A <i>Photorhabdus</i> Natural Product Inhibits Insect Juvenile Hormone Epoxide Hydrolase

Nollmann, Friederike I.; Heinrich, Antje K.; Brachmann, Alexander O.; Morisseau, Christophe; Mukherjee, Krishnendu; Casanova-Torres, Ángel M.; Strobl, Frederic; Kleinhans, David; Kinski, Sebastian; Schultz, Katharina; Beeton, Michael L.; Kaiser, Marcel; Chu, Ya Yun; Ke, Long Phan; Thanwisai, Aunchalee; Bozhüyük, Kenan A. J.; Chantratita, Narisara; Götz, Friedrich; Waterfield, Nick; Vilcinskas, Andreas; Stelzer, Ernst H. K.; Goodrich-Blair, Heidi; Hammock, Bruce D.; Bode, Helge B.

doi:10.1002/cbic.201402650

Cited by 37 publications

(27 citation statements)

References 33 publications

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“…methyl isocyanate ( Figure S7). These resultss how that the chain length tolerance for the incorporation of AFAs is narrower than that for phenethylamides, which correlates well with previousf indings [18] showing the incorporation of C 9 to C 14 alkyl chains in phurealipids. Since in the presentw ork 10 a and 10 d were only detected in trace amounts, it can be concluded that the preferred chain length forA FAsi nt his case is C 9 or C 10 (9b and 9c), whichi si na ccordance with the main natural products if the azide group is regarded as being equivalent in size to an ethyl group rathert han ap ropyl group due to its greater rigidity.…”

Section: Carr Enrichment Of Azidof Atty Acids and Natural Products Desupporting

confidence: 92%

Solid‐Phase Enrichment and Analysis of Azide‐Labeled Natural Products: Fishing Downstream of Biochemical Pathways

Pérez

Wesche

Adihou

et al. 2015

Chemistry A European J

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Many methods have been devised over the decades to trace precursors of specific molecules in cellular environments as, for example, in biosynthesis studies. The advent of click chemistry has facilitated the powerful combination of tracing and at the same time sieving the highly complex metabolome for compounds derived from simple or complex starting materials, especially when the click reaction takes place on a solid support. While the principle of solid-phase click reactions has already been successfully applied for selective protein and peptide enrichment, the successful enrichment of much smaller primary and secondary metabolites, showing great structural diversity and undergoing many different biosynthetic steps, has seen only little development. For bacterial secondary metabolism, a far broader tolerance for "clickable" precursors was observed than in ribosomal proteinogenesis, thus making this method a surprisingly valuable tool for the tracking and discovery of compounds within the cellular biochemical network. The implementation of this method has led to the identification of several new compounds from the bacterial genera Photorhabdus and Xenorhabdus, clearly proving its power.

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Section: Carr Enrichment Of Azidof Atty Acids and Natural Products Desupporting

confidence: 92%

Solid‐Phase Enrichment and Analysis of Azide‐Labeled Natural Products: Fishing Downstream of Biochemical Pathways

Pérez

Wesche

Adihou

et al. 2015

Chemistry A European J

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“…In line with these findings, chemical analysis revealed that the amount of other known secondary metabolites [isopropylstilbene (IPS), GameXPeptides (GXP), photopyrones (PPY) and phurealipids (PL)] [13, 22, 23, 24] is not significantly affected when comparing the wild type with Δ antJ and the complemented strain Δ antJ + antJ + (Fig. S3A).…”

Section: Resultssupporting

confidence: 59%

“…The gene encoding AntJ ( plu4185 ) was deleted using pCKcipB [24], which is a derivative of pDS132 [44]. For the in frame deletion of antJ an upstream (926 bp) and a downstream fragment (788 bp) of antJ were amplified by PCR using primers AKHp06–AKHp09 introducing a PstI and a BamHI restriction site to the 5′end of the upstream fragment and the 3′end of the downstream fragment, respectively.…”

Section: Methodsmentioning

confidence: 99%

Heterogeneous regulation of bacterial natural product biosynthesis via a novel transcription factor

