Mechanisms of degradation of the natural high-potency sweetener (2R,4R)-monatin in mock beverage solutions

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The sodium, potassium, or mixed sodium/potassium salt of the naturally occurring high-potency sweetener (2R,4R)-monatin, also known by the common name arruva, degrades over time in model beverage solutions in the presence of light. By use of UHPLC, LC-MS/MS, and peroxide assays, it has been demonstrated that degradation is accelerated by UV/visible light and the presence of trace metal ions. Data are presented that are consistent with a role for singlet oxygen (¹O₂), free radicals, and peroxides (both H₂O₂ and organic peroxides) in monatin oxidation. Separation of degradation products by UHPLC/HPLC or LC-MS/MS provided evidence for the formation of hydroxylated and peroxide species formed on the indole ring (mass increases 16 and 32, respectively) as well as multiple ring and side-chain oxidation and scission products. Model oxidation systems using the photosensitizer Rose Bengal as a source of ¹O₂ support the proposed photodegradation pathways.

Original languageEnglish
JournalJournal of Agricultural and Food Chemistry
Issue number15
Pages (from-to)3476-87
Number of pages12
Publication statusPublished - 16 Apr 2014
Externally publishedYes

    Research areas

  • Beverages, Glutamic Acid, Indoles, Kinetics, Oxidation-Reduction, Photolysis, Stereoisomerism, Sweetening Agents

ID: 128973642