Lachenalia is the largest endemic genus in the southern African Hyacinthaceae, yet no members have been phytochemically characterised before. Based on chemotaxonomic trends for southern African Hyacinthaceae subfamilies, Lachenalia in the Hyacinthoideae was expected to produce homoisoflavanones. Bulbs of Lachenalia rubida were collected from Bloubergstrand, Western Cape, South Africa. The dried material was extracted with dichloromethane and methanol, and the dichloromethane extract was separated by gravity column chromatography. Structures of isolated compounds were determined using 2D NMR and MS techniques. Two compounds were identified: 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone (1) and the novel 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromone (2). Compound 2 represents the first homoisoflavonoid with a 2,3-double bond reported from the Hyacinthaceae. A parallel phytochemical investigation of the sister taxon L. bulbifera did not detect any homoisoflavanones, suggesting these compounds are not definitive markers for Lachenalia. However, their production appears restricted to the Asparagales.