The current investigation aimed to phytochemically characterise a popular Zulu medicinal plant from a subfamily of the Hyacinthaceae expected to yield bufadienolides. Flowering material of D. delagoensis was harvested from Paris Dam, Vryheid, KwaZulu-Natal, identified by N. Crouch, and a voucher specimen (Crouch 828, NH) retained for verification purposes. The bulbs (3511 g) were dried, chopped and successively extracted on a Labcon mechanical shaker for 48 h with dichloromethane and methanol. The dichloromethane extract (4.661 g) was subjected to column chromatography using gravity and separated over silica gel (Merck 9385, 20% EtOAc in MeCl2) to yield the novel homoisoflavonoid 1 (7.2 mg). The methanol extract (25.3 g) was dry-packed onto a silica gel column and impure compound 2 was eluted (Merck 9385, 20% MeOH in CH2Cl2). The compound was purified by further chromatography using a Pasteur pipette packed with silica gel and using the same solvent system to yield pure compound 2 (4.8 mg). The structures of compounds 1 and 2 were determined using 2D NMR and MS techniques. Compound 1 was identified as the novel homoisoflavonoid, (R)-5,7-dihydroxy-(4-hydroxy-3-methoxybenzyl)chroman-4-one. Compound 2 was identified as 4-hydroxy-3-methoxybenzoic acid. This is the first report of the occurrence of a homoisoflavanone in the Urgineoideae, a subfamily characterised chemotaxonomically by the occurrence of bufadienolides and their glucosides. The present contribution, describing the isolation of a homoisoflavanone rather than bufadienolides from the bulbs, correlates with this early report for non-toxicity. The recent finding of a homoisoflavonoid in Ornithogalum longibracteatum Jacq. of the subfamily Ornithogaloideae, has, together with this report, revealed the more widespread occurrence of homoisoflavonoids in the southern African Hyacinthaceae. It further supports the monophyletic origin of the Hyacinthaceae (excluding Camassia Lindl. and Chlorogalum Kunth.) indicated by plastid DNA sequence studies. However, the more widespread occurrence of homoisoflavanones diminishes their value as strict subfamily chemotaxonomic markers. Of the several regional species of Drimia investigated none besides D. delagoensis have yielded a homoisoflavanone; their occurrence in the Urgineoideae is evidently rare.