Killarniensolide, methyl orsellinates and 9,10-dihydrophenanthrenes from the liverwort Plagiochila killarniensis from Scotland and the Azores

Methyl everninate has been identified as the major constituent of the deute rochloroform extract of ten specimens of the liverwort Plagiochila killarni ensis. Using NMR fingerprinting and GC-MS, the new methyl 6-hydroxy-2-methy l-3,4-methylenedioxybenzoate and three other methyl orsellinate derivatives were identified as minor components. 9,10-Dihydro-3,5-dimethoxyphenanthren -2-ol and 9,10-dihydro-3-methoxyphenanthrene-4,5-diol previously reported f rom a Neotropical Plagiochila, were also present. Killarniensolide, a new p hthalide, was isolated; its structure was elucidated as 3-(2-hydroxy-4,5-di methoxybenzyl)-7-methoxyphthalide by NMR spectroscopy, GC-MS and isolation of an acetate derivative. Chemical differences between specimens from Scotl and and the Azores were relatively minor but characteristic small differenc es between some of the Scottish materials were also observed. (C) 1999 Else vier Science Ltd. All rights reserved.