2, 5-diketopiperazines (cyclic dipeptides) in beef: identification, synthesis, and sensory evaluation

J Food Sci. 2009 Mar;74(2):C100-5. doi: 10.1111/j.1750-3841.2009.01062.x.

Abstract

Stewed beef and grilled dry aged beef were analyzed as part of an in-depth analytical program, with the aim of creating new flavors incorporating only compounds identified in the target foods and identifying new synthesis targets. In-house GC-MS analyses of several types of cooked beef have identified over 1000 volatile and semivolatile components; many for the 1st time. Among the semivolatiles detected were ten 2, 5-diketopiperazines (cyclic dipeptides) previously unreported in beef. These cyclic dipeptides are cis-cyclo(L-Ile-L-Pro), cis-cyclo(L-Leu-L-Pro), cis-cyclo(L-Pro-L-Pro), cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Ala-L-Pro), cyclo(Gly-L-Pro), cyclo(Gly-L-Leu), cis-cyclo(L-Met-L-Pro), cis-cyclo(L-Phe-L-Pro), and cis-cyclo(L-Phe-L-Val). All 10 cyclic dipeptides were synthesized and evaluated organoleptically. Among them cis-cyclo(L-Leu-L-Pro), cis-cyclo(L-Met-L-Pro), and cis-cyclo(L-Phe-L-Pro) were found to be of particular organoleptic interest.

MeSH terms

  • Animals
  • Cattle
  • Chromatography, Gas
  • Cooking
  • Diketopiperazines / analysis*
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification
  • Dipeptides / analysis
  • Dipeptides / isolation & purification
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Meat / analysis*
  • Odorants
  • Taste
  • Volatile Organic Compounds / analysis
  • Volatile Organic Compounds / isolation & purification

Substances

  • Diketopiperazines
  • Dipeptides
  • Volatile Organic Compounds