Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance
A total of 31 compounds were isolated from the ethyl acetate and <i>n</i>-butanol fractions of <i>Anchusa italica</i> Retz., which contained one ursane triterpenoid, 2<i>α</i>,3<i>β</i>,19<i>α</i>-trihydroxy-23-formyl-urs-12-en-28,21<i&g...
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| author | Linchuang Shen Bingchen Han Zhiliang Ma Xianju Huang Guangzhong Yang Yanfeng Zeng Maochuan Liao Ruixi Gao Jun Li |
| author_facet | Linchuang Shen Bingchen Han Zhiliang Ma Xianju Huang Guangzhong Yang Yanfeng Zeng Maochuan Liao Ruixi Gao Jun Li |
| author_sort | Linchuang Shen |
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| description | A total of 31 compounds were isolated from the ethyl acetate and <i>n</i>-butanol fractions of <i>Anchusa italica</i> Retz., which contained one ursane triterpenoid, 2<i>α</i>,3<i>β</i>,19<i>α</i>-trihydroxy-23-formyl-urs-12-en-28,21<i>β-</i>olide (<b>1</b>), and five norisoprenoids: (2<i>R</i>,6<i>R</i>,9<i>S</i>)-9-hydroxy-4-megastigmen-3-one-2<i>-O-β-</i>D-glucopyranoside (<b>3</b>); (2<i>R</i>,6<i>S</i>,9<i>S</i>)-9-hydroxy-megastigman-4,7-dien-3-one-2<i>-O-β-</i>D-glucopyranoside (<b>4</b>); (+)-isololiolide <i>β-</i>D-glucopyranoside (<b>5</b>); (2<i>S</i>,8<i>R</i>)-loliolide <i>β-</i>D-glucopyranoside (<b>6a</b>); and (2<i>R</i>,8<i>S</i>)-loliolide <i>β-</i>D-glucopyranoside (<b>6b</b>). It also contained 25 known compounds (<b>2</b> and <b>7–30</b>). The chemical structures of the compounds, inclusive of their absolute configurations, were ascertained using spectroscopic methods such as NMR, HR-MS, and quantum chemical calculations (computational NMR and ECD), in combination with relevant literature data. Moreover, the chemotaxonomic significance of the isolated substances was discussed, with compounds <b>1</b>, <b>2</b>, and <b>7–13</b> potentially broadening the application of triterpenes as taxonomic markers for the classification of the genus <i>Anchusa</i>. |
| format | Article |
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| spelling | doaj-art-133d8fccfc144209aa268755f0f04b2b2025-08-20T03:52:57ZengMDPI AGPlants2223-77472025-05-01149138510.3390/plants14091385Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic SignificanceLinchuang Shen0Bingchen Han1Zhiliang Ma2Xianju Huang3Guangzhong Yang4Yanfeng Zeng5Maochuan Liao6Ruixi Gao7Jun Li8School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaCollege of Life Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaSchool of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, ChinaA total of 31 compounds were isolated from the ethyl acetate and <i>n</i>-butanol fractions of <i>Anchusa italica</i> Retz., which contained one ursane triterpenoid, 2<i>α</i>,3<i>β</i>,19<i>α</i>-trihydroxy-23-formyl-urs-12-en-28,21<i>β-</i>olide (<b>1</b>), and five norisoprenoids: (2<i>R</i>,6<i>R</i>,9<i>S</i>)-9-hydroxy-4-megastigmen-3-one-2<i>-O-β-</i>D-glucopyranoside (<b>3</b>); (2<i>R</i>,6<i>S</i>,9<i>S</i>)-9-hydroxy-megastigman-4,7-dien-3-one-2<i>-O-β-</i>D-glucopyranoside (<b>4</b>); (+)-isololiolide <i>β-</i>D-glucopyranoside (<b>5</b>); (2<i>S</i>,8<i>R</i>)-loliolide <i>β-</i>D-glucopyranoside (<b>6a</b>); and (2<i>R</i>,8<i>S</i>)-loliolide <i>β-</i>D-glucopyranoside (<b>6b</b>). It also contained 25 known compounds (<b>2</b> and <b>7–30</b>). The chemical structures of the compounds, inclusive of their absolute configurations, were ascertained using spectroscopic methods such as NMR, HR-MS, and quantum chemical calculations (computational NMR and ECD), in combination with relevant literature data. Moreover, the chemotaxonomic significance of the isolated substances was discussed, with compounds <b>1</b>, <b>2</b>, and <b>7–13</b> potentially broadening the application of triterpenes as taxonomic markers for the classification of the genus <i>Anchusa</i>.https://www.mdpi.com/2223-7747/14/9/1385<i>Anchusa italica</i> Retz.structural elucidationursane triterpenenorisoprenoidchemotaxonomic significance |
| spellingShingle | Linchuang Shen Bingchen Han Zhiliang Ma Xianju Huang Guangzhong Yang Yanfeng Zeng Maochuan Liao Ruixi Gao Jun Li Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance Plants <i>Anchusa italica</i> Retz. structural elucidation ursane triterpene norisoprenoid chemotaxonomic significance |
| title | Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance |
| title_full | Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance |
| title_fullStr | Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance |
| title_full_unstemmed | Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance |
| title_short | Ursane Triterpenes and Norisoprenoids from <i>Anchusa italica</i> Retz. and Their Chemotaxonomic Significance |
| title_sort | ursane triterpenes and norisoprenoids from i anchusa italica i retz and their chemotaxonomic significance |
| topic | <i>Anchusa italica</i> Retz. structural elucidation ursane triterpene norisoprenoid chemotaxonomic significance |
| url | https://www.mdpi.com/2223-7747/14/9/1385 |
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