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Structure and absolute configuration of toxic polyketide pigments from the fruiting bodies of the fungus Cortinarius rufo-olivaceus.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2010 Aug 07; Vol. 8 (15), pp. 3543-51. Date of Electronic Publication: 2010 Jun 09. - Publication Year :
- 2010
-
Abstract
- Two new polyketide-derived pigments, named rufoolivacins B (), and D (), with a 4',10-coupled aryl linkage between polysubstituted 1-naphthol and 1,4- or 1,2-anthraquinone, together with nine known metabolites including rufoolivacins A () and C (), have been isolated from the fruiting bodies of the Chinese toadstool Cortinarius rufo-olivaceus (basidiomycetes). Their structures were characterized on the basis of spectroscopic methods, including 2D-NMR experiments (COSY, NOESY, HSQC, and HMBC). The axial chirality of and was assigned through analysis of their CD spectra and ZINDO and TDDFT calculations. Compounds and were found to be unusual natural products incorporating an ortho-anthraquinone chromophore. All the metabolites were shown to be toxic toward the brine shrimp.
- Subjects :
- Animals
Artemia drug effects
Circular Dichroism
Lactams chemistry
Lactams isolation & purification
Lactams toxicity
Macrolides isolation & purification
Models, Molecular
Molecular Conformation
Pigments, Biological isolation & purification
Quantum Theory
Cortinarius chemistry
Fruiting Bodies, Fungal chemistry
Macrolides chemistry
Macrolides toxicity
Pigments, Biological chemistry
Pigments, Biological toxicity
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 8
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 20532365
- Full Text :
- https://doi.org/10.1039/c002773a