VermixocinsA and B, 3-(r-hydroxy-3'-methylbutyl)-and 3-(r-acetoxy-3'-methylbutyl)-l lhydroxy-4-methoxy-9-methyl-5//,7/f-dibenzo [c,/] respectively. A new strain, specified B 5, selected from the above mentioned parental strain formed dehydroaltenusin only4). This compoundin addition to other polyketide metabolites was isolated from the mycelium of T. flavus (ATCC52201) grown on a malt extract medium5). Two new minor metabolites designated vermixocins A (1) and B (2) were found in the mycelium of P. vermiculatum cultivated under conditions optimized for vermiculin production. The structure elucidation of compounds1 and 2 is the subject of this report.
2-Methylsorbic acid (MA), (2Z,4E)-2-methyl-2,4-hexadienoic acid, is a new m e t a b o l i t e o f Penicillium vermiculatum. A n t i f u n g a l activity of this acid was higher than that o f sorbic acid or the b r o m o d e r i v a t i v e s brom o m e t h y l s o r b i c acid and b r o m o s o r b i c acid. M A suppressed the growth of Talaromyces flavus and germination o f its conidia. In P. vermiculatum this acid lowered p r o d u c t i o n of vermiculin and inhibited proteosynthesis in Saccharomyces cerevisiae.
Biosynthesis of vermiculin (1) and vermistatin (2) in Penicillium vermiculatum can be controlled by the carbon and nitrogen sources. Glucose and sucrose affect the levels of the two metabolites; cornsteep liquor influences the quality the biosynthesis. The concentrations of Fe3+ and Cu2+ ions also affect the biosynthesis, the effect being dependent on the type of carbon source utilized. The compounds capable of electron transport generally stimulate the production of 1 and 2 but do not influence the biosynthesis qualitatively.
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