Kangaroo Island propolis types originating from two Lepidosperma species and Dodonaea humilis

The endemic Australian plants Lepidosperma sp. Flinders Chase (Cyperaceae), Lepidosperma viscidum (Cyperaceae) and Dodonaea humilis (Sapindaceae) were found to be the botanical origin of three propolis types found on Kangaroo Island identified by TLC and ¹H NMR matching of propolis and plant resin analytical profiles. Resin samples extracted from the plant, Lepidosperma sp. Flinders Chase, were chromatographically fractionated to give: methyl 3-phenyl-2-(E-cinnamoyloxy)propanoate (1), 3-(E-8-methoxy-8-oxo-3,7-dimethyloct-2-enyl)-4-hydroxy-E-cinnamic acid (2), 3-(E-6,7-dihydroxy-3,7-dimethyloct-2-enyl)-4-hydroxy-E-cinnamic acid (3), previously undescribed; and the known stilbenes, 2-prenyl-3,5-dihydroxy-E-stilbene (6) and 2-prenyl-3-methoxy-5-hydroxy-E-stilbene (7). The resin from L. viscidum gave: 5'-(E-4-hydroxy-3-methylbut-2-enyl)-4,2',4'-trihydroxydihydrochalcone (4); 5'-(E-4-hydroxy-3-methylbut-2-enyl)-4'-methoxy-4,2'-dihydroxydihydrochalcone (5), previously undescribed; and three known flavanones, farrerol (8), 5,7,3',5'-tetrahydroxy-6,8-dimethylflavanone (9) and 5,7,3',5'-tetrahydroxy-6-methylflavanone (10). The major constituent in the propolis identified as being sourced from D. humilis was identified as 6,8-diprenyl-5,7,3',4'-tetrahydroxyflavanone (11), a known compound identified in several unrelated plant species.