UV-guided isolation of verrucines A and B, novel quinazolines from Penicillium verrucosum structurally related to anacine from Penicillium aurantiogriseum

Two novel quinazolines, verrucines A (1) and B (2), have been isolated as a major and a minor metabolite, respectively, of Penicillium verrucosum. Bot h are condensates of one mole each of anthranilic acid, phenylalanine, and glutamine. The structures were elucidated by spectroscopic methods, and the two compounds were found to be epimers. The spectroscopic data for the ost ensible benzodiazepine anacine reported from Penicillium aurantiogriseum, c omposed of one mole each of anthranilic acid, leucine, and glutamine, appea red very similar to those of 1. Therefore, a revised quinazoline structure for anacine is proposed.