Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity
Mogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet...
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MDPI AG
2014-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/8/12676 |
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| author | Lei Wang Ziming Yang Fenglai Lu Jinglei Liu Yunfei Song Dianpeng Li |
| author_facet | Lei Wang Ziming Yang Fenglai Lu Jinglei Liu Yunfei Song Dianpeng Li |
| author_sort | Lei Wang |
| collection | DOAJ |
| description | Mogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet triterpenoid saponin mixture. The reactant concentration, temperature, pH and buffer system were studied. New saponins with the α-glucose group were isolated from the resulting mixtures, and the structures of three components of the extract were determined. The structure-taste relationships of these derivatives were also studied together with those of the natural mogrosides. The number and stereoconfiguration of glucose groups present in the mogroside molecules were found to be the main factor to determine the sweet or bitter taste of a compound. The antioxidant and food safety properties were initially evaluated by their radical scavenging ability and via 7 day mice survival tests, respectively. The results showed that the sweet triterpenoid saponin mixture has the same favorable physiological and safety characteristics as the natural mogrosides. |
| first_indexed | 2024-04-13T14:39:21Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T14:39:21Z |
| publishDate | 2014-08-01 |
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| series | Molecules |
| spelling | doaj.art-060fc487bcc94fcc86d46d3bd18680de2022-12-22T02:42:56ZengMDPI AGMolecules1420-30492014-08-01198126761268910.3390/molecules190812676molecules190812676Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute ToxicityLei Wang0Ziming Yang1Fenglai Lu2Jinglei Liu3Yunfei Song4Dianpeng Li5Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, ChinaGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, ChinaGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, ChinaGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, ChinaGuilin Layn Natural Ingredients Corp., Guilin 541199, ChinaGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, ChinaMogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet triterpenoid saponin mixture. The reactant concentration, temperature, pH and buffer system were studied. New saponins with the α-glucose group were isolated from the resulting mixtures, and the structures of three components of the extract were determined. The structure-taste relationships of these derivatives were also studied together with those of the natural mogrosides. The number and stereoconfiguration of glucose groups present in the mogroside molecules were found to be the main factor to determine the sweet or bitter taste of a compound. The antioxidant and food safety properties were initially evaluated by their radical scavenging ability and via 7 day mice survival tests, respectively. The results showed that the sweet triterpenoid saponin mixture has the same favorable physiological and safety characteristics as the natural mogrosides.http://www.mdpi.com/1420-3049/19/8/12676mogrosidesweetenercucurbitane glycosidescyclodextrin glucanotransferase |
| spellingShingle | Lei Wang Ziming Yang Fenglai Lu Jinglei Liu Yunfei Song Dianpeng Li Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity Molecules mogroside sweetener cucurbitane glycosides cyclodextrin glucanotransferase |
| title | Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity |
| title_full | Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity |
| title_fullStr | Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity |
| title_full_unstemmed | Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity |
| title_short | Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity |
| title_sort | cucurbitane glycosides derived from mogroside iie structure taste relationships antioxidant activity and acute toxicity |
| topic | mogroside sweetener cucurbitane glycosides cyclodextrin glucanotransferase |
| url | http://www.mdpi.com/1420-3049/19/8/12676 |
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