A kind of synthetic method of Ginkgo biloba polyprenol metal complex with light control activity

A technology of metal complex and leaf polyprenol, which is applied in the synthesis field of ginkgo leaf polyprenol metal complex with light control activity, and achieves the effect of good dark stability

Active Publication Date: 2022-06-28
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on the synthesis of GBP-ruthenium polypyridine metal complexes is rarely reported at home and abroad.

Method used

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  • A kind of synthetic method of Ginkgo biloba polyprenol metal complex with light control activity
  • A kind of synthetic method of Ginkgo biloba polyprenol metal complex with light control activity
  • A kind of synthetic method of Ginkgo biloba polyprenol metal complex with light control activity

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthetic route of aminopolypentenol is as follows figure 1 shown.

[0041] Weigh 0.27g of polypentenol, 0.06g of phthalimide and 0.11g of triphenylphosphine into a 35mL thick-walled pressure bottle, add 2.5mL of tetrahydrofuran, and then add 0.08g of diethyl azodicarboxylate The ester was reacted with magnetic stirring at 20°C for 4.0h (nitrogen atmosphere), concentrated after the reaction, and the concentrate was dissolved in ether. A. Concentrate A is in the form of light yellow oil. Dissolve Concentrate A with a small amount of diethyl ether and then apply it to a silica gel column (silica gel is 200-300 mesh, silica gel column is 2cm×40cm, 10g) for elution, and the eluent is diethyl ether: n-hexane Alkane=1:4, eluate A (0.21g) is a light yellow oil with Rf of 0.6 (developing solvent is ether: n-hexane=1:4);

[0042] Weigh 0.44g of eluate A and 0.24g of hydrazine hydrate into a 35mL thick-walled pressure-resistant bottle, respectively, then add 3.5mL of tetrah...

Embodiment 2

[0045] Weigh 30mg of aminopolypentenol ligand, 11.3mg of potassium hydroxide in a mixed solution of 5mL of water-ethanol (1:9), stir for 30min with a collector-type constant temperature heating magnetic stirrer, add 100mg of cis-Ru ( bpy) 2 Cl 2 , refluxed for 2h. The solvent was removed by rotary evaporation to obtain 0.17 g of a concentrate. It is then separated with a silica gel column. Weigh 6 g of silica gel, the silica gel column is 2 cm×40 cm, the silica gel is 200-300 mesh, and the eluent (chloroform-methanol=100:4) is used for rinsing. The collected compounds were dissolved in ethanol and NH was added 4 PF 6 The solid precipitated, filtered with filter paper to obtain a red precipitate, washed with water, and dried.

[0046] The hydrogen spectral shifts of aminopolypentenol metal complexes (e.g. image 3 shown) is analyzed in two parts:

[0047] (1) Aminopolypentenol moiety 1 H NMR, δ: 5.27 (br-t,=C H -CH 2 -N);5.12(m,=CH);3.26(br-d,N-CH 2 ); 1.90~2.08(m,-...

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Abstract

The invention discloses a synthesis method of ginkgo biloba polyprenol metal complex with light control activity. The method comprises the following steps: using high-purity ginkgo biloba polyprenol as a raw material, replacing the terminal hydroxyl group of the polyprenol with an active group with stronger coordination ability by means of chemical modification, and then combining it with a ruthenium polypyridine complex Carry out complexation reaction to synthesize Ginkgo biloba polyprenol-ruthenium polypyridine metal complex; the prepared complex has good photodissociation efficiency and light-controlled anti-tumor properties, and can be used as a high-value Ginkgo biloba polyprene Provide theoretical reference and technical support for the development of alcohol functional products.

Description

technical field [0001] The invention belongs to the field of high-value functional product development of natural products, and particularly relates to a method for synthesizing a metal complex of ginkgo biloba polyprenol with light control activity. Background technique [0002] Ginkgo biloba is a precious and unique forest plant in my country. Ginkgo biloba has many important pharmacological effects and economic value, among which the main bioactive components are flavonoids, terpene lactones, polyprenol (PPs) and polysaccharides. At present, the development and application of ginkgo biloba products in my country are still in the initial stage, mainly using flavonoids and terpene lactones, and the most valuable PPs have not yet been developed and utilized. Ginkgo biloba polyprenol (GBP) is a betulinol PPs composed of 14-24 isopentenyl units. It has become a research hotspot in recent years due to its similar structure to doliol, which is involved in the synthesis of human...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00A61P35/00A61K47/55A61K41/00A61K31/765A61K31/7135
CPCC08G83/008A61K41/0042A61K31/765A61K31/7135A61K47/55A61P35/00
Inventor 王成章张昌伟陶冉
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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