Lyngbyastatins 5–7, Potent Elastase Inhibitors from Floridian Marine Cyanobacteria, <i>Lyngbya</i> spp.

Taori, Kanchan; Matthew, Susan; Rocca, James R.; Paul, Valerie J.; Luesch, Hendrik

doi:10.1021/np0702436

Cited by 119 publications

(141 citation statements)

References 19 publications

Supporting

Mentioning

136

Contrasting

Order By: Relevance

“…This study documents the presence of compounds across a range of species from Fort Lauderdale collections. Previous studies detailed the bioassay-guided fractionation and nuclear magnetic resonance (NMR) methods used to isolate and elucidate structures of the compounds of interest (21,34,35,48,58). For comparisons among chemotypes, an Econosil (Alltech, Deerfield, IL) C 18 10-m column was used with a solvent scheme consisting of methanol-water (80:20) run isocratically for 10 min followed by a linear gradient to 100% methanol over the course of 60 min.…”

Section: Methodsmentioning

confidence: 99%

Phylogenetic and Chemical Diversity of Three Chemotypes of Bloom-Forming Lyngbya Species ( Cyanobacteria : Oscillatoriales ) from Reefs of Southeastern Florida

Sharp

Arthur

et al. 2009

Appl Environ Microbiol

Self Cite

View full text Add to dashboard Cite

The cyanobacterial genus Lyngbya includes free-living, benthic, filamentous cyanobacteria that form periodic nuisance blooms in lagoons, reefs, and estuaries. Lyngbya spp. are prolific producers of biologically active compounds that deter grazers and help blooms persist in the marine environment. Here, our investigations reveal the presence of three distinct Lyngbya species on nearshore reefs in Broward County, FL, sampled in 2006 and 2007. With a combination of morphological measurements, molecular biology techniques, and natural products chemistry, we associated these three Lyngbya species with three distinct Lyngbya chemotypes. One species, identified as Lyngbya cf. confervoides via morphological measurements and 16S rRNA gene sequencing, produces a diverse array of bioactive peptides and depsipeptides. Our results indicate that the other two Lyngbya species produce either microcolins A and B or curacin D and dragonamides C and D. Results from screening for the biosynthetic capacity for curacin production among the three Lyngbya chemotypes in this study correlated that capacity with the presence of curacin D. Our work on these bloom-forming Lyngbya species emphasizes the significant phylogenetic and chemical diversity of the marine cyanobacteria on southern Florida reefs and identifies some of the genetic components of those differences.Marine harmful algal blooms are increasing in frequency and severity as a result of eutrophication in the marine environment, changes in global climate patterns, and increased monitoring and use of marine habitats (22,23,60). The genus Lyngbya consists of filamentous cyanobacteria that cause periodic, but in some cases long-lasting, blooms in shallow (usually Ͻ30 m) tropical and subtropical marine and estuarine environments (42,43). Lyngbya species are prolific producers of secondary metabolites, primarily lipopeptides, cyclic peptides, and depsipeptides. To date, over

show abstract

Section: Methodsmentioning

confidence: 99%

Phylogenetic and Chemical Diversity of Three Chemotypes of Bloom-Forming Lyngbya Species ( Cyanobacteria : Oscillatoriales ) from Reefs of Southeastern Florida

Sharp

Arthur

et al. 2009

Appl Environ Microbiol

Self Cite

View full text Add to dashboard Cite

show abstract

“…The reaction was followed by measuring the absorbance at 405 nm every 30 s. For each assay, enzyme activity of each well was calculated using the initial slope of each progress curve, expressed as a percentage of the slope of the uninhibited reaction. Lyngbyastatin 7 7 was used as a positive control for inhibition of elastase and chymotrypsin, while phenylmethylsulfonyl fluoride was used as a positive control for inhibition of trypsin. 7 …”

mentioning

confidence: 99%

“…Lyngbyastatin 7 7 was used as a positive control for inhibition of elastase and chymotrypsin, while phenylmethylsulfonyl fluoride was used as a positive control for inhibition of trypsin. 7 …”

