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

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

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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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

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通讯作者: 陈斌, bchen63@163.com

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