Isoflavonoids isolated from Cuban propolis.

Chemical investigation of a red-type Cuban propolis sample has led to the isolation of 11 isoflavonoids (2 isoflavones, 3 isoflavans, and 6 pterocarpans), together with gallic acid, isoliquiritigenin, and (-)-liquiritigenin. Structural determination, including the absolute stereochemistry, was accomplished by spectroscopic analysis, particularly CD and 2D NMR techniques. The fragmentation behavior of pterocarpans was studied by electrospray ionization (ESI) tandem mass spectrometry (MS/MS) using an ion-trap analyzer, and a generalized fragmentation pathway, useful in the identification and structural characterization of pterocarpans, is proposed. Isoflavonoids are reported for the first time from propolis samples.