Phytochemical study and biological evaluation of chemical constituents of Platanus orientalis and Platanus × acerifolia buds. (October 2016)

• Record Type: Journal Article
• 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.
• Is Part Of: Phytochemistry. Volume 130(2016:Oct.)
• Page Start: 170
• Page End: 181
• Publication Date: 2016-10
• Subjects: Platanus orientalis -- Platanus × acerifolia -- Platanaceae -- Phytoestrogens -- Estrogenic activity -- Flavonoids -- Coumarins -- Dihydrochalcones -- Osteoblast differentiation; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2016.04.006
• Languages: English
• ISSNs: 0031-9422

Abstract

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 × acerifoli a. 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. Graphical abstract: Highlights: 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.