- Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.
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Two new HIV-inhibitory depsipeptides, stellettapeptins A (1) and B (2), were isolated from an extract of the marine sponge Stelletta sp., collected from northwestern Australia. Structures of these cyclic nonribosomal peptides were elucidated on the basis of extensive NMR data analysis, and chemical degradation and derivatization studies. Stellettapeptins contain numerous nonproteinogenic amino acid residues and they are the first peptides reported to contain a 3-hydroxy-6,8-dimethylnon-4-(Z)-enoic acid moiety. Compounds 1 and 2 potently inhibit infection of human T-lymphoblastoid cells by HIV-1RF with EC50 values of 23 and 27 nM, respectively.
- Shin, Hee Jae,Rashid, Mohammad A.,Cartner, Laura K.,Bokesch, Heidi R.,Wilson, Jennifer A.,McMahon, James B.,Gustafson, Kirk R.
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supporting information
p. 4215 - 4219
(2015/06/22)
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- Lipopeptides from the tropical marine cyanobacterium symploca sp.
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A collection of the tropical marine cyanobacterium Symploca sp., collected near Kimbe Bay, Papua New Guinea, previously yielded several new metabolites including kimbeamides A-C, kimbelactone A, and tasihalide C. Investigations into a more polar cytotoxic fraction yielded three new lipopeptides, tasiamides C-E (1-3). The planar structures were deduced by 2D NMR spectroscopy and tandem mass spectrometry, and their absolute configurations were determined by a combination of Marfeys and chiral-phase GC-MS analysis. These new metabolites are similar to several previously isolated compounds, including tasiamide (4), grassystatins (5, 6), and symplocin A, all of which were isolated from similar filamentous marine cyanobacteria.
- Mevers, Emily,Haeckl, F. P. Jake,Boudreau, Paul D.,Byrum, Tara,Dorrestein, Pieter C.,Valeriote, Frederick A.,Gerwick, William H.
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p. 969 - 975
(2014/05/20)
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- Cytotoxic cyclic depsipeptides from the Australian marine sponge Neamphius huxleyi
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Three new cyclic depsipeptides, neamphamides B (2), C (3), and D (4), were isolated from the Australian sponge Neamphius huxleyi. The planar structural characterization of these molecules was elucidated using 2D NMR experiments and ESI-FTICR-MSn. Their configurations were determined by Marfey's method and J-based NMR analysis. These new metabolites inhibited the growth of human cell lines (A549, HeLa, LNCaP, PC3, and NFF) with IC50 values ranging from 88 to 370 nM. However, neamphamide D causes A549 cell proliferation at subcytotoxic doses and should be treated cautiously as a cytotoxic compound.
- Tran, Trong D.,Pham, Ngoc B.,Fechner, Gregory,Zencak, Dusan,Vu, Hoan T.,Hooper, John N.A.,Quinn, Ronald J.
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p. 2200 - 2208
(2013/02/25)
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- PROTEASE INHIBITORS, COMPOSITIONS AND METHODS OF USE
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This invention relates to grassystatins A, B and C, and their isolated or purified forms. The compounds of the invention are useful as aspartic protease, gamma secretase, or metalloprotease inhibitors. Methods of using the compounds and compositions thereof are also disclosed.
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Page/Page column 34-35
(2011/01/12)
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- Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation
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In our efforts to exploremarine cyanobacteria as a source of novel bioactive compounds, we discovered a statine unit-containing linear decadepsipeptide, grassystatin A (1), which we screened against a diverse set of 59 proteases. We describe the structure
- Kwan, Jason C.,Eksioglu, Erika A.,Liu, Chen,Paul, Valerie J.,Luesch, Hendrik
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experimental part
p. 5732 - 5747
(2010/03/24)
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