RESUMO
Calea pinnatifida (R. Br.) Less. is a plant of Brazilian folk medicine. We evaluated the influence of environmental factors on the chemical profile of C. pinnatifida collected during the winter season. C. pinnatifida leaves, alongside soil samples, were collected from two sites of different altitude. Plant samples were sequentially extracted, while soil samples were subject to compositional analysis. Plant extracts were compared using HPTLC-UV, using chemometric analyses to compare samplings harvested at both altitudes. Two marker metabolites, calein A (1) and acetylportentol (2), were isolated from samples collected at the respective altitudes. The differing metabolic profiles observed may be a result of the influence of environmental factors.
Assuntos
Asteraceae , Plantas Medicinais , Altitude , Brasil , Extratos Vegetais , Folhas de Planta , SoloRESUMO
The phytochemical study of Stereocaulon montagneanum harvested in Sumatra (Indonesia) led to the isolation of 11 known compounds including two metabolites not previously described in the genus Stereocaulon, peristictic acid (8) and menegazziaic acid (10). The complete 1H and 13C NMR spectral assignments of stictic acid derivatives are reported with some revisions. Five depsidones belonging to the stictic acid chemosyndrome were superoxide anion scavengers as potent as ascorbic acid and with no toxicity on two human cell lines.
Assuntos
Antioxidantes/farmacologia , Sequestradores de Radicais Livres/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Líquens/química , Oxepinas/farmacologia , Protetores contra Radiação/farmacologia , Superóxidos/metabolismo , Animais , Antioxidantes/química , Antioxidantes/isolamento & purificação , Linhagem Celular , Avaliação Pré-Clínica de Medicamentos , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Humanos , Indonésia , Queratinócitos/efeitos dos fármacos , Queratinócitos/efeitos da radiação , Melanoma Experimental , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oxepinas/química , Oxepinas/isolamento & purificação , Protetores contra Radiação/química , Protetores contra Radiação/isolamento & purificação , Solventes , Raios UltravioletaRESUMO
BACKGROUND: Natural products from lichens are widely investigated for their biological properties, yet their potential as central nervous system (CNS) therapeutic agents is less explored. PURPOSE: The present study investigated the neuroactive properties of selected lichen compounds (atranorin, perlatolic acid, physodic acid and usnic acid), for their neurotrophic, neurogenic and acetylcholine esterase (AChE) activities. METHODS: Neurotrophic activity (neurite outgrowth) was determined using murine neuroblastoma Neuro2A cells. A MTT assay was performed to assess the cytotoxicity of compounds at optimum neurotrophic activity. Neuro2A cells treated with neurotrophic lichen compounds were used for RT-PCR to evaluate the induction of genes that code for the neurotrophic markers BDNF and NGF. Immunoblotting was used to assess acetyl H3 and H4 levels, the epigenetic markers associated with neurotrophic and/or neurogenic activity. The neurogenic property of the compounds was determined using murine hippocampal primary cultures. AChE inhibition activity was performed using a modified Ellman's esterase method. RESULTS: Lichen compounds atranorin, perlatolic acid, physodic acid and (+)-usnic acid showed neurotrophic activity in a preliminary cell-based screening based on Neuro2A neurite outgrowth. Except for usnic acid, no cytotoxic effects were observed for the two depsides (atranorin and perlatolic acid) and the alkyl depsidone (physodic acid). Perlatolic acid appears to be promising, as it also exhibited AChE inhibition activity and potent proneurogenic activity. The neurotrophic lichen compounds (atranorin, perlatolic acid, physodic acid) modulated the gene expression of BDNF and NGF. In addition, perlatolic acid showed increased protein levels of acetyl H3 and H4 in Neuro2A cells. CONCLUSION: These lichen depsides and depsidones showed neuroactive properties in vitro (Neuro2A cells) and ex vivo (primary neural stem or progenitor cells), suggesting their potential to treat CNS disorders.
Assuntos
Benzoatos/farmacologia , Benzofuranos/farmacologia , Sistema Nervoso Central/efeitos dos fármacos , Depsídeos/farmacologia , Dibenzoxepinas/farmacologia , Hidroxibenzoatos/farmacologia , Lactonas/farmacologia , Líquens/química , Acetilcolinesterase/metabolismo , Animais , Benzoatos/uso terapêutico , Benzofuranos/uso terapêutico , Produtos Biológicos/farmacologia , Produtos Biológicos/uso terapêutico , Fator Neurotrófico Derivado do Encéfalo/genética , Fator Neurotrófico Derivado do Encéfalo/metabolismo , Linhagem Celular , Sistema Nervoso Central/metabolismo , Doenças do Sistema Nervoso Central/tratamento farmacológico , Doenças do Sistema Nervoso Central/metabolismo , Inibidores da Colinesterase/farmacologia , Depsídeos/uso terapêutico , Dibenzoxepinas/uso terapêutico , Expressão Gênica , Hidroxibenzoatos/uso terapêutico , Lactonas/uso terapêutico , Camundongos , Fator de Crescimento Neural/genética , Fator de Crescimento Neural/metabolismo , Células-Tronco Neurais , Neurogênese/efeitos dos fármacos , Neurogênese/genéticaRESUMO
A new aryl-hydrazide l-glutamic acid derivative, pygmeine (3), was isolated from a methanolic extract of Lichina pygmaea, a marine lichen. Synthetic derivatives obtained via a two-step coupling of l-glutamic acid with phenylhydrazine moieties were useful to elucidate the structure of 3 and to carry out biological assays. Thus, the cytotoxicity of the ortho-, meta-, and para-hydroxyl isomers along with their respective benzyl intermediates, and a natural methoxylated analog, were evaluated on murine and human melanoma cells (B16, A375). The para-hydroxyl isomer 6 was found to be the most active (IC(50)=1.6 microM) on B16 cells.