Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba

Journal of Natural Products
K HeJ L McLaughlin

Abstract

Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure-activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1-3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.

References

Jan 1, 1977·International Journal of Cancer. Journal International Du Cancer·A A YunisD J Russin
Nov 1, 1973·Journal of the National Cancer Institute·H D SouleM Brennan
Nov 1, 1973·Journal of the National Cancer Institute·D J GiardW P Parks
May 1, 1982·Planta medica·B N MeyerJ L McLaughlin

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