Estudo químico e avaliação da atividade antioxidante e antimicrobiana dos escapos de Syngonanthus nitens (bong.) Ruhland. (Eriocaulaceae)

Neste trabalho é apresentado o estudo químico dos escapos de Syngonanthus nitens (Bong.) Ruhland, pertencente à família Eriocaulaceae. O extrato metanólico foi preparado por percolação, concentrado e fracionado em coluna de permeação em gel. As frações obtidas foram analisadas por CCDC e purificadas por HSCCC, HPLC-RI e HPLC-PDA. As estruturas foram determinadas usando ultravioleta, técnicas mono e bidimensionais de RMN e espectrometria de massas com fonte electrospray e analisador íon trap (modo de inserção direta). O perfil cromatográfico de HPLC-PDA mostrou que as flavonas derivadas da luteolina são os seus principais constituintes químicos. Foram isoladas as substâncias: 7-metoxiluteolina-8-C-β-D-glicopiranosídeo (SN1), 7-metoxiluteolina-6-C-β-D-glicopiranosídeo (SN2), 3',7-dimetoxiluteolina-6-C-β-D-glicopiranosídeo (SN3), luteolina (SN4), 6-hidroxiluteolina (SN5), luteolina-6-C--D-glicopiranosídeo (Sn6), 6-hidroxiluteolina-7-O--D-galactopiranosideo (Sn7) e 7-metoxiluteolina-6-C- β-D-glicopiranosideo-(3'-O-3''')-7ʹ-metoxiluteolina-8'-C-β-D-glicopiranosídeo (Sn8). Foram avaliadas as atividades antioxidantes do extrato metanólico dos escapos de S. nitens e do biflavonóide identificado, os quais apresentaram atividade significativa quando comparada com os padrões do ácido gálico, rutina e quercetina . A atividade antimicrobiana do extrato metanólico dos escapos e das substâncias identificadas derivadas da luteolina foram também avaliadas. O extrato metanólico dos escapos apresentou melhor atividade antimicrobiana, quando comparada com os demais flavonoides isolados e identificados do mesmo extrato. Finalmente, foi avaliada a atividade antiulcerogênica do extrato metanolico dos escapos, utilizando-se o modelo de lesão ulcerativa induzida por etanol absoluto

Quantification of Flavonoids, Naphthopyranones and Xanthones in Eriocaulaceae Species by LC-PDA

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

Anatomia de espécies brasileiras de Eriocaulaceae: Comanthera e Syngonanthus

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Estudo químico e avaliação da atividade antimicrobiana de fungos endofíticos associados à Paepalanthus chiquitensis (eriocaulaceae) e efeitos de moduladores químicos epigenéticos no cultivo de Pochonia chlamydosporia

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

Anatomia floral e ontogenia de espécies dímeras de Paepalanthus Mart. (Eriocaulaceae, Poales) e seu significado evolutivo

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Flavonoids and a naphthopyranone from Eriocaulon ligulatum and their mutagenic activity

A new acylated flavonoid, 6,4'-dimethoxyquereetin-3-O-beta-D-6 ''[3,4,5-trihydroxy (E)-cinnamoyl]glucopyranoside, and a naphthopyranone dimer, named eriocauline, together with 2 other known flavonoids, 6-methoxyapigenin-7-O-beta-D-glucopyranoside and 6-methoxyapigenin-7-O-beta-D-allopyranoside, have been isolated from the capitulae of Eriocaulon ligulatum. The compounds were identified using spectroscopic methods (HR-ESI-MS, and 1-D and 2-D NMR). The methanol extract exhibited mutagenic activity in the Salmonella/microsome assay, in strains TA100, TA97a and TA102 and for dichloromethane extract tested in strain TA98.

Effect of the isocoumarin paepalantine on the luminol and lucigenin amplified chemiluminescence of rat neutrophils

Paepalantine (9,10-dihydroxy-5,7-dimethoxy-1H-naphto(2,3c)pyran-1-one), a natural isocoumarin isolated from the capitula of Paepalanthus bromelioides (Eriocaulaceae), was assessed for its effect on the respiratory burst (zymosan-stimulated luminol-enhanced chemiluminescence and. PMA-stimulated lucigenin-enhanced chemiluminescence) of polymorphonuclear neutrophils in vitro. Special attention was devoted to establishing the IC50 for neutrophils. Paepalantine was able to decrease luminol and lucigenin chemiluminescence, reflecting an inhibitory effect on the respiratory burst, with an ED50 of 0.44 +/- 0.05 and 0.84 +/- 0.15 mug/ml, respectively. A cell-free system was performed with paepalantine on myeloperoxidase/H2O2 and myeloperoxidase/H2O2/Cl- systems. Paepalantine inhibited luminol oxidation in both systems. This inhibition was related to the interaction of paepalantine-myeloperoxidase and its scavenger effect on HOCl.

Antioxidant activity of isocoumarins isolated from Paepalanthus bromelioides on mitochondria

The isocoumarins (1-50 mu M) paepalantine (9,10-dihydroxy-5,7-dimethoxy-1H-naptho(2,3c)pyran-1-one), 8,8 '-paepalantine dimer, and vioxanthin isolated from Paepalanthus bromelioides, were assessed for antioxidant activity using isolated rat liver mitochondria and non-mitochondrial systems, and compared with the flavonoid quercetin. The paepalantine and paepalantine dimers, but not vioxanthin, were effective at scavenging both 1,1-diphenyl-2-picrylhydrazyl (DPPH*) and superoxide (O-2(-)) radicals in non-mitochondrial systems, and protected mitochondria from tert-butylhydroperoxide-induced H2O2 accumulation and Fe2+ -citrate-mediated mitochondrial membrane lipid peroxidation, with almost the same potency as quercetin. These results point towards paepalantine, followed by paepalantine dimer, as being a powerful agent affording protection, apparently via O-2(-) scavenging, from oxidative stress conditions imposed on mitochondria, the main intracellular source and target of those reactive oxygen species. This strong antioxidant action of paepalantine was reproduced in HepG2 cells exposed to oxidative stress condition induced by H2O2. (C) 2007 Elsevier Ltd. All rights reserved.

