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Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72

Publication Date: March 11, 2014
Journal: PLOS ONE
Authors: Tim A. Schöner, Sebastian W. Fuchs, Barbara Reinhold Hurek & Helge B. Bode
Volume: 9
Issue: 3
Pages: e90922
DOI: https://dx.plos.org/10.1371/journal.pone.0090922
Publisher URL: http://journals.plos.org/plosone/article?id=10.1371%2Fjournal.pone.0090922
PubMed: http://www.ncbi.nlm.nih.gov/pubmed/24618669
PubMed Central: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3949708
Europe PMC: http://europepmc.org/abstract/MED/24618669
Web of Science: 000332842400036
Scopus: 84897506148
Mendeley: http://www.mendeley.com/research/identification-biosynthesis-novel-xanthomonadindialkylresorcinol-hybrid-azoarcus-sp-bh72

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{"title"=>"Identification and biosynthesis of a novel xanthomonadin-dialkylresorcinol- hybrid from Azoarcus sp. BH72", "type"=>"journal", "authors"=>[{"first_name"=>"Tim A.", "last_name"=>"Schöner", "scopus_author_id"=>"56096797900"}, {"first_name"=>"Sebastian W.", "last_name"=>"Fuchs", "scopus_author_id"=>"56669314400"}, {"first_name"=>"Barbara", "last_name"=>"Reinhold-Hurek", "scopus_author_id"=>"7004360449"}, {"first_name"=>"Helge B.", "last_name"=>"Bode", "scopus_author_id"=>"7103361368"}], "year"=>2014, "source"=>"PLoS ONE", "identifiers"=>{"issn"=>"19326203", "pui"=>"372764628", "doi"=>"10.1371/journal.pone.0090922", "sgr"=>"84897506148", "scopus"=>"2-s2.0-84897506148", "pmid"=>"24618669"}, "id"=>"b945eba1-cabf-31ea-8f50-8708fce2af6e", "abstract"=>"A novel xanthomonadin-dialkylresorcinol hybrid named arcuflavin was identified in Azoarcus sp. BH72 by a combination of feeding experiments, HPLC-MS and MALDI-MS and gene clusters encoding the biosynthesis of this non-isoprenoid aryl-polyene containing pigment are reported. A chorismate-utilizing enzyme from the XanB2-type producing 3- and 4-hydroxybenzoic acid and an AMP-ligase encoded by these gene clusters were characterized, that might perform the first two steps of the polyene biosynthesis. Furthermore, a detailed analysis of the already known or novel biosynthesis gene clusters involved in the biosynthesis of polyene containing pigments like arcuflavin, flexirubin and xanthomonadin revealed the presence of similar gene clusters in a wide range of bacterial taxa, suggesting that polyene and polyene-dialkylresorcinol pigments are more widespread than previously realized.", "link"=>"http://www.mendeley.com/research/identification-biosynthesis-novel-xanthomonadindialkylresorcinol-hybrid-azoarcus-sp-bh72", "reader_count"=>15, "reader_count_by_academic_status"=>{"Researcher"=>3, "Student > Ph. D. Student"=>7, "Student > Postgraduate"=>1, "Student > Master"=>3, "Unspecified"=>1}, "reader_count_by_user_role"=>{"Researcher"=>3, "Student > Ph. D. Student"=>7, "Student > Postgraduate"=>1, "Student > Master"=>3, "Unspecified"=>1}, "reader_count_by_subject_area"=>{"Biochemistry, Genetics and Molecular Biology"=>3, "Agricultural and Biological Sciences"=>8, "Chemistry"=>2, "Computer Science"=>1, "Immunology and Microbiology"=>1}, "reader_count_by_subdiscipline"=>{"Chemistry"=>{"Chemistry"=>2}, "Immunology and Microbiology"=>{"Immunology and Microbiology"=>1}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>8}, "Computer Science"=>{"Computer Science"=>1}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>3}}, "reader_count_by_country"=>{"China"=>1, "Denmark"=>1}, "group_count"=>1}

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Figshare 26303 Mar 06:25 UTC

