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  • Pseudoceramines A-D, new antibacterial bromotyrosine alkaloids from themarine sponge Pseudoceratina sp.

    Author(s)
    Yin, Sheng
    Davis, Rohan A
    Shelper, Todd
    Sykes, Melissa L
    Avery, Vicky M
    Elofsson, Mikael
    Sundin, Charlotta
    Quinn, Ronald J
    Griffith University Author(s)
    Quinn, Ronald J.
    Davis, Rohan A.
    Sykes, Melissa L.
    Avery, Vicky M.
    Shelper, Todd B.
    Year published
    2011
    Metadata
    Show full item record
    Abstract
    Bioassay-guided fractionation of the CH2Cl2/MeOH extract of the Australian marine sponge Pseudoceratina sp. resulted in the purification of four new bromotyrosine alkaloids, pseudoceramines A-D (1-4), along with a known natural product, spermatinamine (5). The structures of 1-5 were determined by spectroscopic methods. Pseudoceramines A (1) and B (2) feature a rare bromotyrosyl-spermine-bromotyrosyl sequence, and pseudoceramine C (3) is the first example of bromotyrosine coupled with an N-methyl derivative of spermidine. Compounds 1-5 were screened for inhibition of toxin secretion by the type III secretion (T3S) pathway ...
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    Bioassay-guided fractionation of the CH2Cl2/MeOH extract of the Australian marine sponge Pseudoceratina sp. resulted in the purification of four new bromotyrosine alkaloids, pseudoceramines A-D (1-4), along with a known natural product, spermatinamine (5). The structures of 1-5 were determined by spectroscopic methods. Pseudoceramines A (1) and B (2) feature a rare bromotyrosyl-spermine-bromotyrosyl sequence, and pseudoceramine C (3) is the first example of bromotyrosine coupled with an N-methyl derivative of spermidine. Compounds 1-5 were screened for inhibition of toxin secretion by the type III secretion (T3S) pathway in Yersinia pseudotuberculosis. Compounds 2 and 5 inhibited secretion of the Yersinia outer protein YopE (IC50 = 19 and 6 mM, respectively) and the enzyme activity of YopH (IC50 = 33 and 6 mM, respectively).
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    Journal Title
    Organic & Biomolecular Chemistry
    Volume
    9
    Issue
    6755
    DOI
    https://doi.org/10.1039/C1OB05581J
    Subject
    Medicinal and biomolecular chemistry
    Medicinal and biomolecular chemistry not elsewhere classified
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/43495
    Collection
    • Journal articles

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