Pleonotoquinones, Cytotoxic Oxepinenaphthoquinones from Pleonotoma jasminifolia.

Two unusual naphthoquinones, named here as pleonotoquinones A (1) and B (2), were isolated along with two known anthraquinones (3 and 4) via chromatographic separations of an ethyl acetate extract of the roots of Pleonotoma jasminifolia. Compounds 1 and 2 are the first examples of quinones bearing a 2-methyloxepine moiety. The compounds were isolated with the aid of mass spectrometry and molecular networking, and their structures were resolved using 1D and 2D NMR and HRESIMS data. The isolated compounds were evaluated for their antiproliferative activity against human cancer cell lines, and compounds 1 and 2 displayed cytotoxicity against human colon cancer HCT116 cells (IC50 = 2.6 µM for compound 1 and IC50 = 4.3 µM for compound 2) and human liver cancer HepG2 cells (IC50 = 1.9 µM for compound 1 and IC50 = 6.4 µM for compound 2).

Variability of individuals from a population Varronia curassavica Jacq considering volatile compounds / Variabilidade de indivíduos de uma população de Varonia curassavica Jacq a partir de compostos voláteis

Varronia curassavica is a medicinal species native to Brazil; its anti-inflammatory properties are attributed to α-humulene and ß-caryophyllene. This study to investigated the population variability of V. curassavica. Leaves were collected from 40 individuals of a natural population and transferred to glass flasks (2 mL). The volatiles were extracted and analyzed using static headspace gas chromatography coupled with mass spectrometry (HS-GC-MS). A total of 17 compounds were detected: monoterpenes (1.6% - 68%) and sesquiterpenes (25.7% - 79.0%), including α-humulene and ß-caryophyllene. Multivariate analysis was performed to estimate the dissimilarity of individuals separated the compounds into four groups. Group I was characterized by the content of α-pinene, groups II and IV by ß-caryophyllene, and group III by ß-pinene. The abundance of α-humulene showed small variations; while ß-caryophyllene showed larger variations that contributed to the population variability. This is the first report on the chemical composition analysis of volatile compounds in V. curassavica using the HS-GC-MS technique.

Varronia curassavica é uma espécie medicinal nativa no Brasil e sua propriedade anti-inflamatória é atribuída aos compostos α-humuleno e ß-cariofileno. O objetivo foi estudar a variabilidade de população de V. curassavica. Foram coletadas folhas de 40 indivíduos de população natural, sendo estas transferidas para frascos de vidro (2 mL). Os voláteis foram extraídos e analisados por headspace estático, associado à cromatografia gasosa, acoplada à espectrometria de massas (HS-CG-EM). Detectou-se 17 compostos: monoterpenos (1,6% - 68%) e sesquiterpenos (25,7% - 79,0%), incluindo o α-humuleno e o ß-cariofileno. A análise multivariada foi realizada para estimar a dissimilaridade dos indivíduos, a qual separou quatro grupos. O grupo I foi caracterizado pela presença do α-pineno, os grupos II e IV do ß-cariofileno e o grupo III do ß-pineno. O teor do α-humuleno apresentou pequenas variações, enquanto o do ß-cariofileno contribuiu mais para a variabilidade da população. É o primeiro relato de análise da composição química de compostos voláteis de V. curassavica utilizando a técnica HS-GC-MS.

Seasonal variation in the essential oil from Varronia curassavica jacq. accessions / Variación estacional en el aceite esencial de accesiones de Varronia curassavica Jacq

Varronia curassavica has anti-inflammatory properties because of the terpenes, α-humulene and ß-caryophyllene, present in the essential oil. The objective of this study was to evaluate the influence of seasonality on the essential oil of V. curassavica accessions. Leaves from six accessions were collected from the Germplasm Bank of the Federal University of Minas Gerais over 12 months. Correlations between the essential oil content and meteorological factors were determined. Gas chromatography analysis coupled with mass spectrometry was conducted to determine the chemical composition of the essential oil. The content and chemical composition of the oil varied throughout the year. Relative humidity was correlated with accessions ICA-VC2 (-0.64) and ICA-VC4 (0.68). ß-bourbonene, ß-elemene, spathulenol, germacrene, caryophyllene oxide, α-humulene, and ß-caryophyllene occurred in all accessions. Accession ICA-VC3 exhibited lower variation (22.17%), higher average (0.97%) essential oil, and maintained an average abundance of α-humulene greater than 2.6%, which is the amount necessary for phytotherapeutics.

