Reference - Detail
| RRC ID | 71772 |
|---|---|
| Author | Fayez S, Bruhn T, Feineis D, Assi LA, Awale S, Bringmann G. |
| Title | Ancistrosecolines A-F, Unprecedented seco-Naphthylisoquinoline Alkaloids from the Roots of Ancistrocladus abbreviatus, with Apoptosis-Inducing Potential against HeLa Cancer Cells. |
| Journal | J Nat Prod |
| Abstract |
Ancistrosecolines A-F (8-13) are the first seco-type naphthylisoquinoline alkaloids discovered in Nature. In all these novel compounds, the tetrahydroisoquinoline ring is cleaved, with loss of C-1. They were isolated from the root bark of Ancistrocladus abbreviatus (Ancistrocladaceae), along with 1-nor-8-O-demethylancistrobrevine H (14), which is the first naturally occurring naphthylisoquinoline lacking the otherwise generally present methyl group at C-1. The stereostructures of the new alkaloids were established by HRESIMS, 1D and 2D NMR, oxidative degradation, and experimental and quantum-chemical ECD investigations. Ancistrosecolines A-F (8-13) and 1-nor-8-O-demethylancistrobrevine H (14) are typical Ancistrocladaceae-type metabolites, i.e., oxygenated at C-6 and S-configured at C-3, belonging to the subclasses of 7,1'- and 7,8'-coupled alkaloids. The biaryl linkages of 8-14 are rotationally hindered due to bulky ortho-substituents next to the axes. Owing to the constitutionally unsymmetric substitution patterns on each side of the axis, this C-C single bond represents an element of chirality in 1-nor-8-O-demethylancistrobrevine H (14) and in ancistrosecolines A-D (8-11). In ancistrosecolines E (12) and F (13), however, the likewise rotationally hindered biaryl axes do not constitute chiral elements, due to a symmetric substitution pattern, with its identical two methoxy functions at C-6 and C-8 in the phenyl subunit. And these two methoxy groups are, for the first time, not constitutionally heterotopic, but diastereotopic to each other. Ancistrosecoline D (11) exhibits strong cytotoxicity against HeLa cervical cancer cells. As visualized by Hoechst nuclei staining and by real-time imaging experiments, 11 induced massive nuclei fragmentation in HeLa cells, leading to apoptotic cell death. |
| Volume | 83(4) |
| Pages | 1139-1151 |
| Published | 2020-4-24 |
| DOI | 10.1021/acs.jnatprod.9b01168 |
| PMID | 32125158 |
| MeSH | Alkaloids / chemistry* Alkaloids / isolation & purification Alkaloids / pharmacology Antineoplastic Agents, Phytogenic / chemistry Antineoplastic Agents, Phytogenic / isolation & purification Antineoplastic Agents, Phytogenic / pharmacology* Apoptosis / drug effects* Caryophyllales / chemistry* Cell Line, Tumor HeLa Cells Humans Isoquinolines / chemistry Isoquinolines / isolation & purification Isoquinolines / pharmacology* Magnoliopsida / chemistry* Molecular Structure Plant Roots / chemistry |
| IF | 3.782 |
| Altmetric score |
オルトメトリクス指標項目
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| Total number of mentions | 0 |
| Resource | |
| Human and Animal Cells | HeLa(RCB0007) |