Colman-Saizarbitoria T, Gu Z M, McLaughlin J L
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
J Nat Prod. 1994 Dec;57(12):1661-9. doi: 10.1021/np50114a007.
Xylopien [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 xylomaticin. Their structures were elucidated by spectral analyses of the parent compounds and/or simple chemical derivatives. Their absolute stereochemistries have been established by 1H- 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.
