Chemical investigation of the Australian plant Haemodorum simplex resulted in the isolation of three new phenylphenalenones, haemodorone (10), haemodorol (11), and haemodorose (12), together with the previously reported compounds 5, dilatrin (6), and xiphidone (8). The first complete 2D NMR characterization for all of the compounds isolated, including several chemical shift reassignments for dilatrin (6), is reported. In addition this is one of the few reports to discuss the isolation of new phenylphenalenones from an Australian medicinal plant. The crude extract of both the bulbaceous and aerial components of the plant exhibited varying degrees of antibacterial, antifungal, and antiviral activity, and only the bulbs displayed potent cytotoxic activity.

The crude extract of the roots from the Australian medicinal plant Dianella callicarpa (Liliaceae) displayed significant antimicrobial and antiviral activities. This prompted a chemical investigation, resulting in the isolation of the new naphthalene glycoside, dianellose (10), together with dianellin (1), dianellidin (2), dianellinone (3), stellalderol (9) and 5-hydroxydianellin (11). The structures for compounds 1, 9 and 10 were secured by detailed spectroscopic analyses, while compounds 2, 3 and 11 were identified on the basis of comparisons to literature data. Whilst the chemistry of the genus Dianella has previously been investigated, we report the first isolation of stellalderol (9) from this genus, together with the chemical and biological evaluation of the callicarpa species. Biological evaluation of the isolated compounds established that 2 showed antiviral and mild antimicrobial properties and that compounds 1, 9 and 10 displayed moderate antitumour activities.