Pyrazines from bacteria and ants: convergent chemistry within an ecological niche

Silva-Junior, Eduardo A.; Ruzzini, Antonio C.; Paludo, Camila Raquel; Nascimento, Fábio Santos do; Currie, Cameron R.; Clardy, Jon; Pupo, Mônica Tallarico

doi:10.1038/s41598-018-20953-6

Cited by 59 publications

(73 citation statements)

References 42 publications

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“…Serratia marcescens isolated from Atta sexdens rubropilosa colonies produce volatile pyrazines, including 2,5-dimethylpyrazine (1) and 3-ethyl-2,5-dimethylpyrazine (2) (▶ Fig. 2), that are components of antsʼ trail pheromone [38]. However, the dependence of ants on the microbial biosynthesis of trail pheromones remains to be elucidated.…”

Section: Natural Products Mediating Microbial Symbiosis Fungus-farminmentioning

confidence: 99%

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Chemical Ecology in Insect-microbe Interactions in the Neotropics

2020

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Small molecules frequently mediate symbiotic interactions between microorganisms and their hosts. Brazil harbors the highest diversity of insects in the world; however, just recently, efforts have been directed to deciphering the chemical signals involved in the symbioses of microorganisms and social insects. The current scenario of natural products research guided by chemical ecology is discussed in this review. Two groups of social insects have been prioritized in the studies, fungus-farming ants and stingless bees, leading to the identification of natural products involved in defensive and nutritional symbioses. Some of the compounds also present potential pharmaceutical applications as antimicrobials, and this is likely related to their ecological roles. Microbial symbioses in termites and wasps are suggested promising sources of biologically active small molecules. Aspects related to public policies for insect biodiversity preservation are also highlighted.

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Section: Natural Products Mediating Microbial Symbiosis Fungus-farminmentioning

confidence: 99%

“…ICBG1323 and anthracyclines from Micromonospora sp. ICBG132 (29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39), including the rare quinocyclines 29-34 and the novel compound 39 (▶ Fig. 3).…”

Section: Natural Products Mediating Microbial Symbiosis In Stingless mentioning

confidence: 99%

Chemical Ecology in Insect-microbe Interactions in the Neotropics

2020

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“…In A. sexdens var. rubropilosa (Hymenoptera, Formicidae), Serratia marcences, a common endosymbiotic strain in insects, is involved in pyrazines biosynthesis starting from L-threonine as a precursor [37]. In addition to bacteria, yeast species also contribute to semiochemical communication in Hymenoptera.…”

Section: Bacteria and Eusocial Insect Communicationmentioning

confidence: 99%

“…Specifically, Serratia oderifera, Serratia ficaria, and Serratia rubidea synthesize the alkylated pyrazines 3-isopropyl-2-methoxy-5-methylpyrazine, 3-isopropyl-2-methoxy-methylpyrazine, and 3-isobutyl-methoxy-pyrazine) [129]. A recent study demonstrated that L-trenonine and acetic acid are the precursors for 2,5-dimethylpyrazine and 3-ethyl-2,5-dimethylpyrazine synthesis in Serratia marcescens [37]. Radiolabeled precursors were used in this study and their incorporation into the final compounds was shown, leading to the proposed pathway illustrated in Figure 4.…”

Section: Pyrazine Metabolism In Bacteriamentioning

confidence: 99%

Bacterial Semiochemicals and Transkingdom Interactions with Insects and Plants

Calcagnile

Tredici

Talà

et al. 2019

Insects

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A peculiar feature of all living beings is their capability to communicate. With the discovery of the quorum sensing phenomenon in bioluminescent bacteria in the late 1960s, it became clear that intraspecies and interspecies communications and social behaviors also occur in simple microorganisms such as bacteria. However, at that time, it was difficult to imagine how such small organisms—invisible to the naked eye—could influence the behavior and wellbeing of the larger, more complex and visible organisms they colonize. Now that we know this information, the challenge is to identify the myriad of bacterial chemical signals and communication networks that regulate the life of what can be defined, in a whole, as a meta-organism. In this review, we described the transkingdom crosstalk between bacteria, insects, and plants from an ecological perspective, providing some paradigmatic examples. Second, we reviewed what is known about the genetic and biochemical bases of the bacterial chemical communication with other organisms and how explore the semiochemical potential of a bacterium can be explored. Finally, we illustrated how bacterial semiochemicals managing the transkingdom communication may be exploited from a biotechnological point of view.

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“…Corynebacterium glutamicum synthesizes alkyl pyrazines via acyloins, which are intermediates of branched‐chain amino acid biogenesis . Reports indicate that Serratia and Vibrio threonine dehydrogenases convert threonine into aminoacetone, which is another intermediate of pyrazine synthesis that can condense with itself or with alanine to yield alkyl pyrazines that function as ant pheromones and bacterial autoinducers . However, the enzymes that generate their pyrazine rings remain elusive and an enzymatic mechanism alone cannot explain the biogenesis of pyrazines from amino acids other than threonine, in which the β‐hydroxy residue is oxidized to the carbonyl moiety of aminoketone required for dimerization to form pyrazines (Figure S1).…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Cascade in Pseudomonas that Produces Pyrazine from α‐Amino Acids

et al. 2019

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Pyrazines are widespread chemical compounds that include pheromones and odors. Herein, a novel mechanism used by Pseudomonas fluorescens SBW25 to biosynthesize monocyclic pyrazines is reported. Heterologous expression of the papABC genes that synthesize the natural α‐amino acid 4‐aminophenylalanine (4APhe), together with three adjacent papDEF genes of unknown function, in Escherichia coli resulted in the production of 2,5‐dimethyl‐3,6‐bis(4‐aminobenzyl)pyrazine (DMBAP), which comprised two symmetrical aminobenzyl moieties derived from 4APhe. It is found that PapD is a novel amino acid C‐acetyltransferase, which decarboxylates and transfers acetyl residues to 4APhe, to generate an α‐aminoketone, which spontaneously dehydrates and condenses to give dihydro DMBAP. PapF is a novel oxidase in the amine oxidase superfamily that oxidizes dihydro DMBAP to yield the pyrazine ring of DMBAP. These two enzymes constitute a unique mechanism for synthesizing monocyclic pyrazines and might serve as a novel strategy for the enzymatic synthesis of pyrazine derivatives from natural α‐amino acids.

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Pyrazines from bacteria and ants: convergent chemistry within an ecological niche

Cited by 59 publications

References 42 publications

Chemical Ecology in Insect-microbe Interactions in the Neotropics

Chemical Ecology in Insect-microbe Interactions in the Neotropics

Bacterial Semiochemicals and Transkingdom Interactions with Insects and Plants

Enzymatic Cascade in Pseudomonas that Produces Pyrazine from α‐Amino Acids

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