Navegando por Palavras-chave "Guarea macrophylla"
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- ItemAcesso aberto (Open Access)Estudo fitoquímico da madeira de Guarea macrophylla (Meliaceae)(Sociedade Brasileira de Química, 2009-01-01) Lago, Joao Henrique Ghilardi [UNIFESP]; Roque, Nídia Franca; Universidade Federal de São Paulo (UNIFESP); Universidade Federal da Bahia Instituto de QuímicaIn the present work, the crude ethanol extract from wood of G. macrophylla was submitted to liquid/liquid partition between hexane, CH2Cl2, EtOAc and n-BuOH. Each phase was individually chromatographed over silica gel, Sephadex LH-20 or Amberlite XAD-2 to give eight terpene derivatives, such as five sesquiterpenoids (caryophyllene oxide, guai-6-en-10β-ol, spathulenol, aromadendrane-4β,10α-diol and aloaromadendrane-4α,10β-diol) as well as three triterpenoids (cicloart-24-ene-3β,23(R*)-diol, cicloart-24-ene-3β,23(S*)-diol, and cicloart-23E-ene-3β,25-diol). Additionally, were isolated three fatty acids (linolenic, linoleic and stearic), two steroids (sitosterol and stigmasterol) and sacarose. The structures of all these compounds were characterized by spectrometric analysis, mainly mass spectrometry and NMR and comparison of these data described in the literature.
- ItemAcesso aberto (Open Access)Estudos das variações intraespecíficas/interpopulacionais e avaliação da atividade anti-leishmania dos óleos voláteis das folhas de Guarea macrophylla Vahl. ssp. tuberculata Vellozo (Meliaaceae)(Universidade Federal de São Paulo, 2015-04-29) Oliveira, Emerson Alves de [UNIFESP]; Lago, João Henrique Ghilardi [UNIFESP]; Universidade Federal de São Paulo (UNIFESP)The present work studies the chemical composition of intraspecific and interpopulational variations of the volatile oils contained on G. macrophylla leaves. For the accomplishment of such study were collected five samples of two different specimens located on the cities of São Paulo (I) and Cubatão (II) every three months along the term of one year. Thru CG, CG/EM analysis and calculation of Kovats indices were identified 57 compounds. Besides that, it was noticed a phytogeografical variation, being that the oil collected from (I) showed larger qualitative diversity (57 compounds) in relation to oil collected from (II) (32 compounds). Nonetheless, a chemical similarity was noticed since the sesquiterpenes were majority in both oils 73.27±0.64% to 85.87±0.76% and 68.24±1.72% to 80.78±1.76%, for I and II respectively. Three meteorological variables were monitored during the study, median maximum temperature, median minimum temperature and total precipitation indices. From the meteorological variables analysis and compilation it was possible to identify a different climatic profile for both cities, which according to literature and our field observations may have influenced the oils variations in gain and compounds, being that the gain might have influenced directly by the total precipitation. The raw volatile oils in the five samples collected also underwent anti-Leishmania trials using promastigotes and amastigotes from L. (L.) amazonensis. The anti-promastigote evaluation the volatile oils showed CE50 results varying from 11.8±5.2 to 17.2±5.1 and 12.0±1.2 to 20.5 ±2.7 µg/mL for subjects I and II respectively, indicating a strong anti-promastigote action. In the anti-amastigote evaluation the volatile oils from subject I shows significant dose dependent anti-amastigote action. Nonetheless, the dose dependent anti-amastigote action was not observed on subject II. The results of the anti-amastigote activity observed on subject I are coincidently inverse to the seasonal bicyclogermacrene variation percentage presented by the same subject, which suggests possible direct action of this compound in the infection indexes. The volatile oils also underwent trials for cytotoxicity (macrophage J774) and IS calculation, for cytotoxicity the CC50 varied from 65.6±6.1 to ?100 and 17.7±4.6 to 32.3±2.8 µg/mL for subjects I and II respectively. The verified index selectivity were 4.8 to ?5.8 and 1.2 to 2.7 for subjects I and II respectively. Due to the pharmacological potential observed in this study, the G. macrophylla?s volatile oil may be considered as a potential source for future studies in search of a prototype, thus enabling the development of antiparasitic pharmacos and phytotherapies.
