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Roles of Indole As an Interspecies and Interkingdom Signaling Molecule Jin-Hyung Lee,1 Thomas K

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Roles of Indole As an Interspecies and Interkingdom Signaling Molecule Jin-Hyung Lee,1 Thomas K TIMI 1232 No. of Pages 12 Review Roles of Indole as an Interspecies and Interkingdom Signaling Molecule Jin-Hyung Lee,1 Thomas K. Wood,2 and Jintae Lee1,* A number of bacteria, and some plants, produce large quantities of indole, Trends which is widespread in animal intestinal tracts and in the rhizosphere. Indole, as A variety of bacteria, and some plants, an interspecies and interkingdom signaling molecule, plays important roles in produce large quantities of indole, and bacterial pathogenesis and eukaryotic immunity. Furthermore, indole and its thus, indole and its derivatives are widespread in prokaryotic and eukar- derivatives are viewed as potential antivirulence compounds against antibiotic- yotic communities. Recently, indole resistant pathogens because of their ability to inhibit quorum sensing and was shown to be an intercellular, inter- fl species, and interkingdom signaling virulence factor production. Indole modulates oxidative stress, intestinal in am- molecule. mation, and hormone secretion in animals, and it controls plant defense sys- tems and growth. Insects and nematodes can recognize indole, which controls Indole and its derivatives can suppress the bacterial pathogenesis of several some of their behavior. This review presents current knowledge regarding indole antibiotic-resistant pathogens by inhi- and its derivatives, their biotechnological applications and their role in prokary- biting quorum sensing and virulence otic and eukaryotic systems. factor production. Insects sense indole, which controls Intercellular, Interspecies, and Interkingdom Signaling by Indole and Its their behavior. Furthermore, indole Derivatives controls plant defense systems and Bacteria and eukaryotes coexist in the natural environment, and bacterial metabolites modulate growth, and modulates oxidative eukaryotic immunity. The commensal bacteria colonize the surfaces of animal and plant cells and stress, intestinal inflammation, and hor- mone secretion in animals. Emerging prevent invasion by pathogenic bacteria [1]. In fact, an imbalance between commensal (or data suggest that indoles may influ- symbiotic) and pathogenic bacteria can result in life-threatening infections. Bacteria produce a ence human diseases, such as inflam- wide variety of signaling molecules, siderophores, and antibiotics. Other organisms can sense matory, neurological, and metabolic these signaling molecules, which synchronize multicellular behaviors, such as virulence, biofilm diseases. formation, and antibiotic resistance. Also, bacterial signaling molecules can be manipulated and utilized by animal and plant cells [2]. Indole is synthesized from tryptophan by tryptophanase (TnaA) in a large number of Gram- positive and Gram-negative bacterial species (Figure 1). Extracellular indole concentrations in liquid cultures of Escherichia coli and Vibrio cholerae can reach 0.5 mM [3,4], and indole concentrations of up to 1.1 mM are produced by indole-producing bacteria in the mouse, rat, and human gut [5,6]. Indole is a well-known signaling molecule that modulates spore formation by Gram-positive strains [7,8]; plasmid stability [9], cell division [10], antibiotic toler- ance [11,12], and virulence [13,14] in E. coli; and biofilm formation by E. coli [3,15] and V. cholerae [4]. As an interspecies signaling molecule, indole has recently shown diverse roles in 1School of Chemical Engineering, various non-indole-producing bacteria (Table 1). Yeungnam University, Gyeongsan, 712-749, Republic of Korea 2Department of Chemical Engineering, Several plants, including maize, are able to produce indole using indole-3-glycerol phosphate Pennsylvania State University, lyases [16] (Figure 1). Furthermore, maize releases volatile compounds, including indole, in University Park, PA 16802-4400, USA response to herbivore attack [17,18]. In contrast, animals cannot synthesize indole but can fl sense indole using their olfactory systems [19,20]. Insects, such as mosquitoes and butter ies, *Correspondence:.