New class of algicidal compounds and fungicidal activities derived from a chromene amide of Amyris texana.
A chromene amide, N-[2-(2,2-dimethyl-2H-1-benzopyran-6-yl)ethyl]-N,3-dimethylbutanamide, was isolated from the EtOAc extract of the leaves of Amyris texana and found to have moderate antifungal activity against Colletotrichum spp. and selective algicidal activity against Planktothrix perornata, a cyanobacterium (blue-green alga) that causes musty off-flavor in farm-raised channel catfish (Ictalurus punctatus). To improve the selective algicidal activity and provide water solubility, a series of chromene analogues were synthesized and evaluated for algicidal activity using a 96-well microplate rapid bioassay. In addition, the chromene analogues were evaluated for antifungal and phytotoxic activities. Hydrochloride salts of a chromene amine analogue showed improved water solubility and selectivity toward P. perornata with activity comparable to that of the naturally occurring chromene amide.
Meepagala
Kumudini M
KM
Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 8048, University, Mississippi 38677-8048, USA. kmeepaga@olemiss.edu
Schrader
Kevin K
KK
Burandt
Charles L
CL
Wedge
David E
DE
Duke
Stephen O
SO
D001578:Benzopyrans / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D000458:Cyanobacteria / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D027821:Rutaceae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D001578:Benzopyrans; D005659:Fungicides, Industrial