Antiproliferative activity of essential oils from three plants of the Brazilian Cerrado: Campomanesia adamantium (Myrtaceae), Protium ovatum (Burseraceae) and Cardiopetalum calophyllum (Annonaceae) / Atividade antiproliferativa dos óleos essenciais de três plantas do Cerrado brasileiro: Campomanesia adamantium (Myrtaceae), Protium ovatum (Burseraceae) e Cardiopetalum calophyllum (Annonaceae)

Abstract Essential oils, which may be extracted from several parts of plants, have different biological activities. The Brazilian Cerrado has a large variety of plants that yield essential oils, even though many have not been studied yet. Taking into account the biodiversity of this biome, this study aimed at evaluating the antiproliferative activity of essential oils extracted from three species of plants of the Cerrado in Goiás state: Campomanesia adamantium (Cambess.) O. Berg, Protium ovatum (Engl. in Mart.) and Cardiopetalum calophyllum (Schltdl.). Essential oils were extracted from both C. adamantium and C. calophyllum leaves and from P. ovatum leaves and green fruits by hydrodistillation carried out by a Clevenger-type apparatus. The chemical composition of the essential oils was determined by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following major chemical constituents were identified in the essential oils under investigation: β-myrcene (62.00%), spathulenol (28.78%), germacrene-B (18.27%), β-caryophyllene oxide (16.40%), β-caryophyllene (14.00%), α-pinene (11.30%), viridiflorol (9.99%), limonene (7.30%) and (Z,E)-pharnesol (6.51%). The antiproliferative activity was evaluated in different human tumor cell lines: breast adenocarcinoma (MCF-7), cervical adenocarcinoma (HeLa) and glioblastoma (M059J). A normal human cell line was included (GM07492A, lung fibroblasts). Results showed that essential oils from C. adamantium leaves got the lowest values of IC50 in all strains of tumor cells under evaluation. They were significantly lower than the ones of the normal cell line, an evidence of selectivity. It is worth mentioning that this is the first report of the antiproliferative activity of essential oils from C. adamantium , P. ovatum and C. calophyllum against human tumor cells.

Resumo Os óleos essenciais podem ser extraídos de várias partes das plantas e apresentam diversas atividades biológicas. O Cerrado brasileiro possui uma grande variedade de plantas produtoras de óleos essenciais muitas delas ainda não estudadas. Levando-se em consideração a biodiversidade desse bioma, o objetivo deste trabalho foi avaliar a atividade antiproliferativa dos óleos essenciais extraídos de três espécies de plantas ocorrentes no Cerrado do estado de Goiás: Campomanesia adamantium (Cambess.) O. Berg, Protium ovatum (Engl. in Mart.) e Cardiopetalum calophyllum (Schltdl.). Os óleos essenciais foram obtidos das folhas de C. adamantium e C. calophyllum e das folhas e frutos verdes de P. ovatum por hidrodestilação, usando o aparelho do tipo Clevenger. A composição química dos óleos essenciais foi determinada pelo método de Cromatografia Gasosa acoplada à Espectrometria de Massas (CG-EM). Os constituintes químicos majoritários identificados nos óleos essenciais estudados foram: β-mirceno (62,00%), espatulenol (28,78%), germacreno-B (18,27%), óxido de β-cariofileno (16,40%), β-cariofileno (14,00%), α-pineno (11,30%), viridiflorol (9,99%), limoneno (7,30%) e (Z,E)-farnesol (6,51%). A atividade antiproliferativa foi avaliada em diferentes linhagens de células tumorais humanas: adenocarcinoma de mama (MCF-7), adenocarcinoma cervical (HeLa) e gliobastoma (M059J), além de, uma linhagem celular humana normal (GM07492A, fibroblastos pulmonares). O óleo essencial das folhas de C. adamantium exibiu menores valores de CI50 em todas as linhagens celulares tumorais avaliadas, sendo menores que aquele obtido na linhagem celular normal, indicando seletividade. Este é o primeiro relato da atividade antiproliferativa dos óleos essenciais de C. adamantium , P. ovatum e C. calophyllum contra células tumorais humanas.

