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Communication | Regular issue | Vol 41, No. 2, 1995, pp.229-236
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6943
Isolation and Structural Elucidation of Bioactive C-12,15-cis Non-adjacent Bis-THF Annonaceous Acetogenins

Zhe-Ming Gu, Lu Zeng, and Jerry L. McLaughlin*

*Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, U.S.A.

Abstract

In further investigation on the EtOH extract of the bark of Annona bullata, two novel Annonaceous acetogenins, C-12,15-cis-bullatanocin (1) and C-12,15-cis-bullatalicin (2), were successfully separated by hplc from fractions in which they were mixed with bullatanocin (7) and bullatalicin (8), their respective C-12/15-trans diastereomers. Their relative stereochemistries between the two THF rings were determined through preparations of their respective 16,19-formaldehyde acetal derivatives (1a and 2a). The absolute configurations of 1 and 2 were resolved by analyses of the 1H nmr data of the (S)- and (R)-Mosher ester derivatives (1b,1c and 2b,2c) of 1a and 2a. Compounds (1) and (2) are the first examples of C-12/15-cis non-adjacent bis-THF Annonaceous acetogenins and showed potent bioactivities, comparable to those of 7 and 8, with notable cytotoxic selectivities among six human solid tumor cell lines.