Structure of sepedonin, a tropolone metabolite of <i>Sepedomum</i><i>chrysospermum</i> Fries

Wright, Jeffrey L. C.; McInnes, A. G.; Smith, David George Emslie; Vining, L. C.

doi:10.1139/v70-456

Cited by 18 publications

(7 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4 Mycoparasitic fungi are a diverse and prolific source of compounds with potential therapeutic value. 5 The polyketides sepedonin and derivatives, 6 along with chrysodin, 7 have been isolated previously from this species, while the New Zealand strain CANU E609 has been the source of the cyclic pentapeptide chrysosporide, two aromatic polyketides, and phomalactone. 8 Previously, it had been observed that strain CANU E609 gave an altered metabolic profile under different culture conditions; 8 however even when regrown under identical conditions to those in a previous study the crude extract showed a different metabolite pattern.…”

mentioning

confidence: 99%

Evolving Trends in the Dereplication of Natural Product Extracts. 2. The Isolation of Chrysaibol, an Antibiotic Peptaibol from a New Zealand Sample of the Mycoparasitic Fungus Sepedonium chrysospermum

et al. 2008

View full text Add to dashboard Cite

By the application of an HPLC bioactivity profiling/microtiter technique in conjunction with capillary NMR instrumentation and access to the AntiMarin database the conventional evaluation/isolation dereplication/characterization procedures can be dramatically truncated. This approach is illustrated using the isolation of a new peptaibol, chrysaibol (1), from a New Zealand isolate of the mycoparasitic fungus Sepedonium chrysospermum. The unique nature of chrysaibol was recognized by bioactivity-guided fractionation using HPLC bioactivity profiling/microtiter plate analysis in conjunction with capillary NMR instrumentation and the AntiMarin database. 2D NMR techniques, in combination with MS fragmentation experiments, determined the planar structure of chrysaibol (1), while the absolute configurations of the amino acid residues were defined by Marfey's method. Chrysaibol (1) was cytotoxic against the P388 murine leukemia cell line (IC50 6.61 microM) and showed notable activity against Bacillus subtilis (IC50 1.54 microM).

show abstract

mentioning

confidence: 99%

Evolving Trends in the Dereplication of Natural Product Extracts. 2. The Isolation of Chrysaibol, an Antibiotic Peptaibol from a New Zealand Sample of the Mycoparasitic Fungus Sepedonium chrysospermum

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Metabolites previously isolated from S. chrysospermum include the polyketide sepedonin and its derivatives and the antifungal compound chrysodin, while quinone derivatives and peptaibols have been isolated from S. microspermum Besl. and S. ampullosporum Damon, two species initially included in S. chrysospermum sensu lato…”

mentioning

confidence: 99%

Chrysosporide, a Cyclic Pentapeptide from a New Zealand Sample of the Fungus Sepedonium chrysospermum

et al. 2006

View full text Add to dashboard Cite

A new cyclic pentapeptide, chrysosporide (1), was isolated from a New Zealand sample of the mycoparasitic fungus Sepedonium chrysospermum by bioactivity-guided fractionation. The planar structure was deduced by detailed spectroscopic analysis, and the absolute configurations of the amino acid residues were defined by Marfey's method. As both enantiomers of Leu occurred in chrysosporide, molecular mechanics calculations were applied to the analysis to distinguish between the possible structural isomers. Only the lowest energy conformers of the cyclo-(L-Val-D-Ala-L-Leu-L-Leu-D-Leu) isomer were in agreement with the observed NOEs, suggesting that this was the most probable amino acid sequence for chrysosporide (1).

show abstract

“…One relatively well-investigated necrotrophic mycoparasite is Sepedonium chrysospermum, which parasitises the fruiting bodies of Boletaceae, for instance Boletus edulis. It contains the polyketide sepedonin (104), which exhibits bioactivity against bacteria, yeasts and moulds, 231,232 and chrysodin (105) with antifungal activity. 233 Moreover, peptaibols, antimicrobial peptides that contain high proportions of g-aminoisobutyric acid, such as the antibacterial and antifungal chrysospermins 234 and the antibiotic chrysaibol, 235 occur in S. chrysospermum.…”

Section: Attack and Counter-defencementioning

confidence: 99%

Chemical ecology of fungi

Spiteller

2015

Nat. Prod. Rep.

133

View full text Add to dashboard Cite

Fungi are widespread in nature and have conquered nearly every ecological niche. Fungi occur not only in terrestrial but also in freshwater and marine environments. Moreover, fungi are known as a rich source of secondary metabolites. Despite these facts, the ecological role of many of these metabolites is still unknown and the chemical ecology of fungi has not been investigated systematically so far. This review intends to present examples of the various chemical interactions of fungi with other fungi, plants, bacteria and animals and to give an overview of the current knowledge of fungal chemical ecology.

show abstract

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Cited by 18 publications

References 7 publications

Evolving Trends in the Dereplication of Natural Product Extracts. 2. The Isolation of Chrysaibol, an Antibiotic Peptaibol from a New Zealand Sample of the Mycoparasitic Fungus Sepedonium chrysospermum

Evolving Trends in the Dereplication of Natural Product Extracts. 2. The Isolation of Chrysaibol, an Antibiotic Peptaibol from a New Zealand Sample of the Mycoparasitic Fungus Sepedonium chrysospermum

Chrysosporide, a Cyclic Pentapeptide from a New Zealand Sample of the Fungus Sepedonium chrysospermum

Chemical ecology of fungi

Contact Info

Product

Resources

About