ISOLATION AND SYNTHESIS OF BETA-MIROSIDE AN ANTIFUNGAL FURANONE GLUCOSIDE FROM PRUMNOPITYS FERRUGINEA

The bioactivity-directed isolation and structural determination of bet a-miroside [(beta-D-glucopyranosyloxy)methyl]-2(5H)-furanone} from the New Zealand gymnosperm Prumnopitys ferruginea, is described. Picein { 4-(beta-D-glucopganosyloxy)acetophenone} was also isolated. Sytheses o f beta-miroside, its a-anomer and an isomer with an exocyclic double b ond are described along with an unusual reaction of an exocyclic alkox yallcylidene lactone with N-bromosuccinimide to give a product with an endocyclic double bond. beta-Miroside shows antifungal, antibacterial and cytotoxic activities.