天然产物研究与开发 ›› 2022, Vol. 34 ›› Issue (增刊2): 18-25.

• 研究论文 • 上一篇    下一篇

三尖杉宁碱的核磁共振数据解析研究

刘雅琴*,余明新,何   玲   

  1. 浙江大学化学系,杭州 310027
  • 出版日期:2022-12-07 发布日期:2022-12-07
  • 基金资助:
    浙江大学实验技术项目(SJS202002)

Structural analysis of cephalomannine by nuclear magnetic resonance spectroscopy

LIU Ya-qin*,YU Ming-xin,HE Ling   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027,China
  • Online:2022-12-07 Published:2022-12-07

摘要:

三尖杉宁碱是一种具有抗肿瘤作用的紫杉醇类化合物,采用核磁共振氢谱(1H NMR)、氢-氢相关谱(1H-1H COSY)、核磁共振碳谱(13C NMR和DEPT135)、异核单量子相关谱(HSQC)、异核多键相关谱(HMBC)进行解析,对其所有的NMR 谱信号进行归属。同时,针对三尖杉宁碱分子的结构特点,探索性地引入ROESY谱来表征空间相关以获得更丰富的空间信息。在1H NMR谱中显示有多组质子信号,共30个质子;13C NMR谱显示样品分子有41组碳原子信号,分子中含有45个碳,存在重叠峰;DEPT135谱显示出3组仲碳,29组叔碳,其余为季碳;在二维谱中,确认各组碳与氢的连接关系;化学键上相邻氢原子的偶合、远程相关和空间相关信息。该解析对象的结构相对较复杂,二维核磁共振波谱数据进一步确证了其分子结构。

关键词: 核磁共振二维谱;三尖杉宁碱;结构解析;ROESY谱 

Abstract:

Cephalomannine is a paclitaxel compound with antitumor effect and an important pharmaceutical intermediate. All NMR signals were assigned by using 1H NMR,1H-1H COSY,13C NMR and DEPT135,1H-13C HSQC and HMBC.At the same time,according to the characteristics of cephalomannine molecule,and ROESY is tentatively introduced to characterize spatial correlation in order to obtain richer spatial information.The 1H NMR spectrum of cephalomannine showed multiple groups of proton signals,a total of 30 protons;13C NMR spectrum showed that there were 41 groups of carbon atom signals in the sample molecule,which contained 45 carbon atoms and overlapping peaks;DEPT135 spectrum showed 3 groups of secondary carbon,29 groups of tertiary carbon and the rest were quaternary carbon.The connection information between carbon and hydrogen,the identification of adjacent hydrogen atoms on the chemical bond,the remote correlation information and the spatial correlation information is confirmed by the two-dimensional spectrum.The structure of the analytical object in this study is relatively complex,which is conducive to molecular structure further confirmed by two-dimensional NMR data.

Key words: two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy, cephalomannine, structural analysis, ROESY spectroscopy

中图分类号:  O657