Rapid determination of the relative configuration of diverse 8,4'-oxyneolignans by NMR analysis: Retrospective studies, improvement and structural revision

被引：2

作者：

Zhao, Peng ^{[1
,2
,3
,4
]}

Lou, Li-Li

Xin, Ben-Song

Li, Zhi-Yuan ^{[1
,2
,3
,4
]}

Guo, Rui ^{[1
,2
,3
,4
]}

Zhou, Wei-Yu

Lv, Tian-Ming ^{[1
,2
,3
,4
]}

Huang, Xiao-Xiao ^{[1
,2
,3
,4
]}

Song, Shao-Jiang ^{[1
,2
,3
,4
]}

机构：

[1] Key Lab Computat Chem Based Nat Antitumor Drug Res, Shenyang, Peoples R China

[2] Engn Res Ctr Nat Med Act Mol Res & Dev Liaoning Pr, Shenyang, Peoples R China

[3] Key Lab Nat Bioact Cpds Discovery & Modificat, Shenyang, Peoples R China

[4] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Shenyang 110016, Liaoning, Peoples R China

来源：

PHYTOCHEMISTRY | 2023年 / 214卷

基金：

中国国家自然科学基金;

关键词：

8,4'-oxyneolignans; Configuration determination; NMR methods; Retrospective studies; Structural revision; NEOLIGNANS; LIGNANS; ASSIGNMENT; FRUITS; SEEDS; 8,4'-OXYNEOLIGNANS; FLAVONOLIGNANS; ROOTS;

D O I：

10.1016/j.phytochem.2023.113801

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The characteristic H-1 NMR signals (H-7 and H-2-9) are significant parameters that have been widely used to assess the relative configuration of H-7 and H-8 of 8,4'-oxyneolignans. However, many usual 8,4'-oxyneolignans cannot be accurately determined by existing NMR methods and no research considering their limitations was performed until now. In this study, the application scope of NMR methods was comprehensively studied and the ?d(H9a-H9b) methods have been extended to solve the majority of configuration determination difficulties. The accuracy of extended NMR methods was verified by anisotropic NMR (RCSA measurements), NMR calculation and diverse statistical analysis (MAE(??d), CP3 and DP4+). Furthermore, the theoretical conformational analysis was per-formed to investigate the inherent limitations of existing NMR methods. This study could provide a valuable reference for determining the relative configuration of H-7 and H-8 in 8,4'-oxyneolignans and the relative configuration of 23 recently reported 8,4'-oxyneolignan derivatives should be reassigned as well.

引用

页数：11