title: Phytochemical study and biological evaluation of chemical constituents of Platanus orientalis and Platanus × acerifolia buds.
abstract: One flavonol glycoside, two O-isoprenylated flavonols, one α,α-dimethylallyl flavonol, one dihydrochalcone, two furanocoumarins and one terpenoid previously undescribed, along with 42 known compounds were isolated from the buds of two European Platanaceae, Platanus orientalis and Platanus × acerifolia. Their chemical structures were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR (COSY, NOESY, HSQC, and HMBC) experiments, as well as HRMS data. The estrogen-like and antiestrogen-like activity of dichloromethane and methanol extracts of P. orientalis and P. × acerifolia buds and isolated compounds was evaluated using estrogen-responsive cell lines. The potency of selected estrogen agonists to regulate gene expression through ERα and/or ERβ was compared with their in vitro osteoblastogenic activity. Kaempferol and 8-C-(1,1-dimethyl-2-propen-1-yl)-5,7-dihydroxyflavonol displayed osteoblastogenic as well as ERα-mediated estrogenic activity similar to estradiol.
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece; Laboratoire de Pharmacognosie de l'Université Paris Descartes, UMR/CNRS 8638, Faculté de Pharmacie, 4 Avenue de l'Observatoire, F-75006, Paris, France.
authors.forename: Quoc Dang
authors.initials: QD
authors.lastname: Thai
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece.
authors.forename: Job
authors.initials: J
authors.lastname: Tchoumtchoua
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece; Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece.
authors.forename: Maria
authors.initials: M
authors.lastname: Makropoulou
authors.affiliation: Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece.
authors.forename: Athina
authors.initials: A
authors.lastname: Boulaka
authors.affiliation: Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece.
authors.forename: Aggeliki K
authors.initials: AK
authors.lastname: Meligova
authors.affiliation: Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece.
authors.forename: Dimitra J
authors.initials: DJ
authors.lastname: Mitsiou
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece.
authors.forename: Sophia
authors.initials: S
authors.lastname: Mitakou
authors.affiliation: Laboratoire de Pharmacognosie de l'Université Paris Descartes, UMR/CNRS 8638, Faculté de Pharmacie, 4 Avenue de l'Observatoire, F-75006, Paris, France.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Michel
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece.
authors.forename: Maria
authors.initials: M
authors.lastname: Halabalaki
authors.affiliation: Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, Athens, Greece.
authors.forename: Michael N
authors.initials: MN
authors.lastname: Alexis
authors.affiliation: Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupoli Zografou, 15771, Athens, Greece. Electronic address: skaltsounis@pharm.uoa.gr.
authors.forename: Leandros A
authors.initials: LA
authors.lastname: Skaltsounis
mesh_terms: D004958:Estradiol / Q000378:metabolism; D047628:Estrogen Receptor alpha / Q000378:metabolism; D047629:Estrogen Receptor beta / Q000378:metabolism; D044948:Flavonols / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D006801:Humans; D044949:Kaempferols / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010006:Osteoblasts / Q000187:drug effects
chemical_list: C000614046:8-C-(1,1-dimethyl-2-propen-1-yl)-5,7-dihydroxyflavonol; C506487:ESR1 protein, human; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D044948:Flavonols; D006027:Glycosides; D044949:Kaempferols; D004958:Estradiol
keywords: Coumarins; Dihydrochalcones; Estrogenic activity; Flavonoids; Osteoblast differentiation; Phytoestrogens; Platanaceae; Platanus orientalis; Platanus × acerifolia