organic carbon that was present in organic fertilizers remained incorporated in the soil. [•] Different physical and chemical compositions of organic wastes resulted in different outcomes. [Copyright &y& Elsevier]

Calophyllum brasiliense is a rich source of bioactive coumarins, xanthones and biflavonoids. The aim of the study was to compare the phenol contents and the antioxidant activity of C. brasiliense extracts obtained by conventional and supercritical fluid extraction (SFE) methods, as well as the quantification of crude extracts and (-)-mammea A/BB yields. Dichloromethane and hexane were used as solvents for the conventional extractions and SFE was developed using supercritical CO2; the kinetic curves were modeled using a second-order empirical model. The dichloromethane extract presented the best total yield, although it showed the lowest content of (-)-mammea A/BB. The concentration of the coumarin was considerably higher in extracts obtained by the supercritical fluid method and a higher antioxidant activity was assigned to extracts obtained by this technique. Concerning the total phenolic contents, both the dichloro-methane and the supercritical extractions produced satisfactory amounts. The SFE method proved to be more promising than conventional methods. [ABSTRACT FROM AUTHOR]

Abstract: Treatment of cutaneous leishmaniasis remains limited to a few available options. Recent studies showed in vitro antileishmanial activity of (−) mammea A/BB, a coumarin isolated from leaves of Calophyllum brasiliense. Moreover, the dichloromethane crude extract and hexane fraction from this plant demonstrated in vivo activity in mice infected with Leishmania amazonensis. We evaluated the antileishmanial activity of (−) mammea A/BB in the L. amazonensis BALB/c mice model. The animals were given intramuscular and topical treatment with (−) mammea A/BB for 30 consecutive days. The results demonstrated that 18mg/kg/d intramuscularly or 0.2% topically of (−) mammea A/BB significantly reduced the size of skin lesions in footpads of mice compared with those in the control group (p <0.05). The activity of Glucantime® (corresponding to 27mg/kg/d of pentavalent antimony) administered intramuscularly was similar to that of (−) mammea A/BB (p <0.05) by both routes of administration. The histopathological evaluation showed no changes in the organs analyzed. These results indicate that the coumarin obtained from C. brasiliense is the antileishmanially active compound and can be used to control the development of cutaneous leishmaniasis lesions caused by L. amazonensis. [Copyright &y& Elsevier]

Abstract: Ethnopharmacological relevance: Calophyllum brasiliense Camb. (Clusiaceae), popularly known as ‘guanandi’, is found in the tropical areas and swampy lands. The latex exuding from its bark is used in the treatment of gastric ulcer in folk medicine. Several active compounds have been isolated from its stem bark among them, are the chromanone acids. Therefore, this study aimed to evaluate antiulcer activity and probable mechanism(s) of action of a fraction containing a mixture of chromanone acids (BI), derived by column chromatography fractionation of the hexane extract of the stem bark of Calophyllum brasiliense (HECb), using experimental in vitro and in vivo models. Materials and methods: Ulcer was induced by oral administration of ethanol (75%, v/v) and indomethacin (50mg/kg). Malondialdehyde, reduced glutathione and catalase activity was measured in stomach tissue after ethanol induced ulcer. In order to evaluate the effect of BI on nitric oxide, ulcer was induced by ethanol in l-NAME pretreated animals. Anti-Helicobacter pylori activity was verified in disk diffusion and broth microdilution in vitro assays, using cagA+ and vacA+ Helicobacter pylori strains. Results: BI prevented the gastric ulceration caused by ethanol and indomethacin treatments. Its gastroprotective mechanism in ethanol-induced ulcer was partly due to reduction of MDA and CAT levels in the gastric tissue. BI did not affect the GSH levels and its gastroprotective effect was not reversed by pretreatment with l-NAME. BI showed anti-Helicobacter pylori in the both assays. Conclusion: The results indicate that BI is partly responsible for the HECb antiulcer and anti-Helicobacter pylori effects. [Copyright &y& Elsevier]

