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Method for converting bergenin into special nitrogenous derivative by using penicillium

A technology of petrolatum and Penicillium, which is applied in the field of using Penicillium to transform petrakinin into special nitrogen-containing derivatives, and can solve the problems of poor water solubility, insignificant activity, poor oral absorption and the like of petrolatum

Inactive Publication Date: 2012-02-01
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the water solubility of petracenin is poor, and many activities are not very significant, so it is very necessary to carry out structural modification
Through structural modification, a new petracenin conversion product was discovered, which is expected to solve the problems of poor oral absorption, low bioavailability, and low biological activity

Method used

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  • Method for converting bergenin into special nitrogenous derivative by using penicillium
  • Method for converting bergenin into special nitrogenous derivative by using penicillium
  • Method for converting bergenin into special nitrogenous derivative by using penicillium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Fungal fermentation medium: glucose 20 g, yeast extract 5 g, peptone 5 g, NaCl 5 g, K 2 HPO 4 5 g, distilled water 1000 mL, pH 6.5.

[0055] Pour 50mL of the fungal fermentation medium into a 250mL Erlenmeyer flask, and after autoclaving at 121°C, insert Penicillium clatices ( Penicillium crustosum , CGMCC No. 3.7142) strain, 28°C, 180r / min shake flask fermentation and culture for 48 hours, stop the fermentation, add 2% petracenin DMSO solution to the medium, 28°C, after 96 hours, stop the transformation reaction, filter to remove the mycelia, and the supernatant contains the transformation product of petogenin ( E )-7-((6-acetyl-2-(oximino)-4-methyl-1, 2-dihydropyridine-3-hydrocarbyl)methyl)-3, 4, 8, 10-tetrahydroxy- 2-(Hydroxymethyl)-9-methoxy-2, 3, 4, 4a-tetrahydro[3, 2- c ] Isochromen-6(10b H)-one. The supernatant was extracted three times with 50 mL of ethyl acetate, and then purified by silica gel column chromatography (chloroform:methanol=10:1) and Sephade...

Embodiment 2

[0057] Fungal fermentation medium: glucose 20 g, yeast extract 5 g, peptone 5 g, NaCl 5 g, K 2 HPO 4 5 g, distilled water 1000 mL, pH 6.5.

[0058] Pour 50mL of the fungal fermentation medium into a 250mL Erlenmeyer flask, and after autoclaving at 121°C, insert Penicillium clatices ( Penicillium crustosum , CGMCC No. 3.7142) strain, 28°C, 180r / min shake flask fermentation culture for 48 hours, stop the fermentation, add DMSO solution with a mass fraction of 2% petgenin in the medium, 28°C, after 120 hours, stop the transformation reaction, filter to remove the mycelia, and the supernatant contains the transformation product of petogenin ( E )-7-((6-acetyl-2-(oximino)-4-methyl-1, 2-dihydropyridine-3-hydrocarbyl)methyl)-3, 4, 8, 10-tetrahydroxy- 2-(Hydroxymethyl)-9-methoxy-2, 3, 4, 4a-tetrahydro[3, 2- c ] Isochromen-6(10b H)-one. The supernatant was extracted three times with 50 mL of ethyl acetate, and then purified by silica gel column chromatography (chloroform:methano...

Embodiment 3

[0060] Fungal fermentation medium: glucose 20 g, yeast extract 5 g, peptone 5 g, NaCl 5 g, K 2 HPO 4 5 g, distilled water 1000 mL, pH 6.5.

[0061] Pour 50mL of the fungal fermentation medium into a 250mL Erlenmeyer flask, and after autoclaving at 121°C, insert Penicillium clatices ( Penicillium crustosum , CGMCC No. 3.7142) strain, 28°C, 180r / min shake flask fermentation culture for 48 hours, stop the fermentation, add daidzein DMSO solution with a mass fraction of 2% to the medium, 28°C, after 96 hours, stop the transformation reaction, filter to remove the mycelia, and the supernatant contains the transformation product of petogenin ( E )-7-((6-acetyl-2-(oximino)-4-methyl-1, 2-dihydropyridine-3-hydrocarbyl)methyl)-3, 4, 8, 10-tetrahydroxy- 2-(Hydroxymethyl)-9-methoxy-2, 3, 4, 4a-tetrahydro[3, 2- c ] Isochromen-6(10b H)-one. After supernatant was extracted three times with 50mL ethyl acetate, after HPLC preparative column was prepared again, the petracenin transformat...

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Abstract

The invention relates to a method for converting bergenin into a special nitrogenous derivative by using penicillium. The method comprises the following steps of: inoculating a microbial strain which has bergenin structure modified special enzyme activity into a culture solution, and performing flask shaking fermentation culture; at the middle stage of fermentation, adding a bergenin-containing substrate conversion liquor into a fermentation liquor; after the conversion is finished, removing mycelia, extracting supernatant liquor by using an organic solvent, concentrating an extract liquor, and recrystallizing to obtain a converted product crystal; or concentrating the extract liquor, and performing silica gel chromatographic separation, Sephadex purification or high performance liquid chromatography (HPLC) to obtain a solution containing a converted product; and concentrating or crystallizing the solution or performing low-temperature drying treatment on the solution to obtain converted product crystals or powder. The product has 2,2-diphenyl-1-picrylhydrazyl (DPPH) eliminating capacity and oxidation resistance which are higher than those of the bergenin and has a restraint effect on lipid peroxidation.

Description

technical field [0001] The present invention relates to the use of microbial strains with special enzyme activity in Penicillium to modify the structure of bergenin (bergenin) into ( E )-7-((6-acetyl-2-(hydroxyimino)-4-methyl-1,2-dihydropyridin-3-yl)methyl)3, 4,8,10-tetrahydroxy-2-(hydroxymethyl)-9- methoxy-2,3,4,4a-tetrahydropyrano[3,2- c ] isochromen-6 (10b H)-one, namely ( E )-7-((6-acetyl-2-(oximino)-4-methyl-1, 2-dihydropyridine-3-hydrocarbyl)methyl)-3, 4, 8, 10-tetrahydroxy- 2-(Hydroxymethyl)-9-methoxy-2, 3, 4, 4a-tetrahydro[3, 2- c ] Isochromen-6(10bH)-one method. The conversion product is ( E )-7-((6-acetyl-2-(oximino)-4-methyl-1, 2-dihydropyridine-3-hydrocarbyl)methyl)-3, 4, 8, 10-tetrahydroxy- 2-(Hydroxymethyl)-9-methoxy-2, 3, 4, 4a-tetrahydro[3, 2- c ] Isochromen-6(10b H)-one. technical background [0002] Bergenin is a naturally occurring aromatic carbon glycoside, a dihydroisocoumarin derivative of glucopyranosyl gallic acid, and the molecule contains a ...

Claims

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Application Information

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IPC IPC(8): C12P17/18C12R1/80
Inventor 崔桂友朱志雄陆广念冉昇
Owner YANGZHOU UNIV
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