Asitrocin, (2,4)-cis- and trans-asitrocinones: Novel bioactive mono-tetrahydrofuran acetogenins from Asimina triloba seeds

Asitrocin (1) and the mixture of(2,4)-cis- and trans-asitrocinones (2 and 3 ), new bioactive Annonaceous acetogenins, were isolated from the seeds of A simina triloba by activity-directed fractionation using the brine shrimp le thality test. Asitrocin and the mixture of..(2;4)-cis- and trans-asitrocino nes have a configuration of erythro/trans/threo from C-15 to C-20, the mono -THF moiety with two flanking hydroxyl groups. The structures were determin ed by spectroscopic methods. These acetogenins showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumor ce ll lines with notable selectivity for the prostate (PC-3) and the pancreati c(MIA PaCa-2) cell lines at 10-100 times the potency of adriamycin.