Biomimetic Oxidative Reactions with Acanthoic Acid.
Acanthoic acid, Annona amazônica, Biomimetic oxidation, Jacobsen catalyst, Natural products.
The acanthoic acid, (-)-pimara-9(11),15-dien-19-oic acid, is a type of pimaradiene diterpene mainly isolated from the Korean medicinal plant, Acanthopanax koreanum. Others species as Annona amazonica, Rollinia pittieri, Rollinia exsucca, Aralia racemosa and Croton oblongifolius Roxb also have this diterpene in its constitution. Despite its biological diversity for the treatment of several diseases described in the literature (ulcerative colitis, hepatic fibrosis, type 2 diabetes, inflammatory cardiovascular diseases and periodontal), studies related to its pharmacokinetic parameters such as absorption, products of its metabolism, toxicity and elimination kinetics need to be investigated. This study aimed to investigate the phase I metabolism of acanthoic acid through biomimetic oxidative reactions with the Jacobsen catalyst, using PhIO, m-CPBA and H2O2 as oxygen donors in homogenous medium. The Jacobsen catalyst, that is known by easy synthesis and purification, is observed in the literature together with metalloporphyrins the ability to simulate the catalytic activity of the cytochrome P450 enzymes, which are the main responsible by phase I metabolism. These biomimetic models with chemical catalysts stand out for being less expensive, generate higher concentrations of the oxidized products and minimizing animal experiments when compared to other in vitro studies. Thus, it is expected that the present work will serve as a basis for other in vitro studies of acanthoic acid metabolism and that both will help in the investigation and confirm its reproducibility in vivo. It is also expected to facilitate future pharmacological and toxicological studies to ensure its safety and assist in the discovery of a possible drug candidate. In addition, it is shown a literature review that was submitted to an international Brazilian Journal.