- ItemAcesso aberto (Open Access)Identificação química e avaliação do potencial antitumoral dos metabólitos especiais de guarea macrophylla ssp tuberculata (meliaceae)(Universidade Federal de São Paulo, 2016-08-24) Conserva, Geanne Alexsandra Alves [UNIFESP]; Lago, João Henrique Ghilardi [UNIFESP]; Universidade Federal de São Paulo (UNIFESP)Currently, several researches in phytochemical screening are associated with the evaluation of biological activities, aiming the isolation and structural characterization of bioactive compounds. In this context, the species Guarea macrophylla ssp. tuberculata (Meliaceae), unknown in biological point of view, had the ethanol extract of leaves subjected to evaluation of in vitro cytotoxic activity against the B16F10-Nex2 cell lineage. The bioactive extract was subjected to liquid-liquid partition, where the phases in Hexane, EtOAc and DCM were obtained, being the first, the most active (30% cell viability 100 ?g/ml). Aiming the identification of active compounds, the hexane phase of ethanol extract of G. macrophylla was subjected to several chromatographic fractionation techniques fully bio-guided (silica gel 60, Sephadex LH-20, Florisil® and HPLC), allowing then, isolation and structural characterization of two triterpene with cycloartane skeleton: cycloart-23E-ene-3?, 25-diol (I), 23,24-dihydroxy-cicloart-25-en-3-one (II), and two pimarane diterpenes: isopimara -7,15-diene-2?, 3?-diol (III) and isopimara-7,15-diene, 3?-ol (IV). Compounds (II) and (III) are considered unprecedented in the literature, which structures were identified/elucidated by spectroscopic and spectrometric analysis, such as nuclear magnetic resonance (NMR), Infrared (IR), circular dichroism (CD) and spectrometry and high and low resolution mass spectrometry (MS). Isolated compounds were evaluated for their cytotoxic potential by MTT colorimetric quantitative assay against murine melanoma cell lines (B16F10-Nex2) and, against several human tumoral cell lines: human melanoma (A2058), breast adenocarcinoma (MCF7), leukemia (HL-60) and human cervical carcinoma (HeLa), presenting significative IC50 values, ranging from 8,0 ± 0,2 and 94±3.4 µg/mL. But when comparing the IC50 values obtained with the values of the positive control (cisplatin), it can be inferred that the compounds I, II and III performed better just to MCF7 line. Depth studies of cell death mechanism (morphological study, fragmentation and condensation of DNA and measurement of mitochondrial membrane potential) showed that the tumoral cell line, B16F10-Nex2 (murine melanoma), chosen for ongoing work, when treated with I, actives the programmed cell death mechanism (apoptosis), involving the mitochondria as the main affected organelle.
- ItemAcesso aberto (Open Access)Óleos essenciais de plantas medicinais: estudo químico e avaliação biológica da atividade biológica das espécies Allophylus edulis e Guarea macrophylla(Universidade Federal de São Paulo, 2014-04-28) Ribeiro Filho, Waldemar Alves [UNIFESP]; Sartorelli, Patricia [UNIFESP]; Universidade Federal de São Paulo (UNIFESP)The plant species are a number of sources of volatile substances of low molecular mass, known as secondary metabolites or natural products. The use of many of these metabolites, such as pharmaceuticals or antifungal agents has stimulated research on the plant species to be described from the point of view phytochemical by the pharmaceutical and agrochemical industries. Many of the drugs used in therapy today are derived from plants, and the search for species with antimicrobial and antitumor properties have been intensified in recent years due to the increasing problems associated with the use of various antibiotics. This project aims to study the chemical and biological evaluation of essential oils extracted from two plant species: Allophylus edulis and Guarea macrophylla. This work included the collection of plant species, obtaining essential oils from fresh leaves by hydrodistillation in Clevenger type apparatus, the identification of the chemical constituents and evaluation of antimicrobial and cytotoxic activities. Plants were selected taking into consideration the accessibility and availability of the Parque Estadual da Serra do Mar - Itutinga - Pilões in the city of Cubatão, and in the case of A. edulis, weighed up the lack of scientific studies detailing the chemical composition of volatile oils and biological activity. Gas chromatography was chosen as the analytical technique to effect the separation of the chemical constituents and mass spectrometry for identification and quantification of them. As a parameter for this determination was proposed the use of Kovatz Retention Index (KI), which compares the retention time of a complex mixture with the retention time of a series of alkanes, allowing for a later comparison with values tabulated in the literature. For the first time it was performed the analysis of the chemical composition of the essential oils of A. edulis. Evaluated for antimicrobial activity, essential oils of the two species were inactive. Regarding the evaluation of the cytotoxic potential of the species A. edulis and G. macrophylla showed good activity against the murine melanoma B16F10-Nex2.
- ItemSomente MetadadadosTerpenoids from Leaves of Guarea macrophylla Display In Vitro Cytotoxic Activity and Induce Apoptosis In Melanoma Cells(Georg Thieme Verlag Kg, 2017) Conserva, Geanne Alexandra A. [UNIFESP]; Girola, Natalia [UNIFESP]; Figueiredo, Carlos R. [UNIFESP]; Azevedo, Ricardo A.; Mousdell, Sasha; Sartorelli, Patricia [UNIFESP]; Soares, Marisi G.; Antar, Guilherme M.; Lago, Joao Henrique G.Guarea macrophylla is a Brazilian plant species that has been used in folk medicine to treat a range of diseases. Our ongoing work focuses on the discovery of new bioactive natural products derived from Brazilian flora. The current study describes the identification of cytotoxic compounds from the EtOH extract of leaves from G. macrophylla using bioactivity-guided fractionation. This approach resulted in the isolation and characterization of four compounds: cycloart-23E-ene-3 beta,25-diol (1), (23S*,24S*)-dihydroxycicloart-25-en-3-one (2), isopimara-7,15-diene-2 alpha,3 beta-diol (3), and isopimara-7,15-dien-3 beta-ol (4), in which 2 and 3 are identified as new derivatives. In vitro assays were conducted to evaluate the cytotoxic activity of compounds 1-4 against a panel of cancer cell lines and to determine the possible mechanism(s) related to the activity of the compounds on B16F10Nex2 cells. The most active compound 1 induced cytotoxic effects on tumor cells, with IC50 values of 18.3, 52.1, and 58.9 mu M against HL-60, HeLa, and B16F10-Nex2 tumor cells, respectively. Furthermore, it was observed in melanoma cells that compound 1 induced several specific apoptotic hallmarks, such as morphological changes in the cell shape structure, nuclear DNA condensation, specific chromatin fragmentation, and disruption in the mitochondrial membrane potential, which are related to the intrinsic apoptotic pathway.