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{"files"=>["https://ndownloader.figshare.com/files/1415446"], "description"=>"Annotation colors follow the Azoarcus gene clusters and genes are connected by grey lines if their identity was ≥40% in a BLAST-P analysis. All genes are scaled to the depicted size and are listed in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922.s001\" target=\"_blank\">Table S1</a>, <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922.s002\" target=\"_blank\">S2</a>, <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922.s003\" target=\"_blank\">S3</a>, <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922.s004\" target=\"_blank\">S4</a>.", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "clusters", "xanthomonadin", "xanthomonadin-like", "compounds", "bh72", "campestris", "pv", "atcc", "33913", "rcb", "s110", "es-1"], "article_id"=>958267, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0090922.g002", "stats"=>{"downloads"=>2, "page_views"=>96, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Known_and_proposed_gene_clusters_involved_in_biosynthesis_of_DARs_xanthomonadin_and_xanthomonadin_like_compounds_in_Azoarcus_sp_BH72_A_Xanthomonas_campestris_pv_campestris_ATCC_33913_B_Dechloromonas_aromatica_RCB_C_Variovorax_paradoxus_S110_D_and_Siderox/958267", "title"=>"Known and proposed gene clusters involved in biosynthesis of DARs, xanthomonadin and xanthomonadin-like compounds in Azoarcus sp. BH72 (A), Xanthomonas campestris pv campestris ATCC 33913 (B), Dechloromonas aromatica RCB (C) Variovorax paradoxus S110 (D) and Sideroxydans lithotrophicus ES-1 (E).", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-11 03:23:19"}
{"files"=>["https://ndownloader.figshare.com/files/1415448"], "description"=>"A: MALDI-orbitrap mass spectra of wildtype 8 (I) and from labeling experiments with d3-methionine (II) and 4-Fluoro-3-hydroxybenzoic acid (4F-3HBA) (III). B: MALDI-iontrap-MS2 of 8. MALDI-iontrap-MS3 of m/z 293.3 (C) and m/z 317.2 (D) with m/z 608.4 [M]+• as precursor.", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "spectra"], "article_id"=>958269, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0090922.g004", "stats"=>{"downloads"=>0, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Mass_spectra_of_8_from_Azoarcus_sp_BH72_/958269", "title"=>"Mass spectra of 8 from Azoarcus sp. BH72.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-11 03:23:19"}
{"files"=>["https://ndownloader.figshare.com/files/1415447"], "description"=>"HPLC-UV analysis of wildtype (I), BH0260 (II) and BH3911 extracts with traces showing absorption at 420 nm (solid line) or 310 nm (dotted line). All chromatograms were drawn to the same scale.", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "bh72", "mutant"], "article_id"=>958268, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0090922.g003", "stats"=>{"downloads"=>0, "page_views"=>13, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_HPLC_analysis_of_Azoarcus_sp_BH72_wild_type_and_mutant_strains_/958268", "title"=>"HPLC analysis of Azoarcus sp. BH72 wild type and mutant strains.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-11 03:23:19"}
{"files"=>["https://ndownloader.figshare.com/files/1415444"], "description"=>"Natural occurring DARs (1–4) <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922-Kanda1\" target=\"_blank\">[2]</a>–<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922-Imai1\" target=\"_blank\">[6]</a>, polyene containing pigments like flexirubin (5) from Chitinophaga filiformes<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922-Achenbach2\" target=\"_blank\">[8]</a> or xanthomonadin I (6) <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922-Andrewes1\" target=\"_blank\">[9]</a>, DAR (7) heterologously produced with Azoarcus DAR proteins <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0090922#pone.0090922-Fuchs1\" target=\"_blank\">[1]</a> and the proposed structure of the DAR-xanthomonadin hybrid pigment named arcuflavin (8) from Azoarcus sp. BH72 identified in this study.", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "occurring", "dars", "polyene", "containing", "pigments", "flexirubin", "xanthomonadin", "dar", "heterologously", "produced", "proteins", "dar-xanthomonadin", "hybrid", "pigment", "named", "arcuflavin", "bh72"], "article_id"=>958265, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0090922.g001", "stats"=>{"downloads"=>2, "page_views"=>94, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Natural_occurring_DARs_1_4_2_6_polyene_containing_pigments_like_flexirubin_5_from_Chitinophaga_filiformes_8_or_xanthomonadin_I_6_9_DAR_7_heterologously_produced_with_Azoarcus_DAR_proteins_1_and_the_proposed_structure_of_the_DAR_xanthomonadin_hybrid_pigme/958265", "title"=>"Natural occurring DARs (1–4) [2]–[6], polyene containing pigments like flexirubin (5) from Chitinophaga filiformes[8] or xanthomonadin I (6) [9], DAR (7) heterologously produced with Azoarcus DAR proteins [1] and the proposed structure of the DAR-xanthomonadin hybrid pigment named arcuflavin (8) from Azoarcus sp. BH72 identified in this study.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2014-03-11 03:23:19"}
