Seven naphtho-γ-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties

@article{Shaaban2012SevenNF,
  title={Seven naphtho-$\gamma$-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties},
  author={Mohamed Shaaban and Khaled A. Shaaban and Mohamed S. Abdel-Aziz},
  journal={Organic and Medicinal Chemistry Letters},
  year={2012},
  volume={2},
  pages={6 - 6}
}
Eight bioactive pyrone derivatives were identified from the culture of Alternaria alternata strain D2006, isolated from the marine soft coral Denderonephthya hemprichi, which was selected as its profound antimicrobial activities. The compounds were assigned as pyrophen (1), rubrofusarin B (2), fonsecin (3), and fonsecin B (5) beside to the four dimeric naphtho-γ-pyrones; aurasperone A (6), aurasperone B (7), aurasperone C (8), and aurasperone F (9). Structures of the isolated compounds were… 
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References

SHOWING 1-10 OF 38 REFERENCES
Seven naphtho-g-pyrones from the marine-derived fungus Alternaria alternata : structure elucidation and biological properties
Eight bioactive pyrone derivatives were identified from the culture of Alternaria alternata strain D2006, isolated from the marine soft coral Denderonephthya hemprichi, which was selected as its
Aurasperone F – a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C-433
TLDR
A novel dimeric naphtho-γ-pyrone was isolated from the fermentation broth of the culture extracts of Aspergillus niger C-433, isolated from grapes and established by extensive one- and two-dimensional NMR spectroscopic studies.
Isolation, Structure Elucidation, and Antimycobacterial Properties of Dimeric Naphtho‐γ‐pyrones from the Marine‐Derived Fungus Aspergillus carbonarius
TLDR
Two new dimeric naphtho‐γ‐pyrones, compounds 1 and 2, were isolated from the AcOEt extract of the fungal strain WZ‐4‐11 of Aspergillus carbonarius and showed weak antimycobacterial activities against Mycobacterium tuberculosis H37Rv.
Secondary Metabolites of Marine-Derived Fungi: Natural Product Chemistry and Biological Activity
A marine fungal isolate, identified as Acremonium sp., was mass cultivated and found to produce two novel hydroquinone derivatives, 7-isopropenylbicyclo[4.2.0]octa-1,3,5-triene2,5-diol (1) and
Anthranilamides: new antimicroalgal active substances from a marine Streptomyces sp.
TLDR
All anthranilamide analogues were inactive against Staphylococcus aureus, Escherichia coli, and Mucor miehei, and showed that esters 1b, 1f and 2b were more active than the free acids.
Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties.
TLDR
Of 200 actinomycete isolates, one isolate was found to produce a new substance, altemicidin, which showed not only acaricidal activity but also antitumor activity and showed no antimicrobial activity except the inhibitory activity to Xanthomonas strains.
Antimycobacterial Naphthopyrones from Senna obliqua.
TLDR
This is the first report of antimycobacterial activity associated with naphthopyrone compounds and their structures were determined by spectroscopic means including 1D and 2D NMR techniques and further confirmed by X-ray crystallographic analysis.
Structure and absolute configuration of pyrophen, a novel pryrone derivative of L-phenylalanine from Aspergillus niger.
TLDR
Pyrophen, a novel 4-methoxy-2-pyrone derivative of L-phenylalanine isolated from cultures of Aspergillus niger, crystallizes in the orthorhombic space group P2(1)2( 1)2-1) 2(1), which is the first report of an amino acid-p Pyrone derivative.
New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities
TLDR
Nineteen aromatic nitro compounds were isolated from the culture broth of an Artic sea ice bacterium and 2-Nitro-4-(2′-nitroethenyl)-phenol was the most potent antimicrobial and cytotoxic substance.
New bioactive compounds from Aloe hijazensis
TLDR
The chemical constituents and biological activities of leaves and roots of Aloe hijazensis, collected in Saudi Arabia, are reported here for the first time and potent anti-bacterial and anti-fungal activities were found.
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