Abstract
Ingestion of ponderosa pine needles by late-pregnant cattle causes premature parturition induced by a profound and progressive decrease in uterine blood flow. In vitro perfused placentomes obtained from late-pregnant cows were used in the bioassay-guided fractionation of Pinus ponderosa pine needles to isolate a new class of vasoactive lipid substances. Chromatographically inseparable mixtures of active compounds were isolated by Soxhlet extraction and flash column chromatography. The structures of intact myristate and/or laurate diesters of 1,14-tetradecanediol or 1,12-dodecanediol in these extracts were determined by lH and 13C NMR, IR, and high- and low-resolution FAB mass spectrometric analyses. Saponification of small samples of isolated diesters, derivatization, and GCiMS verified major components as lauric and myristic acids and 1,14-tetradecanediol. Structures of individual components of mixtures of lipids were confirmed by MS-MS analysis.
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