Citation: Xian-Hua Meng, Zhi-Bo Jiang, Cheng-Gen Zhu, Qing-Lan Guo, Cheng-Bo Xu, Jian-Gong Shi. Napelline-type C20-diterpenoid alkaloid iminiums from an aqueous extract of “fu zi”: Solvent-/base-/acid-dependent transformation and equilibration between alcohol iminium and aza acetal forms[J]. Chinese Chemical Letters, ;2016, 27(7): 993-1003. doi: 10.1016/j.cclet.2016.05.013 shu

Napelline-type C20-diterpenoid alkaloid iminiums from an aqueous extract of “fu zi”: Solvent-/base-/acid-dependent transformation and equilibration between alcohol iminium and aza acetal forms

  • Corresponding author: Jian-Gong Shi, shijg@imm.ac.cn
  • Received Date: 3 May 2016
    Revised Date: 15 May 2016
    Accepted Date: 18 May 2016
    Available Online: 27 July 2016

Figures(11)

  • Three new napelline-type C20-diterpenoid alkaloids, named aconicarmichinium A and B trifluoroacetates (1 and 2) and aconicarmichinium C chloride (3), were isolated from an aqueous extract of “fu zi”, the lateral roots of Aconitum carmichaelii. Their structures were elucidated by extensive spectroscopic data analysis. Compounds 1-3 represent the first examples of napelline-type C20-diterpenoid alkaloid alcohol iminiums, of which the structures were fully characterized. In addition, transformation and equilibration between the alcohol iminiums (1-3) and the aza acetals 1a-3a were investigated by measurements of the NMR spectra in protic and aprotic deuteriumsolvents including alkali pyridine-d5, along with evaporation under reduced pressure and gradual additions of TFA, AcOH, and HCl. The results demonstrated that the transformation and equilibration were solvent-, base-, and acid-dependent. Especially, in aqueous biological fluid, these C20-diterpenoid alkaloids would more likely exist as the alcohol iminiums accompanied by anion counterparts in biosystems to increase their solubility, bioavailability, transportations, and functions. The absolute configurations of 1-3 were confirmed by X-ray crystallographic analysis of 2a.
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