On the origin of the branched alkyl substituents on ring B of flexirubin-type pigments

Achenbach, Hans; Böttger-Vetter, Angelika; Fautz, Erich; Reichenbach, Hans

doi:10.1007/bf00407958

Cited by 12 publications

(6 citation statements)

References 12 publications

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“…BH72 and has a xanthomonadin‐like APE that is esterified with a DAR . The third is flexirubin ( 4 ), an APE‐DAR hybrid with tyrosine as precursor for the APE, and its derivatives differ in their degree of methylation and chlorination, polyene chain length and the DAR alkyl chains …”

Section: Introductionmentioning

confidence: 57%

“…[9] The third is flexirubin (4), an APE-DAR hybrid with tyrosine as precursor for the APE, [10] and its derivatives differ in their degree of methylation and chlorination, polyene chain length and the DAR alkyl chains. [11] During previous work on flexirubin and arcuflavin biosynthesis, [9,10] we found that both gene clusters encode ac onserved set of enzymes and that the APE gene clusters can be found in severald ifferent proteobacteria, bacteria from the phylum Bacteroidetes and in one strain from the Spirochaetes. This wasf ollowed by the discoveryo fafourth class of APEs, which was recently found during the development of the gene cluster finder algorithm "ClusterFinder".…”

Section: Introductionmentioning

confidence: 89%

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Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids

et al. 2016

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Bacterial pigments of the aryl polyene type are structurally similar to the well-known carotenoids with respect to their polyene systems. Their biosynthetic gene cluster is widespread in taxonomically distant bacteria, and four classes of such pigments have been found. Here we report the structure elucidation of the aryl polyene/dialkylresorcinol hybrid pigments of Variovorax paradoxus B4 by HPLC-UV-MS, MALDI-MS and NMR. Furthermore, we show for the first time that this pigment class protects the bacterium from reactive oxygen species, similarly to what is known for carotenoids. An analysis of the distribution of biosynthetic genes for aryl polyenes and carotenoids in bacterial genomes is presented; it shows a complementary distribution of these protective pigments in bacteria.

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Section: Introductionmentioning

confidence: 57%

Section: Introductionmentioning

confidence: 89%

Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids

et al. 2016

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“…Their conserved structural feature is a ω-(4-hydroxyphenyl)-polyene carboxylic acid chromophore, esterified with a 2,5-dialkylresorcinol (DAR). Known derivatives differ in methylation and/or chlorination pattern at the polyene ring and the chain lengths of the DAR alkyl chains as well as the polyene chain length (Achenbach et al ., 1982 ). Feeding experiments with radioactive precursors combined with chemical degradation showed that tyrosine is the precursor of the polyene ring and that its methyl group is derived from methionine (Achenbach et al ., 1979 ).…”

Section: Introductionmentioning

confidence: 99%

Initiation of the flexirubin biosynthesis in Chitinophaga pinensis

Schöner

Fuchs

Schönau

et al. 2014

Microbial Biotechnology

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Bacteria from the Bacteroidetes phylum are known producers of the chemotaxonomic relevant flexirubins. These orange pigments comprise a non-isoprenoid aryl-polyene carboxylic acid esterified with a dialkylresorcinol. Herein, we report a gene cluster from Chitinophaga pinensis encoding the biosynthesis of the polyene moiety and the biochemical characterization of a tyrosine ammonia-lyase and a 4-coumarate-CoA ligase responsible for the initiation of the polyene biosynthesis. Additionally, the flexirubin of C. pinensis was characterized by a combination of feeding experiments, high-performance liquid chromatography tandem mass spectrometry and matrix-assisted laser desorption/ionization mass spectrometry.

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“…The major structural variations in the flexirubins are due to the alkyl substituents of this DAR moiety, which sometimes have terminally branched alkyl chains (1,4). The flexirubins are characteristic taxonomic markers for certain Cytophaga, Flexibacter, and Flavobacterium species (5,43,44).…”

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confidence: 99%

“…Achenbach et al initially described incorporation of radiolabeled acetate into the DAR moiety and speculated about the possibility that orsellinic acid is a DAR precursor (2). Sankawa et al subsequently demonstrated incorporation of [1,[2][3][4][5][6][7][8][9][10][11][12][13] C 2 ]acetate into HPR and, based on the observed labeling pattern, proposed that HPR arises by an unusual head-to-head condensation of two polyketide chains (45). Shortly thereafter, Achenbach et al.…”

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confidence: 99%

2,5-Dialkylresorcinol Biosynthesis in Pseudomonas aurantiaca : Novel Head-to-Head Condensation of Two Fatty Acid-Derived Precursors

et al. 2003

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2-Hexyl-5-propylresorcinol is the predominant analog of several dialkylresorcinols produced by Pseudomonas aurantiaca (Pseudomonas fluorescens BL915). We isolated and characterized three biosynthetic genes that encode an acyl carrier protein, a ␤-ketoacyl-acyl carrier protein synthase III, and a protein of unknown function, all of which collectively allow heterologous production of 2-hexyl-5-propylresorcinol in Escherichia coli. Two regulatory genes exhibiting similarity to members of the AraC family of transcriptional regulators are also present in the identified gene cluster. Based on the deduced functions of the proteins encoded by the gene cluster and the observed incorporation of labeled carbons from octanoic acid into 2-hexyl-5-propylresorcinol, we propose that dialkylresorcinols are derived from medium-chain-length fatty acids by an unusual head-tohead condensation of ␤-ketoacyl thioester intermediates. Genomic evidence suggests that there is a similar pathway for the biosynthesis of the flexirubin-type pigments in certain bacteria belonging to the order Cytophagales.

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On the origin of the branched alkyl substituents on ring B of flexirubin-type pigments

Cited by 12 publications

References 12 publications

Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids

Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids

Initiation of the flexirubin biosynthesis in Chitinophaga pinensis

2,5-Dialkylresorcinol Biosynthesis in Pseudomonas aurantiaca : Novel Head-to-Head Condensation of Two Fatty Acid-Derived Precursors

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