In addition to the well known affinin [= spilanthol, (2E,6Z,8E)-deca-2,6,8 trienoic acid isobutylamide (1)], the corresponding 2-methyl-butylamide (2), and two new acetylenic alkamides were isolated from Spilanthes oleracea L. by reversed phase medium pressure chromatography: (Z)-non-2-en-6,8-diynoic acid isobutylamide (3) and (Z)-dec-2-en-6,8-diynoic acid isobutylamide (4). The structures and their stereochemistries were elucidated by 1H-NMR, 13C-NMR (2 and 3), MS, UV, IR, and CD (2). The chemotaxonomic significance of the distribution of alkamides within the Compositae tribe Heliantheae is briefly discussed.