químicos das folhas de Qualea grandiflora: atribuição dos dados de RMN de dois flavonóides glicosilados acilados diastereoisoméricos

Phytochemical investigation from leaves of the Qualea grandiflora (Vochysiaceae) resulted in the isolation and identification of kaempferol-3-O-α-L-(4"-E-p-coumaroyl)-rhamnoside, kaempferol-3-O-α-L-(4"-Z-p-coumaroyl)-rhamnoside, squalene, phytol, lupeol, α-amyrin, β-amyrin, sitosterol, sitostenone, sitosterol-3-O-β-D-glucopyranoside, ursolic and oleanolic acids. The structures of the compounds were identified by 1D- and 2D-NMR experiments, mass and UV spectrometry and comparison with literature data.

REPRODUCTIVE SYSTEM AND POLLEN FLOW IN PROGENIES OF Qualea grandiflora Mart., A TYPICAL SPECIES OF THE BRAZILIAN CERRADO

This study analyzed the reproductive system and the pollen dispersion pattern of Qualea grandiflora progenies. This is a typical species from the Brazilian Cerrado about which there are not too many studies from the genetics point of view. The study was conducted in an area of 2.2 hectares located in the Conservation Unit managed by the Forest Institute of the state of São Paulo, Brazil (Assis State Forest). Total genomic DNA of 300 seeds from 25 plants (12 seeds from each plant) was extracted and amplified using specific primers to obtain microsatellite markers. Results showed that selfing is frequent among adults and progenies, and the species reproduces by outcrossing between related and unrelated individuals (0.913). The single-locus outcrossing rate was 0.632, which indicates that mating between unrelated individuals is more frequent than between related plants. The selfing rate was low (0.087), that is, the species is allogamous and self-fertilization is reduced. About 35% of the plants in the progenies were full-sibs, and about 57%, half-sibs. Besides, about 8% of the progenies were selfing siblings. The genetic differentiation coefficient within progenies was 0.139, whereas the fixation rate was about 27%. The estimate of the effective size revealed that the genetic representativeness of descent was lower than expected in random mating progenies: The analyzed samples corresponded to only 13.2 individuals of an ideal panmictic population. In environmental recovery programs, seeds, preferably from different fruits, should be collected from 95 trees to preserve the genetic diversity of the species.

Genotoxicity of polar and apolar extracts obtained from Qualea multiflora and Qualea grandiflora

Ethnopharmacological relevance: The species Qualea grandiflora and Qualea multiflora, which belong to the Vochysiaceae family, are common in the Brazilian savannah (Cerrado biome), and the local inhabitants use these species to treat external ulcers and gastric diseases and as an anti-inflammatory agent. Studies have demonstrated that these plants contain compounds that exhibit pharmacological activities; however, the risks associated with their consumption are not known.Material and methods: In the present study, the mutagenicity of polar and apolar extracts from Qualea grandiflora and Qualea multiflora were assessed by employing the Ames assay with and without metabolic activation. Additionally, phytochemical analyses (HPLC-ESI-IT-MS, HPLC-UV-PDA and GC-IT-MS) were performed to identify the chemical constituents present in these species, including the evaluation of physico-chemical properties, such as polarity or apolarity of the organic compounds, which are related to each fraction obtained. These studies provide important information regarding the biochemical behaviour of these compounds.Results: All extracts exhibited mutagenicity, inducing frameshift mutations and base substitutions in DNA. Phytochemical analysis identified terpenes, ellagic acid derivatives and phytosteroids.Conclusions: The mutagenicity observed might be due to the presence of pentacyclic triterpenes and polyphenols, which are able to generate reactive oxygen species (ROS) and result in the potential to cause DNA damage. The genetic risk identified in this present work shows that special attention should be considered for the use of compounds obtained from these plant species in medicinal treatments. Further studies must be conducted to identify safe therapeutic doses. (C) 2011 Elsevier B.V. All rights reserved.

Qualea grandiflora, a Brazilian Cerrado medicinal plant presents an important antiulcer activity

Qualea grandiflora is one of the species widely used in folk medicine to treat gastric ulcers in Cerrado of the central region of Brazil. The hydroalcoholic extract of bark (HE) of Qualea grandiflora was investigated for their ability to prevent and heal lesions in the gastric mucosa. The oral administration of HE exhibited antiulcer activity decreasing the ulcerative index induced by HCl/ethanol solution, indomethacin/bethanechol and stress. In the Shay model, results showed that HE (p.o.) only reduced the severity of gastric lesions without effects on pH, gastric acidity or volume. When given by intraduodenal route, HE changed the pH, but did not modify the other parameters of the gastric juice. These data were in accordance with those obtained when HE was administered orally for 14 days after gastric ulcers were induced by acetic acid in rats. HE presented healing process in subacute gastric ulcer induced by acetic acid in rats. Moreover, histological examinations showed the simple columnar epithelium, lamina propria with simple branched tubular glandules with dilated lumen and large amounts of mucus secretion. Phytochemical investigation of HE led to the detection of terpenes, steroids, saponins, phenolic compounds and tannins in this extract, which may be involved in the observed activity. (c) 2005 Elsevier B.V.. All rights reserved.

