Quinolactacins revisited: from lactams to imide and beyond.

  title={Quinolactacins revisited: from lactams to imide and beyond.},
  author={Ben Clark and Robert J. Capon and Ernest Lacey and Shaun Tennant and Jennifer H. Gill},
  journal={Organic \& biomolecular chemistry},
  volume={4 8},
Chemical analysis of a solid phase fermentation of an Australian Penicillium citrinum strain has returned all known examples of a rare class of N-methyl quinolone lactams, quinolactacins A2 (1), B2 (2), C2 (3) and A1 (4), together with the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel derivatives quinolonimide (9) and quinolonic acid (10). Complete stereostructures were assigned to all these compounds by detailed spectroscopic analysis and chemical interconversion… Expand
Bioactive Quinolactacins and Structurally Related Pyrroloquinolones
Abstract Quinolactacins are a small group of structurally related alkaloids containing a N-methyl pyrroloquinolone skeleton, which were initially identified in the fermentation broth ofExpand
Alkaloids from the Fungus Penicillium spathulatum as α-Glucosidase Inhibitors.
The docking studies predicted that the most stable conformers of 1 bind to yeast and mammalian α-glucosidases with a higher affinity than acarbose, and 1 also showed antihyperalgesic activity when tested in the formalin assay in hyperglycemic mice. Expand
Pyrrolyl 4-quinolone alkaloids from the mangrove endophytic fungus Penicillium steckii SCSIO 41025: Chiral resolution, configurational assignment, and enzyme inhibitory activities.
Six undescribed 4-quinolone alkaloids, including four racemic mixtures, (±)-oxypenicinolines A-D, and two related ones, penicinolines F and G, together with seven known analogues, were isolated fromExpand
Total synthesis of quinolactacin-H from marine-derived Penicillium sp. ENP701 and biological activities
  • Jin-xin Zhu, Yaojia Lu, +5 authors Hong Wang
  • Chemistry
  • 2020
The quinolactacins are a family of pyrroloquinoline-type natural products from Penicillium sp. From the organic extract of Penicillium sp. ENP701 fermentation broth, a microorganism from the eastExpand
Quinolactacin Biosynthesis Involves NRPSs Catalyzed Dieckmann Condensation to Form the Quinolone-γ-lactam Hybrid.
The identification of the quinolactacin A2 biosynthetic gene cluster is reported and the enzymatic basis for the formation of thequinolone- γ -lactam structure is elucidated, which expands the paradigm for the biosynthesis of quinlone-γ - lactam natural products via Dieckmann condensation. Expand
Quinoisobutyride A, an acyclic antibacterial tetrapeptide incorporating an unprecedented heterocyclic amino acid residue from the hypersaline lake-derived fungus Penicillium simplicissimum strain WSH17
Abstract Chromatographic refining of the EtOAc extract of a solid rice culture of the hypersaline lake-derived fungus Penicillium simplicissimum strain WSH17 afforded a new linear antibacterialExpand
New N-methyl-4-quinolone alkaloid and citrinin dimer derivatives from the sponge-derived fungus Penicillium sp. SCSIO 41303
  • Tiantian Guo, Meng-Meng Song, Wen-Rong Han, Jun-Heng Zhu, Qingchao Liu, Junfeng Wang
  • Chemistry
  • Phytochemistry Letters
  • 2021
Abstract Four new N-methyl-4-quinolones (1–4) and a new citrinin dimer derivative (10) with fourteen known compounds (5–9, 11–19) were isolated from the sponge-derived fungus Penicillium sp.Expand
Xanthones and Quinolones Derivatives Produced by the Deep-Sea-Derived Fungus Penicillium sp. SCSIO Ind16F01
The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data and were evaluated for their antiviral (EV71 and H3N2) and cytotoxic activities. Expand
Anti-Proliferative and Anti-Plasmodia Activity of Quinolactacin A2, Citrinadin A and Butrecitrinadin co-isolated from a Ghanaian Mangrove Endophytic Fungus Cladosporium oxysporum strain BRS2A-AR2F
  • 2017
The compounds quinolactacin A2 (2) and citrinadin A (13) which are originally considered to be the compounds of fungi genus Penicillium, were co-isolated for the first time from the new fungal strainExpand
Bioactive polyketides and alkaloids from Penicillium citrinum, a fungal endophyte isolated from Ocimum tenuiflorum.
The structures of the isolated compounds were determined by extensive analysis of the 1D, 2D NMR, and MS data, and by comparison with the literature by comparing them with known polyketides and alkaloids. Expand


Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6. II. Physico-chemical properties and structure elucidation.
Three novel quinolone compounds, quinolactacins A (1), B (2) and C (3), have been found from the fermentation broth of Penicillium sp. EPF-6, a fungus isolated from the larvae of mulberry pyralidExpand
Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp.
Chemical analysis of an Australian Streptomyces species yielded a range of known anthracyclines and biosynthetically related metabolites, as well as the hitherto unreported blanchaquinone (8). Expand
Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6. I. Taxonomy, production, isolation and biological properties.
Quinolactacins A (1), B (2) and C (3), novel quinolone antibiotics have been found from the cultured broth of a fungal strain isolated from the larvae of the mulberry pyralid Margaronia pyloalisExpand
Synthesis of 5-substituted imidazo[4,5-b]pyridinones by annelation of 4-amino-5-ethoxalyl-1H-imidazole derivatives with active methylene compounds
A new synthetic route to imidazo[4,5-b]pyridinones with a range of substituents at the 6-position has been developed. These compounds can be prepared in four steps from readily availableExpand
Concise enantioselective syntheses of quinolactacins A and B through alternative Winterfeldt oxidation.
Enantioselective total syntheses of (+)-quinolactacin B and (+)-quinolactacin A2 through asymmetric Pictet-Spengler cyclization and KO(2) oxidation-an alternative Winterfeldt condition-are described.
Synthesis of 1-aryl-1H-pyrazolecarbonitriles and related derivatives
The synthesis of 1-aryl-5-cyano-1H-pyrazole-4-carboxylic acid, ethyl esters 1 is described. Subsequent chemistry led to relatively simple and unique pyrazole derivatives. Most important of these areExpand
Quinolactacins A1 and A2, new acetylcholinesterase inhibitors from Penicillium citrinum.
The cholinergic neurotransmission has been considered as one potential therapeutic approach against Alzheimer disease and the use of acetylcholinesterase inhibitors to increase the amount ofacetylcholine present in the synapses between cholinerential neurons is considered. Expand
Synthese von chinoxalin- und indol-2,3-dicarbonsäureimiden
Zusammenfassung Chinoxalin- und Indol-2,3-dicarbonsaureimide 7, 8 werden durch Umsetzung halogenaktiver Maleinimide 1, 2 mit Natriumazid hergestellt. Weitere Derivate dieser heterocyclischen ReihenExpand