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.
Schmidt
Karen
K
Institute of Pharmacy, Friedrich-Schiller-University Jena, Semmelweisstrasse 10, D-07743 Jena, Germany.
Riese
Ulrike
U
Li
Zengzhi
Z
Hamburger
Matthias
M
D000470:Alkaloids / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002681:China; D002855:Chromatography, Thin Layer; D007313:Insecta / Q000472:pathogenicity; D007770:L-Lactate Dehydrogenase / Q000032:analysis / Q000378:metabolism; D015394:Molecular Structure; D009414:Nerve Growth Factors / Q000378:metabolism; D016716:PC12 Cells / Q000187:drug effects / Q000201:enzymology; D010143:Paecilomyces / Q000737:chemistry*; D010860:Pigments, Biological / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011728:Pyridones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051381:Rats
D000470:Alkaloids; D000970:Antineoplastic Agents; D009414:Nerve Growth Factors; D010860:Pigments, Biological; D011728:Pyridones; D011760:Pyrrolidinones; C476668:militarinone B; C476669:militarinone C; C476670:militarinone D; C009435:tetramic acid; D007770:L-Lactate Dehydrogenase