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Paper | Regular issue | Vol 38, No. 8, 1994, pp.1897-1908
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6765
Bullatin and Bullanin: Two Novel, Highly Cytotoxic Acetogenins from Asimina triloba

Geng-xian Zhao, Jocelyn H. Ng, John F. Kozlowzki, David L. Smith, and Jerry L. McLaughlin*

*Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, 1333 Robert E. Heine Pharmacy Building West Lafayette IN 47907, Indiana 47907, U.S.A.

Abstract

Two new highly cytotoxic adjacent bis-tetrahydrofuran acetogenins, bullatin (2) (10-hydroxy-4-deoxybullatacin) and bullanin (5) (30-hydroxy-4-deoxybullatacin), have been isolated from the ethanolic extract of the stem bark of Asimina triloba by directing the fractionation with brine shrimp lethality. In addition to these two new compounds, two previously reported acetogenins, squamocin (3) (28-hydroxy-4-deoxybullatacin) and motrilin (4) (29-hydroxy-4-deoxybullatacin) which are new to this species, were obtained. Through spectral analysis these four acetogenins were structurally identified as hydroxylation isomers of bullatacin (1) which was recently patented as an antitumor agent. All of these acetogenins showed high potencies in the brine shrimp test (BST) and in cytotoxicity tests against human solid tumor cell lines in culture, with certain potencies quite comparable to those of bullatacin (1) and several orders of magnitude greater than those of adriamycin.