{"files"=>["https://ndownloader.figshare.com/files/1415470", "https://ndownloader.figshare.com/files/1415471", "https://ndownloader.figshare.com/files/1415472", "https://ndownloader.figshare.com/files/1415473", "https://ndownloader.figshare.com/files/1415474", "https://ndownloader.figshare.com/files/1415475", "https://ndownloader.figshare.com/files/1415476", "https://ndownloader.figshare.com/files/1415477", "https://ndownloader.figshare.com/files/1415478", "https://ndownloader.figshare.com/files/1415479", "https://ndownloader.figshare.com/files/1415480", "https://ndownloader.figshare.com/files/1415481"], "description"=>"<div>A novel xanthomonadin-dialkylresorcinol hybrid named arcuflavin was identified in Azoarcus sp. BH72 by a combination of feeding experiments, HPLC-MS and MALDI-MS and gene clusters encoding the biosynthesis of this non-isoprenoid aryl-polyene containing pigment are reported. A chorismate-utilizing enzyme from the XanB2-type producing 3- and 4-hydroxybenzoic acid and an AMP-ligase encoded by these gene clusters were characterized, that might perform the first two steps of the polyene biosynthesis. Furthermore, a detailed analysis of the already known or novel biosynthesis gene clusters involved in the biosynthesis of polyene containing pigments like arcuflavin, flexirubin and xanthomonadin revealed the presence of similar gene clusters in a wide range of bacterial taxa, suggesting that polyene and polyene-dialkylresorcinol pigments are more widespread than previously realized.</div>", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "xanthomonadin-dialkylresorcinol-hybrid", "bh72"], "article_id"=>958291, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0090922.s001", "https://dx.doi.org/10.1371/journal.pone.0090922.s002", "https://dx.doi.org/10.1371/journal.pone.0090922.s003", "https://dx.doi.org/10.1371/journal.pone.0090922.s004", "https://dx.doi.org/10.1371/journal.pone.0090922.s005", "https://dx.doi.org/10.1371/journal.pone.0090922.s006", "https://dx.doi.org/10.1371/journal.pone.0090922.s007", "https://dx.doi.org/10.1371/journal.pone.0090922.s008", "https://dx.doi.org/10.1371/journal.pone.0090922.s009", "https://dx.doi.org/10.1371/journal.pone.0090922.s010", "https://dx.doi.org/10.1371/journal.pone.0090922.s011", "https://dx.doi.org/10.1371/journal.pone.0090922.s012"], "stats"=>{"downloads"=>1, "page_views"=>12, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Identification_and_Biosynthesis_of_a_Novel_Xanthomonadin_Dialkylresorcinol_Hybrid_from_Azoarcus_sp_BH72/958291", "title"=>"Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2014-03-11 03:23:19"}
{"files"=>["https://ndownloader.figshare.com/files/1415450"], "description"=>"Predicted gene clusters for arcuflavin biosynthesis in Azoarcus sp. BH72. Domain guided annotation is based on conserved domains detected by BLAST-P.", "links"=>[], "tags"=>["Biochemistry", "lipids", "Lipid structure", "neutral lipids", "metabolism", "biosynthesis", "Lipid metabolism", "Small molecules", "microbiology", "Bacterial pathogens", "Gram negative", "Host-pathogen interaction", "microbial ecology", "Microbial physiology", "Analytical chemistry", "organic chemistry", "Organic compounds", "clusters", "arcuflavin", "guided", "annotation", "conserved", "domains"], "article_id"=>958271, "categories"=>["Biological Sciences", "Chemistry"], "users"=>["Tim A. Schöner", "Sebastian W. Fuchs", "Barbara Reinhold-Hurek", "Helge B. Bode"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0090922.t001", "stats"=>{"downloads"=>2, "page_views"=>26, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Predicted_gene_clusters_for_arcuflavin_biosynthesis_in_Azoarcus_sp_BH72_Domain_guided_annotation_is_based_on_conserved_domains_detected_by_BLAST_P_/958271", "title"=>"Predicted gene clusters for arcuflavin biosynthesis in Azoarcus sp. BH72. Domain guided annotation is based on conserved domains detected by BLAST-P.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2014-03-11 03:23:19"}

PMC Usage Stats 94717 Mar 18:08 UTC

PMC Usage Stats | Further Information

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Relative Metric 189806 Apr 02:11 UTC

Relative Metric

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F1000Prime07 Apr 11:43 UTC

F1000Prime

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