Temporal dynamics of natural product biosynthesis in marine cyanobacteria.

PubWeight™: 0.98‹?› | Rank: Top 15%

🔗 View Article (PMC 3069200)

Published in Proc Natl Acad Sci U S A on March 10, 2011

Authors

Eduardo Esquenazi1, Adam C Jones, Tara Byrum, Pieter C Dorrestein, William H Gerwick

Author Affiliations

1: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, and Department of Biology, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0212, USA.

Articles citing this

Codon randomization for rapid exploration of chemical space in thiopeptide antibiotic variants. Chem Biol (2012) 1.55

Genomic insights into the physiology and ecology of the marine filamentous cyanobacterium Lyngbya majuscula. Proc Natl Acad Sci U S A (2011) 1.40

Significant natural product biosynthetic potential of actinorhizal symbionts of the genus frankia, as revealed by comparative genomic and proteomic analyses. Appl Environ Microbiol (2011) 1.10

The chemical ecology of cyanobacteria. Nat Prod Rep (2012) 0.98

Recent applications of metabolomics toward cyanobacteria. Metabolites (2013) 0.89

Mass spectrometry-based metabolomics to elucidate functions in marine organisms and ecosystems. Mar Drugs (2012) 0.86

An analysis of the sponge Acanthostrongylophora igens' microbiome yields an actinomycete that produces the natural product manzamine A. Front Mar Sci (2014) 0.81

Enzymatic strategies and biocatalysts for amide bond formation: tricks of the trade outside of the ribosome. Mol Biosyst (2014) 0.81

Comparative mass spectrometry-based metabolomics strategies for the investigation of microbial secondary metabolites. Nat Prod Rep (2016) 0.80

Detailed Mechanistic Study of the Non-enzymatic Formation of the Discoipyrrole Family of Natural Products. J Am Chem Soc (2016) 0.80

Probing the in vivo biosynthesis of scytonemin, a cyanobacterial ultraviolet radiation sunscreen, through small scale stable isotope incubation studies and MALDI-TOF mass spectrometry. Bioorg Med Chem (2011) 0.77

Prioritizing Natural Product Diversity in a Collection of 146 Bacterial Strains Based on Growth and Extraction Protocols. J Nat Prod (2016) 0.76

Expanding the Described Metabolome of the Marine Cyanobacterium Moorea producens JHB through Orthogonal Natural Products Workflows. PLoS One (2015) 0.76

Articles cited by this

Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem Biol (2004) 4.58

Bioactive natural products from marine cyanobacteria for drug discovery. Phytochemistry (2007) 4.27

Marine natural products. Nat Prod Rep (2009) 3.41

Metamorphic enzyme assembly in polyketide diversification. Nature (2009) 2.64

Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages. Proc Natl Acad Sci U S A (2008) 2.23

Light and the transcriptional response of the microcystin biosynthesis gene cluster. Appl Environ Microbiol (2000) 1.97

Rapid typing and elucidation of new secondary metabolites of intact cyanobacteria using MALDI-TOF mass spectrometry. Nat Biotechnol (1997) 1.67

Seaweed dermatitis: structure of lyngbyatoxin A. Science (1979) 1.64

Integrating transcriptional and metabolite profiles to direct the engineering of lovastatin-producing fungal strains. Nat Biotechnol (2003) 1.48

Visualizing the spatial distribution of secondary metabolites produced by marine cyanobacteria and sponges via MALDI-TOF imaging. Mol Biosyst (2008) 1.47

Organization, evolution, and expression analysis of the biosynthetic gene cluster for scytonemin, a cyanobacterial UV-absorbing pigment. Appl Environ Microbiol (2009) 1.28

Activity screening of carrier domains within nonribosomal peptide synthetases using complex substrate mixtures and large molecule mass spectrometry. Biochemistry (2006) 1.24

The unique mechanistic transformations involved in the biosynthesis of modular natural products from marine cyanobacteria. Nat Prod Rep (2010) 1.19

