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Communication | Regular issue | Vol 36, No. 10, 1993, pp.2221-2228
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6452
Bullacin: A New Cytotoxic Annonaceous Acetogenin from Annona bullata

Zhe-ming Gu, Xin-ping Fang, Lu Zeng, Karl V. Wood, and Jerry L. McLaughlin*

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

Abstract

Using the brine shrimp lethality test (BST) to direct fractionation, two additional Annonaceous acetogenins, bullacin (1) and parviflorin (2), were isolated from the ethanol extract of the bark of Annona bullata Rich. Their absoulte stereochemistries were revealed by the use of Mosher’s methodology. Compound (1) is a new adjacent bis-tetrahydrofuran (THF) acetogenin possessing a relatively rare C35 skeleton and an unprecedented C-6 hydroxyl group. The absolute configuration of 1 was assigned as 6S, 13R, 14R, 17R, 18R, 21R, 22R, and 34S. Compound (2) is a known acetogenin but is new to this plant. The absolute configuration of 2 was concluded to be 4R, 13R, 14R, 17R, 18R, 21R, 22R,and 34S. This is the first paper in which the absolute stereochemistry of a new acetogenin is published with the new structure. 1 showed 10 to 1000 times the cytotoxic potency of adriamycin when tested in human tumor cell lines.