Method for efficiently converting sesquiterpene isomer derivative and preparing high-purity monomer and application of sesquiterpene isomer derivative and high-purity monomer in antitumor drugs

A technology of sesquiterpenes and isomers, which is applied in the field of compound preparation and monomer compound separation, can solve the problems such as the separation of three configurations of celeryne, and achieve high purity and good separation Effect

Active Publication Date: 2021-12-21
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, the separation of the three configurational monomer components of celinae has not been studied

Method used

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  • Method for efficiently converting sesquiterpene isomer derivative and preparing high-purity monomer and application of sesquiterpene isomer derivative and high-purity monomer in antitumor drugs
  • Method for efficiently converting sesquiterpene isomer derivative and preparing high-purity monomer and application of sesquiterpene isomer derivative and high-purity monomer in antitumor drugs
  • Method for efficiently converting sesquiterpene isomer derivative and preparing high-purity monomer and application of sesquiterpene isomer derivative and high-purity monomer in antitumor drugs

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preparation example Construction

[0028] In a typical embodiment of the present invention, a method for preparing sesquiterpene isomer derivatives with efficient conversion and high-purity monomers is provided, and the preparation method at least includes:

[0029] Gemacerone is converted into celeryne, and separated and extracted using high-speed countercurrent chromatography and preparative HPLC to obtain three configuration monomers of celeryne; in the high-speed countercurrent chromatography, the solvent system is Ag-containing + of n-hexane / methanol / water.

[0030] Described gemaconone is converted into the concrete method of apigenene as:

[0031] Add silica gel and phosphoric acid aqueous solution to gemaconone solution, and react at high temperature.

[0032] Wherein, the volume mass of the gemacerone and silica gel is 100-500 μL: 1-20 mg, such as 200 μL: 4 mg, 200 μL: 8 mg, 200 μL: 12 mg, 200 μL: 16 mg and 200 μL: 20 mg;

[0033] The concentration of the phosphoric acid aqueous solution is controlle...

Embodiment

[0054] 1. Single factor experiment on the conversion of gemmazone to celrenene isomers

[0055] 1. Process flow:

[0056] Use a pipette gun to accurately draw 200 μL of a crude sample of gemmaquinone into a stoppered test tube, add different amounts of silica gel (200-300 mesh) as a catalyst for the reaction, and react at a certain temperature for a certain period of time in different pH environments. After the reaction was completed, the reaction solution was transferred to a centrifuge tube, centrifuged at 8000r / min for 10min, and 10μL of the supernatant was accurately measured and diluted with 1mL of methanol, and then detected by HPLC.

[0057] 2. Process optimization:

[0058] Select different silica gel addition amounts (0, 4, 8, 12, 16 and 20mg), add 5 μ L of phosphoric acid aqueous solution of different concentrations (0%, 20%, 40%, 60%, 80% and 100%), different Reaction time (10, 20, 30, 40, 50, and 60min), different reaction temperatures (30, 50, 70, 90, 110, and 1...

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Abstract

The invention provides a method for efficiently converting a sesquiterpene isomer derivative and preparing a high-purity monomers and application of the sesquiterpene isomer derivative and the high-purity monomer in antitumor drugs, and belongs to the technical field of compound preparation and monomeric compound separation. The preparation method at least comprises the following steps: converting germacrone into selinene, and separating and extracting by using high-speed counter-current chromatography and preparative HPLC to obtain three configuration monomers of selinene, wherein a solvent system in the high-speed counter-current chromatography is n-hexane/methanol/water containing Ag<+>. The preparation method provided by the invention has the advantages of simplicity, good separation degree, high purity and the like, provides a new solution for extraction and analysis of related compounds such as sesquiterpene isomer derivatives and the like, and has good practical application value.

Description

technical field [0001] The invention belongs to the technical field of compound preparation and monomer compound separation, and specifically relates to a high-efficiency conversion of sesquiterpene isomer derivatives and a high-purity monomer preparation method and its application in antitumor drugs. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Sesquiterpenes are aroma molecules with sedative and anti-inflammatory effects. They have anti-inflammatory and antihistamine-like effects. They also have anti-itching, anti-allergic, analgesic, anti-spasmodic, immune-regulating, disinfecting and anti-bacterial effects, and Qi circulation. Removing stasis, repairing skin and ot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/207C07C7/12C07C13/48A61P35/00
CPCC07C1/2074C07C7/12A61P35/00C07C2602/28C07C2527/173C07B2200/09C07C13/48
Inventor 孙蓉王岱杰吴东进宋祥云杜航黄娜娜钟颖李建超郭崇李晓骄阳刘闰平朴政一
Owner SHANDONG UNIV
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