JBIR-56 and JBIR-57, 2(1H)-pyrazinones from a marine sponge-derived Streptomyces sp. SpD081030SC-03.

@article{Motohashi2011JBIR56AJ,
  title={JBIR-56 and JBIR-57, 2(1H)-pyrazinones from a marine sponge-derived Streptomyces sp. SpD081030SC-03.},
  author={Keiichiro Motohashi and Kennichi Inaba and Shinichiro Fuse and Takayuki Doi and Miho Izumikawa and Shams Tabrez Khan and Motoki Takagi and Takashi Takahashi and Kazuo Shin‐ya},
  journal={Journal of natural products},
  year={2011},
  volume={74 7},
  pages={
          1630-5
        }
}
Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were… 
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References

SHOWING 1-10 OF 16 REFERENCES
Tetrapeptides possessing a unique skeleton, JBIR-34 and JBIR-35, isolated from a sponge-derived actinomycete, Streptomyces sp. Sp080513GE-23.
TLDR
Two new modified indole-containing peptides were isolated from the fermentation broth of a sponge-derived actinomycete identified by phylogenetic methods as a Streptomyces sp.
JBIR-66, a New Metabolite Isolated from Tunicate-Derived Saccharopolyspora sp. SS081219JE-28
In the course of our chemical screening program for new secondary metabolites, we isolated a new compound JBIR-66 (1) from the culture broth of the tunicate-derived actinomycete, Saccharopolyspora
Determination ofD-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene
Abstract1-fluoro-2,4-dinitrophenyl-5-l-alanine amide has been synthesized in high yield (76%) from 1,5-difluoro-2,4-dinitrobenzene andl-Ala-NH2. This compound contains a reactive fluorine atom which
Novel Pyrazines from the Myxobacterium Chondromyces crocatus and Marine Bacteria
The volatiles released by two strains of the myxobacterium Chondromyces crocatus and seven strains of marine Alphaproteobacteria from the North Sea were collected using the CLSA or SPME headspace
Tetracenoquinocin and 5-iminoaranciamycin from a sponge-derived Streptomyces sp. Sp080513GE-26.
TLDR
Two new anthracyclines and 5-iminoaranciamycin were established on the basis of extensive NMR and MS analyses along with (13)C-labeling experiments and the compounds 1-3 were evaluated for cytotoxicity against two cancer cell lines.
Streptomyces associated with a marine sponge Haliclona sp.; biosynthetic genes for secondary metabolites and products.
TLDR
This is the first comprehensive study detailing the isolation of actinobacteria from a marine sponge and novel secondary metabolites from these strains, and JBIR-34 and -35 were particularly interesting because of their unique chemical skeleton.
A new tetrodotoxin-producing actinomycete, Nocardiopsis dassonvillei, isolated from the ovaries of puffer fish Fugu rubripes.
TLDR
Mouse neuroblastoma cell culture, thin-layer chromatography, fluorimetric spectrophotometry, UV-spectrophotometer and electrospray ionization mass spectrometry, together with mouse bioassay demonstrated that the isolated strain produced tetrodotoxin and related toxin during cultivation.
JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02
JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02
Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14
Isolation of 2 new metabolites, JBIR-74 and JBIR-75, from the sponge-derived Aspergillus sp. fS14
Developing a new resource for drug discovery: marine actinomycete bacteria
TLDR
The continued development of improved cultivation methods and technologies for accessing deep-sea environments promises to provide access to this significant new source of chemical diversity.
...
1
2
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