Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark

• Published in: Journal of ethnopharmacology Vol. 147; no. 1; pp. 63 - 73
• Main Authors: Sgariglia, Melina A., Soberón, José R., Poveda Cabanes, Ana, Sampietro, Diego A., Vattuone, Marta A.
• Format: Journal Article
• Language: English
• Published: Ireland Elsevier Ireland Ltd 02.05.2013
• Subjects: Anti-inflammatory; anti-inflammatory activity; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; antioxidant; antioxidant activity; Antioxidants - pharmacology; aspirin; bark; bioassays; Biological Assay; Biphenyl Compounds - chemistry; butylated hydroxytoluene; Caesalpinia; Caesalpinia - chemistry; Caesalpinia paraguariensis stem bark; Chemical Fractionation; Dose-Response Relationship, Drug; ellagic acid; Ellagic acid derivatives; enzyme inhibition; enzyme inhibitors; Enzyme Inhibitors - pharmacology; Erythrocyte Membrane - drug effects; Erythrocyte Membrane - metabolism; free radical scavengers; hyaluronoglucosaminidase; Hyaluronoglucosaminidase - antagonists & inhibitors; Hyaluronoglucosaminidase - metabolism; lactones; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; lipid peroxidation; Lipid Peroxidation - drug effects; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; nitric oxide synthase; Nitric Oxide Synthase Type II - antagonists & inhibitors; Nitric Oxide Synthase Type II - metabolism; Phenolic lactones; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Phytotherapy; Picrates - chemistry; Plant Bark; Plant Preparations - chemistry; Plant Preparations - isolation & purification; Plant Preparations - pharmacology; Plant Stems; Plants, Medicinal; reactive oxygen species; Reactive Oxygen Species - metabolism; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; Caesalpinia paraguariensis stem bark; Ellagic acid derivatives; Phenolic lactones; antioxidant; Anti-inflammatory
• ISSN: 0378-8741; 1872-7573
• DOI: 10.1016/j.jep.2012.12.030

Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their “vulnerary” properties. CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-1H/13C-NMR). Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2–4.5μg/ml, and for DPPH radical (2.5–7.3μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. This work provides scientific validity to the popular usage of CPBI. Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguarienisis stem bark. [Display omitted]