UV-Guided isolation of verrucines A and B, novel quinazolines from penicillium verrucosum structurally related to anacine from penicilliumaurantiogriseum

Two novel quinazolines, verrucines A (1) and B (2), have been isolated as a major and a minor metabolite, respectively, of Penicillium verrucosum. Both 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 ostensible benzodiazepine anacine reported from Penicillium aurantiogriseum, composed of one mole each of anthranilic acid, leucine, and glutamine, appeared very similar to those of 1. Therefore, a revised quinazoline structure for anacine is proposed.

Dichlorodiaportin, diaportinol, and diaportinic acid: three novel isocoumarins from penicillium nalgiovense

Three novel isocoumarin (or isochromen) metabolites, dichlorodiaportin [3-(3, 3-dichloro-2-hydroxy-propyl)-8-hydroxy-6-methoxy-isochromen-1-one] (1), diaportinol [3-(2, 3-dihydroxy-propyl)-8-hydroxy-6-methoxy-isochromen-1-one] (2), and diaportinic acid [2-hydroxy-3-(8-hydroxy-6-methoxy-1-oxo-1H-isochromen-3-yl)-propanoic acid] (3), were isolated from the cultures of Penicillium nalgiovense along with citreoisocoumarin (4) and 6-methyl-citreoisocoumarin (5). Their structures were elucidated by spectroscopic methods including UV, MS, and NMR.