Phytochemical study and biological evaluation of chemical constituents of Platanus orientalis and Platanus × acerifolia buds

• Published in: Phytochemistry (Oxford) Vol. 130; pp. 170 - 181
• Main Authors: Thai, Quoc Dang, Tchoumtchoua, Job, Makropoulou, Maria, Boulaka, Athina, Meligova, Aggeliki K., Mitsiou, Dimitra J., Mitakou, Sophia, Michel, Sylvie, Halabalaki, Maria, Alexis, Michael N., Skaltsounis, Leandros A.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-10-2016
• Subjects: Coumarins; Dihydrochalcones; Estradiol - metabolism; Estrogen Receptor alpha - metabolism; Estrogen Receptor beta - metabolism; Estrogenic activity; Flavonoids; Flavonols - chemistry; Glycosides - chemistry; Humans; Kaempferols - metabolism; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Osteoblast differentiation; Osteoblasts - drug effects; Phytoestrogens; Platanaceae; Platanus orientalis; Platanus × acerifolia; Phytoestrogens; Flavonoids; Coumarins; Platanaceae; Platanus orientalis; Platanus × acerifolia; Dihydrochalcones; Estrogenic activity; Osteoblast differentiation
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2016.04.006

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.
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•Phytochemical and biological studies of the buds of Platanus orientalis and Platanus × acerifolia were performed.•50 compounds, including 8 previously undescribed were isolated in total.•Their chemical structures were elucidated by extensive spectroscopic analyses (1D & 2D NMR, ESI-HRMS).•Kaempferol and 8-C-(1,1-dimethyl-2-propen-1-yl)-5,7-dihydroxyflavonol displayed activities similar to estradiol.