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.

Uma proposta de material didático baseado nas espécies de Vochysiaceae existentes em uma trilha no cerrado de Bauru - SP

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

Fitotoxicidade e análise fitoquímica a partir de folhas de cinco espécies de Cerrado

Pós-graduação em Biociências - FCLAS

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)

Aglacins I-K, three highly methoxylated lignans from Aglaia cordata

Further chemical investigation of the stem bark of Aglaia cordata has led to the isolation and identification of three new lignans, namely, aglacins I-K (1-3), all of which contain two contiguous trimethoxylated phenyl systems. Among them, aglacins I and J (1 and 2) are new members of the aryltetralin cyclic lactol class, while aglacin K (3) is a new example of tetralrydrofuran lignan. The structures of these compounds were established on the basis of spectroscopic data interpretation.

Iridaea cordata (Gigartinales, Rhodophyta): responses to artificial UVB radiation

The effects of UVB radiation on the different developmental stages of the carrageenan-producing red alga Iridaea cordata were evaluated considering: (1) carpospore and discoid germling mortality; (2) growth rates and morphology of young tetrasporophytes; and (3) growth rates and pigment content of field-collected plant fragments. Unialgal cultures were submitted to 0.17, 0.5, or 0.83 W m(-2) of UVB radiation for 3 h per day. The general culture conditions were as follows: 12 h light/12 h dark cycles; irradiance of 55 mu mol photon. per square meter per second; temperature of 9 +/- 1 degrees C; and seawater enriched with Provasoli solution. All UVB irradiation treatments were harmful to carpospores (0.17 W m(-2) = 40.9 +/- 6.9%, 0.5 W m(-2) = 59.8 +/- 13.4%, 0.83 W m(-2) = 49 +/- 17.4% mortality in 3 days). Even though the mortality of all discoid germlings exposed to UVB radiation was unchanged when compared to the control, those germlings exposed to 0.5 and 0.83 W m(-2) treatments became paler and had smaller diameters than those cultivated under control treatment. Decreases in growth rates were observed in young tetrasporophytes, mainly in 0.5 and 0.83 W m(-2) treatments. Similar effects were only observed in fragments of adult plants cultivated at 0.83 W m(-2). Additionally, UVB radiation caused morphological changes in fragments of adult plants in the first week, while the young individuals only displayed this pattern during the third week. The verified morphological alterations in I. cordata could be interpreted as a defense against UVB by reducing the area exposed to radiation. However, a high level of radiation appears to produce irreparable damage, especially under long-term exposure. Our results suggest that the sensitivity to ultraviolet radiation decreases with increased algal age and that the various developmental stages have different responses when exposed to the same doses of UVB radiation.

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.

Preparative droplet counter-current chromatography for the separation of the new nor-seco-triterpene and pentacyclic triterpenoids from Qualea parviflora

The methanolic extract of the bark of the medicinal plant Qualea parviflora (Vochysiaceae) contains new nor-seco-triterpene and pentacyclic triterpenoids. They were separated in a preparative scale using droplet counter-current chromatography. The optimum solvent used was composed of a mixture of CHCl3/MeOH/H2O (43:37:20, v/v) in the descending mode and led to a successful separation of the new compound 28-nor-17, 22-seco-2 alpha, 3 beta, 19, 22, 23-pentahydroxy-Delta(12)-olecinane, besides the known triterpenoids bellericagenin B, bellericaside B and arjunglucoside I. Identification was performed by ESI-MS, H-1 NMR and C-13 NMR analyses.

Qualea parviflora Mart.: An integrative study to validate the gastroprotective, antidiarrheal, antihemorragic and mutagenic action

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

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.

Germinação de sementes de Drymaria cordata (L.) Willd. ex Roem & Schult.: efeito do potencial hídrico

Modelos matemáticos baseados no conceito de graus dia (thermal-time) e Ψw dia (hydrotime) podem ser usados para a elaboração de modelos mais gerais sobre a germinação e emergência de plântulas no campo, podendo ser uma importante ferramenta para estudos sobre a biologia de plantas daninhas e seu controle. Neste trabalho, avaliou-se a germinação de sementes de D. cordata em resposta ao potencial hídrico (Ψw), usando-se o modelo Ψw dia. Tanto a germinabilidade como a velocidade de germinação decresceram linearmente com a redução do Ψw, atingindo valores próximos a zero em -0.8 MPa. em temperatura ótima, a taxa de queda na germinação foi maior em comparação com as temperaturas sub- e supra-ótima. O Ψw base (Ψwb) mediano foi similar entre as temperaturas sub-ótima (19 ºC) e supra-ótima (32 ºC), mas foi maior (menos negativo) à temperatura ótima (25 ºC), mostrando que sementes de D. cordata são menos sensíveis à redução do potencial hídrico à 19 ºC do que à 25 ºC. O Ψw dia foi maior para sementes germinadas à temperatura sub-ótima do que à temperatura ótima, mostrando que a velocidade de germinação num dado potencial hídrico é maior em temperatura ótima. A quantidade de Ψw dia necessária para a germinação foi maior em temperatura supra-ótima do que em temperatura ótima, e menor em temperatura supra-ótima do que em sub-ótima. em geral, Ψw dia foi relativamente constante entre as diferentes sub-populações. O modelo de Ψw dia pode descrever bem o efeito do potencial hídrico sobre as curvas de germinação (porcentagem acumulada x tempo), especialmente às temperaturas sub-ótima e supra-ótima.

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)