Leaves from natural populations of Barbarea vulgaris ssp. arcuata (Brassicaceae) in Denmark were examined for glucosinolate content and resistance to the crucifer specialist flea beetle Phyllotreta nemorum. Two types of the plant (P- and G-type) could be recognized. Leaves of the G-type contained the glucosinolates (only side chains mentioned): (S)-2-hydroxy-2-phenylethyl- (2S), indol-3-ylmethyl- (4) and in trace amount (R)-2-hydroxy-2-phenylethyl- (2R), 2-phenylethyl- (1) and 4-methoxyindol-3-ylmethyl- (5). Leaves of the P-type were dominated by 2R and 4, and had only trace amounts of 1, 2S, and 5 but contained in addition the previously unknown (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl- (3R). The epimer, (S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl- (3S) was found in populations believed to be hybrids, and in B. orthoceras. 2S, 2R, desulfo 2S,-2R, -3S and -3R were isolated and identified by NMR and MS. Acylated glucosinolates or allylglucosinolate were not detected in leaves. The glucosinolate content in August was variable, 3-46 micromol/g dry wt, but was low in most populations, 3-15 micromol/g dry wt. In general, the glucosinolate content increased during the autumn, to 35-75 micromol/g dry wt in November. The G-type was resistant to neonate larvae of Phyllotreta nemorum in August and September (survival in 3-day bioassay typically 0%), and gradually lost the resistance in October and November (survival in 3-day bioassay 40-90%), and there was no correlation between glucosinolate content and resistance. Neither did glucosinolates explain the difference in resistance between the P-type (always susceptible) and the G-type (resistant in the summer season).