BioMed Research International / 2014 / Article / Tab 1

Review Article

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.

SynonymsChemical nameChemical structure, formula name, molecular formula, and formula weight Producing organismsPhenotypes controlledReference

C4-HSLN-Butanoyl-L-homoserine lactone162584.table.001a
(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-butanamid)
MF: C8H13NO3; MW: 171.19
A. hydrophila, A. salmonicida, P. aeruginosa, S. liquefaciens MG1Biofilm formation, exoproteases, virulence factor, swimming motility, and biofilm formation[41, 45, 46, 46]

3-hydroxy-C4-HSLN-(3-Hydroxybutyryl)-L-homoserine lactone162584.table.001b 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[4749]

7 -3-hydroxy-C4-HSLN-(3-Hydroxy-7-cis-tetradecenoyl)-L-homoserine lactone162584.table.001c 3-Hydroxy-tetradec-7-enoic acid (2-oxo-tetrahydro-furan-3-yl)-amide
MF: H13NO4; MW: 325.44
Rhodobacter leguminosarum, 
Rhodococcus sphaeroides
Root nodulation, plasmid transfer[5052]

C6-HSLN-Hexanoyl-L-homoserine lactone 162584.table.001d (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, 5359]

3-oxo-C6-HSLN-(3-Oxo-hexanoyl)-L-homoserine lactone 162584.table.001e (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[6063]

3-hydroxy-C6-HSLN-(3-Hydroxyhexanoyl)-L-homoserine lactone162584.table.001f
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-HSLN-Heptanoyl-L-homoserine lactone 162584.table.001g (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-hexanamide)
MF: C11H19NO3; MW: 213.30
Ed. tarda, S. marcescens SS-1Virulence factor, pigment prodigiosin [54, 57]

C8-HSLN-Octanoyl-L-homoserine lactone162584.table.001h (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 lactone162584.table.001i (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[6569]

C9-HSLN-Nonanoyl-L-homoserine lactone162584.table.001j
(N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-nonanamide)
MF: C13H23NO3; MW: 241.30
Er. carotovora strain SCC 3193Virulence factor, swarming motility[70]

C10-HSLN-Decanoyl-L-homoserine lactone162584.table.001k
(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-HSLN-(3-Oxo-decanoyl)-L-homoserine lactone162584.table.001l (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-HSLN-Undecanoyl-L-homoserine lactone162584.table.001m (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-undecanamide)
MF: C15H27NO3; MW: 269.40
P.  aeruginosa strain PAO1Virulence factor [73]

-HSLN-Dodecanoyl-L-homoserine lactone162584.table.001n (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide)
MF: ; MW: 283.41
Klebsiella pneumonia, P. aeruginosa,andSinorhizobium meliloti Rm1021Virulence factor, exopolysaccharide production, and symbiotic nodulation development[46, 74, 75]

3-oxo-C12-HSLN-(3-Oxo-dodecanoyl)-L-homoserine lactone162584.table.001o (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, 7678]

C13-HSLN-Tridecanoyl-L-homoserine lactone162584.table.001p (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-tridecanamide)
MF: C17H31NO3; MW: 297.4
Yersinia pseudotuberculosis Virulence factor[79]

C14-HSLN-Tetradecanoyl-L-homoserine lactone162584.table.001q (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-tetradecanamide)
MF: C18H33NO3; MW: 311.46
Y. pseudotuberculosis, Proteus mirabilis Virulence factor[79, 80]

3-oxo-C14-HSLN-(3-Oxo-tetradecanoyl)-L-homoserine lactone162584.table.001r (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-Δ7-cis-(L)-HSLN-(3-Oxo-tetradec)-7(Z)-enoyl-L-homoserine lactone162584.table.001s (3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-7-tetradecenamide)
MF: C18H29NO4; MW: 323.40
Rhi. leguminosarum Root nodulation/symbiosis, growth inhibition[69, 8183]

C14: 1-Δ9-cis-(L)-HSLN-cis-Tetradec-9Z-enoyl-L-homoserine lactone162584.table.001t
(S,Z)-N-(2-Oxotetrahydrofuran-3-yl)tetradec-9-enamide)
MF: C18H31NO3; MW: 309.40
Ag. vitis Virulence factor[84]

C15-HSLN-Pentadecanoyl-L-homoserine lactone162584.table.001u (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-pentadecanamide)
MF: C19H35NO3; MW: 325.50
Y. pseudotuberculosis Virulence factor[79]

C16-HSLN-Hexadecanoyl-L-homoserine lactone162584.table.001v (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-hexadecanamide)
MF: C20H37NO3; MW: 339.50
Rh. capsulatus Polyhydroxyalkanoates synthesis[85]

3-oxo-C16-: 1-Δ11-cis-(L)-HSLN-(3-Oxo-hexadec)-11(Z)-enoyl-L-homoserine lactone162584.table.001w (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-HSLN-Octadecanoyl-L-homoserine lactone162584.table.001x (N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-octadecanamide)
MF: C22H41NO3; MW: 367.70
Si. meliloti Symbiotic nodulation development[75]

C18: 1-Δ9-cis-(L)-HSLN-cis-Octadec-9Z-enoyl-L-homoserine lactone162584.table.001y (N-(Tetrahydro-2-oxo-3-furanyl)-9Z-octadecanamide)
MF: C22H39NO3; MW: 365.60
Dinoroseobacter shibae [87]