Honours Projects 2010
Dr Belinda Abbott
Picroroccellin - a lost medicinal product?
(In collaboration with Adj. Prof. Seb Marcuccio)In 1876 John Stenhouse and Charles Groves described a crystalline substance they called picrorocellin, which they had isolated from an unknown species of lichen used for dyeing. It was thought that this compound may have some useful medicinal properties, as it had a bitter taste similar to the antimalarial drug quinine.
Forster and Saville proposed a structure for picrorocellin (shown) in 1922 but the regiochemistry and absolute stereochemistry were not determined. In particular, the substitutions on the nitrogens could have been reversed. In 1983, the structure of picrorocellin was revised to contain the hydroxyl and methoxy substituents on the a rather than b carbons. However substitution of the nitrogens remains unconfirmed.
This project will target the synthesis, structural elucidation and reactions of this lost natural product. Its biological properties will also be investigated.