A new Oligonychus and description of the female allotype of Oligonychus psidium Estebanes & Baker (Acari, Tetranychidae) from Qualea grandiflora Mart. (Vochysiaceae) in northwestern São Paulo, Brazil

Oligonychus longipenis, sp.n. and the female allotype of O. psidium Estebanes & Baker, 1968 from Qualea grandiflora Mart. (Vochysiaceae) is described. The male of O. psidium is redescribed in Northwestern São Paulo (Brazil). This is the first record for 0. psidium in Brazil.

químicos das folhas de Qualea grandiflora: atribuição dos dados de RMN de dois flavonóides glicosilados acilados diastereoisoméricos

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Dereplication of phenolic derivatives of qualea grandiflora and qualea cordata (vochysiaceae) using liquid chromatography coupled with ESI-QToF-MS/MS

A rational and selective method using on-line high-performance liquid chromatography (HPLC) coupled with electrospray quadrupole time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS) was established for the dereplication of phenolic derivatives from Qualea grandiflora and Qualea cordata. The selection of the extracts was based on the antioxidant capacity measured by in vitro DPPH assay. The HPLC-ESI-QToF-MS/MS analysis was conducted by on-flow detection, using high-resolution mass/ratio ions as well as collision induced MS/MS experiments for selected protonated ions. The dereplication of the EtOAc fraction from the hydro alcohol extract from the stem bark of Q. grandiflora allowed the detection of the flavonoids: 3',4',5',5,6,7-hexahydroxy- 8 methylflavanone, 8-methyl-naringenine and 3',7-dimethoxy-8 methyl-4',5,7- trihydroxyflavanone, as well as a benzophenone derivatives: bis(4,6-dimethoxy-2- hydroxy-3-methylphenyl)- metanone, 3',4'-dimethoxy-8-methyl-5,6,7 trihydroxyflavanone, 7-methoxy-6-methyl- 3',4',5 trihydroxyflavanone, 6,8-dimethyl-3' methoxy-4',5,7 trihydroxyflavanone and 3',5'-dimethoxy-6,8- dimethyl-4',5,7 trihydroxyflavanone were detected in the EtOAc fraction from the hydro-alcohol extract from the leaves of Q. cordata. © 2013 Sociedade Brasileira de Química.

Efeitos anti-inflamatório e antitumoral dos constituintes de Qualea grandiflora no tumor de Ehrlich

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

DEVELOPMENT OF MICROSATELLITE MARKERS FOR QUALEA GRANDIFLORA (VOCHYSIACEAE), A TYPICAL SPECIES OF THE BRAZILIAN CERRADO

Premise of the study: Microsatellite primers were developed to investigate genetic diversity and population structure of Qualea grandiflora, a typical species of the Brazilian cerrado. Methods and Results: Eight microsatellite loci were isolated using an enrichment cloning protocol. These loci were tested on a population of 110 individuals of Q. grandiflora collected from a cerrado fragment in Sao Paulo State, Brazil. The loci polymorphism ranges from seven to 19 alleles and the average heterozygosity value is 0.568, while the average polymorphic information content is 0.799. Conclusions: The developed markers were found to be highly polymorphic, indicating their applicability to studies of population genetic diversity in Q. grandiflora

Identification of ellagic acid derivatives in methanolic extracts from Qualea species

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Elaboração de métodos analíticos de desreplicação para o estudo metabolômico em espedies de Qualea (Vochysiaceae) : detecção e elucidação in situ de micromoléculas com potencial antioxidante

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Fenóis totais e atividade antioxidante de cinco plantas medicinais

This paper describes total phenolics content and antioxidant activity in the ethanolic extract of leaves, bark and roots of five medicinal plants: Terminalia brasiliensis Camb., Terminalia fagifolia Mart. & Zucc., Copernicia cerifera (Miller) H.E. Moore, Cenostigma macrophyllum Tul. var. acuminata Teles Freire and Qualea grandiflora Mart. The total phenolics content of the plant extracts, determined by the Folin-Ciocalteu method, varied from 250.0 ±8,2 to 763,63 ± 13.03 mg of gallic acid equivalent/g dry EtOH extract. The antioxidant activity of extracts was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay system. Extract of bark from T. brasiliensis, the most active, with an EC50 value of 27.59 ± 0.82 µg/mL, was comparable to rutin (EC50 = 27.80 ± 1.38) and gallic acid (EC50 = 24.27 ± 0.31), used as positive controls. The relationship between total phenolic content and antioxidant activity was positive and significant for T. brasiliensis, C. macrophyllum and C. cerifera.