Abstract: We have previously demonstrated antileishmanial activity on Leishmania amazonensis of the natural (1–2), synthetic (7) and derivatives of coumarin (−) mammea A/BB (3–6) isolated from the dichloromethane extract of Calophyllum brasiliense leaves. The aim of the present study was to evaluate morphological and ultrastructural alterations in Leishmania amazonensis induced by these compounds. In promastigote forms, all seven compounds produced significant morphological and ultrastructural alterations, as revealed by scanning and transmission electron microscopy. The compound 5,7-dihydroxy-8-(2-methylbutanoyl)-6-(3-methylbutyl)-4-phenyl-chroman-2-one (3), the most active antileishmanial with LD50 of 0.9μM), induced cell shrinkage and a rounded appearance of the cells. Parasites incubated in the presence of compound (3) showed ultrastructural changes, such as the appearance of mitochondrial swelling with a reduction in the density of the mitochondrial matrix and the presence of vesicles inside the mitochondrion, indicating damage and significant change in this organelle; abnormal chromatin condensation, alterations in the nuclear envelope, intense atypical cytoplasmic vacuolization, and the appearance of autophagic vacuoles were also observed. In addition, the compound (3) may be acting to depolarize the mitochondrial membrane potential of the cells, leading to death of the parasite. [Copyright &y& Elsevier]

Abstract: Calophyllum species are sources of calanolides, which inhibit human immunodeficiency virus type 1 reverse transcriptase (HIV-1 RT). The hexane extract of the leaves from C. brasiliense collected in Soconusco, State of Chiapas, Mexico, analyzed by HPLC showed to contain apetalic acid, calanolides B, and C. It showed potent anti-HIV-1 RT inhibition (IC50 =20.2μg/ml), but was not toxic in mice (LD50 =1.99g/kg). The histological study of the mice treated at the highest dose revealed no alteration on hepatocytes, and an increase in the number of spleen megakaryocytes. These results suggest this extract is suitable to continue studies for developing a phytodrug against HIV-1. [Copyright &y& Elsevier]

Calophyllum brasiliense (Cambes) produces calanolide secondary metabolites that are active against human immunodeficiency virus type 1 reverse transcriptase. In this study, it was demonstrated that plant tissue culture is a useful technique for producing these metabolites. Different concentrations and combinations of plant growth regulators were tested in leaf and seed explants to establish callus cultures capable of producing calanolides. Highest callus induction (100%) was achieved when seed explants were incubated in a medium consisting of 8.88 μM 6-benzyladenine and 20 μM picloram. Highest callus induction (80.67%) was observed when leaf explants were incubated on a medium consisting of 0.46 μM kinetin and 5.37 μM α-naphthaleneacetic acid. High-performance liquid chromatography quantitative analysis revealed higher calanolide B and calanolide C production in calluses from seed explants than those developed from leaves (309.25 vs. 8.70 mg kg for calanolide B; 117.70 vs. 0.0 mg kg for calanolide C). [ABSTRACT FROM AUTHOR]

Aim of the study: To investigate the activities of the 217 plant extracts in traditional medicine of the Brazilian Cerrado against protozoans and yeasts. Materials and methods: Plant extracts were prepared by the method of maceration using solvents of different polarities. The growth inhibition of chloroquine-resistant Plasmodium falciparum strain (FcB1) was determined by measuring the radioactivity of the tritiated hypoxanthine incorporated. Activity against Leishmania (Leishmania) chagasi and Trypanosoma cruzi was measured by the MTT colorimetric assay. The antifungal tests were carried out by using the CLSI method. The active extracts were tested also by cytotoxicity assay using NIH-3T3 cells of mammalian fibroblasts. Results: Two hundred and seventeen extracts of plants were tested against Plasmodium falciparum. The eleven active extracts, belonging to eight plant species were evaluated against L. (L.) chagasi, Trypanosoma cruzi, yeasts and in NIH-3T3 cells. The results found in these biological models are consistent with the ethnopharmacological data of these plants. The ethyl acetate extract of Diospyros hispida root showed IC50 values of 1μg/mL against Plasmodium falciparum. This extract demonstrated no toxicity against mammalian cells, resulting in a significant selectivity index (SI) of 435.8. The dichloromethane extract of Calophyllum brasiliense root wood was active against Cryptococcus gattii LMGO 01 with MIC of 1.95μg/mL; and Candida albicans ATCC 10231 and Candida krusei LMGO 174, both with MIC of 7.81μg/mL. The same extract was also active against Plasmodium falciparum and L. (L.) chagasi with IC50 of 6.7 and 27.6μg/mL respectively. The ethyl acetate extract of Spiranthera odoratissima leaves was active against Cryptococcus gattii LMGO 01 with MIC of 31.25μg/mL, and against Plasmodium falciparum with IC50 of 9.2μg/mL and Trypanosoma cruzi with IC50 of 56.3μg/mL. Conclusion: The active extracts for protozoans and human pathogenic yeasts are considered promising to continue the search for the identification and development of leading compounds. [Copyright &y& Elsevier]

