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Applied and Environmental Microbiology, September 2002, p. 4322-4327, Vol. 68, No. 9
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.9.4322-4327.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.

Lactobacillus plantarum MiLAB 393 Produces the Antifungal Cyclic Dipeptides Cyclo(L-Phe-L-Pro) and Cyclo(L-Phe-trans-4-OH-L-Pro) and 3-Phenyllactic Acid

Katrin Ström,1* Jörgen Sjögren,2 Anders Broberg,2 and Johan Schnürer1

Departments of Microbiology,1 Chemistry, Swedish University of Agricultural Sciences, SE-750 07 Uppsala, Sweden2

Received 16 January 2002/ Accepted 26 June 2002

We have isolated a Lactobacillus plantarum strain (MiLAB 393) from grass silage that produces broad-spectrum antifungal compounds, active against food- and feed-borne filamentous fungi and yeasts in a dual-culture agar plate assay. Fusarium sporotrichioides and Aspergillus fumigatus were the most sensitive among the molds, and Kluyveromyces marxianus was the most sensitive yeast species. No inhibitory activity could be detected against the mold Penicillium roqueforti or the yeast Zygosaccharomyces bailii. An isolation procedure, employing a microtiter well spore germination bioassay, was devised to isolate active compounds from culture filtrate. Cell-free supernatant was fractionated on a C18 SPE column, and the 95% aqueous acetonitrile fraction was further separated on a preparative HPLC C18 column. Fractions active in the bioassay were then fractionated on a porous graphitic carbon column. The structures of the antifungal compounds cyclo(L-Phe-L-Pro), cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid (L/D isomer ratio, 9:1), were determined by nuclear magnetic resonance spectroscopy, mass spectrometry, and gas chromatography. MIC values against A. fumigatus and P. roqueforti were 20 mg ml-1 for cyclo(L-Phe-L-Pro) and 7.5 mg ml-1 for phenyllactic acid. Combinations of the antifungal compounds revealed weak synergistic effects. The production of the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) by lactic acid bacteria is reported here for the first time.

* Corresponding author. Mailing address: Department of Microbiology, Swedish University of Agricultural Sciences, P.O. Box 7025, SE-750 07 Uppsala, Sweden. Phone: 46 18 673213. Fax: 46 18 673392. E-mail: katrin.strom{at}mikrob.slu.se.

Applied and Environmental Microbiology, September 2002, p. 4322-4327, Vol. 68, No. 9
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.9.4322-4327.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.



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