Synthesis and cancer chemopreventive activity of zapotin, a natural product from Casimiroa edulis. (1/2)
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. (+info)Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities. (2/2)
(+info)Casimiroa is a genus of plant species that belongs to the family Rutaceae. It includes several trees and shrubs that are native to tropical regions of the Americas. One of the most well-known species in this genus is Casimiroa edulis, which is commonly known as the "white sapote" or "casimiroa." This fruit-bearing tree has large, glossy leaves and produces a white, pulpy fruit that tastes sweet and creamy. The fruit is often used in desserts, drinks, and traditional medicine.
In a medical context, Casimiroa has been studied for its potential sedative and hypnotic effects. Some research suggests that certain compounds found in the plant, such as casimiroin and edulilic acid, may have calming and sleep-promoting properties. However, more research is needed to fully understand the medicinal uses and safety of Casimiroa. It's important to note that consuming large amounts of the fruit or extracts from the plant can cause side effects such as nausea, vomiting, and dizziness. Therefore, it's recommended to consult with a healthcare professional before using Casimiroa for medicinal purposes.