Chlorinated Polyketide Obtained from a Daldinia sp. Treated with the Epigenetic Modifier Suberoylanilide Hydroxamic Acid

@article{Du2014ChlorinatedPO,
  title={Chlorinated Polyketide Obtained from a Daldinia sp. Treated with the Epigenetic Modifier Suberoylanilide Hydroxamic Acid},
  author={Lin Du and Jarrod B. King and Robert H. Cichewicz},
  journal={Journal of Natural Products},
  year={2014},
  volume={77},
  pages={2454 - 2458}
}
A new chlorinated pentacyclic polyketide, daldinone E (1), was purified from a Daldinia sp. fungal isolate treated with the epigenetic modifier suberoylanilide hydroxamic acid (SAHA). A biosynthetically related epoxide-containing daldinone analogue, 2, was also purified from the same fungus. The structures of both compounds were established by spectroscopic methods, and the absolute configurations were assigned by analysis of their NMR data (coupling constants and ROESY correlations) and DFT… 
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References

SHOWING 1-10 OF 28 REFERENCES
Secondary metabolites by chemical screening. XXII: Gabosines, new carba-sugars from Streptomyces
Chemical screening of different Streptomycetes strains resulted in the detection, isolation, and structure elucidation of a number of novel carba-sugars. The constitution of these secondary…
Diarylcyclopentendione metabolite obtained from a Preussia typharum isolate procured using an unconventional cultivation approach.
An uncommon 2,5-diarylcyclopentenone compound, preussidone (1), and a new biphenyl compound, 1',5-dimethoxy-3,5'-dimethyl-2,3'-oxybiphenyl-1,2'-diol (4), together with two known biphenyl compounds,…
Aromatic polyketide production in Cordyceps indigotica, an entomopathogenic fungus, induced by exposure to a histone deacetylase inhibitor.
Cultivation of Cordyceps indigotica, an entomopathogenic fungus, in the presence of suberoyl bis-hydroxamic acid (an HDAC inhibitor) greatly activated its polyketide synthesis apparatus to afford six…
Histone deacetylase inhibitor induced the production of three novel prenylated tryptophan analogs in the entomopathogenic fungus, Torrubiella luteorostrata
Sphaeropsidones, phytotoxic dimedone methyl ethers produced by Diplodia cupressi: a structure-activity relationship study.
TLDR
The conversion of sphaeropsidone into the corresponding 1,4-dione derivative led to a compound showing greater antifungal activity than its precursor, which could be useful in devising new natural fungicides for practical application in agriculture.
Tenuipyrone, a novel skeletal polyketide from the entomopathogenic fungus, Isaria tenuipes, cultivated in the presence of epigenetic modifiers.
The concomitant addition of the histone deacetylase inhibitor and the DNA methyltransferase inhibitor to the culture medium of an entomopathogenic fungus, Isaria tenuipes, greatly enhanced its…
The structure of a glyoxalase I inhibitor and its chemical reactivity with SH-compounds.
The structure of a glyoxalase I inhibitor (I), isolated from a cultured broth of Streptomyces griseosporeus, was found to be 2-crotonyloxymethyl-4,5,6-trihydroxy-cyclohex-2-enone by chemical studies.…
Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor
Aromatic polyketide glycosides from an entomopathogenic fungus, Cordyceps indigotica
Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor
...
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