FUROFURANONAPHTHOQUINONES - BIOACTIVE COMPOUNDS WITH A NOVEL FUSED-RING SYSTEM FROM CRESCENTIA-CUJETE

Bioassay-directed fractionation of the methyl ethyl ketone extract of Crescentia cujete yielded the naphthoquinones 1 and 2. Both compounds are cytotoxic, and 1 shows selective DNA-damaging activity against yeast. Detailed spectroscopic interpretation led to the assignment of the structures of 1 and 2 as 3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione and 9-hydroxy-3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione, respectively. This is the first report of this fused furofuran ring system, either as a product or a synthetic substance.