Trimeric hemibastadin congener from the marine sponge Ianthella basta.

@article{Niemann2013TrimericHC,
  title={Trimeric hemibastadin congener from the marine sponge Ianthella basta.},
  author={Hendrik Niemann and Wenhan Lin and Werner E. G. M{\"u}ller and Michael Kubbutat and Daowan Lai and Peter Proksch},
  journal={Journal of natural products},
  year={2013},
  volume={76 1},
  pages={
          121-5
        }
}
The first naturally occurring trimeric hemibastadin congener, sesquibastadin 1 (1), and the previously reported bastadins 3, 6, 7, 11, and 16 (2-6) were isolated from the marine sponge Ianthella basta, collected in Indonesia. The structure of 1 was elucidated on the basis of 1D and 2D NMR measurements and by HRMS. Among all the isolated compounds, the linear sesquibastadin 1 (1) and bastadin 3 (2) showed the strongest inhibition rates for at least 22 protein kinases (IC(50) = 0.1-6.5 μM), while… 

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References

SHOWING 1-10 OF 18 REFERENCES
New bastadins from the sponge Ianthella basta
From the sponge Ianthella basta collected in Guam, four new bastadin type ethers, bastasin-8 (7), -9 (9), -10 (8), and -11 (10) were isolated together with the known bastadin-2 (4), -4 (3), -5 (5),
Brominated tyrosine-derived metabolites from the sponge Ianthella basta
Seven novel metabolites, each originating from four bromotyrosine units, have been isolated from the sponge Ianthella basta. Bastadin-1 (2), bastadin-2(3) and bastadin-3(4) are derived from a single
Antifouling Bastadin Congeners Target Mussel Phenoloxidase and Complex Copper(II) Ions
Synthetically prepared congeners of sponge-derived bastadin derivatives such as 5,5′-dibromohemibastadin-1 (DBHB) that suppress the settling of barnacle larvae were identified in this study as strong
Bastadin 20 and bastadin O-sulfate esters from Ianthella basta: novel modulators of the Ry1R FKBP12 receptor complex.
TLDR
The problem of dereplication of bastadins was addressed using 1H-NMR "fingerprinting" of MeO signals in the corresponding permethyl bastadin derivatives.
1-O-Sulfatobastadins-1 and -2 from Ianthella basta (Pallas). Antagonists of the RyR1-FKBP12 Ca2+ Channel
Two new sulfate monoesters of hemibastadins-1 and -2 were isolated from the marine sponge Ianthella basta (Pallas) from Guam. A third new compound was tentatively assigned the structure
A new bastadin from the sponge Psammaplysilla purpurea.
TLDR
A new bastadin 2 and the previously reported bastadins 5, 7, and 12 were isolated from the Verongid sponge Psammaplysilla purpurea collected in Pohnpei and inhibited the enzymes topoisomerase II and dehydrofolate reductase.
Lithothamnin A, the first bastadin-like metabolite from the red alga Lithothamnion fragilissimum.
Lithothamnin A (1) is a new bastadin-like metabolite and represents the first report of this class of molecules from the red alga Lithothamnion fragilissimum. Lithothamnin A contains several novel
Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations.
TLDR
This study is the first report on the secondary metabolites from Ianthella cf.
A bastadin with potent and selective delta-opioid receptor binding affinity from the Australian sponge Ianthella flabelliformis.
TLDR
Three new bastadins, bastadin 25 (1), 15-O-sulfonatobastadin 11 (2), and bastadin 26 (3), were isolated from a MeOH extract of the Australian marine sponge Ianthella flabelliformis and showed potent affinity for the guinea pig delta-opioid receptors.
...
1
2
...