Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage
The instability of rebaudioside A (Reb A) in food product applications during storage challenges their utilization. The pathways of Reb A degradation in aged acidic beverages were investigated. Three Reb A degradation compounds of known sensory importance were monitored, consisting of (<b>1<...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/4/1385 |
| _version_ | 1797477570104524800 |
|---|---|
| author | Benjamin S. Gelinas Edisson Tello Devin G. Peterson |
| author_facet | Benjamin S. Gelinas Edisson Tello Devin G. Peterson |
| author_sort | Benjamin S. Gelinas |
| collection | DOAJ |
| description | The instability of rebaudioside A (Reb A) in food product applications during storage challenges their utilization. The pathways of Reb A degradation in aged acidic beverages were investigated. Three Reb A degradation compounds of known sensory importance were monitored, consisting of (<b>1</b>) a rearrangement, (<b>2</b>) a hydration, and (<b>3</b>) an epoxidation/rearrangement product. Using deuterium-labeled water (D<sub>2</sub>O) experiments, compounds <b>1</b>–<b>2</b> were reported to be generated by acid-catalyzed mechanisms involving the formation of a carbocation on carbon position 16, followed by either deprotonation via E<sub>1</sub> elimination on C15 to form the more thermodynamically stable trisubstituted alkene (compound <b>1</b>), or by the Markovnikov addition of water via SN<sub>1</sub> substitution to form a tertiary alcohol (compound <b>2</b>). Compound <b>3</b> was generated by epoxidation of the exomethylene at the C16–17 positions, followed by the opening and rearrangement of the ring to form a new alkene bond between C15–C16 and a primary alcohol on C17. Further analysis of the effect of beverage ingredients indicated the addition of caramel color significantly increased (<i>p</i> < 0.0001) the concentrations of compounds <b>1</b>–<b>2</b> compared to the aged control by 89 and 83%, respectively, whereas a specific coffee flavor and caramel color were reported to significantly reduce (<i>p</i> < 0.0001) the formation of compound <b>3</b> compared to the aged control during storage by 90 and 79%, respectively. |
| first_indexed | 2024-03-09T21:19:35Z |
| format | Article |
| id | doaj.art-32ba0dd6908e4a8784dc5905666bba5e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:19:35Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-32ba0dd6908e4a8784dc5905666bba5e2023-11-23T21:23:12ZengMDPI AGMolecules1420-30492022-02-01274138510.3390/molecules27041385Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during StorageBenjamin S. Gelinas0Edisson Tello1Devin G. Peterson2Department of Food Science and Technology, The Ohio State University, 2015 Fyffe Rd., Columbus, OH 43210, USADepartment of Food Science and Technology, The Ohio State University, 2015 Fyffe Rd., Columbus, OH 43210, USADepartment of Food Science and Technology, The Ohio State University, 2015 Fyffe Rd., Columbus, OH 43210, USAThe instability of rebaudioside A (Reb A) in food product applications during storage challenges their utilization. The pathways of Reb A degradation in aged acidic beverages were investigated. Three Reb A degradation compounds of known sensory importance were monitored, consisting of (<b>1</b>) a rearrangement, (<b>2</b>) a hydration, and (<b>3</b>) an epoxidation/rearrangement product. Using deuterium-labeled water (D<sub>2</sub>O) experiments, compounds <b>1</b>–<b>2</b> were reported to be generated by acid-catalyzed mechanisms involving the formation of a carbocation on carbon position 16, followed by either deprotonation via E<sub>1</sub> elimination on C15 to form the more thermodynamically stable trisubstituted alkene (compound <b>1</b>), or by the Markovnikov addition of water via SN<sub>1</sub> substitution to form a tertiary alcohol (compound <b>2</b>). Compound <b>3</b> was generated by epoxidation of the exomethylene at the C16–17 positions, followed by the opening and rearrangement of the ring to form a new alkene bond between C15–C16 and a primary alcohol on C17. Further analysis of the effect of beverage ingredients indicated the addition of caramel color significantly increased (<i>p</i> < 0.0001) the concentrations of compounds <b>1</b>–<b>2</b> compared to the aged control by 89 and 83%, respectively, whereas a specific coffee flavor and caramel color were reported to significantly reduce (<i>p</i> < 0.0001) the formation of compound <b>3</b> compared to the aged control during storage by 90 and 79%, respectively.https://www.mdpi.com/1420-3049/27/4/1385steviastabilitysweet beveragesflavor interactionsrebaudioside Adegradation |
| spellingShingle | Benjamin S. Gelinas Edisson Tello Devin G. Peterson Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage Molecules stevia stability sweet beverages flavor interactions rebaudioside A degradation |
| title | Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage |
| title_full | Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage |
| title_fullStr | Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage |
| title_full_unstemmed | Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage |
| title_short | Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage |
| title_sort | mechanisms of rebaudioside a degradation and ingredient sweetener interactions in beverages during storage |
| topic | stevia stability sweet beverages flavor interactions rebaudioside A degradation |
| url | https://www.mdpi.com/1420-3049/27/4/1385 |
| work_keys_str_mv | AT benjaminsgelinas mechanismsofrebaudiosideadegradationandingredientsweetenerinteractionsinbeveragesduringstorage AT edissontello mechanismsofrebaudiosideadegradationandingredientsweetenerinteractionsinbeveragesduringstorage AT devingpeterson mechanismsofrebaudiosideadegradationandingredientsweetenerinteractionsinbeveragesduringstorage |