Extracts of six lichen species collected from Brazil and Antarctica were investigated for their potential toxicity and radical-scavenging properties. The composition of the extracts was investigated using TLC and NMR, leading to identification of atranorin (1), along with salazinic (2), barbatic (3), α-alectoronic (4), α-collatolic (5), cryptochlorophaeic (6), caperatic (7), lobaric (8), and protolichesterinic (9) acids. All acetone extracts were evaluated for their 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability and subjected to Artemia salina bioassay. The free-radical-scavenging activities of each extract (100 µg) ranged from 8.9 ± 0.1% to 38.7 ± 2.5% and the EC50 values ranged from 0.24 ± 2.10 to 3.54 ± 0.28 mg mL-1, while the toxicity of the extracts against A. salina were low (151.0 to >600 µg mL-1).
Several technologies for the development of new sugarcane cultivars have mainly focused on the increase in productivity and greater disease resistance. Sugarcane cultivars are usually identified by the organography of the leaves and stems, the analysis of peroxidase and esterase isoenzyme activities and the total soluble protein as well as soluble solid content. Nuclear magnetic resonance (NMR) associated with chemometric analysis has proven to be a valuable tool for cultivar assessment. Thus, this article describes the potential of chemometric analysis applied to ¹H high resolution magic angle spinning (HRMAS) and NMR in solution for the investigation of sugarcane cultivars. For this purpose, leaves from eight different cultivars of sugarcane were investigated by ¹H NMR spectroscopy in combination with chemometric analysis. The approach shows to be a useful tool for the distinction and classification of different sugarcane cultivars as well as to access the differences on its chemical composition.
Várias tecnologias para o desenvolvimento de novas cultivares de cana-de-açúcar têm focado, principalmente, no aumento da produtividade e maior resistência à doença. Cultivares de cana-de-açúcar são, geralmente, identificadas pela organografia das folhas e caule, análise de peroxidase e atividade da isoenzima esterase, proteínas solúveis totais e teor de sólidos solúveis. A ressonância magnética nuclear (RMN) associada às análises quimiométricas provou ser uma técnica valiosa para avaliação de plantas. Assim, este trabalho descreve o potencial das análises quimiométricas aplicadas a RMN de ¹H de alta resolução com giro no ângulo mágico (HRMAS) e em solução para investigação de cultivares de cana-de-açúcar. Para esta proposta, folhas de oito diferentes cultivares de cana-de-açúcar foram analisadas por espectroscopia de RMN de ¹H aliada à quimiometria. As técnicas empregadas apresentaram-se como ferramentas úteis para a distinção e classificação das diferentes cultivares, bem como para acessar as diferenças na composição química das cultivares.
Campomanesia adamantium (Cambess.) O. Berg, Myrtaceae, is a native species. The extracts of ethyl acetate and hexane showed little variation in their chemical composition at different seasons of the year associated with the development of the plant, while the ethanol extract showed significant change in relationship to chemical composition. All ethanol extracts showed high antioxidant activity against DPPH method and from moderate to high antioxidant activity for β-carotene/linoleic acid.
Campomanesia adamantium (Cambess.) O. Berg, Myrtaceae, é uma espécie nativa. As folhas são utilizadas na medicina popular. Os extratos hexânico e acetato de etila das folhas mostraram pouca variação na sua composição química em diferentes estações do ano associado com o desenvolvimento do vegetal, enquanto o extrato etanólico mostrou alteração significativa em relação à composição química. Todos os extratos etanólicos mostraram alta atividade antioxidante frente ao método DPPH e de moderada a alta para β-caroteno/ácido linoléico.
The effects of isolated compounds from Brazilian lichens and their derivatives on H2O2 and NO production were studied using murine macrophages as a part of an attempt to understand their possible immunomodulatory properties. The compound cytotoxicity was studied using MTT assay. Macrophage stimulation was evaluated by the determination of NO (Griess assay) and H2O2 (horseradish peroxidase/phenol red) in supernatants of peritoneal macrophage cultures of Swiss mice. This research demonstrated stimulatory activities of some phenolic compounds isolated from lichens and their derivatives on H2O2 and NO production. Structure-activity relationships suggest several synthetic directions for further improvement of immunological activity.
Os efeitos dos compostos isolados de líquens brasileiros e seus derivados na produção de NO e H2O2 foram estudados utilizando macrófagos murinos na tentativa de desvendar suas possíveis propriedades imunomodulatórias. A citotoxicidade dos compostos foi estudada utilizando o ensaio de MTT. A estimulação dos macrófagos foi avaliada através da determinação de NO (metodologia de Griess) e H2O2 (peroxidase de raíz forte/vermelho de fenol) no sobrenadante de culturas de macrófagos peritoneais de camundongos Swiss. Este estudo demonstrou atividade estimulante de alguns compostos fenólicos e seus derivados na produção de NO e H2O2. A relação estrutura atividade sugere inúmeras direções sintéticas para futuros melhoramentos da atividade imunológica.
From the lichen Parmotrema lichexantonicum were isolated the depsidone salazinic acid, the xanthone lichexanthone, and the depside atranorin. The two major compounds, salazinic acid and lichexanthone, were selected for structure modifications. Salazinic acid afforded O-alkyl salazinic acids, some of them potentially cytotoxic against tumor cell lines (HCT-8, SF-295 and MDA/ MB - 435). From lichexanthone were obtained norlichexanthone, 3-O-methylnorlichexanthone, 3-O-methyl-6-O-prenylnorlichexanthone, 3,6-di-O-prenyl-norlichexanthone, 3,6-bis[(3,3-dimethyloxyran-2-il)methoxy]-1-hydroxy-8-methyl-9H-xanten-9-one and 3,6-bis[3-(dimethylamine)propoxy]-1-hydroxy-8-methyl-9H-xanten-9-one. The last compound was the most active against S. aureus.
Chemical studies with aerial parts of Microgramma vacciniifolia (Langsd. & Fisch.) Copel. afforded ²-sitosterol, hopan-22-ol, 6-metoxiapinenin-7-O-²-D-allopyranoside and a mixture containing ethyl esters of carboxilic acids. The structures of the coumpounds were elucidated by spectroscopy and GC-MS analysis. The total phenolics contents of the crude extract and fractions were determined by Folin-Ciocalteau method. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH). The AcOEt fraction showed better activity in DPPH assay (9.9 ± 0.03 µg/mL), and presented also higher contents of the total phenolic (93.60 ± 1.11 µg/mg). Antimicrobial and allelopathic effects of the crude etanolic extract and fractions also were evaluated. In addition, the combination of biological activities was discussed.
Chemical studies of green leaves of A. tetraphyllum afforded beta-sitosterol, a mixture containing the ethyl esters of long chain carboxylic acids, 30-normethyl-lupan-20-one, hopan-22-ol, phytol, phyten-3(20)-1,2-diol, quercetin and quercetin-3-O-beta-D-glucoside. The structures of the compounds were elucidated by spectroscopic and GC analysis. The allelopathic potentials of the crude ethanolic extract and fractions were evaluated against Lactuca sativa (letuce) and Allium cepa (onion) seeds.
With the aim of obtaining new compounds with potential antifungal activity, lecanoric acid, a chemical constituent of the lichen Parmotrema tinctorum and its derivatives prepared from structural modification were tested against the fungus Cladosporium sphaerospermum, by employing the bioautographic method. Activity of the derivatives ranged from 10- to 1-μg concentrations. Results demonstrated this series of compounds to have potent fungitoxic activity.