Chirality of the gamma-lactones formed by Fusarium poae INRA 45
Résumé
A filamentous fungus, Fusarium poae INRA 45, was grown in two liquid Czapek-type media (a Czapek medium, and a yeast extract plus casaminoacids-enriched Czapek medium). Eight γ-lactones, i.e., γ-penta-, γ-octa-, γ-nona-, γ-deca-, and γ-dodecalactone, (6Z)-γ- and (6E)-γ-dodecenolactones, and a di-unsaturated γ-dodecalactone, were tentatively, or conclusively, identified by capillary gas chromatography (GC) and coupled GC-MS, in the volatile fractions of the cultures. Kinetics of the formation of γ-decalactone, (6Z)-γ- and (6E)-γ-dodecenolactones, (three major lactones), and γ-dodecalactone (a minor lactone) were quantitatively studied by computerized GC integration. Variations of the (R/S) ratios of the lactone enantiomers were quantitatively studied by computerized multidimensional gas chromatography (MDGC) integration. The levels of the lactones were superior in the enriched Czapek-type medium to those of the Czapek medium, but the compositions of these media did not influence significantly the (R/S) ratios of these lactones. Formation of the enantiomers is discussed in terms of metabolism of potential precursors.