Varronia curassavica tiene propiedades antiinflamatorias debido a los terpenos, α-humuleno y ß-cariofileno, presentes en el aceite esencial. El objetivo de este estudio fue evaluar la influencia de la estacionalidad en el aceite esencial de las accesiones de V. curassavica. Se recolectaron hojas de seis accesiones del Banco de Germoplasma de la Universidad Federal de Minas Gerais durante 12 meses. Se determinaron las correlaciones entre el contenido de aceite esencial y los factores meteorológicos. Se realizó un análisis de cromatografía de gases junto con espectrometría de masas para determinar la composición química del aceite esencial. El contenido y la composición química del aceite varió a lo largo del año. La humedad relativa se correlacionó con las accesiones ICA-VC2 (-0,64) e ICA-VC4 (0,68). En todas las accesiones aparecieron ß-bourboneno, ß-elemeno, espatulenol, germacreno, óxido de cariofileno, α-humuleno y ß-cariofileno. La accesión ICA-VC3 mostró una menor variación (22,17%), un promedio más alto (0,97%) de aceite esencial y mantuvo una abundancia media de α-humuleno superior al 2,6%, que es la cantidad necesaria para los fitoterápicos.

Physico-mechanical properties of the wood of freijó, Cordia goeldiana (Boraginacea), produced in a multi-stratified agroforestry system in the southwestern Amazon / Propriedades físico-mecânicas da madeira de freijó, Cordia goeldiana (Boraginacea), produzida em sistema agroflorestal multiestratificado no sudoeste da Amazônia

Agroforestry systems (AFSs) integrate, through sustainable practices, agricultural and forest crops for the production of wood and food, providing environmental services, and conserving biodiversity. The freijó (Cordia goeldiana) has potential for cultivation in the Amazon for timber purposes, but data on the characteristics of its wood produced in AFSs are scarce. Our objective was to determine the physical-mechanical properties and suggest technological applications of freijó wood produced in a multi-stratified AFS established in the state of Rondônia, Brazil in 1996. Agricultural and forest species were established in the AFS in double rows with 5.0-m x 2.5-m spacing. Three 19-year-old freijó trees were harvested for chemical, physical (density and dimensional stability), and mechanical (compression, static bending, Janka hardness, and shear strength) characterization of the wood. The wood presented a chemical composition similar to tropical hardwoods, was moderately heavy (582.63 kg m-3), and had high dimensional stability in comparison with other consecrated woods on the market (longitudinal, radial, and tangential retraction = 0.25, 4.27, and 6.83%, respectively). The values determined for parallel (32.32 MPa) and perpendicular compression (8.02 MPa), specific strength (55.32 MPa kg-1 m-3), parallel (2373.33 N) and perpendicular Janka hardness (2326.67 N), strength to static bending (63.5 MPa), and shear (5.94 MPa) were similar to the values ​​observed in other high-density tropical woods grown in either monoculture plantations or natural forests. The wood under study is suitable for manufacture of high-value-added products, such as fine furniture, residential floors, musical instruments and structural pieces.(AU)

Os sistemas agroflorestais (SAFs) integram, com práticas sustentáveis, culturas agrícolas e florestais para produção de madeira e alimentos, conservando os serviços ambientais e a biodiversidade. O freijó, Cordia goeldiana, tem potencial para cultivo na Amazônia para fins madeireiros, porém dados sobre as características de sua madeira em SAFs são escassas. Objetivou-se determinar as propriedades físico-mecânicas e aplicações tecnológicas da madeira de freijó produzida em um SAF multiestratificado estabelecido no estado de Rondônia, Brasil em 1996. No SAF, as espécies agrícolas e madeireiras foram estabelecidas em renques duplos no espaçamento 5,0 m x 2,5 m. Abateram-se três árvores de freijó com 19 anos de idade, para caracterização química, física (densidade e estabilidade dimensional) e mecânica (compressão, flexão estática, dureza Janka e cisalhamento) da madeira. A madeira de freijó apresentou composição química similar à de madeiras nobres tropicais, peso moderado (582,63 kg m-3) e estabilidade dimensional elevada em comparação com outras madeiras consagradas no mercado (retração longitudinal, radial e tangencial = 0,25, 4,27 e 6,83%, respectivamente). Os valores de resistência à compressão paralela (32,32 MPa) e perpendicular (8.02 MPa), resistência específica (55,32 MPa kg-1 m-3), dureza Janka paralela (2373,33 N) e perpendicular (2326,67 N), resistência à flexão estática (63,5 MPa) e ao cisalhamento (5,94 MPa) foram semelhantes aos valores observados em outras madeiras tropicais de alta densidade, produzidas em monocultivo e florestas naturais. A madeira em estudo é adequada para fabricação de produtos de alto valor agregado, como móveis finos, pisos residenciais, instrumentos musicais e peças estruturais.(AU)

