Flavonoid constituents of Sideritis caesarea


Abstract: The acetone extract of the aerial parts of Sideritis caesarea Duman, Aytaç & Başer (Lamiaceae) afforded the flavonoids penduletin (1) and apigenin (2) and 6 glycosylated flavonoids, 4'-O-methyl-isoscutellarein-7-O-[6'''-O-acetyl-\beta-D-allopyranosyl- (1 \to 2)]-6\"-O-acetyl-\beta -D-glucopyranoside (3), 4'-O-methylhypolaetin- 7-O-[6'''-O-acetyl-\beta -D-allopyranosyl-(1 \to 2)]-6\"-O-acetyl-\beta- D-glucopyranoside (4), isoscutellarein-7-O-[6'''-O-acetyl-\beta- D-allopyranosyl-(1 \to 2)]-6\"-O-acetyl-\beta -D-glucopyranoside (5), isoscutellarein-7-O-[6'''-O-acetyl-\beta -D-allopyranosyl-(1 \to 2)]- \beta-D-glucopyranoside (6), 4'-O-methylhypolaetin-7-O- [6'''-O-acetyl-\beta -D-allopyranosyl-(1 \to 2)]-\beta-D- glucopyranoside (7), and hypolaetin-7-O-[6'''-O-acetyl-\beta- D-allopyranosyl-(1 \to 2)]-\beta -D-glucopyranoside (8). The compounds were identified by the use of 1D- and 2D-NMR and UV spectroscopic techniques and by comparisons with the reported data. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of the acetone, methanol, and water extracts of the plant and of the flavones penduletin and apigenin were evaluated at 200 \mu g/mL. The water extract exhibited better activity against the enzyme AChE as compared to both the acetone and the methanol extracts. Penduletin (1) showed significant activity against BChE (66.58%) while apigenin (2) showed weak activity against both enzymes.

Keywords: Penduletin, methoxyflavones, flavone glycosides, Sideritis caesarea, anticholinesterase activity, Lamiaceae

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