Goniodenin, a New Bioactive Annonaceous Acetogenin from Goniothalamus giganteus and Its Conversion to Tri-THF Acetogenins
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Abstract
Using activity-directed fractionation, a novel bioactive his-THF acetogenin, goniodenin (I), has been isolated from the hark of Goniothalamus giganteus (Annonaceae).1 is the first reported bis-THF acetogenin which bears a double hond in the aliphatic chain.The cis C-21/22 double hond in 1 was efficiently oxidized to the epoxides and cyclized to produce a pair of tri-THF acetogenins, cyclogoniodenins T and C (8 and 13).These are the first reported semi-synthesized tri-THF acetogenins, and 13 represents a new type of acetogenin.The absolute stereochemistries were assigned using Mosher ester and nmr analyses.8 and 13 show interesting selectivities among several human tumor cell lines.Asimilobin (19), concurrently found in the seeds of Asimina triloba, was also isolated and characterized.Goniothalamus giganteus Hook.f. &Thomas (Annonaceae) is a tropical tree which has a great reputation as a drug among the Malays.l The hark of this plant, obtained from Thailand, showed toxicities in the brine shrimp lethality test (BST) and showed murine toxicities in the 3PS (P388) leukemia bioassay.2Thirteen bioactive Annonaceous acetogenins have been previously isolated from the bark.? In our further bioactivity-directed search for antitumor compounds, two additional bioactive acetogenins,
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