A Conformational Isomer of Soulattrolide from the Stem Bark of Calophyllum symingtonianum and Its Antibacterial Activity

Callophylum symingtonianum (Guttiferae), an evergreen broad-leaved tree that usually grows in hill forests, can be found distributed in the Malay Peninsula. The barks, leaves, flowers and seeds is often used medicinally to treat diarrhea and rheumatism. In the present study, we isolated two inophyllum type coumarins, 12-O-ethylinophyllum D (1) and iso-soulattrolide (2) from the stembarks of C. symingtonianum together with their antibacterial activity. The compounds were isolated by chromatographic methods on a silica gel. The structures were established by spectroscopic methods including UV, IR, (1D and 2D) NMR and mass spectrometry as well as by comparison with several literature sources. The antibacterial activity of those compounds was tested using a disc-diffusion assay against Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa. Both compound exhibited mild inhibition against P. aeruginosa with both 111 µg/ml MIC value. Compound 2 also inhibits S. aureus with 25 µg/ml MIC value.

Storage of Calophyllum brasiliense Cambess. seeds / Armazenamento de sementes de Calophyllum brasiliense Cambess

Abstract Calophyllum brasiliense is a species native to Brazil and has potential for use in the timber industry, in the reforestation of degraded areas, besides having medicinal properties. Its propagation is mainly by seeds which, depending on their recalcitrant characteristics, leads to difficulty in conservation, due to changes in its physiological potential during storage. Aiming to contribute to the expansion of its cultivation, rational use and conservation, the objective of this study was to investigate the behavior of C. brasiliense seeds during storage. Different packings (paper, aluminum and polyethylene) and environmental conditions (room temperature and cold chamber) were quarterly tested over 12 months, by evaluating germination viability and vigor. Based on the results, it was concluded that packaging in polyethylene and freezer storage provided the best conditions for the conservation of seeds, keeping them viable for a period of nine months.

Resumo Calophyllum brasiliense é uma espécie nativa do Brasil e está na lista de espécies recomendadas para o reflorestamento de áreas degradadas, além de possuir propriedades medicinais e madeireiras. Sua propagação se dá principalmente via sementes, as quais, em função das suas características recalcitrantes, apresentam dificuldade de conservação, devido a alterações no seu potencial fisiológico ao longo do armazenamento. Visando contribuir com a ampliação de seu cultivo, uso racional e conservação, objetivou-se investigar o comportamento das sementes de C. brasiliense durante 12 meses de armazenamento. Testou-se diferentes embalagens (papel, alumínio e polietileno) e condições ambientais (câmara fria e temperatura ambiente), avaliando-se trimestralmente a germinação, viabilidade e vigor. Com base nos resultados obtidos conclui-se que o acondicionamento em embalagem de polietileno e o armazenamento em câmara fria proporcionou a melhor condição para a conservação das sementes, mantendo essas viáveis por um período de nove meses.

Micropropagation of Calophyllum brasiliense (Cambess) from nodal segments / Micropropagação de Calophyllum brasiliense (Cambess) a partir de segmentos nodais

Abstract Micropropagation of Calophyllum brasiliense Cambess. (Clusiaceae) is a way to overcome difficulties in achieving large-scale plant production, given the recalcitrant nature of the seeds, irregular fructification and absence of natural vegetative propagation of the species. Cultures were established using nodal segments 2 cm in length, obtained from 1-2 year old seedlings, maintained in a greenhouse. Mercury chloride and Plant Preservative Mixture™ were used in the surface sterilizing stage, better results being achieved with Plant Preservative Mixture™ incorporation in culture medium, at any concentration. Polyvinylpyrrolidone, activated charcoal, cysteine, ascorbic acid or citric acid were added to the culture medium to avoid oxidation. After 30 days of culture, polyvinylpirrolidone and ascorbic acid gave better results, eliminating oxidation in most explants. For shoot multiplication, benzylaminopurine was used in concentrations of 4.4 and 8.8 µM in Woody Plant Medium, resulting in an average of 4.43 and 4.68 shoots per explant, respectively, after 90 days. Indole-3-butyric acid and α-naphthalene acetic acid were used to induce root formation, reaching a maximum rooting rate of 24% with 20µM α-naphthalene acetic acid. For acclimatization. the rooted plants were transferred to Plantmax® substrate and cultured in a greenhouse, reaching 79% of survival after 30 days and 60% after one year.