[4_TD$IF][email protected] sense indole, which then controls some of their behavior [21,22]. More recently, several studies (J. Lee) Trends in Microbiology, August 2015, Vol xx. No. x http://dx.doi.org/10.1016/j.tim.2015.08.001 1 © 2015 Elsevier Ltd. All rights reserved. TIMI 1232 No. of Pages 12 Animals Animals O NH NH OH O 2 OH O O S O OH HO O O N N N N N N H H H H H H Serotonin Melatonin Indole-3-propionic acid Indoxyl sulfate Isan Hydroxyindoles Oxygenases or P450 family O OH HO Indigoids Tryptophanase Oxygenases or NH Metabolism 2 Indole-producing N N bacteria H H N Indole Hydroxyindoles H OH L-tryptophan CN O Indole-3-glycerol Indole-metabolizing phosphate lyase bacteria N N H H Indole-3-acetonitrile Indole-3-acec acid O Plants Plants OH OH CN OH O N N N N N H H H H H Indole Indole-3-acec acid Indole-3-acetonitrile Indole-3-carbinol Indole-3-butyric acid Figure 1. Biosynthesis of Indole and Its Derivatives in Prokaryotes and Eukaryotes. Indole is produced from amino acid L-tryptophan by tryptophanase (TnaA) in various indole-producing bacteria. Some plants, including maize, synthesize indole using indole-3-glycerol phosphate lyases, but animal cells cannot synthesize indole. Indole can be oxidized to hydroxyindoles by diverse oxygenases produced by non-indole-producing bacteria or eukaryotes. Hence, indole and its derivatives are widespread in prokaryotic and eukaryotic systems. In addition, hormone tryptophan- derivatives, such as serotonin, melatonin, indole-3-acetic acid, indole-3-acetonitrile, indole-3-carbinol, and indole-3-butyric acid, possess a core indole moiety. have suggested that indole may have several beneficial effects on human health by influencing oxidative stresses [23], intestinal inflammation [5,24], and hormone secretion [25]. Indole is stable in indole-producing bacteria, but many non-indole-producing bacteria and eukaryotes can modify or degrade indole using diverse oxygenases, such as monooxygenases, dioxygenases, and P450 family members [23,26]. Hence, indole derivatives are widely present in prokaryotic and eukaryotic communities (Figure 1). However, little is known of the biological role, metabolism, or mechanisms of action of indole derivatives. A small number of reviews have summarized the biological roles of indole, mostly in indole- producing bacteria [27,28], or the approaches used to synthesize indole-based small molecules [29,30]. In this review, we discuss current knowledge of indole and its derivatives in indole- producing bacteria, in non-indole-producing pathogenic bacteria, and in eukaryotic systems (such as animals, plants, insects, and nematodes); potential biotechnological applications of indoles are also discussed. Functions and Applications of Indole and Its Derivatives in Indole-Producing Bacteria Indole biosynthesis and its regulation were well studied during the last century, and its biological functions have been extensively investigated during the last decade, mostly in indole-producing bacteria [3,27]. Indole is considered by some authors to be an intercellular signaling molecule, 2 Trends in Microbiology, August 2015, Vol xx. No. x TIMI 1232 No. of Pages 12 Table 1. Roles of Indole and Its Derivatives in Non-Indole-Producing Microorganisms Bacteria Indole Compound Phenotypic Change Mechanism Refs Acinetobacter baumannii, Indole-derived flustramine, Inhibition of biofilm Unknown [46] Staphylococcus aureus pyrroloindoline triazole formation amides Acinetobacter oleivorans Indole Inhibition of biofilm Inhibition of QSa [54] formation and regulator folding motility Agrobacterium tumefaciens Indole Increase of biofilm Change of [65] formation and biofilm-, stress-,[3_TD$IF] antibiotic tolerance and efflux- related genes Bdellovibrio bacteriovorus Indole Reduction of Downregulation of [60] predation flagellar and ribosome assembly genes Burkholderia unamae Indole and gallic acid Induction of biofilm Unknown [59] formation Candida albicans Indole and Reduction of biofilm Stimulation of [56] 3-indolylacetonitrile formation and transcriptional virulence factor Chromobacterium Indole Inhibition of QS- QS inhibition [55] violaceum, Pseudomonas regulated chlororaphis, pigmentation Serratia marcescens Cyanobacterial Indole Inhibition of Formation of [58] microsystis aeruginosa cyanobacterial periphyton blooms biofilms Cylindrotheca sp. Indole and its derivatives Inhibition of growth Induction of [66] and biofilm formation cellular Ca2+ efflux Pseudomonas putida Indole Increase of Activation of [64] antibiotic tolerance efflux pump Pseudomonas aeruginosa Indole, 3-indolylacetonitrile, Inhibition of QS inhibition [42,48, 7-fluoroindole, indole- virulence factor 51–53,69] based N-acylated production L-homoserine lactones Pseudomonas aeruginosa Indole, 7-hydroxyindole Increase of Activation of [48,53] antibiotic tolerance efflux pump Pseudomonas aeruginosa 2-Aminobenzimidazoles Inhibition of biofilm Partly by QS [68] formation inhibition Salmonella enterica Indole Increase of Oxidative stress [61] serovar Typhimurium antibiotic tolerance response Salmonella enterica Indole Increase of Activation of [62,63] serovar Typhimurium antibiotic tolerance efflux pump and decrease of and suppression motility of flagellar genes Staphylococcus aureus Indole and Attenuation of Reduction of [57] 7-benzyloxyindole virulence staphyloxanthin and hemolysin Staphylococcus aureus Desformylflustrabromine Inhibition of biofilm Unknown [45] formation aQS, quorum sensing. Trends in Microbiology, August 2015, Vol xx. No. x 3 TIMI 1232 No. of Pages 12 like a quorum-sensing (QS) signal [11,12,31],
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