| Autor: |
Shaimaa Fayez, Torsten Bruhn, Doris Feineis, Laurent Aké Assi, Prem Prakash Kushwaha, Shashank Kumar, Gerhard Bringmann |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
RSC Advances. 12:28916-28928 |
| ISSN: |
2046-2069 |
| Popis: |
The West African liana Ancistrocladus abbreviatus is a rich source of structurally most diverse naphthylisoquinoline alkaloids. From its roots, a series of four novel representatives, named ancistrobrevolines A–D (14–17) have now been isolated, displaying an unprecedented heterocyclic ring system, where the usual isoquinoline entity is replaced by a ring-contracted isoindolinone part. Their constitutions were elucidated by 1D and 2D NMR and HR-ESI-MS. The absolute configurations at the chiral axis and at the stereogenic center were assigned by using experimental and computational electronic circular dichroism (ECD) investigations and a ruthenium-mediated oxidative degradation, respectively. For the biosynthetic origin of the isoindolinones from ‘normal’ naphthyltetrahydroisoquinolines, a hypothetic pathway is presented. It involves oxidative decarboxylation steps leading to a ring contraction by a benzilic acid rearrangement. Ancistrobrevolines A (14) and B (15) were found to display moderate cytotoxic effects (up to 72%) against MCF-7 breast and A549 lung cancer cells and to reduce the formation of spheroids (mammospheres) in the breast cancer cell line. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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