Resumo A micropropagação de Calophyllum brasiliense Cambess. (Clusiaceae) é uma maneira de superar dificuldades para sua produção em larga escala, devido à natureza recalcitrante das sementes, frutificação irregular e ausência de propagação vegetativa natural da espécie. Culturas foram estabelecidas utilizando segmentos nodais com 2 cm de comprimento, obtidos de plantas com 1 a 2 anos de idade, mantidas em casa de vegetação. Cloreto de mercúrio e Plant Preservative Mixture™ foram utilizados durante a etapa de desinfestação, com melhores resultados alcançados com a incorporação de Plant Preservative Mixture™ ao meio de cultura. Polivinilpirrolidona, carvão ativado, cisteína, ácido ascórbico ou ácido cítrico foram adicionados ao meio de cultura para evitar a oxidação dos explantes. Após 30 dias de cultivo, o uso de polivinilpirrolidona ou ácido ascórbico proporcionou melhores resultados, eliminando a oxidação na maioria dos explantes. Para multiplicação das brotações, benzilaminopurina foi usada em concentrações de 4.4 e 8.8 µM em meio WPM, resultando em uma média de 4.43 e 4.68 brotações por explante, respectivamente, após 90 dias. Ácido indol-3-butírico e ácido α-naftaleno acético foram usados para a indução de raízes, alcançando um enraizamento máximo de 24% com o uso de 20µM de ácido α-naftaleno acético. As plantas enraizadas foram transferidas para substrato Plantmax® e cultivadas em casa de vegetação, alcançando 79% de sobrevivência após 30 dias e 60% após um ano.

Cytotoxic, Anti-Inflammatory and Adipogenic Effects of Inophyllum D, Calanone, Isocordato-oblongic acid, and Morelloflavone on Cell Lines

This paper reports in vitro cytotoxic, anti-inflammatory and adipocyte diffentiation with adipogenic effects of coumarins inophyllum D (1) and calanone (2), and a chromanone carboxylic acid namely isocordato-oblongic acid (3) isolated from Calophyllum symingtonianum as well as a biflavonoid morelloflavon e (4) isolated from Garcinia prainiana on MCF-7 breast adenocarcinoma RAW 264.7 macrophages and 3T3-L1 preadipocytes cells, respectively. The cytotoxicity study on MCF-7 cell was conducted by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Meanwhile, the study of anti-inflammatory effects in RAW 264.7 macrophages and adipogenic effects on 3T3-L1 pre-adipocytes were conducted through nitrite determination assay and induction of adipocyte differentiation, respectively. In the cytotoxicity study, inophyllum D (1) was the only compounds that exhibited significant cytotoxic effect against MCF-7 cell with IC₅₀ of 84 µg/mL. Further, all by inhibiting the compounds have shown anti-inflammatory effects in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages of nitrite concentration with production. In addition, the compounds also exhibited adipogenic effects on 3T3-L1 pre-adipocytes by stimulating lipid formation. Thus, this study may provide significant input in discovery of the potential effects cytotoxic, anti-inflammatory and adipogenic agents.

Effect of seed coat on the seed germination and seedling development of Calophyllum brasiliense Cambess. (Clusiaceae) / Efeito do envoltório na germinação da semente e no desenvolvimento de plântulas de Calophyllum brasiliense Cambess. (Clusiaceae)

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.

