Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata.

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J Nat Prod. 1996 Feb;59(2):100-8.

Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata.

Rieser MJ, Gu ZM, Fang XP, Zeng L, Wood KV, McLaughlin JL.
AgrEvo Research Center, Pikeville, North Carolina 27863, USA.
Bioactivity-directed
fractionation of the seeds of Annona muricata L. (Annonaceae) resulted
in the isolation of five new compounds: cis-annonacin (1),
cis-annonacin-10-one (2), cis-goniothalamicin (3), arianacin (4), and
javoricin (5). Three of these (1-3) are among the first cis
mono-tetrahydrofuran ring acetogenins to be reported. NMR analyses of
published model synthetic compounds, prepared cyclized formal acetals,
and prepared Mosher ester derivatives permitted the determinations of
absolute stereochemistries. Bioassays of the pure compounds, in the
brine shrimp test, for the inhibition of crown gall tumors, and in a
panel of human solid tumor cell lines for cytotoxicity, evaluated
relative potencies. Compound 1 was selectively cytotoxic to colon
adenocarcinoma cells (HT-29) in which it was 10,000 times the potency
of adriamycin.