Asymmetric dihydroxylation of piperine (PIP) was investigated under various reaction conditions. Using AD-mix-α in the presence of methanesulfonamide, the reaction yield was approximately 51% at 25 °C, whereas the reactions with RuCl3/NaIO4 were less efficient. The product was purified, and its structure was determined using 1H and 13C NMR spectroscopy. The carcinogenicity and anticarcinogenicity of PIP and 4,5-dihydroxypiperine (dhPIP) were evaluated using the Epithelial Tumor Test (ETT) in Drosophila melanogaster and no carcinogenic activity was observed in the presence of PIP or dhPIP at 60, 120, 180, or 360 μM. Co-treatment with doxorubicin (0.4 mM) and either PIP (180 μM) or dhPIP (60 μM) inhibited tumor occurrence by 81% and 83%, respectively.
Aguiar et al. (Mon,) studied this question.