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化学学报
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化学学报 ›› 1981, Vol. 39 ›› Issue (5): 445-452. 上一篇    下一篇

论文

几个新乌头碱型——二萜生物碱的13C核磁共振谱研究

杨崇仁, 王德祖, 吴大刚, 郝小江, 周俊   

  1. 中国科学院昆明植物研究所植物化学研究室
  • 投稿日期:1979-08-02 发布日期:2013-06-03

13C NMR SPECTROSCOPIC STUDIES OF SEVERAL NEW DITERPENOID ALKALOIDS FROM ACONITUM SPECIES

YANG CHONG-REN, WANG DE-ZU, WU DA-GANG, HAO XIAO-JIANG, ZHOU JUN   

  1. Laboratory of Phytochemistry, Kunming Institute of Botany, Academia Sinica
  • Received:1979-08-02 Published:2013-06-03

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本文报道云南药用乌头属植物中乌头碱型二萜生物碱乌头碱(aconitine,1),滇乌碱(yunaconitine,3),黄草乌碱甲(vilmorrianine A,5)、碱乙(vilmorrianine B,即karakoline,8)、碱丙(vilmorrianine C,7)、碱丁(vilmorrianine D,9)和鹤乌碱(scopaline,10)及3-乙酰乌头碱(2),3-乙酰滇乌碱(4)和3-乙酰黄草乌碱甲(6)的13C核磁共振谱。根据偏共振去偶及取代基加和律计算,并与类似物比较,对这些化合物各碳原子的共振讯号给予了指定,且进一步确定了新生物碱3,5,7,9的结构。对1,3,5,8及2,4,6中的羟基和乙酰基取代效应也作了分析,并通过对1,3,5及2,4,6的比较而修正了Pelletier对1中C2和C12化学位移的指定。还证明8中因C1为α-OH而形成分子内氢键,使A环呈船式构型,所以A环上碳的化学位移与一般的椅式构型有显著差异。本文还报道了从鹤庆紫草乌(Aconitum episcopale Levl.)中分到的一新生物碱——鹤乌碱(scopaline)。根据红外光谱、质谱及1H和13C核磁共振谱,确定其结构为10。

The 13C NMR spectra of aconitin)-type diterpanoid alkaloids and derivatives:yunaconitine(8),vilmorrianines A (5), B (karakoline, 8),C (7) and D (9),soopaline(10), 3-acetyl-yunaconitine (4) and 3-acetyl-vilmorrianine A (6) have been determined at 22.63 MHz in the PFT mode. These alkaloids were recently isolated from Aconitum, species used in medicine in Yunnan.The structures of new alkaloids 3, 5, 7, 9 and 10 wore further proved by 13C NMR spectra. The chemical shifts due to eaoh carbon atoms in these compounds were assigned with the help of off-resonance decoupling, additive relationship and comparison with similar alkaloids (see Tables 1 and 3).The substituent effects of hydroxyl and acetyl groups in aconitine-type ester alkaloids are analysed (see Tables 4 and 5).