New class of algicidal compounds and fungicidal activities derived from a chromene amide of Amyris texana

J Agric Food Chem. 2010 Sep 8;58(17):9476-82. doi: 10.1021/jf101626g.

Abstract

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.

MeSH terms

  • Benzopyrans / chemistry*
  • Chromatography, Thin Layer
  • Cyanobacteria / drug effects*
  • Fungicides, Industrial / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Rutaceae / chemistry*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Benzopyrans
  • Fungicides, Industrial