Absolute Configuration of 12S-Deoxynortryptoquivaline from Ascidian-Derived Fungus Aspergillus clavatus Determined by Anisotropic NMR and Chiroptical Spectroscopy
文献类型：期刊论文
| 作者 | Doro-Goldsmith, Elisa4,5; Song, Qi1 ; Li, Xiao-Lu5; Li, Xiao-Ming1; Hu, Xue-Yi1; Li, Hong-Lei1; Liu, Hao-Ran3,5; Wang, Bin-Gui1,2; Sun, Han3,5
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| 刊名 | JOURNAL OF NATURAL PRODUCTS
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| 出版日期 | 2024-01-30 |
| 卷号 | 87期号:2页码:381-387 |
| ISSN号 | 0163-3864 |
| DOI | 10.1021/acs.jnatprod.3c01157 |
| 通讯作者 | Wang, Bin-Gui(wangbg@ms.qdio.ac.cn) ; Sun, Han(hsun@fmp-berlin.de) |
| 英文摘要 | Tryptoquivalines are highly toxic metabolites initially isolated from the fungus Aspergillus clavatus. The relative and absolute configuration of tryptoquivaline derivates was primarily established by comparison of the chemical shifts, NOE data, and ECD calculations. A de novo determination of the complete relative configuration using NMR spectroscopy was challenging due to multiple spatially separated stereocenters, including one nonprotonated carbon. In this study, we isolated a new tryptoquivaline derivative, 12S-deoxynortryptoquivaline (1), from the marine ascidian-derived fungus Aspergillus clavatus AS-107. The correct assignment of the relative configuration of 1 was accomplished using anisotropic NMR spectroscopy, while the absolute configuration was determined by comparing calculated and experimental ECD spectra. This case study highlights the effectiveness of anisotropic NMR parameters over isotropic NMR parameters in determining the relative configuration of complex natural products without the need for crystallization. |
| WOS关键词 | RESIDUAL DIPOLAR COUPLINGS ; RELATIVE CONFIGURATION |
| 资助项目 | Deutsche Forschungsgemeinschaft ; Leibniz-Forschungsinstitut fur Molekulare Pharmakologie (FMP)[418729698] ; Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under the DFG/CAPES Collaborative Research Initiative ; Chinese Scholarship Council |
| WOS研究方向 | Plant Sciences ; Pharmacology & Pharmacy |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:001161238900001 |
| 源URL | [http://ir.qdio.ac.cn/handle/337002/184474]  |
| 专题 | 海洋研究所_实验海洋生物学重点实验室 |
| 通讯作者 | Wang, Bin-Gui; Sun, Han |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, CAS & Shandong Prov Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany 4.Univ Edinburgh, Sch Chem, Edinburgh EH9 3FJ, Scotland 5.Leibniz Forschungsinstitut Mol Pharmakol FMP, D-13125 Berlin, Germany |
| 推荐引用方式 GB/T 7714 | Doro-Goldsmith, Elisa,Song, Qi,Li, Xiao-Lu,et al. Absolute Configuration of 12S-Deoxynortryptoquivaline from Ascidian-Derived Fungus Aspergillus clavatus Determined by Anisotropic NMR and Chiroptical Spectroscopy[J]. JOURNAL OF NATURAL PRODUCTS,2024,87(2):381-387. |
| APA | Doro-Goldsmith, Elisa.,Song, Qi.,Li, Xiao-Lu.,Li, Xiao-Ming.,Hu, Xue-Yi.,...&Sun, Han.(2024).Absolute Configuration of 12S-Deoxynortryptoquivaline from Ascidian-Derived Fungus Aspergillus clavatus Determined by Anisotropic NMR and Chiroptical Spectroscopy.JOURNAL OF NATURAL PRODUCTS,87(2),381-387. |
| MLA | Doro-Goldsmith, Elisa,et al."Absolute Configuration of 12S-Deoxynortryptoquivaline from Ascidian-Derived Fungus Aspergillus clavatus Determined by Anisotropic NMR and Chiroptical Spectroscopy".JOURNAL OF NATURAL PRODUCTS 87.2(2024):381-387. |
入库方式： OAI收割
来源：海洋研究所
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