Quorum sensing in Cyanobacteria: N-octanoyl-homoserine lactone release and response, by the epilithic colonial cyanobacterium Gloeothece PCC6909. ISME J (2008) 1.04

Temperature-responsive sensing regulates biocontrol factor expression in Pseudomonas fluorescens CHA0. ISME J (2009) 1.03

Chemical deterrence of a cyanobacterial metabolite against generalized and specialized grazers. J Chem Ecol (2006) 0.97

15N-labeling to determine chlorophyll synthesis and degradation in Synechocystis sp. PCC 6803 strains lacking one or both photosystems. Biochim Biophys Acta (2005) 0.92

A mass spectrometry method for measuring 15N incorporation into pheophytin. Anal Biochem (2002) 0.84

Transcriptional analysis of the jamaicamide gene cluster from the marine cyanobacterium Lyngbya majuscula and identification of possible regulatory proteins. BMC Microbiol (2009) 0.84

Hydrogen, carbon and nitrogen isotopic fractionations during chlorophyll biosynthesis in C3 higher plants. Phytochemistry (2005) 0.80

Articles by these authors

Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature. Nat Prod Rep (2013) 5.38

Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem Biol (2004) 4.58

ncRNA- and Pc2 methylation-dependent gene relocation between nuclear structures mediates gene activation programs. Cell (2011) 4.26

A monovalent streptavidin with a single femtomolar biotin binding site. Nat Methods (2006) 3.89

Mass spectral molecular networking of living microbial colonies. Proc Natl Acad Sci U S A (2012) 3.56

Discovery of a widely distributed toxin biosynthetic gene cluster. Proc Natl Acad Sci U S A (2008) 3.20

Marine natural products as anticancer drugs. Mol Cancer Ther (2005) 2.93

PHF8 mediates histone H4 lysine 20 demethylation events involved in cell cycle progression. Nature (2010) 2.91

Single cell genome amplification accelerates identification of the apratoxin biosynthetic pathway from a complex microbial assemblage. PLoS One (2011) 2.73

Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula. J Nat Prod (2004) 2.71

Metamorphic enzyme assembly in polyketide diversification. Nature (2009) 2.64

Translating metabolic exchange with imaging mass spectrometry. Nat Chem Biol (2009) 2.47

The genomisotopic approach: a systematic method to isolate products of orphan biosynthetic gene clusters. Chem Biol (2007) 2.32

A sliding docking interaction is essential for sequential and processive phosphorylation of an SR protein by SRPK1. Mol Cell (2008) 2.29

Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages. Proc Natl Acad Sci U S A (2008) 2.23

MS/MS networking guided analysis of molecule and gene cluster families. Proc Natl Acad Sci U S A (2013) 2.12

Proteasomal protein degradation in Mycobacteria is dependent upon a prokaryotic ubiquitin-like protein. J Biol Chem (2008) 2.12

The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit. Gene (2002) 2.09

A mass spectrometry-guided genome mining approach for natural product peptidogenomics. Nat Chem Biol (2011) 2.05

Imaging mass spectrometry in microbiology. Nat Rev Microbiol (2011) 2.04

Imaging mass spectrometry of intraspecies metabolic exchange revealed the cannibalistic factors of Bacillus subtilis. Proc Natl Acad Sci U S A (2010) 1.90

Convergence of isoprene and polyketide biosynthetic machinery: isoprenyl-S-carrier proteins in the pksX pathway of Bacillus subtilis. Proc Natl Acad Sci U S A (2006) 1.80

Direct cloning and refactoring of a silent lipopeptide biosynthetic gene cluster yields the antibiotic taromycin A. Proc Natl Acad Sci U S A (2014) 1.78

Lyngbyatoxin biosynthesis: sequence of biosynthetic gene cluster and identification of a novel aromatic prenyltransferase. J Am Chem Soc (2004) 1.73

Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster. J Biol Chem (2007) 1.71

Moorea producens gen. nov., sp. nov. and Moorea bouillonii comb. nov., tropical marine cyanobacteria rich in bioactive secondary metabolites. Int J Syst Evol Microbiol (2011) 1.71

