Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

Saalim, Muhammad; Villegas‐Moreno, Jessica; Clark, Benjamin R.

doi:10.3390/molecules25235689

Cited by 36 publications

(30 citation statements)

References 112 publications

(177 reference statements)

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“…The "Pseudomonas quorum signal" (6, PQS) is a unique AQ signal possessing a hydroxyl group at the third carbon, and a heptyl alkyl side chain (Figure 1). It should be noted that there is considerable structural diversity of AQs in nature, which are beyond the scope of this review [16,17].…”

Section: Quorum Sensing Compounds and Their Relativesmentioning

confidence: 99%

How do Quorum Sensing Signals Mediate Algae–Bacteria Interactions?

Dow¹

2021

Preprint

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Quorum sensing (QS) describes a process by which bacteria can sense the local cell density of their own species, thus enabling them to coordinate gene expression and physiological processes on a community-wide scale. Small molecules called autoinducers or QS signals, which act as intraspecies signals, mediate quorum sensing. As our knowledge of QS has progressed, so too has our understanding of the structural diversity of QS signals, along with the diversity of bacteria conducting QS and the range of ecosystems in which QS takes place. It is now also clear that QS signals are more than just intraspecies signals. QS signals mediate interactions between species of prokaryotes, and between prokaryotes and eukaryotes. In recent years, our understanding of QS signals as mediators of algae–bacteria interactions has advanced such that we are beginning to develop a mechanistic understanding of their effects. This review will summarize the recent efforts to understand how different classes of QS signals contribute to the interactions between planktonic microalgae and bacteria in our oceans, primarily N-acyl-homoserine lactones, their degradation products tetramic acids, and 2-alkyl-4-quinolones. In particular, this review will discuss the ways in which QS signals alter microalgae growth and metabolism, namely as direct effectors of photosynthesis, regulators of the cell cycle, and as modulators of other algicidal mechanisms. Furthermore, the contribution of QS signals to nutrient acquisition is discussed, and finally how microalgae can modulate these small molecules to dampen their effects.

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Section: Quorum Sensing Compounds and Their Relativesmentioning

confidence: 99%

How do Quorum Sensing Signals Mediate Algae–Bacteria Interactions?

Dow¹

2021

Preprint

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“…While this article explicitly focuses on synthetic strategies of microbial 2-alkyl-4(1H)-quinolones, several excellent reviews provide more detailed overviews about naturally produced 2-alkyl-4(1H)-quinolone derivatives and their biological activities. 6,21,[25][26]…”

Section: Natural Diversity Of 2-alkyl-4(1h)-quinolonesmentioning

confidence: 99%

“…The geranyl side chain at 2-position was introduced via the corresponding boronic ester 64. the position followed by spontaneous rearrangement resulted in an isothiocyanate moiety 66. Finally, the isothiocyanate was captured by methyl thiolate and methylated by MeI to afford intervenolin (6). 56 Scheme 20.…”

Section: Synthesis Of Intervenolin Of Nocardiamentioning

confidence: 99%

“…[2][3][4][5] These compounds have many interesting biological activities which are in part reviewed elsewhere. 6 Some of them function as quorum sensing signals that allow their producers to coordinate virulence and other behaviours in dependence of population density. Others are mainly considered to act as anti-bacterial weapons deployed against competing species.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of bacterial 2-alkyl-4(1H)-quinolone derivatives

Böttcher¹,

Nguyen²,

Szamosvári³

2021

Arkivoc

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“…The “Pseudomonas quorum signal” (6, PQS) is a unique AQ signal possessing a hydroxyl group at the third carbon, and a heptyl alkyl side chain ( Figure 1 ). It should be noted that there is considerable structural diversity of AQs in nature, which are beyond the scope of this review [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

How Do Quorum-Sensing Signals Mediate Algae–Bacteria Interactions?

Dow

2021

Microorganisms

View full text Add to dashboard Cite

Quorum sensing (QS) describes a process by which bacteria can sense the local cell density of their own species, thus enabling them to coordinate gene expression and physiological processes on a community-wide scale. Small molecules called autoinducers or QS signals, which act as intraspecies signals, mediate quorum sensing. As our knowledge of QS has progressed, so too has our understanding of the structural diversity of QS signals, along with the diversity of bacteria conducting QS and the range of ecosystems in which QS takes place. It is now also clear that QS signals are more than just intraspecies signals. QS signals mediate interactions between species of prokaryotes, and between prokaryotes and eukaryotes. In recent years, our understanding of QS signals as mediators of algae–bacteria interactions has advanced such that we are beginning to develop a mechanistic understanding of their effects. This review will summarize the recent efforts to understand how different classes of QS signals contribute to the interactions between planktonic microalgae and bacteria in our oceans, primarily N-acyl-homoserine lactones, their degradation products of tetramic acids, and 2-alkyl-4-quinolones. In particular, this review will discuss the ways in which QS signals alter microalgae growth and metabolism, namely as direct effectors of photosynthesis, regulators of the cell cycle, and as modulators of other algicidal mechanisms. Furthermore, the contribution of QS signals to nutrient acquisition is discussed, and finally, how microalgae can modulate these small molecules to dampen their effects.

show abstract

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

Cited by 36 publications

References 112 publications

How do Quorum Sensing Signals Mediate Algae–Bacteria Interactions?

How do Quorum Sensing Signals Mediate Algae–Bacteria Interactions?

Synthesis of bacterial 2-alkyl-4(1H)-quinolone derivatives

How Do Quorum-Sensing Signals Mediate Algae–Bacteria Interactions?

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