Effects of isocoumarins isolated from Paepalanthus bromelioides on mitochondria: Uncoupling, and induction/inhibition of mitochondrial permeability transition

Isolated mitochondria may undergo uncoupling, and in presence of Ca2+ at different conditions, a mitochondrial permeability transition (MPT) linked to protein,thiol oxidation, and demonstrated by CsA-sensitive mitochondrial swelling; these processes may cause cell death either by necrosis or by apoptosis. Isocoumarins isolated from the Brazilian plant Paepalanthus bromelioides (Eriocaulaceae) paepalantine (9,10-dihydroxy-5,7-dimethoxy-1H-naptho(2,3c)pyran-1-one), 8,8'-paepalantine dimer, and vioxanthin were assayed at 1-50 mu M on isolated rat liver mitochondria, for respiration, MPT, protein thiol oxidation, and interaction with the mitochondrial membrane using 1,6-diphenyl-1,3,5-hexatriene (DPH). The isocoumarins did not significantly affect state 3 respiration of succinate-energized mitochondria; they did however, stimulate 4 respiration, indicating mitochondrial uncoupling. Induction of MPT and protein thiol oxidation were assessed in succinate-energized mitochondria exposed to 10 mu M Ca2+; inhibition of these processes was assessed in non-energized organelles in the presence of 300 mu M t-butyl hydroperoxide plus 500 mu M Ca2+. Only paepalantine was an effective MPT/protein thiol oxidation inducer, also releasing cytochrome c from mitochondria; the protein thiol oxidation, unlike mitochondrial swelling, was neither inhibited by CsA nor dependent on the presence of Ca2+. Vioxanthin was an effective inhibitor of MPT/protein thiol oxidation. All isocoumarins inserted deeply into the mitochondrial membrane, but only paepalantine dimer and vioxantin decreased the membrane's fluidity. A direct reaction with mitochondrial membrane protein thiols, involving an oxidation of these groups, is proposed to account for MPT induction by paepalantine, while a restriction of oxidation of these same thiol groups imposed by the decrease of membrane fluidity, is proposed to account for MPT inhibition by vioxanthin. (c) 2006 Published by Elsevier B.V..

Ascorbic acid potentiates the cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin

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

Intestinal anti-inflammatory activity of paepalantine, an isocoumarin isolated from the capitula of Paepalanthus bromelioides, in the trinitrobenzenesulphonic acid model of rat colitis

The preventative intestinal anti-inflammatory activity of paepalantine, an isocoumarin isolated from the capitula of Paepalarithus bromelioides, was tested in the trinitrobenzenesulphonic acid (TNBS) model of rat colitis. This was performed in two different experimental settings, i. e. when the colonic mucosa is intact or when the mucosa is in process of recovery after an initial insult. The results obtained revealed that the paepalantine pretreatment, at doses of 5 and 10 mg/kg, significantly attenuated the colonic damage induced by TNBS in both situations, as it was evidenced both histologically and biochemically. This beneficial effect was associated with an improvement in the colonic oxidative status, since paepalantine prevented the glutathione depletion that occurred as a consequence of the colonic inflammation. In addition, the intestinal anti-inflammatory effect exerted by this isocoumarin was associated with an inhibition of colonic nitric oxide activity, which is upregulated as a consequence of the inflammatory process. In conclusion, the preventative effect exerted by paepalantine in the TNBS model of rat colitis is probably related with its antioxidant properties.

Composição de espécies vasculares de campo sujo e campo úmido em área de cerrado, Itirapina - SP, Brasil

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Handicrafts from Jalapao (TO), Brazil, and their relationship to plant anatomy

EICHEMBERG, M. T. and V. L. SCATENA (Universidade Estadual Paulista, Departamento de Botanica, Rio Claro, São Paulo, Brazil). J. Torrey Bot. Soc. 138:34-40. 2011.-Handicrafts from Jalapao (TO), Brazil, and their Relationship to Plant Anatomy. In the state of Tocantins, midwestern Brazil, communities from the region of Jalapao use scapes of "capim dourado" (golden grass - Syngonanthus nitens- Eriocaulaceae) and leaves of "buriti" (Mauritia flexuosa - Arecaceae) to make handicrafts (baskets and ornaments). The predominant biome of this area is cerrado (savanna), with a notable presence of buriti in the "veredas" (swampy forest-like vegetation), and of golden grass, which is one of the most common plants in humid grasslands. These traditional handicrafts represent a significant source of income for local communities. The whole scapes of Syngonanthus nitens are used due to their golden color, which is a reflection of such internal structures as thick walled cells and lignin in the epidermis and cortex. The strips called "seda" (silk) used to sew the scapes in the making of handicrafts come from young leaves of Mauritia,flexuosa. They are constituted by the adaxial epidermis and bundles of subepidermic fibers, both showing thick-walled cells. Since the cells of the bundles of sclerenchymatic fibers from the abaxial surface of buriti leaves present stegmata containing silica bodies, their mechanical properties are less adapted to the production of "silk", justifying the use of the leaf adaxial surface. Anatomical characteristics such as the thickening and composition of the cell walls of both species together with sociocultural factors, allow a better knowledge of the use of plant structures in the making of handicrafts.

Characterization of flavonoid and naphthopyranone derivatives from Eriocaulon ligulatum using liquid chromatography tandem mass spectrometry

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