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
Year published
2011
Metadata
Show full item recordAbstract
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 ...
View more >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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View more >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
Subject
Medicinal and biomolecular chemistry
Medicinal and biomolecular chemistry not elsewhere classified
Organic chemistry