ABSTRACT
This work evaluated the in vitro inhibitory activity of the crude ethanolic extract from the aerial parts of Cuspidaria pulchra (Cham.) L.G. Lohmann against 15-lipoxygenase (15-LOX). The bioassay-guided fractionation of the n-butanol fraction, which displayed the highest activity, led to the isolation of three compounds: caffeoylcalleryanin (1), verbascoside (2) and 6-hydroxyluteolin-7-O-ß-glucoside (3). Assessment of the ability of the isolated compounds to inhibit 15-LOX revealed that compounds 1, 2 and 3 exerted strong 15-LOX inhibitory activity; IC50 values were 1.59, 1.76 and 2.35 µM respectively. The XTT assay showed that none of the isolated compounds seemed to be significantly toxic.
Subject(s)
Bignoniaceae/chemistry , Caffeic Acids/pharmacology , Lipoxygenase Inhibitors/pharmacology , Plant Extracts/pharmacology , Caffeic Acids/chemistry , Caffeic Acids/isolation & purification , Glucosides/chemistry , Glucosides/isolation & purification , Luteolin/chemistry , Luteolin/isolation & purification , Molecular Structure , Phenols/chemistry , Phenols/isolation & purification , Plant Components, Aerial/chemistryABSTRACT
Chemical investigation of the n-hexane and EtOAc fractions of the ethanolic extract from Styrax pohlii (Styracaceae) aerial parts resulted in the isolation of the benzofuran nor-neolignan derivatives egonol (1), homoegonol (2), homoegonol gentiobioside (3), homoegonol glucoside (4) and egonol gentiobioside (5). This is the first report of compounds 1-5 in S. pohlii. Compounds 1-5, the acetyl derivatives 1 a and 2 a, the ethanolic extract (EE), the n-hexane fraction (HF) and EtOAc fraction (EF) were tested for their inhibitory activities against COX-1 and COX-2. The results showed that EE, HF, EF and compounds 1-5 and 1 a-2 a shown weak to moderate inhibition of COX-1 and COX-2. Among the assayed nor-neolignans, 4 gave a COX-1 inhibition of 35.7% at 30 µM. Compound 5 displayed a COX-2 inhibition of 19.7% at 30 µM.
Subject(s)
Cyclooxygenase Inhibitors/pharmacology , Lignans/pharmacology , Plant Extracts/pharmacology , Styrax/chemistry , Benzofurans/isolation & purification , Benzofurans/pharmacology , Brazil , Cyclooxygenase Inhibitors/chemistry , Cyclooxygenase Inhibitors/isolation & purification , Disaccharides/isolation & purification , Disaccharides/pharmacology , Ethanol , Glucosides/isolation & purification , Glucosides/pharmacology , Hexanes , Lignans/chemistry , Lignans/isolation & purification , Molecular Structure , Plant Extracts/isolation & purificationABSTRACT
Styrax camporum Pohl, known in Brazil as 'estoraque do campo' or 'cuia de brejo', has been used in the treatment of gastrointestinal diseases. The therapeutic action of S. camporum has been attributed to the ethyl acetate fraction, although the chemical composition of this fraction has not yet been analyzed. In this study, a high-performance liquid chromatography photodiode array detection (HPLC-PAD) method for analysis of Brazilian Styrax species has been developed. The compounds egonol (1) and homoegonol (2) were found to be present in all the samples investigated by HPLC. These compounds were isolated by open column chromatography followed by preparative TLC, and were identified by ¹H NMR. Compounds 1 and 2 were thus proposed as phytochemical markers for Styrax, owing to their biological properties and presence in other Styrax species. The developed method has been validated and successfully applied for quantification of 1 and 2 in S. camporum dried leaves and crude ethanolic extracts from S. ferrugineus and S. pohlii aerial parts.
Subject(s)
Benzofurans/analysis , Chromatography, High Pressure Liquid/methods , Plant Extracts/chemistry , Styrax/chemistry , Benzofurans/chemistry , Brazil , Chromatography, High Pressure Liquid/standards , Linear Models , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial/chemistry , Reproducibility of Results , Sensitivity and SpecificityABSTRACT
The in vitro activity of the crude hydroalcoholic extract of the aerial parts of Miconia langsdorffii Cogn. was evaluated against the promastigote forms of L. amazonensis, the causative agent of cutaneous leishmaniasis in humans. The bioassay-guided fractionation of this extract led to identification of the triterpenes ursolic acid and oleanolic acid as the major compounds in the fraction that displayed the highest activity. Several ursolic acid semi-synthetic derivatives were prepared, to find out whether more active compounds could be obtained. Among these ursolic acid-derived substances, the C-28 methyl ester derivative exhibited the best antileishmanial activity.