N-Acyl-homoserine Lactones from Enterobacter sakazakii (Cronobacter spp.) and Their Degradation by Bacillus cereus Enzymes

• Published in: Journal of agricultural and food chemistry 2012-01, Vol.60 (2), p.585-592
• Main Authors: da Silva Araújo, Francisca Diana, Esper, Luciana Maria Ramires, Kuaye, Arnaldo Yoshiteru, Sircili, Marcelo Palma, Marsaioli, Anita Jocelyne
• Format: Article
• Language: English
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemistry; 4-Butyrolactone - metabolism; Acyl-Butyrolactones - metabolism; amidase; Amidohydrolases - metabolism; Bacillus cereus; Bacillus cereus - enzymology; Biological and medical sciences; biotransformation; Coculture Techniques; Cronobacter sakazakii; Cronobacter sakazakii - chemistry; Cronobacter sakazakii - metabolism; dodecanoic acid; Food industries; Food microbiology; Fundamental and applied biological sciences. Psychology; General aspects; homoserine; Homoserine - analogs & derivatives; Homoserine - chemistry; Homoserine - metabolism; Hydrolysis; Hygiene and safety; lactones; monitoring; Spectrometry, Mass, Electrospray Ionization; spectroscopy
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf203846f

A chemical study of acyl-homoserine lactones (acyl-HSLs) produced by Enterobacter sakazakii resulted in the identification of three molecules: (S)-N-heptanoyl-HSL, (S)-N-dodecanoyl-HSL and (S)-N-tetradecanoyl-HSL. Mixed cultures of E. sakazakii and Bacillus cereus depleted E. sakazakii acyl-HSLs, suggesting acyl-HSL degradation by B. cereus hydrolases (hydrolysis of the lactone or amide moiety). The expression of B. cereus acyl-HSL lactonase and acyl-homoserine acylase was confirmed by monitoring the biotransformation of (S)-N-dodecanoyl-HSL into (S)-N-dodecanoyl-homoserine, dodecanoic acid and homoserine in the presence of B. cereus whole cells, using electrospray-mass spectrometry (ESI-MS).