acacetin and naringin

Naringin, as a component universal existing in the peel of some fruits or medicinal plants, was usually selected as the material to synthesise bioactive derivates since it was easy to gain with low cost. In present investigation, eight new acacetin-7-O-methyl ether Mannich base derivatives (1-8) were synthesised from naringin. The bioactivity evaluation revealed that most of them exhibited moderate or potent acetylcholinesterase (AChE) inhibitory activity. Among them, compound 7 (IC

Topics: Acetylcholinesterase; Animals; Butyrylcholinesterase; Catalytic Domain; Chemistry Techniques, Synthetic; Cholinesterase Inhibitors; Drug Evaluation, Preclinical; Flavanones; Flavones; Inhibitory Concentration 50; Kinetics; Mannich Bases; Methyl Ethers; Molecular Docking Simulation; Rats

Apigenin-7-O-β-D-glycosides 1-8 and acacetin-7-O-β-D-glycosides 9-16 were semisynthesized from 4'-O-benzyl apigenin 17 and acacetin 18 by glycosidation and deprotection with the corresponding α-acetylglycosyl bromide, respectively. Compounds 17 and 18 were prepared by iodination followed by base-induced elimination, 4'-O-benzylation, or 4'-O-methylation and acid hydrolysis using naringin as starting material which is readily available and cheap. Their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) was evaluated by standard MTT method. The results show that compounds 2, 9, and 19 exhibit moderate cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480, while compound 3 exhibits potent cytotoxicity against MCF-7 selectively. Among the synthesized target compounds, 3, 4, 7, 11, 12, 15, and 16 were new compounds, the natural product 8 was the first synthesized and the synthesis of natural products 5, 6, 13, and 14 was efficiently improved by the new synthetic routes.

Topics: Antineoplastic Agents; Apigenin; Cell Line, Tumor; Drug Evaluation, Preclinical; Flavanones; Flavones; Glycosides; Halogenation; Humans; Inhibitory Concentration 50