Light-Mediated Antifungal Activity of Echinacea Extracts

Abstract

This study demonstrated that plant extracts containing acetylenic isobutylamides and polyacetylenes, previously reported as occurring in Echinacea, have phototoxic antimicrobial activity against fungi, including clinically relevant pathogenic fungi. Results show that hexane extracts of Echinacea variably inhibit growth of yeast strains of Saccharomyces cerevisiae, Candida shehata, C. kefyr, C. albicans, C. steatulytica and C. tropicalis under near UV irradiation (phototoxicity) and to a lower extent without irradiation (conventional antifungal activity). The presence of polyacetylenes and alkylamides 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, undeca-2E,4Z-diene-8,10-diynoic acid isobutylamide and dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide, were isolated from Echinacea purpurea root extracts, and compared in a disk assay (5 μg/disk) with the highly conjugated 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 was induced by the other two acetylenic compounds. Phototoxic activity of Echinacea spp. is primarily attributed to the ketoalkenes and ketoalkynes abundantly present in the roots.

Echinacea - Asteraceae - phototoxicity - polyacetylenes - alkylamides - Candida

References

• 1 Brevoort  P.. HerbalGram. 1996;;  36 49-57
• 2 Bauer  R.. Phytomedicines of Europe. (Lawson LD, Bauer R, eds.) pp. 140-57, American Chemical Society Symposium Series 691, Washington, D.C.; 1998
• 3 Hobbs  C.. HerbalGram. 1994;;  30 34-47
• 4 Shemluck  M.. J. Ethnopharm.. 1982;;  5 303-58
• 5 Towers  G HN,, Arnason  J T,, Wat  C-K,, Graham  E A,, Lam  J,, Mitchell  J C.. Contact Dermatitis. 1979;;  5 40-144
• 6 Camm  E L,, Towers  G HN,, Mitchell  J C.. Phytochem.. 1975;;  14 2007-11
• 7 Guillet  G,, Philogene  B JR,, O'Meara  J,, Durst  T,, Arnason  J T.. Phytochem.. 1997;;  46 495-8
• 8 Schulte  K E,, Rucker  G,, Perlick  J.. Arzneim.-Forsch.. 1967;;  17 825-9
• 9 McLachlan  D,, Arnason  J T,, Lam  J.. Biochem. Syst. and Ecol.. 1986;;  14 17-23
• 10 Marchant  Y Y,, Cooper  G K.. In: Light Activated Pesticides. (Heitz JR, Downum KR, eds.) pp. 241 - 54, American Chemical Society Symposium Series 339, Washington, D.C.; 1987
• 11 Bauer  R,, Wagner  H.. Economic and Medicinal Plant Research,. (Wagner H, Farnsworth N, eds.) pp. 253-321, Academic Press, London; 1991
• 12 McGregor  R L.. University of Kansas Science Bulletin. 1968;;  118 113-42
• 13 Arnason  J T,, Philogene  B JR,, Towers  G HN.. In: Herbivores: their interactions with secondary plant metabolites,. vol. 2,: pp. 317-341, Academic Press, London; 1992
• 14 Law  D,, Moore  C B,, Denning  D W.. J. Antimicrob. Chemother.. 1997;;  40 109-12
• 15 Bauer  R,, Remiger  P,, Wagner  H.. Phytochem.. 1988;;  27 2339-42
• 16 Bauer  R,, Khan  I A,, Wagner  H.. Planta Med.. 1988;;  54 426-30
• 17 Bergeron  C,, Livesey  J F,, Awang  D VC,, Arnason  J T,, Rana  J,, Baum  B R,, Letchamo  W.. Phytochem. Anal.. submitted 1999; 
• 18 Towers  G HN,, Page  J E,, Hudson  J B.. Curr. Org. Chem.. 1997;;  1 395-414
• 19 Bourque  G,, Arnason  J T,, Madhosingh  C,, Orr  W.. Can. J. Bot.. 1984;;  63 899-902
• 20 Bourque  G,, Arnason  J T,, Madhosingh  C,, Orr  W.. Biochem. Syst. Ecol.. 1986;;  14 569-73
• 21 Bauer  R,, Remiger  P.. Planta Med.. 1989;;  55 367-71