chiniofon and viridicatol

A systematic chemical investigation of the deep-sea-derived fungus

Topics: Animals; Antineoplastic Agents; Aquatic Organisms; Cell Line, Tumor; Humans; Hydroxyquinolines; Inhibitory Concentration 50; Penicillium; Quinolones; Structure-Activity Relationship

Viridicatol is a quinoline alkaloid isolated from the deep-sea-derived fungus

Topics: Anaphylaxis; Animals; Anti-Allergic Agents; Aquatic Organisms; B-Lymphocytes; beta-N-Acetylhexosaminidases; Calcium; Cell Line, Tumor; Disease Models, Animal; Food Hypersensitivity; Histamine; Hydroxyquinolines; Immunoglobulin E; Interleukin-10; Intestines; Mast Cells; Mice; Ovalbumin; Penicillium; Peptide Hydrolases; Quinolones; Rats; T-Lymphocytes, Regulatory; Tumor Necrosis Factor-alpha

A new isoquinolone alkaloid named 5-hydroxy-8-methoxy-4-phenylisoquinolin-1(2H)-one (3), together with two known quinolinone alkaloids 3-O-methylviridicatin (1) and viridicatol (2) were isolated from the fermentation of an endophytic fungus Penicillium sp. R22 in Nerium indicum. Their structures were elucidated by NMR, IR and MS data, and were also confirmed by comparing with the reported data in the literature. Meanwhile, the antibacterial and antifungal activities of all compounds were tested, and the results showed that three compounds had strong antifungal activity. Among them, compound 2 revealed potent antibacterial activity against Staphylococcus aureus with MIC value of 15.6 μg/mL.

Topics: Alkaloids; Anti-Bacterial Agents; Antifungal Agents; Drug Evaluation, Preclinical; Endophytes; Hydroxyquinolines; Isoquinolines; Microbial Sensitivity Tests; Molecular Structure; Nerium; Penicillium; Quinolones; Staphylococcus aureus

Penicillium crustosum is common in food and feed both in subtropical and temperate regions. Recently, it has also been found occurring frequently in glacier ice, sea ice and sea water of Arctic regions of Svalbard. The aim of the study was to compare isolates of the same fungal species from widely different habitats and geographic regions to see if the nutritional physiology and the profile of secondary metabolites were consistent or depended on the isolation source. All 121 strains examined produced the following families of secondary metabolites: penitrems (100%), roquefortines (100%), terrestric acids (99.2%) and viridicatols (100%), whereas 81 of 83 Arctic isolates additionally produced andrastin A. However, only 8 of 38 non-Arctic isolates produced detectable andrastin A. The quantitative profiles of 96 strains were compared using cluster, principal component and correspondence analyses. There was no clear grouping of Arctic versus non-Arctic, creatine positive versus creatine negative strains.

Topics: Androstadienes; Arctic Regions; Chromatography, High Pressure Liquid; Cluster Analysis; Environment; Geography; Heterocyclic Compounds, 4 or More Rings; Hydroxyquinolines; Indoles; Mycotoxins; Penicillium; Piperazines; Principal Component Analysis; Quinolones

The new species Penicillium discolor, frequently isolated from nuts, vegetables and cheese is described. It is characterised by rough, dark green conidia, synnemateous growth on malt agar and the production of the secondary metabolites chaetoglobosins A, B and C, palitantin, cyclopenin, cyclopenol, cyclopeptin, dehydrocyclopeptin, viridicatin and viridicatol. It also produces the mouldy smelling compounds geosmin and 2-methyl-isoborneol, and a series of specific orange to red pigments on yeast extract sucrose agar, hence the epithet discolor. P. discolor resembles P. echinulatum morphologically but on basis of the secondary metabolites is also related to P. expansum, P. solitum and P. crustosum.

Topics: Benzodiazepinones; Camphanes; Cheese; Culture Media; Cyclohexanols; Cyclohexanones; Food Microbiology; Hydroxyquinolines; Indole Alkaloids; Indoles; Microscopy, Electron, Scanning; Naphthols; Nuts; Penicillium; Pigments, Biological; Quinolones; Sucrose; Vegetables

Topics: Benzodiazepinones; Chromatography; Hydroxyquinolines; Metabolism; Penicillium; Quinolines; Quinolones; Research