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Mar Drugs
2010 Jun 04;86:1803-16. doi: 10.3390/md8061803.
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Intramolecular modulation of serine protease inhibitor activity in a marine cyanobacterium with antifeedant properties.
Matthew S
,
Ratnayake R
,
Becerro MA
,
Ritson-Williams R
,
Paul VJ
,
Luesch H
.
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Extracts of the Floridian marine cyanobacterium Lyngbya cf. confervoides were found to deter feeding by reef fish and sea urchins (Diadema antillarum). This antifeedant activity may be a reflection of the secondary metabolite content, known to be comprised of many serine protease inhibitors. Further chemical and NMR spectroscopic investigation led us to isolate and structurally characterize a new serine protease inhibitor 1 that is formally derived from an intramolecular condensation of largamide D (2). The cyclization resulted in diminished activity, but to different extents against two serine proteases tested. This finding suggests that cyanobacteria can endogenously modulate the activity of their protease inhibitors.
Figure 1. Structures of largamide D oxazolidine (1) and the parent compound, largamide D (2).
Figure 2. Feeding experiments with the crude extracts of L. cf. confervoides. The bars represent the mean amount of food eaten and the error bars are +1 SE. Different letters above the bars represent means that are statistically different. (a). Feeding experiments with a natural assemblage of reef fish. (b). Feeding experiments with the sea urchin Diadema antillarum.
Figure 3. Expanded regions of the 13C NMR spectra (125 MHz) of 1 in CD3OD (bottom panel) and 1:1 CD3OD/CD3OH (top) showing peak splitting for carbons attached to the free hydroxyl groups.
Figure 4. Selected key ROESY correlations among Ahp and Thr-1 for 1.
Figure 5. Effect of compounds 1 and 2 on chymotrypsin and elastase activity.
Asai,
TMC-66, a new endothelin converting enzyme inhibitor produced by Streptomyces sp. A5008.
1999, Pubmed
Asai,
TMC-66, a new endothelin converting enzyme inhibitor produced by Streptomyces sp. A5008.
1999,
Pubmed
Baumann,
Planktocyclin, a cyclooctapeptide protease inhibitor produced by the freshwater cyanobacterium Planktothrix rubescens.
2007,
Pubmed
Botes,
Isolation and characterization of four toxins from the blue-green alga, Microcystis aeruginosa.
1982,
Pubmed
Cardellina,
Seaweed dermatitis: structure of lyngbyatoxin A.
1979,
Pubmed
Carmichael,
Cyanobacteria secondary metabolites--the cyanotoxins.
1992,
Pubmed
Cruz-Rivera,
Chemical deterrence of a cyanobacterial metabolite against generalized and specialized grazers.
2007,
Pubmed
Gunasekera,
Carriebowmide, a new cyclodepsipeptide from the marine cyanobacterium Lyngbya polychroa.
2008,
Pubmed
Gunasekera,
Molassamide, a depsipeptide serine protease inhibitor from the marine cyanobacterium Dichothrix utahensis.
2010,
Pubmed
He,
New diterpene alkaloids from the roots of Spiraea japonica.
2001,
Pubmed
Hopp,
Citreamicins with potent gram-positive activity.
2008,
Pubmed
Humpage,
Toxin types, toxicokinetics and toxicodynamics.
2008,
Pubmed
Kunimoto,
Kigamicins, novel antitumor antibiotics. I. Taxonomy, isolation, physico-chemical properties and biological activities.
2003,
Pubmed
Kwan,
Lyngbyastatins 8-10, elastase inhibitors with cyclic depsipeptide scaffolds isolated from the marine cyanobacterium Lyngbya semiplena.
2009,
Pubmed
Linington,
Symplocamide A, a potent cytotoxin and chymotrypsin inhibitor from the marine Cyanobacterium Symploca sp.
2008,
Pubmed
Matthew,
Lyngbyastatin 4, a dolastatin 13 analogue with elastase and chymotrypsin inhibitory activity from the marine cyanobacterium Lyngbya confervoides.
2007,
Pubmed
Matthew,
Tiglicamides A-C, cyclodepsipeptides from the marine cyanobacterium Lyngbya confervoides.
2009,
Pubmed
Nakano,
Neutralization of microcystin shock in mice by tumor necrosis factor alpha antiserum.
1991,
Pubmed
Paul,
Chemical defenses: from compounds to communities.
2007,
Pubmed
Plaza,
Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp.
2006,
Pubmed
Schatz,
Towards clarification of the biological role of microcystins, a family of cyanobacterial toxins.
2007,
Pubmed
Sharp,
Phylogenetic and chemical diversity of three chemotypes of bloom-forming lyngbya species (Cyanobacteria: Oscillatoriales) from reefs of southeastern Florida.
2009,
Pubmed
Taori,
Lyngbyastatins 5-7, potent elastase inhibitors from Floridian marine cyanobacteria, Lyngbya spp.
2007,
Pubmed
