ArticlePloS one2013
A branched biosynthetic pathway is involved in production of roquefortine and related compounds in Penicillium chrysogenum.
Article in PloS one, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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41 citing papers in PubMed, 90 citations in OpenAlex.
- Article
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- Elucidation of the Verrucofortine Biosynthetic Pathway Enables Identification of a Cyclodipeptide Prenyltransferase with High Catalytic Efficiency.Journal of agricultural and food chemistry · 2026Article
- Expansinine, a novel indole alkaloid-ergosteroid conjugate from the endophytic fungusRSC advances · 2025Article
- Characterization and structural analysis of a versatile aromatic prenyltransferase for imidazole-containing diketopiperazines.Nature communications · 2025Article
- Comparative genome analysis of patulin-producingPeerJ · 2025Article
- Biocatalytic Stereoselective Oxidation of 2-Arylindoles.Journal of the American Chemical Society · 2024Article
- Secondary Metabolites Produced by the Blue-Cheese Ripening MoldJournal of fungi (Basel, Switzerland) · 2023Review
- Discovery, Antitumor Activity, and Fermentation Optimization of Roquefortines fromMolecules (Basel, Switzerland) · 2023Article
- Review
- Review
- Nonribosomal peptide synthetases and their biotechnological potential in Penicillium rubens.Journal of industrial microbiology & biotechnology · 2021Review
- N-Heterocyclization in Gliotoxin Biosynthesis is Catalyzed by a Distinct Cytochrome P450 Monooxygenase.Chembiochem : a European journal of chemical biology · 2021Article
- A Penicillium rubens platform strain for secondary metabolite production.Scientific reports · 2020Article
- Anticancer activity and metabolite profiling data ofData in brief · 2020Article
- Mass Spectrometry Guided Discovery and Design of Novel Asperphenamate Analogs FromFrontiers in microbiology · 2020Article
- Bacterial MbtH-like Proteins Stimulate Nonribosomal Peptide Synthetase-Derived Secondary Metabolism in Filamentous Fungi.ACS synthetic biology · 2019Article
- Reprogramming Escherichia coli for the production of prenylated indole diketopiperazine alkaloids.Scientific reports · 2019Article
- Deregulation of secondary metabolism in a histone deacetylase mutant of Penicillium chrysogenum.MicrobiologyOpen · 2018Article
- Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway.Organic & biomolecular chemistry · 2018Article
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Authors and funding
8 authors at 4 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Profiling and structural elucidation of secondary metabolites produced by the filamentous fungus Penicillium chrysogenum and derived deletion strains were used to identify the various metabolites and enzymatic steps belonging to the roquefortine/meleagrin pathway. Major abundant metabolites of this pathway were identified as histidyltryptophanyldiketopiperazine (HTD), dehydrohistidyltryptophanyldi-ketopiperazine (DHTD), roquefortine D, roquefortine C, glandicoline A, glandicoline B and meleagrin. Specific genes could be assigned to each enzymatic reaction step. The nonribosomal peptide synthetase RoqA accepts L-histidine and L-tryptophan as substrates leading to the production of the diketopiperazine HTD. DHTD, previously suggested to be a degradation product of roquefortine C, was found to be derived from HTD involving the cytochrome P450 oxidoreductase RoqR. The dimethylallyltryptophan synthetase RoqD prenylates both HTD and DHTD yielding directly the products roquefortine D and roquefortine C without the synthesis of a previously suggested intermediate and the involvement of RoqM. This leads to a branch in the otherwise linear pathway. Roquefortine C is subsequently converted into glandicoline B with glandicoline A as intermediates, involving two monooxygenases (RoqM and RoqO) which were mixed up in an earlier attempt to elucidate the biosynthetic pathway. Eventually, meleagrin is produced from glandicoline B involving a methyltransferase (RoqN). It is concluded that roquefortine C and meleagrin are derived from a branched biosynthetic pathway.
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