Shahidine, a novel and highly labile oxazoline from Aegle marmelos: the parent compound of aegeline and related amides

A rare alkaloid, shahidine (1), having an unstable oxazoline core has been isolated as a major constituent from the fresh leaves of Aegle marmelos. It is moisture-sensitive, and found to be the parent compound of aegeline and other amides, however, it is stable in dimethyl sulfoxide. Its structure was established by spectroscopic analysis. Biogenetically, oxazolines may be considered as the precursor of hydroxy amides and oxazoles found in plants. Shahidine (1) showed activity against a few Gram-positive bacteria.