Objetivou-se com este trabalho estudar o efeito do envoltório da semente de Calophyllum brasiliense no processo de germinação. Foram montados três experimentos, sendo estes conduzidos em laboratório, casa de vegetação e telado. Avaliaram-se seis tratamentos, sendo cinco relacionados ao envoltório (escarificação mecânica; escarificação mecânica seguido por 2h em água; escarificação química; imersão em água quente; e retirada total do envoltório) e a testemunha. Os experimentos em laboratório e casa de vegetação foram conduzidos em delineamento inteiramente casualizado. No telado, o experimento foi conduzido em delineamento em blocos casualizados. Avaliaram-se a percentagem total; o índice de velocidade e o tempo médio de germinação ou emergência. Os dados foram submetidos à análise de variância e as médias comparadas pelo teste t (LSD) a 5% de probabilidade. Foi possível inferir que no laboratório, a escarificação mecânica, seguido por 2h em água, aumenta a percentagem e o índice de velocidade de germinação (IVG); na casa de vegetação, a retirada total do envoltório aumenta a percentagem e o índice de velocidade de emergência (IVE); e no telado, a escarificação mecânica, seguida por 2h em água, e a escarificação química apresentam os melhores resultados. O tempo de germinação não apresentou diferença significativa nos três experimentos avaliados.

Morphology and anatomy of the seedling and the tirodendro of Calophyllum brasiliense Cambess. (Clusiaceae) / Morfoanatomia da plântula e do tirodendro de Calophyllum brasiliense Cambess. (Clusiaceae)

Calophyllum brasiliense Cambess. is a tree species that is presented as an alternative to replace endangered species of hardwood. The morphology and anatomy of the seedling of this species is the object of the present study. Seedlings at different stages of development were obtained in greenhouse and analyzed fresh and fixed in FAA (Formalin- Acetic-Alcohol) 50. The anatomical analysis was done by the freehand and microtome sections, according to standard techniques in plant anatomy. The seedling and/or tirodendro is cryptocotylar and hypogeal, has cataphylls, and presents eophylls and metaphylls simple with venation pinnate craspedodromous simple. The root is polyarch, the hypocotyl is very short, the cotyledons have an oily and starchy reserve, the epicotyl has stem structure, and eophylls and metaphylls are dorsiventral. The seedling may be classified in the Horsfieldia type/subtype.

Calophyllum brasiliense Cambess. é uma planta arbórea que se apresenta como possível alternativa para substituir espécies em extinção com madeira nobre. A morfologia e anatomia da plântula desta espécie é objeto do presente trabalho. As plântulas, em diferentes fases de desenvolvimento, foram obtidas em casa de vegetação e analisadas a fresco e fixadas em FAA 50. A análise anatômica foi feita mediante seções a mão livre e microtômicas, de acordo com técnicas usuais em anatomia vegetal. A plântula e/ou tirodendro é criptocotiledonar e hipogeia, possui catafilos, e apresenta eófilos e metafilos simples de venação pinada craspedódroma simples. A raiz é poliarca, o hipocótilo é muito reduzido, os cotilédones possuem reserva amilácea e oleaginosa, o epicótilo tem natureza caulinar e os eofilos e metafilos são dorsiventrais. A plântula enquadra-se no tipo e subtipo Horsfieldia.

Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae)

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.

Efecto del extracto atomizado de las hojas de Calophyllum brasiliense ôlagarto caspiõ sobre la glicemia / Effect of the atomized of calophylum brasiliense ôlagarto caspiõ leaves on the glycemia

