title: Peltogynoids and 2-phenoxychromones from Peltophorum pterocarpum and evaluation of their estrogenic activity.
abstract: Phytochemical investigation of the dichloromethane extract of the leaves of Peltophorum pterocarpum, a tropical ornamental tree, led to the isolation of twelve compounds (1-12). One new derivative of peltogynoid ophioglonin (1) and a new 2-phenoxychromone (2) with its 3'-O-β-D-glucoside derivative (3) are described here for the first time. In addition, nine flavonoid derivatives, including peltogynoid ophioglonin (4), were isolated for the first time from this plant. The structures were determined by spectroscopic and chemical methods. Evaluation of the estrogenic activities of 1, 2, and 4 using different model cell systems revealed that 4 was estrogenic and that 2 was largely inactive. Interestingly, 1 was unable to stimulate the proliferation of breast and endometrial cancer cells but exhibited substantial estrogen receptor α-mediated activation of gene expression. This observation indicates that 1 can be further evaluated for its cancer chemopreventive potential.
authors.affiliation: School of Pharmaceutical Sciences, Phytochemistry and Bioactive Natural Products, University of Geneva, University of Lausanne, Geneva, Switzerland.
authors.forename: Johanne
authors.initials: J
authors.lastname: Polasek
authors.forename: Emerson Ferreira
authors.initials: EF
authors.lastname: Queiroz
authors.forename: Laurence
authors.initials: L
authors.lastname: Marcourt
authors.forename: Aggeliki K
authors.initials: AK
authors.lastname: Meligova
authors.forename: Maria
authors.initials: M
authors.lastname: Halabalaki
authors.forename: Alexios-Leandros
authors.initials: AL
authors.lastname: Skaltsounis
authors.forename: Michael N
authors.initials: MN
authors.lastname: Alexis
authors.forename: Bambang
authors.initials: B
authors.lastname: Prajogo
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Wolfender
authors.forename: Kurt
authors.initials: K
authors.lastname: Hostettmann
mesh_terms: D049109:Cell Proliferation; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D047628:Estrogen Receptor alpha / Q000378:metabolism; D004967:Estrogens / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007887:Fabaceae / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D057809:HEK293 Cells; D006801:Humans; D061986:MCF-7 Cells; D018515:Plant Leaves / Q000737:chemistry; D014407:Tumor Cells, Cultured
chemical_list: C584170:5-hydroxy-7-methoxy-2-(3',4'-dihydroxy)phenoxychromone; C584171:7-methoxyophioglonin; D002867:Chromones; D047628:Estrogen Receptor alpha; D004967:Estrogens; D005419:Flavonoids; D005960:Glucosides; C584169:pterophenoxychromone-3'-O-glucoside