4-DEOXYANNOMONTACIN AND (2,4-CIS AND TRANS)-ANNOMONTACINONE, NEW BIOACTIVE MONO-TETRAHYDROFURAN ANNONACEOUS ACETOGENINS FROM GONIOTHALAMUS-GIGANTEUS

4-Deoxyannomontacin (1) and a mixture of (2,4-cis and trans)-annomonta cinone (2), new bioactive mono-tetrahydrofuran (THF) gamma-lactone and keto-lactone acetogenins, respectively, as well as five known mono-TH F acetogenins [xylomaticin, longifolicin, longicoricin, (2,4-cis and t rans)-gigantetrocinone, and (2,4-cis and trans)-gigantetroneninone], w ere isolated from the bark of Goniothalamus giganteus (Annonaceae) by activity-directed fractionation using the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemi cal methods. The absolute stereochemistries of 1 and 2 were determined by the advanced Mosher ester method and by circular dichroism (CD). D etermination of the absolute stereochemistry at C-10 as R for 1 is the first example of the direct determination of the absolute stereochemi stry of a carbinol position isolated from other functional groups in t he annonaceous acetogenins. 1 and 2 showed selective and potent cytoto xicities to certain human tumor cell lines and were comparable to the activity of rotenone against yellow fever mosquito larvae. (C) 1997 El sevier Science Ltd.