title: Mansoins C-F, Oligomeric Flavonoid Glucosides Isolated from Mansoa hirsuta Fruits with Potential Anti-inflammatory Activity.
abstract: Continued investigation of the polyphenolic pool of the fruits of Mansoa hirsuta afforded four additional members of the new class of glucosylated oligomeric flavonoids comprising a flavanone core linked to 1,3-diarylpropane C6-C3-C6 units. The structures and absolute configurations of mansoins C-F (3-6) were established by analysis of NMR and electronic circular dichroism data. Mansoin C (3) was identified as a diglucosylated heterodimer, whereas mansoins D (4), E (5), and F (6) were identified as triglucosylated heterotrimers, isomeric with mansoin A (1). Mansoin F (6) inhibited TNF-α release by lipopolysaccharide-stimulated THP-1 cells (IC50 of 19.3 ± 1.3 μM) and, as with mansoin A (1), reduced the phosphorylation levels of p-65-NF-κB, when assayed at 50 μM. These results indicate that the potential anti-inflammatory properties of mansoin F (6) are probably due to inhibition of the NF-κB pathway and inhibition of TNF-α release.
authors.affiliation: Pharmaceutical and Technological Development Department, Fundação Ezequiel Dias , Belo Horizonte, MG 30.510-010, Brazil.
authors.forename: Priscilla R V
authors.initials: PR
authors.lastname: Campana
authors.affiliation: Department of Biomolecular Sciences, Division of Pharmacognosy and the Research Institute of Pharmaceutical Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Christina M
authors.initials: CM
authors.lastname: Coleman
authors.forename: Lirlândia P
authors.initials: LP
authors.lastname: Sousa
authors.forename: Mauro M
authors.initials: MM
authors.lastname: Teixeira
authors.affiliation: Department of Biomolecular Sciences, Division of Pharmacognosy and the Research Institute of Pharmaceutical Sciences, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Fernão C
authors.initials: FC
authors.lastname: Braga
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029402:Bignoniaceae / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors
chemical_list: D000893:Anti-Inflammatory Agents; D005419:Flavonoids; D005960:Glucosides; D008070:Lipopolysaccharides; D016328:NF-kappa B; D014409:Tumor Necrosis Factor-alpha