Parapiptadenia rigida (Benth.) Brenan (Fabaceae), popularly known in Brazil as „Angico vermelho“, is a perennial tree native in South America. Preparations from its bark are used in traditional medicine because of its astringent, expectorant, antiseptic and antihemorrhagic properties [1–2], but no detailed phytochemical analysis has yet been performed. To increase our knowledge on the biologically active compounds from P. rigida, the ethanolic extract of its bark was phytochemically analysed and 10 catechin derivatives were isolated and identified by 1D and 2D NMR (1H, 13C, COSY, HSQC, HMBC, NOESY, 2D-ROESY) and ESI-MS spectroscopy analyses. 3″, 4′-O-methyl-apocynin (1), 3″,4′-O-methyl-apocynin-B (2), epigallocatechin-(4β-8)-4′-O-methyl-gallocatechin (3), 4′-O-methyl-gallocatechin-(4α-8)-4′-O-methyl-gallocatechin (4) and (–)-epigallocatechin-3-O-ferulate (5) have been found for the first time and 4′-O-methyl-(–)-epigallocatechin-3-O-gallate (6) for the first time from natural sources, in addition to the four known compounds 4′-O-methyl-gallocatechin (7), 4′-O-methyl-epigallocatechin (8), 3′-O-methyl-(–)-epicatechin (9) and (–)-epigallocatechin-3-O-gallate (10). Comprehensive conformational analyses were performed for the dimeric procyanidins 3 and 4. Absolute configuration of 2 was determined by CD analysis. The extract and some of the catechin derivatives were studied for their wound healing effect in the scratch assay and gave promising results which suggest that plant preparations from P. rigida and their effective ingredients may have beneficial effects as a wound healing remedy.
Ethnopharmacological relevance: Preparation from leaves of Cordia americana have been widely used in traditional medicine in South Brazil to treat wounds and various inflammations.Aim of the study: The objective of this work was to identify the effective compounds in the ethanolic extract prepared from the leaves of Cordia americana, which is used in traditional South Brazilian medicine as anti-inflammatory and wound healing remedy.Materials and methods: Isolation and structure elucidation techniques were performed in order to identify the compounds of Cordia americana and HPLC analysis was used for the quantification. The major constituent and the ethanolic extract were investigated for inhibition of 5-lipoxygenase, p38 alpha MAPK, TNF alpha release and NF-kappa B as well as in the fibroblast scratch assay.Results: Rosmarinic acid (1) was identified as the major compound with an amount of 8.44% in the ethanolic extract of the leaves of Cordia americana. The ethanolic extract as well as (1) exhibited the highest inhibitory effects on 5-lipoxygenase (IC50=0.69 and 0.97 mu g/mL, resp., IC50 of BWA4C as reference: 0.3 mu M) and p38 alpha (IC50=3.25 and 1.16 mu g/mL, rasp., IC50 of SB203580 as reference: 0.046 mu M) and moderate inhibitory effects on TNF alpha release. Slight effects were observed in the fibroblast scratch assay.Conclusions: This study increases our knowledge on the effective compound in Cordia americana and supports its use in traditional medicine. We demonstrated for the first time pharmacological effects of Cordia americana and we provide evidences for a crucial role of rosmarinic acid as the major key player. (C) 2010 Elsevier Ireland Ltd. All rights reserved.
In Brazil medicinal plants have been widely used for the treatment of diseases in folk medicine. However, the effective compounds responsible for the biological effects are widely unknown. The objective of this study was to characterize the phytochemical profile and to identify bioactive compounds in the leaves of Cordia americana (Boraginaceae) [1]. The biological activity of the constituents and the ethanolic extract were investigated for the inhibition of 5-lipoxygenase, p38α MAPK, TNFα release and fibroblast scratch assay, targeting different aspects of inflammatory and wound healing processes. The phytochemical studies (i.e., 1D, 2D NMR and MS) have led to the identification of flavonols, phenolic compounds and phytosterols. Quantification analysis showed that rosmarinic acid (RA) is the main compound with an amount of 8.44% in the ethanolic extract. RA as well as the ethanolic extract exhibited the highest inhibitory effects on 5-lipoxygenase (IC50=0.97 and 0.69µg/ml, resp.) and p38α MAPK (IC50=1.16 and 3.25µg/ml, resp.). Additionally, RA inhibited the release of TNFα to 36.75±1.55% at a concentration of 36.03µg/ml, which can be considered as moderately active. The ethanolic extract showed a lower inhibition of 30.3±0.75% at a concentration of 100µg/mL. RA also exhibited slight stimulatory activity on proliferation and migration of fibroblasts indicating that it may partially contribute to the wound healing effects of this plant. We demonstrated for the first time pharmacological effects of C. americana and we provided evidences for a crucial role of RA as the major player.
Aim of the study: n-Hexanic and ethanolic extracts from twelve plants (Brugmansia suaveolens Brecht. et Presl., Eupatorium laevigatum Lam., Galinsoga parviflora Cav., Iresine herbstii Hook., Kalanchoe tubiflora Hamet-Ahti, Petiveria alliacea L, Pluchea sagittalis (Lam.) Cabrera, Piper regnellii DC., Schinus molle L., Sedum dendroideum Moc et Sesse ex DC., Waltheria douradinha St. Hill., Xanthium cavanillesii Schouw.) used in traditional South Brazilian medicine as wound healing agents were investigated in various biological assays, targeting different aspects in this complex process.Materials and methods:The extracts were investigated on NF-kappa B DNA binding, p38 alpha MAPK,TNF-alpha release, direct elastase inhibition and its release as well as on caspase-3. Fibroblasts migration to and proliferation into the wounded monolayers were evaluated in the scratch assay, the agar diffusion test for antibacterial and the MTT assay for cytotoxic effects.Results: The hydrophilic extracts from Galinsoga parviflora, Petiveria alliacea, Schinus molle, Waltheria douradinha and Xanthium cavanillesii as well as the lipophilic extract of Waltheria douradinha turned out to be the most active ones.Conclusions: These results increase our knowledge on the wound healing effects of the investigated medicinal plants. Further studies are necessary to find out the effective secondary metabolites responsible for the observed effects. (C) 2009 Elsevier Ireland Ltd. All rights reserved.