title: Antifungal Quinoline Alkaloids from Waltheria indica.
abstract: Chemical investigation of a dichloromethane extract of the aerial parts of Waltheria indica led to the isolation and characterization of five polyhydroxymethoxyflavonoids, namely, oxyanin A (1), vitexicarpin (3), chrysosplenol E (4), flindulatin (5), 5-hydroxy-3,7,4'-trimethoxyflavone (6), and six quinolone alkaloids, waltheriones M-Q (2, 7, 8, 10, 11) and 5(R)-vanessine (9). Among these, compounds 2, 7, 8, 10, and 11 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C, HSQC, HMBC, COSY, and NOESY NMR experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by ECD. The isolated constituents and 10 additional quinoline alkaloids previously isolated from the roots of the plant were evaluated for their in vitro antifungal activity against the human fungal pathogen Candida albicans, and 10 compounds (7, 9, 11-16, 18, 21) showed growth inhibitory activity on both planktonic cells and biofilms (MIC ≤ 32 μg/mL). Their spectrum of activity against other pathogenic Candida species and their cytotoxicity against human HeLa cells were also determined. In addition, the cytological effect of the antifungal isolated compounds on the ultrastructure of C. albicans was evaluated by transmission electron microscopy.
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Sylvian
authors: S
authors: Cretton
authors: Institute of Microbiology, University of Lausanne and University Hospital Center , Lausanne, Switzerland.
authors: Stéphane
authors: S
authors: Dorsaz
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Antonio
authors: A
authors: Azzollini
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Quentin
authors: Q
authors: Favre-Godal
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Laurence
authors: L
authors: Marcourt
authors: Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University , G. C., Evin, Tehran, Iran.
authors: Samad Nejad
authors: SN
authors: Ebrahimi
authors: Agroscope, Institute for Plant Production Sciences IPS, Mycology and Biotechnology , Route de Duiller 50, CP 1012, 1260 Nyon, Switzerland.
authors: Francine
authors: F
authors: Voinesco
authors: Agroscope, Institute for Plant Production Sciences IPS, Mycology and Biotechnology , Route de Duiller 50, CP 1012, 1260 Nyon, Switzerland.
authors: Emilie
authors: E
authors: Michellod
authors: Institute of Microbiology, University of Lausanne and University Hospital Center , Lausanne, Switzerland.
authors: Dominique
authors: D
authors: Sanglard
authors: Agroscope, Institute for Plant Production Sciences IPS, Mycology and Biotechnology , Route de Duiller 50, CP 1012, 1260 Nyon, Switzerland.
authors: Katia
authors: K
authors: Gindro
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Jean-Luc
authors: JL
authors: Wolfender
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Muriel
authors: M
authors: Cuendet
authors: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, 1211 Geneva 4, Switzerland.
authors: Philippe
authors: P
authors: Christen
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D019660:Malvaceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D046529:Microscopy, Electron, Transmission; D015394:Molecular Structure; D009548:Niger; D019906:Nuclear Magnetic Resonance, Biomolecular; D035261:Plant Components, Aerial / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000470:Alkaloids; D000935:Antifungal Agents; D005419:Flavonoids; D011804:Quinolines; C054133:casticin