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Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
Li, Xin1,2; Li, Xiao-Ming1,2; Wang, Bin-Gui1,2
2019
Source PublicationMARINE DRUGS
ISSN1660-3397
Volume17Issue:1Pages:8
Corresponding AuthorWang, Bin-Gui(wangbg@ms.qdio.ac.cn)
AbstractWentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against ,-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydroxymethyl)-3-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, 2) on the basis of a methylation and subsequent NMR measurements, and was confirmed by X-ray crystallographic analysis. The method established in this paper could be applied to the structural re-examination or revision for some of the reported seco-anthraquinone derivatives.
KeywordStructure revision Wentiquinone C Methylation method Xanthones Anthraquinones Aspergillus wentii
DOI10.3390/md17010008
Indexed BySCI
Language英语
Funding ProjectNatural Science Foundation of China[31330009] ; Natural Science Foundation of China[41706182] ; Shandong Provincial Natural Science Foundation[ZR2017BB073]
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000458053200008
PublisherMDPI
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/160880
Collection实验海洋生物学重点实验室
Corresponding AuthorWang, Bin-Gui
Affiliation1.Chinese Acad Sci, Pilot Natl Lab Marine Sci & Technol Qingdao, Key Lab Expt Marine Biol, Inst Oceanol,Lab Marine Biol & Biotechnol, Nanhai Rd 7, Qingdao 266071, Peoples R China
2.Chinese Acad Sci, Ctr Ocean Mega Sci, Nanhai Rd 7, Qingdao 266071, Peoples R China
First Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Corresponding Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Recommended Citation
GB/T 7714
Li, Xin,Li, Xiao-Ming,Wang, Bin-Gui. Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis[J]. MARINE DRUGS,2019,17(1):8.
APA Li, Xin,Li, Xiao-Ming,&Wang, Bin-Gui.(2019).Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis.MARINE DRUGS,17(1),8.
MLA Li, Xin,et al."Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis".MARINE DRUGS 17.1(2019):8.
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