mentioning

confidence: 99%

Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

et al. 2009

Self Cite

View full text Add to dashboard Cite

A new dolastatin 13 analogue, molassamide (1), was isolated from cyanobacterial assemblages of Dichothrix utahensis collected from the Molasses Reef, Key Largo, Florida, and from Brewer's Bay, St. Thomas, U.S. Virgin Islands. This is the first peptide reported from the cyanobacterial genus Dichothrix and the first natural product isolated from marine Dichothrix spp. Its planar structure was determined by NMR spectroscopic techniques, and the configurations of the asymmetric centers were assigned after chiral HPLC analysis of the hydrolysis products. The depsipeptide 1 exhibited protease-inhibitory activity, with IC 50 values of 0.032 and 0.234 µM against elastase and chymotrypsin, respectively. There was no apparent inhibition of trypsin at 10 µM, the highest concentration tested.Marine cyanobacteria have emerged as a rich source of biologically and ecologically active secondary metabolites, in particular peptides and depsipeptides. 1 While marine cyanobacteria are common inhabitants of tropical and subtropical coastal waters worldwide, under favorable environmental conditions they can grow rapidly and form harmful algal blooms. 2 Grounding of the M/V Wellwood on Molasses Reef in Key Largo, Florida Keys National Marine Sanctuary (FKNMS), on August 4, 1984, resulted in massive destruction to living corals and underlying reef framework. Further injury to this restoration site was caused during the 1998 storm season. Artificial reef structures were placed at the Wellwood grounding site in 2002 as a restoration action by FKNMS. National Oceanic and Atmospheric Administration scientists have attempted to settle larval corals in situ on these Wellwood restoration structures (WRS) for several years, and from 2003-2005, Southeast Fisheries Science Center and academic partners "seeded" tens of thousands of reef-building coral larvae and out-planted a few thousand newly settled coral polyps to the WRS for restoration purposes. They have identified only two survivors from this effort. The WRS has an obvious algal mat cover dominated by the cyanobacterium Dichothrix utahensis, which appears as "black puff balls". The cyanobacterial mat was 14 times more abundant on the WRS than on adjacent natural reef surfaces at similar depth (5-7 m). Preliminary experiments conducted using the cyanobacterial mat exudates with swimming coral larvae indicated significant reduction of larval settlement, 3 leading NOAA scientists to hypothesize that algal mat exudates inhibit coral success on the WRS and possibly other nearby restoration structures. 4 Therefore, we selectively collected a cyanobacterial assemblage of D. utahensis from the WRS and investigated the natural products chemistry of this bloom-forming cyanobacterium to better understand the chemical ecology of this species.Here we report the isolation, structure elucidation, and proteaseinhibitory studies of a new dolastatin 13 analogue, trivially named molassamide (1), as a component of the polar n-BuOH-soluble fraction. Molassamide contains the six common amino acid residues Val,...

show abstract

“…Lyngbyastatins 4-6 (108-110), three depsipeptides containing the unusual amino acid homotyrosine and a 3-amino-6-hydroxy-2-piperidone (Ahp) or 3-amino-6-methoxyl-2-piperidone (Amp) residue, were isolated from the marine cyanobacterium Lyngbya confervoides off the Florida Atlantic coast Taori et al, 2007). A sample of the marine cyanobacterium Lyngbya sp.…”

Section: Cyclic Polypeptides With Branchesmentioning

confidence: 99%

“…A sample of the marine cyanobacterium Lyngbya sp. collected from a mangrove channel at Summerland Key in the Florida Keys produced two lyngbyastatin analogues, termed lyngbyastatin 7 (111) and a previously identified cyanobacterial metabolite somamide B (78) (Taori et al, 2007;Nogle et al, 2001b). Lyngbyastatin 4-7 (108-111) and somamide…”

Section: Cyclic Polypeptides With Branchesmentioning

confidence: 99%

Absolute Configuration and Biosynthesis of Pahayokolide A from Lyngbya sp. Strain 15-2 of the Florida Everglades

Liu¹

View full text Add to dashboard Cite

show abstract

Lyngbyastatins 5–7, Potent Elastase Inhibitors from Floridian Marine Cyanobacteria, Lyngbya spp.

Cited by 119 publications

References 19 publications

Phylogenetic and Chemical Diversity of Three Chemotypes of Bloom-Forming Lyngbya Species ( Cyanobacteria : Oscillatoriales ) from Reefs of Southeastern Florida

Phylogenetic and Chemical Diversity of Three Chemotypes of Bloom-Forming Lyngbya Species ( Cyanobacteria : Oscillatoriales ) from Reefs of Southeastern Florida

Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

Absolute Configuration and Biosynthesis of Pahayokolide A from Lyngbya sp. Strain 15-2 of the Florida Everglades

Contact Info

Product

Resources

About