Evaluación del fruto del Muyuyo (Cordia lutea Lamarck, boraginaceae), como ingrediente cosmético para la elaboración de fijadores de cabello / Evaluation of Muyuyo fruit (Cordia lutea Lamarck, boraginaceae), as a cosmetic ingredient for the preparation of hair fixatives

Las plantas contienen numerosos activos hidratantes, nutritivos, antioxidantes, suavizantes y estimulantes, ya sea en la corteza, en las hojas, en la raíz o en los granos. Los avances en materia de extracción y evaluación de los activos vegetales han sido realmente notables en la última década. El proyecto 'Agrocos', financiado con 2,9 millones de euros por la UE, está rastreando el mundo vegetal para encontrar sustitutivos naturales de los ingredientes sintéticos que se utilizan actualmente en los cosméticos. La especie Cordia lutea L. (Muyuyo, nombre originario de la zona litoral, peninsular de la Provincia del Guayas); está dentro de los arbustos que usualmente florecen en condiciones normales en zonas de clima cálido. Es decir, aquellas zonas con inviernos más o menos suaves, libres de frío y de vientos salinos. El muyuyo tiene muchas propiedades medicinales desde la flores, hojas, y frutos. Es conocido que la goma del fruto se la usa como goma arábiga, y para fijar el cabello. De acuerdo a las investigaciones realizadas sobre la composición química del fruto del muyuyo, nos encontramos que; es desconocida, de ahí que nace la importancia y se plantea en realizar su primer estudio fitoquímico, identificándose los metabolitos secundarios como: Lactonas, catequinas, azúcares reductores, saponinas, fenoles, taninos, aminoácidos y mucílagos.

Temporal variation of chemical composition and antimicrobial activity of the essential oil of Cordia curassavica (Jacq) Roemer and Schultes: Boraginaceae / Variación temporal de la composición química y la actividad antimicrobiana del aceite esencial de Cordia curassavica (Jacq) Roemer y Schultes: Boraginaceae

The people of San Rafael Coxcatlán use Cordia curassavica to treat gastrointestinal and respiratory disorders. The aim of this work was to investigate the temporal variation of chemical composition and antimicrobial activity of the essential oil of C. curassavica in two seasons of the year (dry and rainy). The essential oil of aerial parts was obtained by steam distillation, 12 and 17 compounds were identified for dry and rainy seasons respectively by GC-MS. The major component was for the dry season 1,7,7-trimethyl tricyclo (2.2.1.0(2,6)) heptane (20.3 percent), and for the rainy season was germacrene (24.41 percent). The antibacterial activity of essential oils varies temporarily because was active in nine strains in the dry season and four in the wet. The more sensitive strains were Stapahylococcus epidermidis and Vibrio cholera. The essential oil obtained in dry season presented a MIC of 0.75 and 0.125 mg/mL, and for the rainy season a MIC of 1.00 and 0.375 mg/mL respectively. Rhizoctonia solani was the more sensitive fungi strain (IC25 0.1300 mg/mL) in the rainy season. These results show that the chemical composition and biological properties of essential oil of the C. curassavica have temporal variation.

La población de San Rafael para tratar padecimientos gastrointestinales y respiratorios emplean Cordia curassavica. El objetivo del presente trabajo fue investigar la variación temporal de la composición química y la actividad antimicrobiana del aceite esencial de C. curassavica colectada en dos épocas del año (sequía y lluvias). El aceite esencial se obtuvo mediante la técnica de arrastre de vapor y los componentes se identificaron por CG-MS. En la época de secas se detectaron 12 compuestos y 17 en la de lluvias. El principal componente para la época de secas fue el 1,7,7 trimetil triciclo (2.2.1.0(2,6)) heptano (20.3 por ciento) y para la temporada de lluvias fue el germacrano (24.41 por ciento). La actividad antibacteriana del aceite esencial varía temporalmente porque fue activo sobre nueve cepas en la época seca y sobre cuatro cepas en la época lluviosa. Las cepas más sensibles para ambas estaciones fueron Stapahylococcus epidermidis y Vibrio cholerae. En la época de seca, el aceite esencial presentó la concentración mínima inhibitoria (CMI) de 0.75 y 0.125mg/mL, mientras que en la época de lluvias fueron de 1.00 y 0.375 mg/mL respectivamente. La cepa fúngica más sensible fue Rhizoctonia solani (IC25 0.130 mg/mL) en la época de lluvia. Estos resultados muestran que la composición química y las propiedades biológicas de los aceites esenciales de Cordia curassavica varian de acuerdo a la época del año.

