text: The phomoxanthones are named after the fungus Phomopsis, from which they were first isolated, and after their xanthonoid structure, which means they have structures similar to the compound xanthone (pictured on the left). Chemically, the phomoxanthones are dimers of two tetrahydroxanthones, meaning that they consist of two subunits of xanthonoids that have four hydroxy groups each. The two subunits of the phomoxanthones are covalently linked to each other. PXA itself is a homodimer, meaning that it consists of two identical subunits. Both of these subunits are diacetylated tetrahydroxanthones, so two of their hydroxy groups have been replaced by acetyl groups. The position of the link between the two dimer subunits is the only structural difference between PXA and its less toxic isomers phomoxanthone B (PXB) and dicerandrol C: In PXA, the two xanthonoid monomers are symmetrically linked at the position C-4,4’, while in PXB, they are asymmetrically linked at C-2,4’, and in dicerandrol C, they are symmetrically linked at C-2,2’. Otherwise, these three compounds are structurally identical. The phomoxanthones are structurally closely related to the secalonic acids, another class of dimeric tetrahydroxanthone mycotoxins, with which they share several properties. Notably, both the phomoxanthones and the secalonic acids are unstable when dissolved in polar solvents such as DMSO, with the covalent bond between the two monomers shifting between 2,2′-, 2,4′-, and 4,4′-linkage. The two phomoxanthones PXA and PXB can thus slowly isomerise into each other as well as into the essentially non-toxic dicerandrol C, resulting in a loss of activity of PXA over time when dissolved in a polar solvent.