2 NEW BIOACTIVE MONOTETRAHYDROFURAN ANNONACEOUS ACETOGENINS FROM THE BARK OF XYLOPIA-AROMATICA

Xyloplen [1] and xylomatenin [2], two new bioactive monotetrahydrofuran Annonaceous acetogenins, have been isolated from an EtOH extract of the bark of Xylopia aromatica, using bioactivity-directed fractionation employing lethality to brine shrimp. These new compounds each have a double bond in the hydrocarbon chain and have been identified as C-23, C-24 dehydro analogs of xylopiacin and zylomaticin. Their structures were elucidated by spectral analyses of the parent compounds and/or simple chemical derivatives. Their absolute stereochemistries have been established by H-1- and 2D nmr experiments utilizing the production of Mosher esters. These acetogenins showed cytotoxic potencies superior to adriamycin against three human solid tumor cell lines.