Monoacylglycerol from Punica granatum seed oil

The seeds of Punica granatum, known as hap roman in the Arabian Peninsula, are commonly eaten as a dessert. As part of an ongoing project to find nonnutritional natural products which have health benefits, or that can be exploited to protect crops, the chloroform-soluble extract of the fermented seeds of P. granatum was found to be rich in 1-O-trans, cis, trans-9,11,13-octadecatrienoyl glycerol (1). The seed oil is not lethal to brine shrimp larvae. 1-O-isopentyl-3-O-octadec-2-enoyl glycerol (2) and the known cis-9-octadecenoic, octadecanoic, and eicosanoic acids were also detected in small amounts in the seed oil by LC and MS. The structure of 1 was determined from NMR and MS spectral data.