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1: J Med Chem. 2007 Jan 25;50(2):350-5.Click here to read Click here to read Links

Synthesis and cancer chemopreventive activity of zapotin, a natural product from Casimiroa edulis.

Maiti A, Cuendet M, Kondratyuk T, Croy VL, Pezzuto JM, Cushman M.

Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy Purdue University, West Lafayette, Indiana 47907, USA.

An efficient method has been developed to synthesize zapotin (5,6,2',6'-tetramethoxyflavone), a component of the edible fruit Casimiroa edulis, on a multigram scale. The synthesis utilizes a regioselective C-acylation of a dilithium dianion derived from a substituted o-hydroxyactophenone to afford a beta-diketone intermediate that can be cyclized to zapotin in good overall yield, thus avoiding the inefficient Baker-Venkataraman rearrangement pathway. Zapotin was found to induce both cell differentiation and apoptosis with cultured human promyelocytic leukemia cells (HL-60 cells). In addition, the compound inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity with human bladder carcinoma cells (T24 cells), and TPA-induced nuclear factor-kappa B (NF-kappaB) activity with human hepatocellular liver carcinoma cells (HepG2 cells). These data suggest that zapotin merits further investigation as a potential cancer chemopreventive agent.

PMID: 17228877 [PubMed - indexed for MEDLINE]

PMCID: PMC2523270