Occurrence of 2-Acetyl-1-pyrroline and Its Nonvolatile Precursors in Celtuce (Lactuca sativa L. var. augustana)

J Agric Food Chem. 2019 Oct 23;67(42):11710-11717. doi: 10.1021/acs.jafc.9b05434. Epub 2019 Oct 10.

Abstract

Lactuca sativa L. var. augustana has a basmati rice-like odor with a green note in the background. This typical odor is due to the release of 2-acetyl-1-pyrroline (2-AP) after heating, which is confirmed by volatile analysis. Recent metabolomic and genomic studies of different rice varieties highlighted that the presence of 2-AP was linked to the accumulation of γ-aminobutyraldehyde; genome-wide association studies also indicated that acyltransferases were involved. These results prompted us to analyze nonvolatile compound precursors in L. sativa L. var. augustana (celtuce) to search for compound derivatives with a 4,5-dioxohexan alkyl amine-like structure. Hypothetical synthetic compounds were prepared from a reductive amination between 4,5-dioxohexanal and glycine, alanine, aspartic acid, and glutamic acid to give 2-(2-acetylpyrrolidin-1-yl) alkanoic acid. We proved that 2-(2-acetylpyrrolidin-1-yl) propionic acid is present in L. sativa, which, when thermally treated, released 2-AP. Other 2-AP precursors occurring in this plant are discussed.

Keywords: 2-acetyl-1-pyrroline; 6-methyl-5,6-dihydropyridine; Lactuca sativa L. var. augustana; basmati rice; precursors.

MeSH terms

  • Genome, Plant
  • Lactuca / chemistry*
  • Lactuca / genetics
  • Mass Spectrometry
  • Odorants / analysis
  • Plant Extracts / chemistry*
  • Pyrroles / chemistry*

Substances

  • Plant Extracts
  • Pyrroles
  • 2-acetyl-1-pyrroline