Heinrich

Glaeser

Tobias

et al. 2016

Heliyon

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Biological diversity arises among genetically equal subpopulations in the same environment, a phenomenon called phenotypic heterogeneity. The life cycle of the enteric bacterium Photorhabdus luminescens involves a symbiotic interaction with nematodes as well as a pathogenic association with insect larvae. P. luminescens exists in two distinct phenotypic forms designated as primary (1°) and secondary (2°). In contrast to 1° cells, 2° cells are non-pigmented due to the absence of natural compounds, especially anthraquinones (AQs). We identified a novel type of transcriptional regulator, AntJ, which activates expression of the antA-I operon responsible for AQ production. AntJ heterogeneously activates the AQ production in single P. luminescens 1° cells, and blocks AQ production in 2° cells. AntJ contains a proposed ligand-binding WYL-domain, which is widespread among bacteria. AntJ is one of the rare examples of regulators that mediate heterogeneous gene expression by altering activity rather than copy number in single cells.

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“…Upregulation of all PLs also could be seen in ΔluxS G in an additional analysis. PL biosynthesis also starts with fatty-acid-derived aldehydes (Nollmann et al, 2015). The role of spermidine in this process was concluded from reduced expression of several genes encoding proteins related to polyamine metabolism.…”

Section: Discussionmentioning

confidence: 99%

“…10 ml LB medium with or without 2% of Amberlite® XAD-16 (Sigma-Aldrich) (XAD) were inoculated with a starting OD 600 = 0.1 using an overnight culture. After 72 h of cultivation at 30°C either XAD or ethyl acetate (EE) culture extracts were prepared as described before (Nollmann et al, 2015;Heinrich et al, 2016) HPLC-UV/MS analysis was done as previously stated (Reimer et al, 2011). 5 µl of each sample was separated on a C 18 -UHPLC column (Acquity UPLC BEH C18 1.7 lmRP 2.1 x 50 mm (Waters)) with a C 18 -pre-column (Acquity UPLC BEH C18 1.7 lmRP 2.1 x 5 mm (Waters)) using a H 2 O in acetonitrile (ACN) gradient.…”

Section: Np Quantificationmentioning

confidence: 99%

Peer Review #2 of "LuxS-dependent AI-2 production is not involved in global regulation of natural product biosynthesis in Photorhabdus and Xenorhabdus (v0.1)"

2017

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The Gram-negative bacteria Photorhabdus and Xenorhabdus are known to produce a variety of different natural products (NP). These compounds play different roles since the bacteria live in symbiosis with nematodes and are pathogenic to insect larvae in the soil. Thus, a fine tuned regulatory system controlling NP biosynthesis is indispensable. Global regulators such as Hfq, Lrp, LeuO and HexA have been shown to influence NP production of Photorhabdus and Xenorhabdus. Additionally, photopyrones as quorum sensing (QS) signals were demonstrated to be involved in the regulation of NP production in Photorhabdus. In this study, we investigated the role of another possible QS signal, autoinducer 2 (AI-2), in regulation of NP production. The AI-2 synthase (LuxS) is widely distributed within the bacterial kingdom and has a dual role as a part of the activated methyl cycle pathway, as well as being responsible for AI-2 precursor production. We deleted luxS in three different entomopathogenic bacteria and compared NP levels in the mutant strains to the wild type (WT) but observed no difference to the WT strains. Furthermore, the absence of the small regulatory RNA micA, which is encoded directly upstream of luxS, did not influence NP levels. Phenotypic differences between the P. luminescens luxS deletion mutant and an earlier described luxS deficient strain of P. luminescens suggested that two phenotypically different strains have evolved in different laboratories.

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A Photorhabdus Natural Product Inhibits Insect Juvenile Hormone Epoxide Hydrolase

Cited by 37 publications

References 33 publications

Solid‐Phase Enrichment and Analysis of Azide‐Labeled Natural Products: Fishing Downstream of Biochemical Pathways

Solid‐Phase Enrichment and Analysis of Azide‐Labeled Natural Products: Fishing Downstream of Biochemical Pathways

Heterogeneous regulation of bacterial natural product biosynthesis via a novel transcription factor

Peer Review #2 of "LuxS-dependent AI-2 production is not involved in global regulation of natural product biosynthesis in Photorhabdus and Xenorhabdus (v0.1)"

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