Method for converting aconite diester-type alkaloids into ester-type alkaloids

A technology of diester-type alkaloids and lipid-type alkaloids, which is applied in organic chemistry and other fields, and can solve problems such as high equipment requirements, low solubility, and reduced conversion rate

Active Publication Date: 2009-12-02
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
View PDF1 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method is effective, it needs to be completed in a sublimation device, which requires high equipment conditions.
In addition, there are also reports on the method of converting aconitum diester alkaloids into lipid alkaloids in the aqueous phase, but fatty acids and aconitum diester alkaloids have low solubility in water, which is not conducive to large-scale production, and Reaction in water is easy to generate hydrolyzate, thereby reducing the conversion rate (Chinese patent: "Synthetic method of fatty acid lipid aconitum alkaloid", application number: 200410010868.3)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for converting aconite diester-type alkaloids into ester-type alkaloids
  • Method for converting aconite diester-type alkaloids into ester-type alkaloids
  • Method for converting aconite diester-type alkaloids into ester-type alkaloids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1 mg of aconitine standard substance into 50 mL of toluene, and at this time, toluene has submerged the hypoconitine standard substance, then add 4.2 mg of palmitic acid and 0.25 mL of pyridine, and heat to reflux in a water bath at 95 ° C for 4 hours to obtain Lipid alkaloid: 8-palmitoyl-benzoyl aconitine (m / z 812).

[0021] The obtained reaction product was diluted 100 times with methanol and detected by electrospray mass spectrometry. According to the relative abundance ratio equal to the molar concentration ratio in electrospray mass spectrometry, the conversion rate of hypoaconitine was 97%. The alkaloid components generated by the reaction are: 8-palmitoyl-benzoyl aconitine (m / z812).

Embodiment 2

[0023] Add 1 mg of aconitine standard substance into 100 mL of toluene, at this time, the toluene has submerged the hypoconitine standard substance, then add 22 mg of oleic acid and 1 mL of pyridine into toluene, and heat to reflux in a 97°C water bath for 8 hours, Lipid alkaloid: 8-oleoyl-benzoyl aconitine (m / z 838) was obtained.

[0024] The obtained reaction product was diluted 100 times with methanol and then detected by electrospray mass spectrometry. According to its relative abundance ratio equal to molar concentration ratio in electrospray mass spectrometry, the conversion rate of hypoaconitine was 95%. The alkaloid component generated by the reaction is: 8-oleoyl-benzoyl aconitine (m / z838).

Embodiment 3

[0026] Add 1mg of aconitine standard substance into 100mL of toluene, and then add 40mg of linoleic acid and 5mL of pyridine to toluene, and heat to reflux in a water bath at 100°C for 12 hours , to obtain lipid alkaloid: 8-linoleoyl-benzoyl aconitine (m / z 836).

[0027] The resulting reaction product was diluted 100 times with methanol and then detected by electrospray mass spectrometry. According to its relative abundance ratio equal to the molar concentration ratio in electrospray mass spectrometry, the conversion rate of hypoaconitine was 94%. The alkaloid component generated by the reaction is: 8-linoleoyl-benzoyl aconitine (m / z836).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a method for converting aconite diester-type alkaloids into ester-type alkaloids. The method comprises the following steps: adding an aconite diester-type alkaloids material into methylbenzene, making the methylbenzene submerge the material, adding long-chain fatty acid into the methylbenzene, then adding pyridine into the methylbenzene, and heating and refluxing the mixture to obtain an ester-type alkaloids product. The aconite diester-type alkaloids material is an aconitine standard product, a medium aconitine standard product or a defective aconitine standard product, or dried powder of Chinese medicinal aconite root or radix aconiti agrestis or monkshood. The electric spray mass spectrometry shows that the method converts the virulent aconite diester-type alkaloids into the ester-type alkaloids, and the conversion rate is more than 90 percent; in addition, the method can realize direct use of Chinese medicinal plants as reaction raw materials, and can avoid the early extraction and purification operations of reactants.

Description

technical field [0001] The invention belongs to the technical field of traditional Chinese medicines, and in particular relates to a method for converting aconitum diester alkaloids into lipid alkaloids. technical background [0002] Aconitum alkaloids include diester-type alkaloids, mono-ester-type alkaloids and lipid-type alkaloids, which are mainly found in traditional Chinese medicines such as Chuanwu, Aconitum, and Fuzi, and are pharmacologically active ingredients. Ester alkaloids are highly toxic alkaloids, which can easily lead to poisoning events. Therefore, the derivatization of aconitum diester alkaloids has become an important research topic. Some work has been carried out around the conversion from aconitum diester alkaloids to lipid alkaloids. Pelletier et al. reported in J.Nat.Prod.1994, 57 (7), 963-970 that aconitum Diester-type alkaloids and long-chain fatty acids react in the sublimation device (0.1-0.5mmHg) for more than 3 hours, then the diester-type alk...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/22
Inventor 刘淑莹刘文龙宋凤瑞刘志强董欣
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap