Novel Tetramic Acids and Pyridone Alkaloids, Militarinones B, C, and D, from the Insect Pathogenic Fungus Paecilomyces militaris

Three yellow pigments were isolated from a mycelial extract of the entomopathogenic fungus Paecilomyces militaris. With the aid of spectroscopic means, one compound was identified as a new pyridone alkaloid, militarinone D (1). The two other metabolites were characterized as two novel 3-acyl tetramic acids, militarinones B (2) and C (3). In contrast to the structurally related pyridone militarinone A (4), compounds 1-3 showed only negliable neuritogenic activity in PC-12 cells, whereas militarinone D (1) exhibited cytotoxicity. On the basis of a co-occurrence of 3-acyl tetramic acids and biogenetically related pyridone alkaloids in P. militaris, a revised biosynthetic pathway for pyridone alkaloids is proposed.