This study demonstrated that plant extracts containing acetylenic isobutyla
mides and polyacetylenes, previously reported as occurring in Echinacea, ha
ve phototoxic antimicrobial activity against fungi, including clinically re
levant pathogenic fungi. Results show that hexane extracts of Echinacea var
iably inhibit growth of yeast strains of Saccharomyces cerevisiae, Candida
shehata, C. kefyr, C. albicans, C. steatulytica and C. tropicalis under nea
r UV irradiation (phototoxicity) and to a lower extent without irradiation
(conventional antifungal activity). The presence of polyacetylenes and alky
lamides in extracts of different organs was confirmed in Echinacea purpurea
by HPLC in agreement with previously reported data in the literature, and
was related to phototoxic activity. Two representative pure compounds, unde
ca-2E,4Z-diene-8,10-diynoic acid isobutylamide and dodeca-2E,4E,8Z,10E/Z-te
traenoic acid isobutylamide, were isolated from Echinacea purpurea root ext
racts, and compared in a disk assay (5 mu g/disk) with the highly conjugate
d trideca-1-ene-3,5,7,9,10-pentayne (previously isolated in our laboratory
and found here in E. purpurea). Significant phototoxicity was demonstrated
by pure trideca-1-ene-3,5,7,9,10-pentayne, while only minor phototoxicity w
as induced by the other two acetylenic compounds. Phototoxic activity of Ec
hinacea spp. is primarily attributed to the ketoalkenes and ketoalkynes abu
ndantly present in the roots.