OBJETIVO: Evaluar el efecto hipoglicemiante del Calophylum brasiliense. MATERIAL Y MÉTODO: Preparamos los extractos atomizado, acuoso, hexánico, diclorometánico, metanólico y etanólico de las hojas de Calophyllum brasiliense. La diabetes experimental fue inducida por administración intraperitoneal de 100 mg/kg de estreptozotocina. El efecto hipoglicemiante de Calophyllum brasiliense fue evaluado en ratas hiperglicémicas, con niveles de glucosa superiores a 300 mg/dLy la dosis usada fue 250, 500, 1000 y 1500 mg/kg, comparándolo con el grupo control negativo que recibió 10 ml de agua destilada vía oral y un grupo control positivo al que se le administró Glibenclamida a la dosis de 10 mg/Kg. Los valores de glucosa fueron determinados a las 1, 2, 3 y 4 horas, después de administrar los extractos y los controles. Finalmente el extracto atomizado fue fraccionado con el fin de caracterizar los principios activos de la planta. RESULTADOS: Observamos efecto hipoglicemiante una hora después de administrados los extractos. El mayor efecto observado con la dosis de 1000 mg/Kg, fue 69.28% superior a la Glibenclamida, duró todo el tiempo del experimento (4 horas), y demostramos la presencia de Calanólidas por Resonancia Magnética Nuclear (RMNH/RMNC). CONCLUSIONES: El extracto atomizado de Calophyllum brasiliense posee un buen efecto hipoglicemiante a la dosis de 1000 mg/Kg (100%), en comparación con Glibenclamida.

OBJETIVE: To evaluate the hypoglycemic effect of Calophylum brasiliense. MATERIALS AND METHOD: We prepared the atomized, aqueous, methanolic, hexanic, dicloromethanic and ethanolic, extracts from the leaves of Calophyllum brasiliense. The experimental diabetes was induced by intraperitoneal administration of 100 mg/kg of streptozotocin. The hypoglycemic effect of Calophyllum brasiliense was evaluated on hyperglycemic rats with levels of glucose higher than 300 mg/dL and the doses used were 250, 500, 1000 and 1500 mg/kg, compared with negative control group that received 10 ml of distilled water by mouth and the positive control group that received 10 mg of Glibenclamide. The blood glucose was determined at 1, 2, 3 and 4 hours after the administration of the extracts and the controls. Finally the atomized extract was fractioned in order to elucidate the active principles of the plant. RESULTS: We observed hypoglycemic effect since one hour after the administration of the extracts, the greatest effect was observed with the dose of 1000 mg/kg, even superior to Glibenclamide. The effect persisted all the time that we did the experiments (4 hours). We demonstrated the presence of calanolides with nuclear magnetic resonance (RMNH / RMNC). CONCLUSIONS: Our results indicate that Calophyllum brasiliense has a good hypoglycemic effect even superior to the Glibenclamide.

Research progress of chromanone derivatives from Calophyllum / 中国中药杂志

Calophyllum plants have great pharmaceutical value. Some species of this genus are used in folk medicine to treat and cure diseases, such as toothache, rheumatism, diarrhea, chronic ulcers, skin infections, and wounds. The genus is known to be rich in chromanone derivatives, and some of these compounds have antiviral, antifungal, antibacterial, cytotoxic, and other activities. In order to come to a more complete understanding of chromanone derivatives and gain new bioactive constituents from Calophyllum, chemical structures, pharmacological activities, and biogenesis of chromanone derivatives from Calophyllum have been discussed in this review.

Evaluation of the proliferative activity of methanol extracts from six medicinal plants in murine spleen cells

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 percent 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 (p<0.03) and percentage growth of 88.2 percent, 73.1 percent and 52.7 percent, respectively, suggesting T lymphocyte stimulation. By contrast, M. robusta, R. imperialis and V. scorpioides extracts showed significance only with a negative percentage of growth, suggesting inhibition of cell proliferation (p<0.04). Further biomonitoring studies will enable the fractions and isolated substances responsible for the immunomodulatory activities to be identified.

Várias 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 por cento 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<0,03), com percentagem de crescimento de, respectivamente, 88,2 por cento, 73,1 por cento e 52,7 por cento, sugerindo estímulo de linfócitos T. Contrariamente, os extratos de M. robusta, R. imperialis e V. scorpioides apresentaram significância apenas com percentagem de crescimento negativa, indicando inibição da proliferação celular (p<0,04). A continuidade no estudo biomonitorado permitirá a identificação das frações e substâncias isoladas responsáveis pelas atividades imunomoduladoras.

