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■ Absolute Stereochemistries of Giganin and Longanin, Bioactive Non-tetrahydrofuran Ring Annonaceous Acetogenins from Asimina longifolia

Qing Ye, Jerry L. McLaughlin,* and Dean Evert

*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 cytotoxic Annonaceous aetogenins, giganin (1) and longanin (2), were isolated from the leaves and twings of Asimina longifolis (Annonaceae). These compounds represented the type of Annonaceous astogenin lacking either tetrahydrofuran or epoxide rings along the aliphatic chain. Compound (2) is novel and giganin is previously known. The planar structures and absolute configurations of both were elucidated by ¹H and ¹³C nmr and ms before and after certain chemical derivatizations. Compound (2) gave cytotoxic ED₅₀ values comparable to those of adriamycin in a panel of human solid tumor cell lines.