Citrinin revisited: from monomers to dimers and beyond.
Detailed chemical analysis of the solid phase fermentation of an Australian Penicillium citrinum isolate has returned the known compounds citrinin (1), phenol A acid (6), dihydrocitrinone (7) and dihydrocitrinin (8), together with a novel cytotoxic dimer, dicitrinin A (5). Dicitrinin A (5) was determined to be a dimerised artefact of the major co-metabolite citrinin, and its structure solved by spectroscopic analysis and chemical modification. Analysis of the products encountered during the controlled decomposition of citrinin led to the discovery of additional citrinin dimers and delineated a plausible mechanistic pathway linking all monomeric and dimeric citrinin degradation products.
Clark
Benjamin R
BR
Centre for Molecular Biodiversity, Institute for Molecular Bioscience, University of Queensland, Brisbane, QLD 4072, Australia.
Capon
Robert J
RJ
Lacey
Ernest
E
Tennant
Shaun
S
Gill
Jennifer H
JH
D001572:Benzofurans / Q000737:chemistry*; D001578:Benzopyrans / Q000737:chemistry*; D002953:Citrinin / Q000031:analogs & derivatives* / Q000737:chemistry*; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry* / Q000145:classification; D012988:Soil Microbiology
D001572:Benzofurans; D001578:Benzopyrans; C521725:dicitrinin A; D002953:Citrinin