Xanthones from leaves of Calophyllum inophyllum Linn / 药学学报

To study the xanthones from the leaves of Calophyllum inophyllum Linn., several chromatography methods were employed to isolate the constituents. Investigation on the CHCl3 extract led to the isolation of a new xanthone named inophyxanthone A (1) and four known compounds, which were pancixanthone A (2), gerontoxanthone B (3), jacareubin (4) and pyranojacareubin (5). Among them, compound 2 was obtained from this plant firstly, and compound 3 was obtained for the first time from this genus. The structure of inophyxanthone A (1) was identified as 1, 3, 5-trihydroxy-2-(1, 1-dimethylallyl)xanthone by spectral analysis.

Evaluación de los efectos antioxidante, antibacteriano y antifúngico de Calophyllum Brasilense Cambes (Lagarto Caspi) / Evaluation of antioxidant effects, antibacterial and antifungal Brasilense Calophyllum Cambes (Caspi Lizard)

Objetivo: Evaluar el efecto antibacteriano, antifúngico y antioxidante de diferentes extractos del Calophyllum brasiliense Cambess. Material y Métodos: El efecto antioxidante fue determinado por captación de radicales libres, midiendo la decoloración de una solución de 2,2-difenil-1-picril hidrazilo (DPPH); La actividad antibacteriana y antifúngica, in Vitro, se determinó mediante la prueba de dilución. El efecto antibacteriano se evaluó en cepas de E. coli ATCC25922 y Staphylococcus aureus ATCC25923, utilizando medios de cultivo: Caldo y Agar Mueller Hinton. Para evaluar el efecto antifúngico, se utilizó cepas de Cándida albicans en medio de Agar Sabouraud. Resultados: La actividad antioxidante de los extractos acuoso, metanólico y etanólico fue muy satisfactoria, siendo de 110.56 por ciento, 99.17 por ciento y 99.57 por ciento, respectivamente, a una concentración de 100 ug/mL, en comparación con la Vitamina C que presentó 86,5 por ciento. Asimismo, observamos un buen efecto antifúngico para los extractos acuoso y etanólico al 20 por ciento p/v a los volúmenes de 3, 3.5 y 4mL. y en el caso del extracto etanólico también presentó un buen efecto a una concentración del 10 por ciento a un volumen de 1.6mL. Conclusiones: Los extractos: acuoso, metanólico y etanólico, presentaron un buen efecto antioxidante y antifúngico, en las cepas estudiadas.

Objetive: To evaluate, in vitro, the antibacterial, antifungal andantioxidant effects of different extracts of Calophyllum brasiliense Cambess. Material and Methods: The antioxidant effect was tested by free radicals capture, measuring discoloration of the 2,2-diphenyl-1-pycryl hydrazyle solution (DPPH). We used a dilution to measure antibacterial and antifungal in vitro activity. Strains of E. coli ATCC25922 and Staphylococcus aureus ATCC25923 were used to evaluate antibacterial effect; using Broth and Mueller Hinton Agar as culture medium. Strains of Candida albicans and Agar Sabouraud as culture medium were usedto evaluate antifungal effect. Results: Aqueous, methanolic and ethanolic extracts, showed good antioxidant activity having 110.56 per cent, 99.17 per cent and 99.57 per cent of antioxidant activity at 100 ug/mL concentration, respectively. This is superior to the vitamin C referencepattern that showed 86,5 per cent activity. Good antifungal effect for aqueous and ethanol extracts at a 20 per cent concentration for 3, 3.5 and 4 ml of volume was determined. Ethanol extracts had the same antifungal effect at a 10 per cent concentration for 1.6mL. of volume. Conclusions: The aqueous, methanolic and ethanolic extracts showed a good antioxidant and antifungal activity on the strains studied.

