Molecular Biology; Biochemistry; Endocrinology, Diabetes and Metabolism
Abstract :
[en] Isocaloteysmannic acid (1), a new chromanone, was isolated from the leaf extract of the medicinal species Calophyllum tacamahaca Willd. along with 13 known metabolites belonging to the families of biflavonoids (2), xanthones (3–5, 10), coumarins (6–8) and triterpenes (9, 11–14). The structure of the new compound was characterized based on nuclear magnetic resonance (NMR), high-resolution electrospray mass spectrometry (HRESIMS), ultraviolet (UV) and infrared (IR) data. Its absolute configuration was assigned through electronic circular dichroism (ECD) measurements. Compound (1) showed a moderate cytotoxicity against HepG2 and HT29 cell lines, with IC50 values of 19.65 and 25.68 µg/mL, respectively, according to the Red Dye method. Compounds 7, 8 and 10–13 exhibited a potent cytotoxic activity, with IC50 values ranging from 2.44 to 15.38 µg/mL, against one or both cell lines. A feature-based molecular networking (FBMN) approach led to the detection of a large amount of xanthones in the leaves extract, and particularly analogues of the cytotoxic isolated xanthone pyranojacareubin (10).
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Gerometta, Elise; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France
Herbette, Gaëtan ; Spectropole, FSCM, Centrale Marseille, CNRS, Aix-Marseille Université, Campus de St Jérôme–Service 511, 13397 Marseille, France
Garayev, Elnur; IMBE, CNRS, IRD, Aix Marseille Université, Faculté de Pharmacie, Service de Pharmacognosie, 13331 Marseille, France
Marvilliers, Arnaud; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France
Naubron, Jean-Valère; Spectropole, FSCM, Centrale Marseille, CNRS, Aix-Marseille Université, Campus de St Jérôme–Service 511, 13397 Marseille, France
Di Giorgio, Carole; IMBE, CNRS, IRD, Aix-Marseille Université, Faculté de Pharmacie, Service de Mutagénèse Environnementale, 13385 Marseille, France
Campos, Pierre-Eric ; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France ; Institut de Chimie Organique et Analytique, UMR 6759, Université d’Orléans–CNRS, Pôle de Chimie, Rue de Chartres, BP6759, CEDEX 2, 45067 Orléans, France
Clerc, Patricia; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France
Ledoux, Allison ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Baghdikian, Béatrice; IMBE, CNRS, IRD, Aix Marseille Université, Faculté de Pharmacie, Service de Pharmacognosie, 13331 Marseille, France
Grondin, Isabelle; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France
Gauvin-Bialecki, Anne ; Laboratoire de Chimie et de Biotechnologie des Produits Naturels, Faculté des Sciences et Technologies, Université de La Réunion, Campus du Moufia, 97744 St Denis, France
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