Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism
Although enormous efforts have been made to prepare tasty and soluble steviol glycosides (SGs), the structure–property relationship of SGs still remains unclear, neither in experiment fact nor in the mechanism, such as the influence of linkage type and position of substituted glucosyl on physiochemi...
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2025-05-01
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| Series: | Foods |
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| author | Zhuoyu Zhou Wanjie Wang Qinbing Guo Haijun Wang Yongmei Xia |
| author_facet | Zhuoyu Zhou Wanjie Wang Qinbing Guo Haijun Wang Yongmei Xia |
| author_sort | Zhuoyu Zhou |
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| description | Although enormous efforts have been made to prepare tasty and soluble steviol glycosides (SGs), the structure–property relationship of SGs still remains unclear, neither in experiment fact nor in the mechanism, such as the influence of linkage type and position of substituted glucosyl on physiochemical properties and sensory features of SGs. The favorable SGs, rebaudioside D (RD) and rebaudioside A (RA), possess good edulcorant quality, poor solubility, and other significantly different physical properties. This research chose two pairs of isomeric SGs, RA and its isomer rebaudioside E (RE) and RD and its isomer RA1G (a synthetic SG, <i>α</i>-1,6-mono-glucosylated RA), to conduct a comparative study, aiming to reveal the structure–property relevance on their solubility, sweetness, stability, and crystal structure. The RA1G presents an aqueous solubility 13 times that of RA and 137 times that of RD and exhibits better edulcorant quality than that of RA, similar to RD. The results indicate that the glucosyl linkage type and position have a stronger impact on the properties of the SGs than the number of glucosyl moieties. The underlying mechanism of their structure–property relevance was elucidated by analyzing the interaction energies between the SGs with solvent and human receptor proteins, respectively. |
| format | Article |
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| institution | OA Journals |
| issn | 2304-8158 |
| language | English |
| publishDate | 2025-05-01 |
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| series | Foods |
| spelling | doaj-art-eb6e50a2455e4ceca4bb5b5d1d7b109a2025-08-20T02:33:08ZengMDPI AGFoods2304-81582025-05-011411191710.3390/foods14111917Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying MechanismZhuoyu Zhou0Wanjie Wang1Qinbing Guo2Haijun Wang3Yongmei Xia4Key Laboratory of Synthetic and Biological Colloids, School of Chemical and Materials Engineering, Jiangnan University, Wuxi 214122, ChinaKey Laboratory of Synthetic and Biological Colloids, School of Chemical and Materials Engineering, Jiangnan University, Wuxi 214122, ChinaState Key Laboratory of Food Nutrition and Safety, Tianjin University of Science and Technology, Tianjin 300457, ChinaKey Laboratory of Synthetic and Biological Colloids, School of Chemical and Materials Engineering, Jiangnan University, Wuxi 214122, ChinaKey Laboratory of Synthetic and Biological Colloids, School of Chemical and Materials Engineering, Jiangnan University, Wuxi 214122, ChinaAlthough enormous efforts have been made to prepare tasty and soluble steviol glycosides (SGs), the structure–property relationship of SGs still remains unclear, neither in experiment fact nor in the mechanism, such as the influence of linkage type and position of substituted glucosyl on physiochemical properties and sensory features of SGs. The favorable SGs, rebaudioside D (RD) and rebaudioside A (RA), possess good edulcorant quality, poor solubility, and other significantly different physical properties. This research chose two pairs of isomeric SGs, RA and its isomer rebaudioside E (RE) and RD and its isomer RA1G (a synthetic SG, <i>α</i>-1,6-mono-glucosylated RA), to conduct a comparative study, aiming to reveal the structure–property relevance on their solubility, sweetness, stability, and crystal structure. The RA1G presents an aqueous solubility 13 times that of RA and 137 times that of RD and exhibits better edulcorant quality than that of RA, similar to RD. The results indicate that the glucosyl linkage type and position have a stronger impact on the properties of the SGs than the number of glucosyl moieties. The underlying mechanism of their structure–property relevance was elucidated by analyzing the interaction energies between the SGs with solvent and human receptor proteins, respectively.https://www.mdpi.com/2304-8158/14/11/1917rebaudioside Drebaudioside Atransglycosylationalternansucraseedulcorantphysiochemical properties |
| spellingShingle | Zhuoyu Zhou Wanjie Wang Qinbing Guo Haijun Wang Yongmei Xia Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism Foods rebaudioside D rebaudioside A transglycosylation alternansucrase edulcorant physiochemical properties |
| title | Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism |
| title_full | Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism |
| title_fullStr | Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism |
| title_full_unstemmed | Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism |
| title_short | Structure–Property Relevance of Two Pairs of Isomeric Steviol Rebaudiosides and the Underlying Mechanism |
| title_sort | structure property relevance of two pairs of isomeric steviol rebaudiosides and the underlying mechanism |
| topic | rebaudioside D rebaudioside A transglycosylation alternansucrase edulcorant physiochemical properties |
| url | https://www.mdpi.com/2304-8158/14/11/1917 |
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