Iodo–sesquiterpene hydroquinone and brominated indole alkaloids from the Thai sponge Smenospongia sp.

@article{Prawat2012IodosesquiterpeneHA,
  title={Iodo–sesquiterpene hydroquinone and brominated indole alkaloids from the Thai sponge Smenospongia sp.},
  author={Hunsa Prawat and Chulabhorn Mahidol and Wirongrong Kaweetripob and Sawangjitt Wittayalai and Somsak Ruchirawat},
  journal={Tetrahedron},
  year={2012},
  volume={68},
  pages={6881-6886}
}
6′-Iodoaureol, an iodo–sesquiterpene hydroquinone, 6′-aureoxyaureol, a bissesquiterpene hydroquinone, and four brominated indole alkaloids 3–6 were isolated from the Thai sponge Smenospongia sp. Additionally, four known sesquiterpene hydroquinones 12–15, ten known brominated indole alkaloids 7–11, 17–18, and 20–22, ergosterol, and furospinosulin-1 were also isolated. Compound 1 is the first reported iodo–sesquiterpene hydroquinone and compounds 7–11 were isolated for the first time from natural… 
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References

SHOWING 1-10 OF 23 REFERENCES
Secondary metabolites from three Florida sponges with antidepressant activity.
TLDR
There is ample evidence that marine natural products with the diversity of brominated marine alkaloids will provide potential leads for antidepressant and anxiolytic drugs.
Structure and synthesis of bromoindoles from the marine sponge Pseudosuberites hyalinus
TLDR
Four new 6-bromoindoles have been isolated from the marine sponge Pseudouberitesd hyalinus collected in the North Atlantic around the Faroe Islands.
Investigation of brominated tryptophan alkaloids from two thorectidae sponges: Thorectandra and Smenospongia.
TLDR
Six new brominated tryptophan derivatives are yielded and compounds 1, 3-8, 10, and 11 were found to inhibit the growth of Staphylococcus epidermidis with either weak or moderate MICs.
Polyprenyl derivatives from the sponge Ircinia spinosula
Abstract Unsubstituted prenylated benzoquinones, a novel group of terpenoid quinones, the corresponding quinols, together with the hydroxylated 2-octaprenyl-quinol (VII) have been identified in the
Biologically active quinone and hydroquinone sesquiterpenoids from the sponge smenospongia sp.
Abstract This work describes isolation, structure and biological activity of quinone- and hydroquinone sesquiterpenoids biosynthesized by a sponge Snenospongia sp. Structures were established by
New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea.
TLDR
Eight indole alkaloids including the new N-3'-ethylaplysinopsin (9) have been isolated from the Jamaican sponge Smenospongia aurea, showing significant antimalarial and antimycobacterial activity in vitro and displaced high-affinity [(3)H]antagonist ligands from cloned human serotonin 5-HT(2) receptor subtypes.
Cytotoxic ergosterols frompaecilomyces sp. J300
Seven ergosterol derivatives (1~7) were isolated from silkworm larvae infected withPaecilomyces sp. J300. On the basis of spectroscopic means, their structures have been elucidated
Novel neuronal nitric oxide synthase (nNOS) selective inhibitor, aplysinopsin-type indole alkaloid, from marine sponge Hyrtios erecta.
TLDR
Two novel aplysinopsin-type indole alkaloids and new quinolone 7 were isolated from the marine sponge Hyrtios erecta and exhibited selective inhibitory activity against the neuronal isozyme of nitric oxide synthase.
Synthesis and antitumoral activities of marine ent-chromazonarol and related compounds.
TLDR
Efficient syntheses of ent-isozonarol, 6a, 7a and 7a show a significative antitumoral activity and ent-chromazonarol from (-)-sclareol is described.
New Access to Sesquiterpene Hydroquinones: Synthesis of (+)‐ent‐Chromazonarol
Abstract A facile access to optically active (+)‐ent‐chromazonarol ent‐1, isolated from the sponge Disidea pallescens, is reported from commercially available (+)‐manool 4.
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3
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