Magnetic nanosystem for cancer therapy using oncocalyxone a, an antitomour secondary metabolite isolated from a Brazilian plant.

This paper describes the investigation and development of a novel magnetic drug delivery nanosystem (labeled as MO-20) for cancer therapy. The drug employed was oncocalyxone A (onco A), which was isolated from Auxemma oncocalyx, an endemic Brazilian plant. It has a series of pharmacological properties: antioxidant, cytotoxic, analgesic, anti-inflammatory, antitumor and antiplatelet. Onco A was associated with magnetite nanoparticles in order to obtain magnetic properties. The components of MO-20 were characterized by XRD, FTIR, TGA, TEM and Magnetization curves. The MO-20 presented a size of about 30 nm and globular morphology. In addition, drug releasing experiments were performed, where it was observed the presence of the anomalous transport. The results found in this work showed the potential of onco A for future applications of the MO-20 as a new magnetic drug release nanosystem for cancer treatment.

Antioxidant effects in the quinone fraction from Auxemma oncocalyx TAUB.

In previous studies in vitro we showed that the quinone fraction (QF) from the heartwood of Auxemma oncocalyx TAUB. presented antiplatelet and antioxidant activities. In the present work, the QF antioxidant property was evaluated in models of CCl(4)-induced hepatotoxicity in rats, and prolongation of pentobarbital-induced sleeping time in mice. Our results showed that levels of plasma glutamate-pyruvate-transaminase (GPT), as well as glutamate-oxalate-transaminase (GOT), were increased by the administration of CCl(4). On the other hand, only GPT levels were reduced by the QF treatment. Pentobarbital sleeping time was prolonged by the administration of CCl(4) and reduced by the QF treatment. Moreover, QF did not alter the pentobarbital-induced sleeping time. In conclusion, we showed that QF, represented mainly by oncocalyxone A, has hepatoprotective activity, and this effect is at least in part due to the antioxidant activity of this quinone.

Oncocalyxone A from Auxemma oncocalyx lacks genotoxic activity in phytohemagglutinin-stimulated lymphocytes.

Inadequate doses or prolonged chemotherapy can be cytotoxic or genotoxic to cancer patients, increasing the risk for the development of a second cancer, particularly acute leukemia. The association between therapeutic and genotoxic properties of oncocalyxone A (Onco A), make cytotoxic tests (mitotic index and chromosomal aberrations) fundamental in the accompaniment of the effects of this active compound. Therefore, the aim of the present study was to determine the genotoxic action of Onco A in vitro, during different phases of the cell cycle, utilizing primary cultures of lymphocytes of healthy individuals. The results showed that Onco A is cytotoxic during the cell cycle phases G1, G1/S, and S, however, not in G2. Onco A did not demonstrate a genotoxic effect in any of the cell cycle phases at the concentration studied. It is concluded that during the period of exposure, this active substance inhibits DNA synthesis and consequently cell division. Therefore, the absence of such genotoxicity for Onco A in the tests performed in this study provides important information in regard to the therapeutic use of this agent. Further studies are necessary to better understand the molecular mechanism of action of Onco A.

Toxicity to sea urchin egg development of the quinone fraction obtained from Auxemma oncocalyx.

Auxemma oncocalyx Taub. belongs to the Boraginaceae family and is native to the Brazilian northeast where it is known as "pau-branco". We investigated the ability of the water soluble fraction isolated from the heartwood of A. oncocalyx to inhibit sea urchin egg development. This fraction contains about 80% oncocalyxone A (quinone fraction), a compound known to possess strong cytotoxic and antitumor activities. In fact, the quinone fraction inhibited cleavage in a dose-dependent manner [IC50 of 18.4 (12.4-27.2) microg/ml, N = 6], and destroyed the embryos in the blastula stage [IC50 of 16.2 (13.7-19.2) microg/ml, N = 6]. We suggest that this activity is due to the presence of oncocalyxone A. In fact, these quinones present in A. oncocalyx extract have strong toxicity related to their antimitotic activity.

Heliotropium huascoense resin exudate: chemical constituents and defensive properties.

From the resinous exudate of Heliotropium huascoense a new compound, rel-(8R,9R)-carrizaloic acid, (1) (3-[rel-(8R,9R-9-hydroxy-9,13,13-trimethyl-12-oxo-10-cyclohexenyl)methyl]-4-methoxybenzoic acid), and three known flavonoids, [3-methylgalangin, 3,7-dimethylgalangin, and (-)-alpinone] have been isolated. The structure of 1 was determined by spectral and chemical methods. Several plant defensive properties of 1 (insecticidal and antifungal) have been evaluated.