Bioactive Cyclopentenone Derivatives from Marine Isolates of Fungi

@article{Feng2009BioactiveCD,
  title={Bioactive Cyclopentenone Derivatives from Marine Isolates of Fungi},
  author={Zhile Feng and Alain S Leutou and Guohua Yang and Viviane N. Nenkep and Xavier Noudou Siwe and Hong Dae Choi and Jung Sook Kang and Byeng Wha Son},
  journal={Bulletin of The Korean Chemical Society},
  year={2009},
  volume={30},
  pages={2345-2350}
}
As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the… Expand
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References

SHOWING 1-10 OF 24 REFERENCES
Myrothenones A and B, cyclopentenone derivatives with tyrosinase inhibitory activity from the marine-derived fungus Myrothecium sp.
TLDR
New 3-amino-5-ethenylcyclopentenones, myrothenones A and B, were isolated together with known 6-n-pentyl-alpha-pyrone, which exhibited a tyrosinase inhibitory activity more active than kojic acid currently being used as a functional personal-care compound. Expand
Bromomyrothenone B and botrytinone, cyclopentenone derivatives from a marine isolate of the fungus botrytis.
TLDR
The absolute stereostructures of compounds 1 and 2 were elucidated on the basis of chemical and physicochemical evidence including quantum chemistry calculation, X-ray analysis, and CD exciton chirality method. Expand
Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor.
From a marine-derived strain of the fungus Emericella variecolor, varitriol (1), varioxirane (2), dihydroterrein (3), and varixanthone (4), besides the known mold metabolites ergosterol, terrein,Expand
Cyclopentenones, scaffolds for organic syntheses produced by the endophytic fungus mitosporic dothideomycete sp. LRUB20.
TLDR
Endophytic fungi may be a source for the production of building blocks for organic syntheses, and two new natural products, 2-hydroxymethyl-3-methylcyclopent-2-enone and cis-2,4-dinitrophenylhydrazone, were isolated from the endophytic fungus mitosporic Dothideomycete sp. Expand
New Cyclopentenone Derivatives from an Endophytic Streptomyces sp. Isolated from the Mangrove Plant Aegiceras comiculatum
From the mangrove plant Aegiceras comiculatum collected in South China an endophytic Streptomyces sp. was isolated. Following cultivation in a seawater-based medium, four new cyclopentenoneExpand
Isolation and Structures of Acremolactones B and C, Novel Plant-Growth Inhibitory γ-Lactones from Acremonium roseum I4267
TLDR
The structure of acremolactone B having a phenylpyridyl γ-lactone was elucidated by spectroscopic methods and showed plant growth inhibitory activity toward Chinese cabbage seedlings. Expand
Synthesis and revision of the stereochemistry of a cyclopentenone natural product isolated from ascomycete strain A23-98
The 2-propenyl-4,5-dihydroxycyclopent-2-enones 4, 10 and 14 have been synthesised in optically active form. NMR data suggest the compounds 10 and 14 (but not 4) correspond to compounds isolated fromExpand
Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes).
TLDR
Twenty new 5-(hydroxyalkyl)-2-cyclopentenone derivatives (hygrophorones) could be isolated from Hygrophorus latitabundus, H. persoonii, and H. pustulatus, and have structural similarities to the antibiotic pentenomycin. Expand
Africane-type sesquiterpenoids from the Argentine liverwort Porella swartziana and their antibacterial activity.
TLDR
Seven africanes, all of them swartzianin-type, have been isolated from an Argentine collection of the endemic liverwort Porella swartziana, and none were found to exhibit significant antibacterial activity. Expand
Cyclopentenone: a special moiety for anticancer drug design
TLDR
It appears that the addition of cyclopentenone groups to target-orienting molecules, in order to inactivate specific proteins in cells, could be a helpful general strategy for the development of novel therapeutic molecules. Expand
...
1
2
3
...