Marine natural products as novel antioxidant prototypes. J Nat Prod (2003) 1.70

Biosynthesis of the thiazole moiety of thiamin pyrophosphate (vitamin B1). Biochemistry (2003) 1.70

The identification and characterization of the marine natural product scytonemin as a novel antiproliferative pharmacophore. J Pharmacol Exp Ther (2002) 1.59

Molecular networking as a dereplication strategy. J Nat Prod (2013) 1.57

Interspecies interactions stimulate diversification of the Streptomyces coelicolor secreted metabolome. MBio (2013) 1.56

Codon randomization for rapid exploration of chemical space in thiopeptide antibiotic variants. Chem Biol (2012) 1.55

Microbial metabolic exchange--the chemotype-to-phenotype link. Nat Chem Biol (2011) 1.55

Metabolic coupling of dehydration and decarboxylation in the curacin A pathway: functional identification of a mechanistically diverse enzyme pair. J Am Chem Soc (2006) 1.55

Deconvolution and database search of complex tandem mass spectra of intact proteins: a combinatorial approach. Mol Cell Proteomics (2010) 1.53

Metabolic engineering of lipid catabolism increases microalgal lipid accumulation without compromising growth. Proc Natl Acad Sci U S A (2013) 1.51

Saccharomyces cerevisiae THI4p is a suicide thiamine thiazole synthase. Nature (2011) 1.50

Visualizing the spatial distribution of secondary metabolites produced by marine cyanobacteria and sponges via MALDI-TOF imaging. Mol Biosyst (2008) 1.47

Interkingdom metabolic transformations captured by microbial imaging mass spectrometry. Proc Natl Acad Sci U S A (2012) 1.46

The evolving field of imaging mass spectrometry and its impact on future biological research. J Mass Spectrom (2011) 1.43

Biologically active secondary metabolites from marine cyanobacteria. Curr Opin Biotechnol (2010) 1.42

Enzymatic synthesis of resorcylic acid lactones by cooperation of fungal iterative polyketide synthases involved in hypothemycin biosynthesis. J Am Chem Soc (2010) 1.41

Dereplication and de novo sequencing of nonribosomal peptides. Nat Methods (2009) 1.41

Reconstitution of a new cysteine biosynthetic pathway in Mycobacterium tuberculosis. J Am Chem Soc (2005) 1.40

Genomic insights into the physiology and ecology of the marine filamentous cyanobacterium Lyngbya majuscula. Proc Natl Acad Sci U S A (2011) 1.40

Crystal structures of dehydratase domains from the curacin polyketide biosynthetic pathway. Structure (2010) 1.39

Structure of oxalate decarboxylase from Bacillus subtilis at 1.75 A resolution. Biochemistry (2002) 1.39

Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteria. Org Lett (2005) 1.39

Interpretation of tandem mass spectra obtained from cyclic nonribosomal peptides. Anal Chem (2009) 1.37

Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp. J Am Chem Soc (2008) 1.36

GNAT-like strategy for polyketide chain initiation. Science (2007) 1.36

A phosphopantetheinylating polyketide synthase producing a linear polyene to initiate enediyne antitumor antibiotic biosynthesis. Proc Natl Acad Sci U S A (2008) 1.36

Structural and mechanistic studies on ThiO, a glycine oxidase essential for thiamin biosynthesis in Bacillus subtilis. Biochemistry (2003) 1.35

Polyketide decarboxylative chain termination preceded by o-sulfonation in curacin a biosynthesis. J Am Chem Soc (2009) 1.35

Top-down mass spectrometry on low-resolution instruments: characterization of phosphopantetheinylated carrier domains in polyketide and non-ribosomal biosynthetic pathways. Bioorg Med Chem Lett (2007) 1.33

Synergistic allelochemicals from a freshwater cyanobacterium. Proc Natl Acad Sci U S A (2010) 1.33