Fitossociologia de sub-bosque de cerrado em talhão de Eucalyptus grandis W. Hill ex Maiden no município de Bom Despacho-MG

O Cerrado, o segundo maior bioma brasileiro, apresenta uma crescente área sujeita a impactos variados, o que desperta a necessidade de conservá-lo e desenvolver métodos para seu uso sustentável. Os objetivos do presente trabalho foram realizar um levantamento florístico e fitossociológico de regeneração em um Cerrado no município de Bom Despacho - MG e embasar tomadas de decisões para conservação da biodiversidade. Para o estudo foram instaladas 15 parcelas de 200 m² (10 x 20 m) em uma área originalmente de Cerrado, que atualmente encontra-se ocupada por um plantio de Eucalyptus grandis. A distribuição das parcelas foi feita sistematicamente. Foram amostradas todas as plantas lenhosas eretas com CAB - ao nível do solo - maior ou igual a 10 cm. A composição florística apresentou 39 espécies, distribuídas em 24 famílias. As famílias com maior número de espécies foram Leguminosae Caesalpinioideae, com cinco espécies, Myrtaceae, com quatro, e Melastomataceae, com três, seguidas de Annonaceae, Leguminosae Papilionoideae, Nyctaginaceae, Rubiaceae e Vochysiaceae, com duas. A espécie que apresentou o maior VI foi Eucalyptus grandis (42,03%), seguida das Miconia albicans (7,69%), Brosimum gaudichaudii (6,9%), Eugenia dysenterica (4,99%), Qualea grandiflora (3,11%) e Xylopia aromatica (3,01%). Das 39 espécies lenhosas nativas encontradas no sub-bosque de Eucalyptus grandis, 27 são peculiares do Cerrado e as demais são acessórias, vindas de florestas da região. Esses dados mostram que o Cerrado está em regeneração.

Fitossociologia e análise comparativa da composição florística do cerrado da flora de Paraopeba-MG

Foi conduzido um estudo fitossociológico no Cerrado sentido restrito da Floresta Nacional de Paraopeba, comparando-se os resultados (qualitativos) com os de outras amostras. Foram estabelecidas 10 parcelas de 0,1 ha (20 x 50 m), sendo incluídas no estudo todas as árvores (C30 > 15,7 cm). Foram registrados 1.990 indivíduos/ha (densidade total) e 18,13 m²/ha (área basal total). Os valores de riqueza (73 espécies/38 famílias), de diversidade Shannon (3,57) e de uniformidade (0,83) indicaram grande heterogeneidade e baixa dominânica ecológica. Leguminosae e Vochysiaceae foram as famílias mais ricas em espécies. O grupo das árvores mortas alcançou o maior valor de importância, seguido por Qualea parviflora, Pera glabrata, Erythroxylum suberosum e Qualea grandiflora. A análise comparativa de composições florísticas de 11 cerrados indicou uma forte influência da flora de Floresta Atlântica em Cerrado marginal do interior de São Paulo. Houve influência da localização geográfica na similaridade do Cerrado de Palmas, TO, com as outras áreas.

Análise da estrutura de uma comunidade lenhosa em área de cerrado sensu stricto no município de Senador Modestino Gonçalves, norte de Minas Gerais, Brasil

Com a finalidade de conhecer a estrutura de uma comunidade arbórea de uma área de Cerrado, fez-se um estudo fitossociológico no Município de Senador Modestino Gonçalves. Para tal foram delimitadas 30 parcelas de 10 x 20m para levantamento dos dados, utilizando-se como critério de inclusão os indivíduos com circunferência do tronco à altura do solo (CAS) = 10 cm. Foram encontradas 91 espécies de 38 famílias. As espécies que se destacaram como as mais importantes foram Qualea grandiflora, Eriotheca pubescens, Caryocar brasiliense, Byrsonima coccolobaefolia, Myrsine guianensis, Qualea parviflora, Dalbergia miscolobium, Stryphnodendron adstringens, Plathymenia reticulata e Lafoensia pacari. Essas 10 espécies representaram 49,32% do VI e 51,26% dos indivíduos amostrados. A área não apresentou espécie com dominância marcante, como mostrou o valor de equabilidade (J'= 0,80). Além de se destacar pela riqueza, o cerrado estudado destacou-se também pelos altos valores de densidade (6.476,67 ind/ha), de área basal (28,93 m²/ha) e pelo alto índice de diversidade (H'=3,61).