New cytotoxic annonaceous acetogenins: Bullatanocin and cis- and trans-Bullatanocinone, from Annona bullata (Annonaceae)

Abstract Further bioactivity-directed fractionation of the ethanol extract of the bark of Annona bullata Rich. (Annonaceae) has led to the isolation of the new nonadjacent bis-tetrahydrofuran acetogenins, bullatanocin ( 1 ), cis- bullatanocinone ( 2 ) and trans-bullatanocinone ( 3 ). A known adjacent bis-tetrahydrofuran acetogenin, desacetyluvaricin ( 4 ), which is new to this species, was also isolated. Brine shrimp lethality test (BST) data and cytotoxicities against human solid tumor cell lines of 1–4 were compared with those of the diastereoisomers, bullatalicin ( 5 ), cis- and trans-bullatalicinone ( 6 and 7 ) and 4-deoxyasimicin ( 8 ). 1 shows cytotoxic potencies 10,000 times those of adriamycin in the lung and colon cancer cell lines.