Chemical Synthesis Study Establishes the Correct Structure of the Potent Anti-Inflammatory Agent Myrsinoic Acid F

Abstract

In 2002, Hirota and co-workers reported(1) the isolation and structural elucidation of a series of anti-inflammatory agents, named myrsinoic acids, from the fresh leaves and twigs of Myrsine seguinii, a hardwood of the Myrsinaceae family found in various parts of Asia from Myanmar to Japan. The most active of these compounds was myrsinoic acid F (MA-F) and to which structure 1 (Figure 1) was assigned(1) on the basis of a range of NMR spectroscopic and mass spectrometric studies. This compound and various structurally related co-metabolites have since been encountered in certain other plants (e.g., Rapanea ferruginea and Myrsine coriacea) found in several parts of the globe, and a number of these have been shown to exhibit potentially useful biological properties including selective cytotoxic, anti-microbial, and anti-leishmanial effects.(2) The anti-inflammatory properties of these compounds may arise through their inhibition of DNA polymerase λ.(3)