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 4,5; Song, Qi 1; Li, Xiao-Lu 5; Li, Xiao-Ming 1; Hu, Xue-Yi 1; Li, Hong-Lei 1; Liu, Hao-Ran 3,5; Wang, Bin-Gui 1,2; Sun, Han 3,5
刊名	JOURNAL OF NATURAL PRODUCTS
	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.
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关键词	RESIDUAL DIPOLAR COUPLINGS ; RELATIVE CONFIGURATION
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
内容类型	期刊论文
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.