Biosynthesis of penitrems and roquefortine by Penicillium crustosum.
Roquefortine and the penitrems were biosynthesised concurrently at an approximately equimolar rate by Penicillium crustosum after growth and sporulation. [14C]mevalonic acid was incorporated (15% efficiency) into the isoprenoid regions of the penitrem and roquefortine molecules to an extent consistent with their 6:1 molar ratio of isoprenoid components. [14C]penitrem A (specific activity, 3.4 X 10(2) mu Ci mmol-1) and 14C-penitrems B, C, and E readministered to young cultures were metabolically interconverted, indicating considerable metabolic flux, though generally directed towards penitrem A as the end product and suggesting a metabolic grid for the penitrem metabolites. Addition of bromide to the medium preferentially favored the production of bromo-analogs rather than the usual chloropenitrems.
D004873:Ergolines / Q000096:biosynthesis*; D005285:Fermentation; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D007700:Kinetics; D009183:Mycotoxins / Q000096:biosynthesis*; D010407:Penicillium / Q000254:growth & development / Q000378:metabolism*; D010879:Piperazines; D013329:Structure-Activity Relationship
D004873:Ergolines; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D009183:Mycotoxins; D010879:Piperazines; C003626:tremortin; C012536:roquefortine