Expansion of the mycobacterial "PUPylome". Mol Biosyst (2009) 1.31

Bacterial biosynthesis and maturation of the didemnin anti-cancer agents. J Am Chem Soc (2012) 1.29

Apratoxin D, a potent cytotoxic cyclodepsipeptide from papua new guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida. J Nat Prod (2008) 1.29

Cloning and biochemical characterization of the hectochlorin biosynthetic gene cluster from the marine cyanobacterium Lyngbya majuscula. J Nat Prod (2007) 1.28

Organization, evolution, and expression analysis of the biosynthetic gene cluster for scytonemin, a cyanobacterial UV-absorbing pigment. Appl Environ Microbiol (2009) 1.28

Oxo-phytodienoic acid-containing galactolipids in Arabidopsis: jasmonate signaling dependence. Plant Physiol (2007) 1.27

Venturamides A and B: antimalarial constituents of the panamanian marine Cyanobacterium Oscillatoria sp. J Nat Prod (2007) 1.26

Marinopyrrole A target elucidation by acyl dye transfer. J Am Chem Soc (2009) 1.26

Clostridiolysin S, a post-translationally modified biotoxin from Clostridium botulinum. J Biol Chem (2010) 1.25

Characterization of the initial enzymatic steps of barbamide biosynthesis. J Nat Prod (2006) 1.25

Antimalarial peptides from marine cyanobacteria: isolation and structural elucidation of gallinamide A. J Nat Prod (2009) 1.25

Activity screening of carrier domains within nonribosomal peptide synthetases using complex substrate mixtures and large molecule mass spectrometry. Biochemistry (2006) 1.24

Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica. J Am Chem Soc (2009) 1.23

Evolved diversification of a modular natural product pathway: apratoxins F and G, two cytotoxic cyclic depsipeptides from a Palmyra collection of Lyngbya bouillonii. Chembiochem (2010) 1.22

Primer on agar-based microbial imaging mass spectrometry. J Bacteriol (2012) 1.22

New tricks from ancient algae: natural products biosynthesis in marine cyanobacteria. Curr Opin Chem Biol (2009) 1.22

Incorporation of nonmethyl branches by isoprenoid-like logic: multiple beta-alkylation events in the biosynthesis of myxovirescin A1. Chem Biol (2007) 1.21

Imaging mass spectrometry of natural products. Nat Prod Rep (2009) 1.20

The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J Nat Prod (2003) 1.20

The unique mechanistic transformations involved in the biosynthesis of modular natural products from marine cyanobacteria. Nat Prod Rep (2010) 1.19

Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly. J Nat Prod (2002) 1.19

Underestimated biodiversity as a major explanation for the perceived rich secondary metabolite capacity of the cyanobacterial genus Lyngbya. Environ Microbiol (2011) 1.18

Crystal structure of the ECH2 catalytic domain of CurF from Lyngbya majuscula. Insights into a decarboxylase involved in polyketide chain beta-branching. J Biol Chem (2007) 1.18

Acyltransferase mediated polyketide release from a fungal megasynthase. J Am Chem Soc (2009) 1.18

Antimalarial linear lipopeptides from a Panamanian strain of the marine cyanobacterium Lyngbya majuscula. J Nat Prod (2007) 1.17

Lyngbouilloside, a novel glycosidic macrolide from the marine cyanobacterium Lyngbya bouillonii. J Nat Prod (2002) 1.17

The Bacillus subtilis cannibalism toxin SDP collapses the proton motive force and induces autolysis. Mol Microbiol (2012) 1.17

Oxylipin profiling of the hypersensitive response in Arabidopsis thaliana. Formation of a novel oxo-phytodienoic acid-containing galactolipid, arabidopside E. J Biol Chem (2006) 1.16

Antileishmanial constituents of the Panamanian endophytic fungus Edenia sp. J Nat Prod (2008) 1.16

Palmyramide A, a cyclic depsipeptide from a Palmyra Atoll collection of the marine cyanobacterium Lyngbya majuscula. J Nat Prod (2010) 1.16