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Antimicrobial Agents and Chemotherapy, December 2005, p. 5037-5045, Vol. 49, No. 12
0066-4804/05/$08.00+0     doi:10.1128/AAC.49.12.5037-5045.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Novel Cyclic Lipodepsipeptide from Pseudomonas syringae pv. lachrymans Strain 508 and Syringopeptin Antimicrobial Activities

Dipartimento di Scienze Biochimiche "A. Rossi Fanelli," Università "La Sapienza" di Roma, P.le A. Moro 5, 00185 Roma, Italy,¹ Department of Biology, Utah State University, Logan, Utah 84322-5305,² Centro Internazionale di Servizi di Spettrometria di Massa, Istituto di Scienze dell'Alimentazione del CNR, Via Roma 52, I-83100 Avellino, Italy,³ Dipartimento di Scienze e Tecnologie Agroalimentari, Ambientali e Microbiologiche, Università del Molise, 86100 Campobasso, Italy,⁴ Institute of Chemical Methodologies, National Research Council, 00016 Monterotondo Stazione, Rome, Italy,⁵ Dipartimento di Scienza degli Alimenti, Università di Napoli "Federico II," Parco Gussone, Edificio 84, 80055 Portici, Naples, Italy,⁶ Department of Life Sciences, Snow College, Ephraim, Utah 84627⁷

Received 25 July 2005/ Returned for modification 19 August 2005/ Accepted 30 September 2005

The syringopeptins are a group of antimicrobial cyclic lipodepsipeptides produced by several plant-associated pseudomonads. A novel syringopeptin, SP508, was shown to be produced as two homologs (A and B) by Pseudomonas syringae pv. lachrymans strain 508 from apple and to structurally resemble syringopeptin SP22. SP508 differed from SP22 and other syringopeptins by having three instead of four ,ß-unsaturated amino acids and a longer ß-hydroxy acyl chain. Both SP508 and SP22 displayed growth-inhibitory activities against Mycobacterium smegmatis, other gram-positive bacteria, and yeasts but not against gram-negative bacteria. Structure-activity analyses of the SP508 and SP22 homologs indicated chemical structural features that lead to enhanced antimycobacterial activity by these pseudomonad cyclic lipodepsipeptides.

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