Abstract: Leishmanicide potential of Calophyllum brasiliense leaves on promastigote and amastigote of Leishmania (Leishmania) amazonensis is evaluated. The LD50 of dichloromethane extract and hexane fraction for promastigotes was respectively 40μg/ml and 20μg/ml. In mouse peritoneal macrophages infected with Leishmania amastigotes the Infection Index decreased respectively 100% and 84.2% in 80μg/ml and 40μg/ml concentrations of dichloromethane extract. Hexane fraction decreased infection index respectively by 98.7% and 91.3% within the same concentrations. It was found that pretreatment with dichloromethane extract or with hexane fraction of experimentally infected BALB/c mice decrease the volume of the lesions by L. (L.) amazonensis. Moreover, animals treated topically also revealed healing lesions. Besides, the parasite load in the animals’ popliteal lymph nodes was significantly reduced in treated animals, showing that plant components actually control infection. Results show that crude extract and hexane fraction of C. brasiliense reveal a significant in vitro and in vivo leishmanicide activity. [Copyright &y& Elsevier]

A simple, rapid, and specific high performance liquid chromatographic (HPLC) method was established for analysis of the bioactive compound (-) mammea A/BB in C. brasiliense leaves. In the present study, a method was developed and validated for quantitative determination of (-) mammea A/BB in extracts of C. brasiliense Cambess (Clusiaceae). The analyses were carried out on a Metasil ODS column at 30°C by gradient elution using different concentrations of acetonitrile-water as the mobile phase, flow rate of 0.6 mL/min and detection wavelength of 280 nm. The validation using (-) mammea A/BB as the standard demonstrated that the method shows linearity (linear correlation coefficient = 0.9989), precision (relative standard deviation <1.35%) and accuracy (mean recovery = 88.6%) in the concentration range 15.56-250.0 µg/mL. The limit of detection (LOD) and limit of quantification (LOQ) were 7.61 and 25.36 µg/mL, respectively. This method allowed the identification and quantification of (-) mammea A/BB in extracts obtained from the leaves, stems, and fruits by maceration. The extracts showed different chromatographic profiles: the leaves presented the highest concentration of (-) mammea A/BB, and the dichloromethane extract of leaves showed a larger quantity of this compound than did the hydroethanolic extract. This HPLC method is suitable for routine quantitative analysis of (-) mammea A/BB in extracts of C. brasiliense and phytopharmaceuticals containing this herb. [ABSTRACT FROM AUTHOR]

Abstract: To study the structure–activity relationship of coumarin (−) mammea A/BB isolated from the CH2Cl2 extract of Calophyllum brasiliense leaves, we evaluated the antileishmanial activity of natural, synthetic and derivatives of this coumarin, against promastigote and intracellular amastigote forms of Leishmania amazonensis, and their cytotoxicity to J774G8 murine macrophages. The derivatives were obtained by hydrogenation and methoxylation reactions. The compound structures were elucidated on the basis of spectroscopic data. The compounds 5,7-dihydroxy-8-(2-methylbutanoyl)-6-(3-methylbutyl)-4-phenyl-chroman-2-one (3), 7-hydroxy-5-methoxy-8-(2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenylcoumarin (4) and 5,7-dimethoxy-8-(1-methoxy-2-methylbutyl)-6-(3-methylbut-2-en-1-yl)-4 phenylcoumarin (6) were more biologically active than the compound (−) mammea A/BB (1) (7.4μM), with IC50 values from 0.9, 2.4 and 1.9μM respectively; compound (3) displayed the highest activity. The compounds mammea B/BB (2), 5,7-dimethoxy-8-(2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenylcoumarin (5) and 5,7-dihydroxy-4-phenylcoumarin (7) were less active than (−) mammea A/BB (1), with IC50 of 30.1, 15.1 and 60.2μM respectively; compound (7) showed the lowest antileishmanial activity of all. Compounds (1), (3), (4) and (6) were active not only against promastigote forms of L. amazonensis, but also against intracellular amastigote forms with IC50 of 14.3, 0.6, 34.0 and 22.2μM, respectively. Interestingly, compound (3) showed the most antileishmanial activity of all. This study demonstrated that several aspects of the structure were important for antileishmanial activity. [Copyright &y& Elsevier]