Asitrilobins A and B: cytotoxic mono-THF Annonaceous acetogenins from the seeds of Asimina triloba

The seeds of Asimina triloba have yielded two novel cytotoxic mono-tetrahyd rofuran (THF) Annonaceous acetogenins, asitrilobins A (1) and B (2). In add ition. annonacin, asimin and asiminacin, which are known, and annomontacin and xylomaticin. which are known but are new in this species, were obtained . Compounds 1 and 2 have a relative stereochemical relationship of erythro/ cis/threo across the mono-THF rin with its two flanking hydroxyls and they, thus. represent a new type of acetogenin. Their structures were establishe d on the basis of chemical and spectral evidence. I and 2 showed potent bio activities in the brine shrimp lethality test (BST) and among six human sol id tumor cell lines with notable selectivity for the pancreatic cell line ( MIA PaCa-2) at ten to one-hundred times the potency of adriamycin. (C) 1999 Elsevier Science Ltd. All rights reserved.