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Chirality of the γ‐lactones formed by Fusarium poae INRA 45
Author(s) -
Latrasse Alain,
Guichard Elisabeth,
Piffaut Catherine,
Fournier Nicole,
Dufosse Laurent
Publication year - 1993
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530050520
Subject(s) - chemistry , chirality (physics) , stereochemistry , fusarium , botany , chiral symmetry , particle physics , biology , physics , nambu–jona lasinio model , quark
Abstract 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. © 1993 Wiley‐Liss, Inc.