N-Acyl Homoserine Lactone-Mediated Quorum Sensing with Special Reference to Use of Quorum Quenching Bacteria in Membrane Biofouling Control

Table 1

Structures of common N-acyl homoserine lactones produced by different Gram-negative bacteria and the phenotype controlled.

Synonyms	Chemical name	Chemical structure, formula name, molecular formula, and formula weight	Producing organisms	Phenotypes controlled	Reference
C4-HSL	N-Butanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-butanamid); MF: C8H13NO3; MW: 171.19	A. hydrophila, A. salmonicida, P. aeruginosa, S. liquefaciens MG1	Biofilm formation, exoproteases, virulence factor, swimming motility, and biofilm formation	[41, 45, 46, 46]
3-hydroxy-C4-HSL	N-(3-Hydroxybutyryl)-L-homoserine lactone	3-Hydroxy-N-(2-oxo-tetrahydro-furan-3-yl)-butyramide; MF: C8H13NO4; MW: 187.19	V. harveyi, Xenorhabdus nematophilus	Bioluminescence, polyhydroxybutyrate metabolism, virulence factor, and extracellular lipase	[47–49]
7Δ-3-hydroxy-C4-HSL	N-(3-Hydroxy-7-cis-tetradecenoyl)-L-homoserine lactone	3-Hydroxy-tetradec-7-enoic acid (2-oxo-tetrahydro-furan-3-yl)-amide; MF: C18H13NO4; MW: 325.44	Rhodobacter leguminosarum,; Rhodococcus sphaeroides	Root nodulation, plasmid transfer	[50–52]
C6-HSL	N-Hexanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-hexanamide); MF: C10H17NO3; MW: 199.25	Chromobacterium  violaceum, Edwardsiella tarda, Bur. cepacia, S. marcescens SS-1, S. liquefaciens MG1, and P. chlororaphis	Exoenzyme, cyanide, pigment, virulence factor, biofilm formation, pigment prodigiosin, swimming motility, biofilm formation, and phenazine synthesis	[41, 53–59]
3-oxo-C6-HSL	N-(3-Oxo-hexanoyl)-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-hexanamide); MF: C10H15NO4; MW: 213.20	V. fischeri, Enterobacter agglomerans, Erwinia carotovora, and Pectobacterium chrysanthemi	Bioluminescence, virulence factor, swarming motility, exoenzymes, antibiotic carbapenem, and pectinases	[60–63]
3-hydroxy-C6-HSL	N-(3-Hydroxyhexanoyl)-L-homoserine lactone	3-Hydroxy-hexanoic acid (2-oxo-tetrahydro-furan-3-yl)-amide; MF: C10H17NO4; MW: 215.25	V. anguillarum	Regulate the production of C10-HSL via vanRI	[64]
C7-HSL	N-Heptanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-hexanamide); MF: C11H19NO3; MW: 213.30	Ed. tarda, S. marcescens SS-1	Virulence factor, pigment prodigiosin	[54, 57]
C8-HSL	N-Octanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-octanamide); MF: C12H21NO3; MW: 227.30	Bur. cepacia, Rho. rubrum	Siderophore production, virulence factor, biofilm formation, photosynthetic membrane production	[55, 56, 65]
3-oxo-C8-HSL	N-(3-Oxo-octanoyl)-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide); MF: C12H19NO4; MW: 241.30	Rho. rubrum, Agrobacterium tumefaciens, Rhizobium sp.strain NGR234, Rhizobium leguminosarum bv. viciae	Photosynthetic membrane production, conjugal transfer of pTi, and root nodulation/symbiosis	[65–69]
C9-HSL	N-Nonanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-nonanamide); MF: C13H23NO3; MW: 241.30	Er. carotovora strain SCC 3193	Virulence factor, swarming motility	[70]
C10-HSL	N-Decanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-decanamid); MF: C14H25NO3; MW: 255.35	Rho. rubrum, Er. carotovora strain SCC 3193, and Bur. vietnamiensis	Photosynthetic membrane production, virulence factor, and exoproteases	[65, 70, 71]
3-oxo-C10-HSL	N-(3-Oxo-decanoyl)-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-decanamid); MF: C14H23NO4; MW: 269.34	P. aeruginosa, P. putida	Virulence factor, biofilm formation	[46, 72]
C11-HSL	N-Undecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-undecanamide); MF: C15H27NO3; MW: 269.40	P.  aeruginosa strain PAO1	Virulence factor	[73]
C12-HSL	N-Dodecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide); MF: C16H29NO3; MW: 283.41	Klebsiella pneumonia, P. aeruginosa,andSinorhizobium meliloti Rm1021	Virulence factor, exopolysaccharide production, and symbiotic nodulation development	[46, 74, 75]
3-oxo-C12-HSL	N-(3-Oxo-dodecanoyl)-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide); MF: C16H27NO4; MW: 297.39	P. aeruginosa, P. putida, and Rho. rubrum	Biofilm formation, virulence factor, and photosynthetic membrane production	[65, 72, 76–78]
C13-HSL	N-Tridecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-tridecanamide); MF: C17H31NO3; MW: 297.4	Yersinia pseudotuberculosis	Virulence factor	[79]
C14-HSL	N-Tetradecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-tetradecanamide); MF: C18H33NO3; MW: 311.46	Y. pseudotuberculosis, Proteus mirabilis	Virulence factor	[79, 80]
3-oxo-C14-HSL	N-(3-Oxo-tetradecanoyl)-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-tetradecanamide); MF: C18H31NO4; MW: 325.44	Rhi. leguminosarum, P. aeruginosa, and Si. meliloti	Root nodulations, virulence factor, and symbiotic nodulation development	[75, 81]
3-oxo-C14: 1-Δ^7-cis-(L)-HSL	N-(3-Oxo-tetradec)-7(Z)-enoyl-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-7-tetradecenamide); MF: C18H29NO4; MW: 323.40	Rhi. leguminosarum	Root nodulation/symbiosis, growth inhibition	[69, 81–83]
C14: 1-Δ^9-cis-(L)-HSL	N-cis-Tetradec-9Z-enoyl-L-homoserine lactone	(S,Z)-N-(2-Oxotetrahydrofuran-3-yl)tetradec-9-enamide); MF: C18H31NO3; MW: 309.40	Ag. vitis	Virulence factor	[84]
C15-HSL	N-Pentadecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-pentadecanamide); MF: C19H35NO3; MW: 325.50	Y. pseudotuberculosis	Virulence factor	[79]
C16-HSL	N-Hexadecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-hexadecanamide); MF: C20H37NO3; MW: 339.50	Rh. capsulatus	Polyhydroxyalkanoates synthesis	[85]
3-oxo-C16-: 1-Δ^11-cis-(L)-HSL	N-(3-Oxo-hexadec)-11(Z)-enoyl-L-homoserine lactone	(3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-(11Z)-hexadecanamide); MF: C20H33NO4; MW: 351.50	Ag. vitis, Si. meliloti	Virulence factor, symbiotic nodulation development	[75, 86]
C18-HSL	N-Octadecanoyl-L-homoserine lactone	(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-octadecanamide); MF: C22H41NO3; MW: 367.70	Si. meliloti	Symbiotic nodulation development	[75]
C18: 1-Δ^9-cis-(L)-HSL	N-cis-Octadec-9Z-enoyl-L-homoserine lactone	(N-(Tetrahydro-2-oxo-3-furanyl)-9Z-octadecanamide); MF: C22H39NO3; MW: 365.60	Dinoroseobacter shibae	—	[87]