Solid acid-catalyzed one-step synthesis of oleacein from oleuropein
Abstract In this study, we developed a new synthetic strategy to convert secoiridoid glucosides into unique dialdehydic compounds using solid acid catalysts. Specifically, we succeeded in the direct synthesis of oleacein, a rare component of extra-virgin olive oil, from oleuropein, which is abundant...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-05-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-35423-x |
| _version_ | 1797818087643283456 |
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| author | Yasuhiro Shimamoto Tadahiro Fujitani Eriko Uchiage Hiroko Isoda Ken-ichi Tominaga |
| author_facet | Yasuhiro Shimamoto Tadahiro Fujitani Eriko Uchiage Hiroko Isoda Ken-ichi Tominaga |
| author_sort | Yasuhiro Shimamoto |
| collection | DOAJ |
| description | Abstract In this study, we developed a new synthetic strategy to convert secoiridoid glucosides into unique dialdehydic compounds using solid acid catalysts. Specifically, we succeeded in the direct synthesis of oleacein, a rare component of extra-virgin olive oil, from oleuropein, which is abundant in olive leaves. Whereas the conventional total synthesis of oleacein from lyxose requires more than 10 steps, these solid acid catalysts enabled the one-step synthesis of oleacein from oleuropein. A key step in this synthesis was the selective hydrolysis of methyl ester. Density functional theory calculations at the B3LYP/631+G (d) level of theory revealed the formation of a tetrahedral intermediate bonded to one H2O molecule. These solid acid catalysts were easily recovered and reused at least five times by simple cleaning. Importantly, this synthetic procedure was not only applicable to other secoiridoid glucosides, but could also be employed for the corresponding scale-up reaction using oleuropein extracted from olive leaves as the starting material. |
| first_indexed | 2024-03-13T09:02:58Z |
| format | Article |
| id | doaj.art-b523f7813f2949e89ea598cc71f25976 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-03-13T09:02:58Z |
| publishDate | 2023-05-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-b523f7813f2949e89ea598cc71f259762023-05-28T11:14:00ZengNature PortfolioScientific Reports2045-23222023-05-0113111210.1038/s41598-023-35423-xSolid acid-catalyzed one-step synthesis of oleacein from oleuropeinYasuhiro Shimamoto0Tadahiro Fujitani1Eriko Uchiage2Hiroko Isoda3Ken-ichi Tominaga4National Institute of Advanced Industrial Science and Technology (AIST), Interdisciplinary Research Center of Catalytic ChemistryNational Institute of Advanced Industrial Science and Technology (AIST), Interdisciplinary Research Center of Catalytic ChemistryNational Institute of Advanced Industrial Science and Technology (AIST), Open Innovation Laboratory for Food and Medicinal Resource EngineeringNational Institute of Advanced Industrial Science and Technology (AIST), Open Innovation Laboratory for Food and Medicinal Resource EngineeringNational Institute of Advanced Industrial Science and Technology (AIST), Interdisciplinary Research Center of Catalytic ChemistryAbstract In this study, we developed a new synthetic strategy to convert secoiridoid glucosides into unique dialdehydic compounds using solid acid catalysts. Specifically, we succeeded in the direct synthesis of oleacein, a rare component of extra-virgin olive oil, from oleuropein, which is abundant in olive leaves. Whereas the conventional total synthesis of oleacein from lyxose requires more than 10 steps, these solid acid catalysts enabled the one-step synthesis of oleacein from oleuropein. A key step in this synthesis was the selective hydrolysis of methyl ester. Density functional theory calculations at the B3LYP/631+G (d) level of theory revealed the formation of a tetrahedral intermediate bonded to one H2O molecule. These solid acid catalysts were easily recovered and reused at least five times by simple cleaning. Importantly, this synthetic procedure was not only applicable to other secoiridoid glucosides, but could also be employed for the corresponding scale-up reaction using oleuropein extracted from olive leaves as the starting material.https://doi.org/10.1038/s41598-023-35423-x |
| spellingShingle | Yasuhiro Shimamoto Tadahiro Fujitani Eriko Uchiage Hiroko Isoda Ken-ichi Tominaga Solid acid-catalyzed one-step synthesis of oleacein from oleuropein Scientific Reports |
| title | Solid acid-catalyzed one-step synthesis of oleacein from oleuropein |
| title_full | Solid acid-catalyzed one-step synthesis of oleacein from oleuropein |
| title_fullStr | Solid acid-catalyzed one-step synthesis of oleacein from oleuropein |
| title_full_unstemmed | Solid acid-catalyzed one-step synthesis of oleacein from oleuropein |
| title_short | Solid acid-catalyzed one-step synthesis of oleacein from oleuropein |
| title_sort | solid acid catalyzed one step synthesis of oleacein from oleuropein |
| url | https://doi.org/10.1038/s41598-023-35423-x |
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