Annocherin and (2,4)-cis- and trans-annocherinones, monotetrahydrofuran annonaceous acetogenins with a C-7 carbonyl group from Annona cherimolia seeds

The new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annocherin ( 1) and a mixture of (2,4)-cis- and trans-annocherinones (2 and 3), were iso lated from the bioactive methanolic extract of Annona cherimolia seeds. Com pounds 1-3 each possess an unusual 7-carbonyl group. Their structures were established on the basis of chemical and spectral evidence. Compounds 1-3 s howed significant toxicity in the brine shrimp lethality test and cytotoxic ity for six human solid tumor cell lines, with selectivity for the renal ce ll line (A-498) at potencies equivalent to Adriamycin.