Halogenated anthraquinones from the rare southern Illinois lichen Lasallia papulosa

Four anthraquinones were isolated from the foliose lichen, Lasallia papulosa (Ach.) Llano. Two of the anthraquinones are known compounds, previously isolated from Lasallia papulosa, while the other two were reported previously as secondary metabolites from laboratory-cultured Nephroma laevigatum, and are isolated here for the first time from lichens in their natural habitat. All compounds were characterized by UV spectrophotometry, mass spectrometry, H-1 NMR and C-13 NMR. The products were identified as 7-chloroemodin, valsarin (7-chloro-5-hydroxyemodin), 5-chloro-1-O-methylemodin and 5-chloro-1-O-methyl-omega-hydroxyemodin. (C) 2002 The British Lichen Society. Published by Elsevier Science Ltd. All rights reserved.