Estudio químico de la resina de la especie endémica Calophyllum pinetorum Bisse / Chemical study of the resin of the endemic species Calophyllum pinetorum Bisse

Objetivos: aislar e identificar los componentes principales presentes en el extracto metanólico de la resina de la especie Calophyllum pinetorum Bisse.Métodos: la cromatografía líquida de alta resolución se utilizó para la separación de los compuestos. Para la caracterización estructural se emplearon las técnicas de resonancia magnética nuclear y la espectrometría de masas.Resultados: el proceso de separación permitió el aislamiento de 3 compuestos que fueron reconocidos como derivados de cromonas. Los compuestos 1-3 fueron identificados como: ácido calolóngico, ácido apetálico y ácido isoapetálico.Conclusiones: la presencia de cromonas se corresponde con los estudios realizados con otras especies de este género, pero es la primera vez que estos compuestos se aíslan e identifican desde una misma especie. Por otra parte, es la primera vez que se informa la presencia de cromonas en la resina de este género.

Objectives: to isolate and identify the main components in the methanolic extract of the resin of the species Calophyllum pinetorum Bisse.Methods: high resolution liquid chromatography was used for the separation of the compounds. Magnetic resonance imaging and mass spectrometry were used for the structural characterization.Results: the separation process allowed the isolation of 3 compounds that were recognized as derivatives of chromans. The compounds 1-3 were identified as calolongic acid, apetalic acid and isoapetalic acid.Conclusions: the presence of chromans corresponds with the studies conducted with other species of this genus, but it is the first time that these compounds are isolated and identified from the same species. On the other hand, it is reported for the first time, too, the presence of chromans in the resin of this genus.

Marcadores y efecto antitumoral, anti-VIH de las hojas y corteza de Calophyllum brasiliense C, ôLagarto caspi, Santa María, Baríõ de las zonas de Satipo y Pucallpa. Perú Sudamérica / Markers, anti tumoral, and anti-HIV effect of leaves and bark of Calophyllum brasiliensi. C ôLagarto caspi Santa Maria, Bariõ of Satipo and Pucallpa regions (Peru-South America)

Se evaluó la actividad antitumoral y antiviral de los extractos al 10% p/v de hojas y corteza de Calophylum brasiliense Cambess de Satipo y Pucallpa. Se utilizaron técnicas del CYTED, Skehan y Simmons. En Artemia salina la CL50 fue 70.5 ppm, con un limite superior e inferior al 95% de 136.50ppm y de 36.4ppm por Probits, asimismo se observó una inhibición sobre líneas celulares tumorales: U251 (Cáncer del SNC), PC-3 (Cáncer de Próstata), HCT15 (Cáncer de Colon), MCF7 (Cáncer de Mama) y K562 (Cáncer de Tejido Linfoide) de 109.42%, 95.67%, 96.16%, 102.68% y 95.69% respectivamente, con una p< 0,01. En la evaluación antimitótica en cebolla, al cabo de 6 horas el IM de las células meristemáticas decreció de 13 a 1.0 a la concentración de 0.5% a 25ºC. La actividad antiviral sobre la Transcriptasa Reversa (RT) del HIV-1, realizada con el Kit Lenti RT, presentó una CL50 de 70.2905 ug/ml (límites al 95%:138.89ug/ml-35.5707ug/ml). Se detectó: alcaloides, cumarinas, lactonas, triterpenos pentacíclicos, habiéndose aislado tres compuestos CBHS5, CbHS16, CbHS525354, realizándose la elucidación estructural de los dos componentes mayoritarios por RMNH1, RMNC13 y Espectrometría de Masas que fueron caracterizados como Betulina, que posee un efecto antiinflamatorio y el Ácido betulínico, que posee efectos: antitumoral y anti-VIH. La Betulina y el Acido betulínico podrían estar implicados en la acción farmacológica del extracto de hojas de Satipo, que presentó un buen efecto antitumoral y antiviral de 72.05% sobre la RT, frente a Nevirapine utilizado en la terapia de pacientes con SIDA, que presentó 71.59%.

