Absolute Configuration of 12<i>S</i>-Deoxynortryptoquivaline from Ascidian-Derived Fungus <i>Aspergillus clavatus</i> Determined by Anisotropic NMR and Chiroptical Spectroscopy

doi:10.1021/acs.jnatprod.3c01157

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	*Absolute Configuration of 12S-Deoxynortryptoquivaline from Ascidian-Derived Fungus Aspergillus clavatus* Determined by Anisotropic NMR and Chiroptical Spectroscopy**
	Doro-Goldsmith, Elisa 1,2; Song, Qi3 ; Li, Xiao-Lu 1; Li, Xiao-Ming 3; Hu, Xue-Yi3 ; Li, Hong-Lei3 ; Liu, Hao-Ran 1,4; Wang, Bin-Gui3,5 ; Sun, Han 1,4
	2024-01-30
发表期刊	JOURNAL OF NATURAL PRODUCTS
ISSN	0163-3864
卷号	87 期号:2 页码:381-387
通讯作者	Wang, Bin-Gui(wangbg@ms.qdio.ac.cn) ; Sun, Han(hsun@fmp-berlin.de)
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.
DOI	10.1021/acs.jnatprod.3c01157
收录类别	SCI
语种	英语
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
WOS类目	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
WOS记录号	WOS:001161238900001
出版者	AMER CHEMICAL SOC
WOS关键词	RESIDUAL DIPOLAR COUPLINGS ; RELATIVE CONFIGURATION
引用统计
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/184475
专题	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.Leibniz Forschungsinstitut Mol Pharmakol FMP, D-13125 Berlin, Germany 2.Univ Edinburgh, Sch Chem, Edinburgh EH9 3FJ, Scotland 3.Chinese Acad Sci, Inst Oceanol, CAS & Shandong Prov Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 4.Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany 5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
通讯作者单位	中国科学院海洋研究所
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.