We evaluated the antitumoral and antiviral activity of extracts at 10% (w/v) of leaves and bark of Calophyllum brasiliense Cambess of Satipo and Pucallpa. METHODS: CYTED, Skehan and Simmons techniques were used. RESULTS: In Artemia salina the LC50 was at 70, 5 ppm, with 95% superior and inferior limits of 136.50ppm and 36.4ppm with Probits. An inhibition on tumoral cell lines: U251(CNS Cancer), PC-3(Prostate Cancer), HCT15 (Colon cancer), MCF7(Breast cancer) and K562 (Lymphoid tissue cancer) of 109,42%, 95,67%, 96,16%, 102,68% and 95,69% respectively, with p< 0,01 was observed. In the antimitotic evaluation using Allium cepa, after 6 hours the MI of meristematic cells decreased from 13 to 1,0 at a concentration of 0,5% at 25ºC. The antiviral activity on Reverse Transcriptase (RT) of the HIV-1, performed with the Lenti RT Kit, presented a LC50 of 70,2905 ug/ml (limit of 95%:138.89ug/ml-35.5707ug/ml). We detected: alkaloids, coumarins, lactones, pentacyclic compounds, triterpens, and three compounds were isolated CBHS5, CbHS16, CbHS525354. Structural elucidation of the major components were characterized by RMNH1, RMNC13 and Mass Spectrometry and were Betulin, that has an anti-inflammatory effect and betulinic acid, that has antitumoral and anti-HIV effects. DISCUSSION: Betulin and betulinic acid could be implied in the pharmacologic action of the leaves extracts of Satipo, that presented a good antitumoral and antiviral activity of 72,05% on RT, as opposed to Nevirapine used in the therapy of patients with AIDS, that presented 71.59%activity.

Studies on flavonoids from stems and leaves of Calophyllum inophyllum / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents from the stems and leaves of Calophyllum inophyllum.</p><p><b>METHOD</b>The compounds were isolated by column chromatography on silica gel, Sephadex LH-20 and preparative TLC. Their structures were elucidated by chemical methods and NMR, MS spectroscopic data.</p><p><b>RESULT</b>Nine compounds were identified as 2-hydroxyxanthone (1), 4-hydroxyxanthone (2), 1, 5-dihydroxyxanthone (3), 1, 7-dihydroxyxanthone (4), 1, 3, 5-trihydroxy-2-methoxyxanthone (5), 6-deoxyjacareubin (6), amentoflavone (7), kaempferol-3-O-alpha-L-rhamnoside (8) and quercetin-3-O-alpha-L-rhamnoside (9).</p><p><b>CONCLUSION</b>Compounds 8 and 9 were isolated from the genus Calophyllum and compounds 1, 2, 4-6 were isolated from this plant for the first time.</p>

Effects of fungal elicitor on inophyllums production in suspension cultured cells of Calophyllum inophyllum L / 药学学报

<p><b>AIM</b>To investigate the effects of fungal elicitors on inophyllums production in suspension cultured cell of Calophyllum inophyllum Linn.</p><p><b>METHODS</b>The pathogen of leaf spot disease of C. inophyllum L. was isolated and prepared as fungal elicitor. The fungal elicitor was added to the medium with different concentrations and culture period. Their effects on biomass and inophyllums content of the suspension of cultured cells were studied.</p><p><b>RESULTS</b>The optimum effects of S-I fungal elicitor concentrations on inophyllums content was 60 mg GE x L(-1). Adding the fungi elicitor into the cell suspension culture system at stationary phase (being cultured for 18 days) resulted in a highest inophyllum content of 59.174 mg x L(-1) at the 3rd day with 27% higher than control. Fungal elicitor treatment promoted the inophyllums accumulation in medium.</p><p><b>CONCLUSION</b>Adding the Stagonospora curtisii (Berk.) Sacc. to the medium was effective approaches to enhance inophyllums yield in the suspension of C. inophyllum L culture cell.</p>